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The Info List - Hydrogen Peroxide





Hydrogen
Hydrogen
peroxide is a chemical compound with the formula H 2O 2. In its pure form, it is a pale blue, clear liquid, slightly more viscous than water. Hydrogen
Hydrogen
peroxide is the simplest peroxide (a compound with an oxygen–oxygen single bond). It is used as an oxidizer, bleaching agent and antiseptic. Concentrated hydrogen peroxide, or "high-test peroxide", is a reactive oxygen species and has been used as a propellant in rocketry.[4] Its chemistry is dominated by the nature of its unstable peroxide bond. Hydrogen
Hydrogen
peroxide is unstable and slowly decomposes in the presence of base or a catalyst. Because of its instability, hydrogen peroxide is typically stored with a stabilizer in a weakly acidic solution. Hydrogen
Hydrogen
peroxide is found in biological systems including the human body. Enzymes that use or decompose hydrogen peroxide are classified as peroxidases.

Contents

1 Properties

1.1 Aqueous solutions 1.2 Structure 1.3 Comparison with analogues

2 Discovery 3 Manufacture

3.1 Availability

4 Reactions

4.1 Decomposition 4.2 Redox
Redox
reactions 4.3 Organic reactions 4.4 Precursor to other peroxide compounds

5 Biological function 6 Uses

6.1 Bleaching 6.2 Detergents 6.3 Production of organic compounds 6.4 Disinfectant

6.4.1 Cosmetic applications 6.4.2 Use in alternative medicine

6.5 Propellant 6.6 Other uses

7 Safety

7.1 Historical incidents

8 See also 9 References 10 External links

Properties[edit] The boiling point of H 2O 2 has been extrapolated as being 150.2 °C, approximately 50 °C higher than water. In practice, hydrogen peroxide will undergo potentially explosive thermal decomposition if heated to this temperature. It may be safely distilled at lower temperatures under reduced pressure.[5] Aqueous solutions[edit] In aqueous solutions hydrogen peroxide differs from the pure material due to the effects of hydrogen bonding between water and hydrogen peroxide molecules. Hydrogen
Hydrogen
peroxide and water form a eutectic mixture, exhibiting freezing-point depression; pure water has a melting point of 0 °C and pure hydrogen peroxide of −0.43 °C. The boiling point of the same mixtures is also depressed in relation with the mean of both boiling points (125.1 °C). It occurs at 114 °C. This boiling point is 14 °C greater than that of pure water and 36.2 °C less than that of pure hydrogen peroxide.[6]

Phase diagram
Phase diagram
of H 2O 2 and water: Area above blue line is liquid. Dotted lines separate solid+liquid phases from solid+solid phases.

Density
Density
of aqueous solution of H2O2

H2O2 (w/w) Density
Density
(g/cm3) Temperature
Temperature
(°C)

3% 1.0095 15

27% 1.10 20

35% 1.13 20

50% 1.20 20

70% 1.29 20

75% 1.33 20

96% 1.42 20

98% 1.43 20

100% 1.45 20

Structure[edit] Hydrogen
Hydrogen
peroxide (H 2O 2) is a nonplanar molecule with (twisted) C2 symmetry. Although the O−O bond is a single bond, the molecule has a relatively high rotational barrier of 2460 cm−1 (29.45 kJ/mol);[7] for comparison, the rotational barrier for ethane is 12.5 kJ/mol. The increased barrier is ascribed to repulsion between the lone pairs of the adjacent oxygen atoms and results in hydrogen peroxide displaying atropisomerism. The molecular structures of gaseous and crystalline H 2O 2 are significantly different. This difference is attributed to the effects of hydrogen bonding, which is absent in the gaseous state.[8] Crystals of H 2O 2 are tetragonal with the space group D4 4P4121.[9]

Structure and dimensions of H2O2 in the gas phase

Structure and dimensions of H2O2 in the solid (crystalline) phase

Properties of H2O2 and its analogues values marked * are extrapolated

Name Formula Molar mass (g/mol) TM (°C) TB (°C)

Hydrogen
Hydrogen
peroxide HOOH 34.01 −0.43 150.2*

Water HOH 18.02 0.00 99.98

Hydrogen
Hydrogen
disulfide HSSH 66.15 −89.6 70.7

Hydrazine H2NNH2 32.05 2 114

Hydroxylamine NH2OH 33.03 33 58*

Diphosphane H2PPH2 65.98 −99 63.5*

Comparison with analogues[edit] Hydrogen
Hydrogen
peroxide has several structural analogues with Hm−X−X−Hn bonding arrangements (water also shown for comparison). It has the highest (theoretical) boiling point of this series (X = O, N, S). Its melting point is also fairly high, being comparable to that of hydrazine and water, with only hydroxylamine crystallising significantly more readily, indicative of particularly strong hydrogen bonding. Diphosphane
Diphosphane
and hydrogen disulfide exhibit only weak hydrogen bonding and have little chemical similarity to hydrogen peroxide. All of these analogues are thermodynamically unstable. Structurally, the analogues all adopt similar skewed structures, due to repulsion between adjacent lone pairs. Discovery[edit] Alexander von Humboldt
Alexander von Humboldt
synthesized one of the first synthetic peroxides, barium peroxide, in 1799 as a by-product of his attempts to decompose air. Nineteen years later Louis Jacques Thénard
Louis Jacques Thénard
recognized that this compound could be used for the preparation of a previously unknown compound, which he described as oxidized water – subsequently known as hydrogen peroxide.[10][11] An improved version of this process used hydrochloric acid, followed by addition of sulfuric acid to precipitate the barium sulfate byproduct. Thénard's process was used from the end of the 19th century until the middle of the 20th century.[12] Thénard and Joseph Louis Gay-Lussac
Joseph Louis Gay-Lussac
synthesized sodium peroxide in 1811. The bleaching effect of peroxides and their salts on natural dyes became known around that time, but early attempts of industrial production of peroxides failed, and the first plant producing hydrogen peroxide was built in 1873 in Berlin. The discovery of the synthesis of hydrogen peroxide by electrolysis with sulfuric acid introduced the more efficient electrochemical method. It was first implemented into industry in 1908 in Weißenstein, Carinthia, Austria. The anthraquinone process, which is still used, was developed during the 1930s by the German chemical manufacturer IG Farben
IG Farben
in Ludwigshafen. The increased demand and improvements in the synthesis methods resulted in the rise of the annual production of hydrogen peroxide from 35,000 tonnes in 1950, to over 100,000 tonnes in 1960, to 300,000 tonnes by 1970; by 1998 it reached 2.7 million tonnes.[13] Pure hydrogen peroxide was long believed to be unstable, as early attempts to separate it from the water, which is present during synthesis, all failed. This instability was due to traces of impurities (transition-metal salts), which catalyze the decomposition of the hydrogen peroxide. Pure hydrogen peroxide was first obtained in 1894—almost 80 years after its discovery—by Richard Wolffenstein, who produced it by vacuum distillation.[14] Determination of the molecular structure of hydrogen peroxide proved to be very difficult. In 1892 the Italian physical chemist Giacomo Carrara (1864–1925) determined its molecular mass by freezing-point depression, which confirmed that its molecular formula is H2O2.[15] At least half a dozen hypothetical molecular structures seemed to be consistent with the available evidence.[16] In 1934, the English mathematical physicist William Penney and the Scottish physicist Gordon Sutherland proposed a molecular structure for hydrogen peroxide that was very similar to the presently accepted one.[17] Manufacture[edit] Previously, hydrogen peroxide was prepared industrially by hydrolysis of the ammonium peroxydisulfate, which was itself obtained by the electrolysis of a solution of ammonium bisulfate (NH 4HSO 4) in sulfuric acid:

(NH 4) 2S 2O 8 + 2 H 2O → H 2O 2 + 2 (NH 4)HSO 4

Today, hydrogen peroxide is manufactured almost exclusively by the anthraquinone process, which was formalized in 1936 and patented in 1939. It begins with the reduction of an anthraquinone (such as 2-ethylanthraquinone or the 2-amyl derivative) to the corresponding anthrahydroquinone, typically by hydrogenation on a palladium catalyst; the anthrahydroquinone then undergoes autoxidation to regenerate the starting anthraquinone, with hydrogen peroxide as a by-product. Most commercial processes achieve oxidation by bubbling compressed air through a solution of the derivatized anthracene, whereby the oxygen present in the air reacts with the labile hydrogen atoms (of the hydroxy groups), giving hydrogen peroxide and regenerating the anthraquinone. Hydrogen
Hydrogen
peroxide is then extracted, and the anthraquinone derivative is reduced back to the dihydroxy (anthracene) compound using hydrogen gas in the presence of a metal catalyst. The cycle then repeats itself.[18][19]

The simplified overall equation for the process is simple:[18]

H 2 + O 2 → H 2O 2

The economics of the process depend heavily on effective recycling of the quinone (which is expensive) and extraction solvents, and of the hydrogenation catalyst. A process to produce hydrogen peroxide directly from the elements has been of interest for many years. Direct synthesis is difficult to achieve, as the reaction of hydrogen with oxygen thermodynamically favours production of water. Systems for direct synthesis have been developed, most of which are based around finely dispersed metal catalysts.[20][21] None of these has yet reached a point where they can be used for industrial-scale synthesis.

ISO tank container for hydrogen peroxide transportation

A tank car designed for transporting hydrogen peroxide by rail

Availability[edit] Hydrogen
Hydrogen
peroxide is most commonly available as a solution in water. For consumers, it is usually available from pharmacies at 3 and 6 wt% concentrations. The concentrations are sometimes described in terms of the volume of oxygen gas generated; one milliliter of a 20-volume solution generates twenty milliliters of oxygen gas when completely decomposed. For laboratory use, 30 wt% solutions are most common. Commercial grades from 70% to 98% are also available, but due to the potential of solutions of more than 68% hydrogen peroxide to be converted entirely to steam and oxygen (with the temperature of the steam increasing as the concentration increases above 68%) these grades are potentially far more hazardous and require special care in dedicated storage areas. Buyers must typically allow inspection by commercial manufacturers. In 1994, world production of H 2O 2 was around 1.9 million tonnes and grew to 2.2 million in 2006,[22] most of which was at a concentration of 70% or less. In that year bulk 30% H 2O 2 sold for around 0.54 USD/kg, equivalent to 1.50 USD/kg (0.68 USD/lb) on a "100% basis".[23] Hydrogen
Hydrogen
peroxide occurs in surface water, groundwater and in the atmosphere. It forms upon illumination or natural catalytic action by substances contained in water. Sea water contains 0.5 to 14 μg/L of hydrogen peroxide, freshwater 1 to 30 μg/L and air 0.1 to 1 parts per billion.[13] Reactions[edit] Decomposition[edit] Hydrogen
Hydrogen
peroxide is thermodynamically unstable and decomposes to form water and oxygen with a ΔHo of −98.2 kJ/mol and a ΔS of 70.5 J/(mol·K):

2 H 2O 2 → 2 H 2O + O 2

The rate of decomposition increases with rising temperature, concentration and pH, with cool, dilute, acidic solutions showing the best stability. Decomposition is catalysed by various compounds, including most transition metals and their compounds (e.g. manganese dioxide, silver, and platinum).[24] Certain metal ions, such as Fe2+ or Ti3+, can cause the decomposition to take a different path, with free radicals such as (HO·) and (HOO·) being formed. Non-metallic catalysts include potassium iodide, which reacts particularly rapidly and forms the basis of the elephant toothpaste experiment. Hydrogen peroxide can also be decomposed biologically by the enzyme catalase. The decomposition of hydrogen peroxide liberates oxygen and heat; this can be dangerous, as spilling high-concentration hydrogen peroxide on a flammable substance can cause an immediate fire. Redox
Redox
reactions[edit] Hydrogen
Hydrogen
peroxide exhibits oxidizing and reducing properties, depending on pH. In acidic solutions, H 2O 2 is one of the most powerful oxidizers known—stronger than chlorine, chlorine dioxide, and potassium permanganate. Also, through catalysis, H 2O 2 can be converted into hydroxyl radicals (·OH), which are highly reactive.

Oxidant/reduced product Oxidation
Oxidation
potential, V

fluorine/hydrogen fluoride 3.0

ozone/oxygen 2.1

hydrogen peroxide/water 1.8

potassium permanganate/manganese dioxide 1.7

chlorine dioxide/HClO 1.5

chlorine/chloride 1.4

In acidic solutions Fe2+ is oxidized to Fe3+ (hydrogen peroxide acting as an oxidizing agent):

2 Fe2+(aq) + H 2O 2 + 2 H+(aq) → 2 Fe3+(aq) + 2 H 2O(l)

and sulfite (SO2− 3) is oxidized to sulfate (SO2− 4). However, potassium permanganate is reduced to Mn2+ by acidic H 2O 2. Under alkaline conditions, however, some of these reactions reverse; for example, Mn2+ is oxidized to Mn4+ (as MnO 2). In basic solution, hydrogen peroxide can reduce a variety of inorganic ions. When it acts as a reducing agent, oxygen gas is also produced. For example, hydrogen peroxide will reduce sodium hypochlorite and potassium permanganate, which is a convenient method for preparing oxygen in the laboratory:

NaOCl + H 2O 2 → O 2 + NaCl + H 2O 2 KMnO 4 + 3 H 2O 2 → 2 MnO 2 + 2 KOH + 2 H 2O + 3 O 2

Organic reactions[edit] Hydrogen
Hydrogen
peroxide is frequently used as an oxidizing agent. Illustrative is oxidation of thioethers to sulfoxides:[25][26]

Ph−S−CH 3 + H 2O 2 → Ph−S(O)−CH 3 + H 2O

Alkaline hydrogen peroxide is used for epoxidation of electron-deficient alkenes such as acrylic acid derivatives, and for the oxidation of alkylboranes to alcohols, the second step of hydroboration-oxidation. It is also the principal reagent in the Dakin oxidation process. Precursor to other peroxide compounds[edit] Hydrogen
Hydrogen
peroxide is a weak acid, forming hydroperoxide or peroxide salts with many metals. It also converts metal oxides into the corresponding peroxides. For example, upon treatment with hydrogen peroxide, chromic acid(CrO 3 + H 2SO 4) forms an unstable blue peroxide CrO(O 2) 2. This kind of reaction is used industrially to produce peroxoanions. For example, reaction with borax leads to sodium perborate, a bleach used in laundry detergents:

Na 2B 4O 7 + 4 H 2O 2 + 2 NaOH → 2 Na 2B 2O 4(OH) 4 + H 2O

H 2O 2 converts carboxylic acids (RCO2H) into peroxy acids (RC(O)O2H), which are themselves used as oxidizing agents. Hydrogen
Hydrogen
peroxide reacts with acetone to form acetone peroxide and with ozone to form trioxidane. Hydrogen
Hydrogen
peroxide forms stable adducts with urea (hydrogen peroxide - urea), sodium carbonate (sodium percarbonate) and other compounds.[27] An acid-base adduct with triphenylphosphine oxide is a useful "carrier" for H 2O 2 in some reactions. The peroxide anion is a stronger nucleophile than hydroxide and displaces hydroxyl from oxyanions e.g. forming perborates and percarbonates. Sodium perborate
Sodium perborate
and sodium percarbonate are important consumer and industrial bleaching agents; they stabilize hydrogen peroxide and limit side reactions (e.g. reduction and decomposition note below). The peroxide anion forms an adduct with urea, hydrogen peroxide–urea. Hydrogen
Hydrogen
peroxide is both an oxidizing agent and reducing agent. The oxidation of hydrogen peroxide by sodium hypochlorite yields singlet oxygen. The net reaction of a ferric ion with hydrogen peroxide is a ferrous ion and oxygen. This proceeds via single electron oxidation and hydroxyl radicals. This is used in some organic chemistry oxidations, e.g. in the Fenton's reagent. Only catalytic quantities of iron ion is needed since peroxide also oxidizes ferrous to ferric ion. The net reaction of hydrogen peroxide and permanganate or manganese dioxide is manganous ion; however, until the peroxide is spent some manganous ions are reoxidized to make the reaction catalytic. This forms the basis for common monopropellant rockets. Biological function[edit]

Ascaridole

Hydrogen
Hydrogen
peroxide is formed in human and animals as a short-lived product in biochemical processes and is toxic to cells. The toxicity is due to oxidation of proteins, membrane lipids and DNA
DNA
by the peroxide ions.[28] The class of biological enzymes called SOD (superoxide dismutase) is developed in nearly all living cells as an important antioxidant agent. They promote the disproportionation of superoxide into oxygen and hydrogen peroxide, which is then rapidly decomposed by the enzyme catalase to oxygen and water.[29]

2

O

2

+ 2

H

+

SOD

H

2

O

2

+

O

2

displaystyle ce 2O2^ - +2H+->[ atop ce SOD ] H2O2 +O2

Formation of hydrogen peroxide by superoxide dismutase (SOD)

Peroxisomes are organelles found in virtually all eukaryotic cells.[30] They are involved in the catabolism of very long chain fatty acids, branched chain fatty acids, D-amino acids, polyamines, and biosynthesis of plasmalogens, etherphospholipids critical for the normal function of mammalian brains and lungs.[31] Upon oxidation, they produce hydrogen peroxide in the following process:[32]

R

CH

2

CH

2

CO

SCoA

+

O

2

FAD

R

CH

=

CH

CO

SCoA

+

H

2

O

2

displaystyle ce R-CH2-CH2-CO-SCoA +O2->[ atop ce FAD ] R-CH=CH-CO-SCoA +H2O2

FAD = flavin adenine dinucleotide

Catalase, another peroxisomal enzyme, uses this H2O2 to oxidize other substrates, including phenols, formic acid, formaldehyde, and alcohol, by means of the peroxidation reaction:

H

2

O

2

+

R ′

H

2

R ′

+ 2

H

2

O

displaystyle ce H2O2 + R'H2 -> R' + 2H2O

, thus eliminating the poisonous hydrogen peroxide in the process.

This reaction is important in liver and kidney cells, where the peroxisomes neutralize various toxic substances that enter the blood. Some of the ethanol humans drink is oxidized to acetaldehyde in this way.[33] In addition, when excess H2O2 accumulates in the cell, catalase converts it to H2O through this reaction:

H

2

O

2

CAT

1 2

O

2

+

H

2

O

displaystyle ce H2O2->[ atop ce CAT ] 1/2O2 +H2O

Another origin of hydrogen peroxide is the degradation of adenosine monophosphate which yields hypoxanthine. Hypoxanthine
Hypoxanthine
is then oxidatively catabolized first to xanthine and then to uric acid, and the reaction is catalyzed by the enzyme xanthine oxidase:[34]

Hypoxanthine

Xanthine
Xanthine
oxidase

 H2O, O2 H2O2

Xanthine

Xanthine
Xanthine
oxidase

 H2O, O2 H2O2

Uric acid

Degradation of hypoxanthine through xanthine to uric acid to form hydrogen peroxide.

Australian bombardier beetle

The degradation of guanosine monophosphate yields xanthine as an intermediate product which is then converted in the same way to uric acid with the formation of hydrogen peroxide.[34] Eggs of sea urchin, shortly after fertilization by a sperm, produce hydrogen peroxide. It is then quickly dissociated to OH· radicals. The radicals serve as initiator of radical polymerization, which surrounds the eggs with a protective layer of polymer.[35] The bombardier beetle has a device which allows it to shoot corrosive and foul-smelling bubbles at its enemies. The beetle produces and stores hydroquinone and hydrogen peroxide, in two separate reservoirs in the rear tip of its abdomen. When threatened, the beetle contracts muscles that force the two reactants through valved tubes into a mixing chamber containing water and a mixture of catalytic enzymes. When combined, the reactants undergo a violent exothermic chemical reaction, raising the temperature to near the boiling point of water. The boiling, foul-smelling liquid partially becomes a gas (flash evaporation) and is expelled through an outlet valve with a loud popping sound.[36][37][38] Hydrogen
Hydrogen
peroxide is a signaling molecule of plant defense against pathogens.[39] Hydrogen
Hydrogen
peroxide has roles as a signalling molecule in the regulation of a wide variety of biological processes.[40] The compound is a major factor implicated in the free-radical theory of aging, based on how readily hydrogen peroxide can decompose into a hydroxyl radical and how superoxide radical byproducts of cellular metabolism can react with ambient water to form hydrogen peroxide.[41] These hydroxyl radicals in turn readily react with and damage vital cellular components, especially those of the mitochondria.[42][43][44] At least one study has also tried to link hydrogen peroxide production to cancer.[45] These studies have frequently been quoted in fraudulent treatment claims.[citation needed] The amount of hydrogen peroxide in biological systems can be assayed using a fluorimetric assay.[46] Uses[edit] Bleaching[edit] About 60% of the world's production of hydrogen peroxide is used for pulp- and paper-bleaching.[22] Detergents[edit] The second major industrial application is the manufacture of sodium percarbonate and sodium perborate, which are used as mild bleaches in laundry detergents. Sodium percarbonate, which is an adduct of sodium carbonate and hydrogen peroxide, is the active ingredient in such products as OxiClean
OxiClean
and Tide laundry detergent. When dissolved in water, it releases hydrogen peroxide and sodium carbonate:[47]

2 Na2CO3·3 H2O2 → 2 Na2CO3 + 3 H2O2

Production of organic compounds[edit] It is used in the production of various organic peroxides with dibenzoyl peroxide being a high volume example. It is used in polymerisations, as a flour bleaching agent and as a treatment for acne. Peroxy acids, such as peracetic acid and meta-chloroperoxybenzoic acid are also produced using hydrogen peroxide. Hydrogen
Hydrogen
peroxide has been used for creating organic peroxide-based explosives, such as acetone peroxide. Disinfectant[edit]

Skin
Skin
shortly after exposure to 35% H 2O 2

Hydrogen
Hydrogen
peroxide is used in certain waste-water treatment processes to remove organic impurities. In advanced oxidation processing, the Fenton reaction[48][49] gives the highly reactive hydroxyl radical (·OH). This degrades organic compounds, including those that are ordinarily robust, such as aromatic or halogenated compounds.[50] It can also oxidize sulfur based compounds present in the waste; which is beneficial as it generally reduces their odour.[51] Hydrogen
Hydrogen
peroxide can be used for the sterilization of various surfaces,[52] including surgical tools[53] and may be deployed as a vapour (VHP) for room sterilization.[54] H2O2 demonstrates broad-spectrum efficacy against viruses, bacteria, yeasts, and bacterial spores.[55] In general, greater activity is seen against Gram-positive
Gram-positive
than Gram-negative
Gram-negative
bacteria; however, the presence of catalase or other peroxidases in these organisms can increase tolerance in the presence of lower concentrations.[56] Higher concentrations of H2O2 (10 to 30%) and longer contact times are required for sporicidal activity.[57] Hydrogen
Hydrogen
peroxide is seen as an environmentally safe alternative to chlorine-based bleaches, as it degrades to form oxygen and water and it is generally recognized as safe as an antimicrobial agent by the U.S. Food and Drug Administration
Food and Drug Administration
(FDA).[58] Historically hydrogen peroxide was used for disinfecting wounds, partly because of its low cost and prompt availability compared to other antiseptics. It is now thought to inhibit healing and to induce scarring because it destroys newly formed skin cells.[59] Only a very low concentration of H2O2 can induce healing, and only if not repeatedly applied.[60] Surgical use can lead to gas embolism formation.[61][62] Despite this, it is still used for wound treatment in many developing countries.[63][64] Dermal exposure to dilute solutions of hydrogen peroxide cause whitening or bleaching of the skin due to microembolism caused by oxygen bubbles in the capillaries.[65] Cosmetic applications[edit] Diluted H 2O 2 (between 1.9% and 12%) mixed with ammonium hydroxide is used to bleach human hair. The chemical's bleaching property lends its name to the phrase "peroxide blonde".[66] Hydrogen
Hydrogen
peroxide is also used for tooth whitening. It can be found in most whitening toothpastes. Hydrogen
Hydrogen
peroxide has shown positive results involving teeth lightness and chroma shade parameters. It works by oxidizing colored pigments onto the enamel where the shade of the tooth can indeed become lighter. Hydrogen
Hydrogen
peroxide can be mixed with baking soda and salt to make a home-made toothpaste.[67] Hydrogen
Hydrogen
peroxide may be used to treat acne,[68] although benzoyl peroxide is a more common treatment. Use in alternative medicine[edit] Practitioners of alternative medicine have advocated the use of hydrogen peroxide for various conditions, including emphysema, influenza, AIDS
AIDS
and cancer,[69] although there is no evidence of effectiveness and in some cases it may even be fatal.[70][71][72][73][74] The practice calls for the daily consumption of hydrogen peroxide, either orally or by injection and is, in general, based around two precepts. First, that hydrogen peroxide is naturally produced by the body to combat infection; and second, that human pathogens (including cancer: See Warburg hypothesis) are anaerobic and cannot survive in oxygen-rich environments. The ingestion or injection of hydrogen peroxide is therefore believed to kill disease by mimicking the immune response in addition to increasing levels of oxygen within the body. This makes it similar to other oxygen-based therapies, such as ozone therapy and hyperbaric oxygen therapy. Both the effectiveness and safety of hydrogen peroxide therapy is scientifically questionable. Hydrogen
Hydrogen
peroxide is produced by the immune system but in a carefully controlled manner. Cells called phagocytes engulf pathogens and then use hydrogen peroxide to destroy them. The peroxide is toxic to both the cell and the pathogen and so is kept within a special compartment, called a phagosome. Free hydrogen peroxide will damage any tissue it encounters via oxidative stress; a process which also has been proposed as a cause of cancer.[75] Claims that hydrogen peroxide therapy increase cellular levels of oxygen have not been supported. The quantities administered would be expected to provide very little additional oxygen compared to that available from normal respiration. It should also be noted that it is difficult to raise the level of oxygen around cancer cells within a tumour, as the blood supply tends to be poor, a situation known as tumor hypoxia. Large oral doses of hydrogen peroxide at a 3% concentration may cause irritation and blistering to the mouth, throat, and abdomen as well as abdominal pain, vomiting, and diarrhea.[70] Intravenous injection of hydrogen peroxide has been linked to several deaths.[72][73][74] The American Cancer
Cancer
Society states that "there is no scientific evidence that hydrogen peroxide is a safe, effective or useful cancer treatment."[71] Furthermore, the therapy is not approved by the U.S. FDA. Propellant[edit] Further information: High-test peroxide

Rocket-belt hydrogen-peroxide propulsion system used in a jet pack

High-concentration H 2O 2 is referred to as "high-test peroxide" (HTP). It can be used either as a monopropellant (not mixed with fuel) or as the oxidizer component of a bipropellant rocket. Use as a monopropellant takes advantage of the decomposition of 70–98% concentration hydrogen peroxide into steam and oxygen. The propellant is pumped into a reaction chamber, where a catalyst, usually a silver or platinum screen, triggers decomposition, producing steam at over 600 °C (1,112 °F), which is expelled through a nozzle, generating thrust. H 2O 2 monopropellant produces a maximal specific impulse (Isp) of 161 s (1.6 kN·s/kg). Peroxide
Peroxide
was the first major monopropellant adopted for use in rocket applications. Hydrazine
Hydrazine
eventually replaced hydrogen-peroxide monopropellant thruster applications primarily because of a 25% increase in the vacuum specific impulse.[76] Hydrazine
Hydrazine
(toxic) and hydrogen peroxide (less-toxic [ACGIH TLV 0.01 and 1 ppm respectively]) are the only two monopropellants (other than cold gases) to have been widely adopted and utilized for propulsion and power applications. The Bell Rocket
Rocket
Belt, reaction-control systems for X-1, X-15, Centaur, Mercury, Little Joe, as well as the turbo-pump gas generators for X-1, X-15, Jupiter, Redstone and Viking used hydrogen peroxide as a monopropellant.[77] As a bipropellant, H 2O 2 is decomposed to burn a fuel as an oxidizer. Specific impulses as high as 350 s (3.5 kN·s/kg) can be achieved, depending on the fuel. Peroxide
Peroxide
used as an oxidizer gives a somewhat lower Isp than liquid oxygen, but is dense, storable, noncryogenic and can be more easily used to drive gas turbines to give high pressures using an efficient closed cycle. It can also be used for regenerative cooling of rocket engines. Peroxide
Peroxide
was used very successfully as an oxidizer in World War II
World War II
German rocket motors (e.g. T-Stoff, containing oxyquinoline stabilizer, for both the Walter HWK 109-500
Walter HWK 109-500
Starthilfe RATO
RATO
externally podded monopropellant booster system, and for the Walter HWK 109-509
Walter HWK 109-509
rocket motor series used for the Me 163B), most often used with C-Stoff in a self-igniting hypergolic combination, and for the low-cost British Black Knight and Black Arrow
Black Arrow
launchers. In the 1940s and 1950s, the Hellmuth Walter KG-conceived turbine used hydrogen peroxide for use in submarines while submerged; it was found to be too noisy and require too much maintenance compared to diesel-electric power systems. Some torpedoes used hydrogen peroxide as oxidizer or propellant. Operator error in the use of hydrogen-peroxide torpedoes was named as possible causes for the sinkings of HMS Sidon and the Russian submarine Kursk.[78] SAAB Underwater Systems is manufacturing the Torpedo
Torpedo
2000. This torpedo, used by the Swedish Navy, is powered by a piston engine propelled by HTP as an oxidizer and kerosene as a fuel in a bipropellant system.[79][80] Other uses[edit]

Chemiluminescence
Chemiluminescence
of cyalume, as found in a glow stick

Hydrogen
Hydrogen
peroxide has various domestic uses, primarily as a cleaning and disinfecting agent.

Glow sticks

Hydrogen
Hydrogen
peroxide reacts with certain di-esters, such as phenyl oxalate ester (cyalume), to produce chemiluminescence; this application is most commonly encountered in the form of glow sticks.

Horticulture

Some horticulturalists and users of hydroponics advocate the use of weak hydrogen peroxide solution in watering solutions. Its spontaneous decomposition releases oxygen that enhances a plant's root development and helps to treat root rot (cellular root death due to lack of oxygen) and a variety of other pests.[81][82]

Fish aeration

Laboratory tests conducted by fish culturists in recent years have demonstrated that common household hydrogen peroxide can be used safely to provide oxygen for small fish. The hydrogen peroxide releases oxygen by decomposition when it is exposed to catalysts such as manganese dioxide. Safety[edit] Regulations vary, but low concentrations, such as 6%, are widely available and legal to buy for medical use. Most over-the-counter peroxide solutions are not suitable for ingestion. Higher concentrations may be considered hazardous and are typically accompanied by a Material Safety Data Sheet
Material Safety Data Sheet
(MSDS). In high concentrations, hydrogen peroxide is an aggressive oxidizer and will corrode many materials, including human skin. In the presence of a reducing agent, high concentrations of H 2O 2 will react violently. High-concentration hydrogen peroxide streams, typically above 40%, should be considered hazardous due to concentrated hydrogen peroxide's meeting the definition of a DOT oxidizer according to U.S. regulations, if released into the environment. The EPA Reportable Quantity (RQ) for D001 hazardous wastes is 100 pounds (45 kg), or approximately 10 US gallons (38 L), of concentrated hydrogen peroxide. Hydrogen
Hydrogen
peroxide should be stored in a cool, dry, well-ventilated area and away from any flammable or combustible substances. It should be stored in a container composed of non-reactive materials such as stainless steel or glass (other materials including some plastics and aluminium alloys may also be suitable).[83] Because it breaks down quickly when exposed to light, it should be stored in an opaque container, and pharmaceutical formulations typically come in brown bottles that block light.[84] Hydrogen
Hydrogen
peroxide, either in pure or diluted form, can pose several risks, the main one being that it forms explosive mixtures upon contact with organic compounds.[85] Highly concentrated hydrogen peroxide itself is unstable and can cause a boiling liquid expanding vapour explosion (BLEVE) of the remaining liquid. Distillation
Distillation
of hydrogen peroxide at normal pressures is thus highly dangerous. It is also corrosive, especially when concentrated, but even domestic-strength solutions can cause irritation to the eyes, mucous membranes and skin.[86] Swallowing hydrogen peroxide solutions is particularly dangerous, as decomposition in the stomach releases large quantities of gas (10 times the volume of a 3% solution), leading to internal bloating. Inhaling over 10% can cause severe pulmonary irritation.[87] With a significant vapour pressure (1.2 kPa at 50 °C[88]), hydrogen-peroxide vapour is potentially hazardous. According to U.S. NIOSH, the immediately dangerous to life and health (IDLH) limit is only 75 ppm.[89] The U.S. Occupational Safety and Health Administration (OSHA) has established a permissible exposure limit of 1.0 ppm calculated as an 8-hour time-weighted average (29 CFR 1910.1000, Table Z-1).[85] Hydrogen
Hydrogen
peroxide has also been classified by the American Conference of Governmental Industrial Hygienists (ACGIH) as a "known animal carcinogen, with unknown relevance on humans".[90] For workplaces where there is a risk of exposure to the hazardous concentrations of the vapours, continuous monitors for hydrogen peroxide should be used. Information on the hazards of hydrogen peroxide is available from OSHA[85] and from the ATSDR.[91] Historical incidents[edit]

On 16 July 1934, in Kummersdorf, Germany, a propellant tank containing an experimental monopropellant mixture consisting of hydrogen peroxide and ethanol exploded during a test, killing three people. During the Second World War, doctors in German concentration camps experimented with the use of hydrogen peroxide injections in the killing of human subjects.[92] Several people received minor injuries after a hydrogen peroxide spill on board a flight between the U.S. cities of Orlando and Memphis on 28 October 1998.[93] The Russian submarine K-141 Kursk sailed to perform an exercise of firing dummy torpedoes at the Pyotr Velikiy, a Kirov-class battlecruiser. On 12 August 2000, at 11:28 local time (07:28 UTC), there was an explosion while preparing to fire the torpedoes. The only credible report to date is that this was due to the failure and explosion of one of the Kursk's hydrogen peroxide-fueled torpedoes. It is believed that HTP, a form of highly concentrated hydrogen peroxide used as propellant for the torpedo, seeped through its container, damaged either by rust or in the loading procedure back on land where an incident involving one of the torpedoes accidentally touching ground went unreported. The vessel was lost with all hands. A similar incident was responsible for the loss of HMS Sidon in 1955. On 15 August 2010, a spill of about 30 US gallons (110 L) of cleaning fluid occurred on the 54th floor of 1515 Broadway, in Times Square, New York City. The spill, which a spokesperson for the New York City fire department said was of hydrogen peroxide, shut down Broadway between West 42nd and West 48th streets as fire engines responded to the hazmat situation. There were no reported injuries.[94]

See also[edit]

FOX reagent, used to measure levels of hydrogen peroxide in biological systems. Hydrogen
Hydrogen
chalcogenide

References[edit] Notes

^ Easton, M. F.; Mitchell, A. G.; Wynne-Jones, W. F. K. (1952). "The behaviour of mixtures of hydrogen peroxide and water. Part 1.?Determination of the densities of mixtures of hydrogen peroxide and water". Transactions of the Faraday Society. 48: 796. doi:10.1039/TF9524800796.  ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0335". National Institute for Occupational Safety and Health (NIOSH).  ^ a b c " Hydrogen
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Hydrogen
Peroxide
Peroxide
Technical Library" (PDF). Retrieved 3 March 2016.  ^ Hunt, Robert H.; Leacock, Robert A.; Peters, C. Wilbur; Hecht, Karl T. (1965). "Internal-Rotation in Hydrogen
Hydrogen
Peroxide: The Far-Infrared Spectrum and the Determination of the Hindering Potential" (PDF). The Journal of Chemical Physics. 42 (6): 1931. Bibcode:1965JChPh..42.1931H. doi:10.1063/1.1696228.  ^ Dougherty, Dennis A.; Anslyn, Eric V. (2005). Modern Physical Organic Chemistry. University Science. p. 122. ISBN 1-891389-31-9.  ^ Abrahams, S. C.; Collin, R. L.; Lipscomb, W. N. (1 January 1951). "The crystal structure of hydrogen peroxide". Acta Crystallographica. 4 (1): 15–20. doi:10.1107/S0365110X51000039.  ^ Gilbert, L. W. (1820). "Der tropfbar flüssige Sauerstoff, oder das oxygenierte Wasser". Annals of Physics (in German). 65–66: 3. Bibcode:1820AnP....64....1T. doi:10.1002/andp.18200640102.  ^ Thénard, L. J. (1818). "Observations sur des nouvelles combinaisons entre l'oxigène et divers acides". Annales de chimie et de physique. 2nd series. 8: 306–312.  ^ C. W. Jones, J. H. Clark. Applications of Hydrogen
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Peroxide
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and Derivatives. Royal Society of Chemistry, 1999. ^ a b Offermanns, Heribert; Dittrich, Gunther; Steiner, Norbert (2000). "Wasserstoffperoxid in Umweltschutz und Synthese". Chemie in unserer Zeit. 34 (3): 150. doi:10.1002/1521-3781(200006)34:3<150::AID-CIUZ150>3.0.CO;2-A.  ^ Wolffenstein, Richard (October 1894). "Concentration und Destillation von Wasserstoffsuperoxyd". Berichte der deutschen chemischen Gesellschaft (in German). 27 (3): 3307–3312. doi:10.1002/cber.189402703127.  ^ G. Carrara (1892) "Sul peso molecolare e sul potere rifrangente dell' acqua ossigenata" (On the molecular weight and on the refractive power of oxygenated water [i.e., hydrogen peroxide]), Atti della Reale Accademia dei Lincei, series 5, 1 (2) : 19–24. Carrara's findings were confirmed by: W. R. Orndorff and John White (1893) "The molecular weight of hydrogen peroxide and of benzoyl peroxide," American Chemical Journal, 15 : 347–356. ^ See, for example:

In 1882, Kingzett proposed as a structure H2O=O. See: Thomas Kingzett, Charles (29 September 1882). "On the activity of oxygen and the mode of formation of hydrogen dioxide". The Chemical News. 46 (1192): 141–142.  In his 1922 textbook, Joseph Mellor considered three hypothetical molecular structures for hydrogen peroxide, admitting (p. 952): "... the constitution of this compound has not been yet established by unequivocal experiments". See: Joseph William Mellor, A Comprehensive Treatise on Inorganic and Theoretical Chemistry, vol. 1 (London, England: Longmans, Green and Co., 1922), p. 952–956. W. C. Schumb, C. N. Satterfield, and R. L. Wentworth (1 December 1953) "Report no. 43: Hydrogen
Hydrogen
peroxide, Part two", Office of Naval Research, Contract No. N5ori-07819 On p. 178, the authors present six hypothetical models for hydrogen peroxide's molecular structure. On p. 184, the present structure is considered almost certainly correct—although a small doubt remained. (Note: The report by Schumb et al. was reprinted as: W. C. Schumb, C. N. Satterfield, and R. L. Wentworth, Hydrogen
Hydrogen
Peroxide
Peroxide
(New York, New York: Reinhold Publishing Corp. (American Chemical Society Monograph), 1955).)

^ See:

Penney, W. G.; Sutherland, G. B. B. M. (1934). "The theory of the structure of hydrogen peroxide and hydrazine". Journal of Chemical Physics. 2 (8): 492–498. doi:10.1063/1.1749518.  Penney, W. G.; Sutherland, G. B. B. M. (1934). "A note on the structure of H2O2 and H4N2 with particular reference to electric moments and free rotation". Transactions of the Faraday Society. 30: 898–902. doi:10.1039/tf934300898b. 

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Bibliography

J. Drabowicz; et al. (1994). G. Capozzi; et al., eds. The Syntheses of Sulphones, Sulphoxides and Cyclic Sulphides. Chichester UK: John Wiley & Sons. pp. 112–6. ISBN 0-471-93970-6. CS1 maint: Explicit use of et al. (link) N.N. Greenwood; A. Earnshaw (1997). Chemistry of the Elements (2nd ed.). Oxford UK: Butterworth-Heinemann.  A great description of properties & chemistry of H 2O 2. J. March (1992). Advanced Organic Chemistry (4th ed.). New York: Wiley. p. 723.  W.T. Hess (1995). " Hydrogen
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Peroxide". Kirk-Othmer Encyclopedia of Chemical Technology. 13 (4th ed.). New York: Wiley. pp. 961–995. 

External links[edit]

Wikiversity has learning resources about Observing the Effects of Concentration on Enzyme
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Hydrogen
Hydrogen
Peroxide
Peroxide
at The Periodic Table of Videos
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(University of Nottingham) Material Safety Data Sheet ATSDR Agency for Toxic Substances and Disease Registry
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FAQ International Chemical Safety Card 0164 NIOSH Pocket Guide to Chemical Hazards Process flow sheet of Hydrogen
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H3AsO3 H3AsO4 HAt HSO3F HBF4 HBr HBrO HBrO2 HBrO3 HBrO4 HCl HClO HClO2 HClO3 HClO4 HCN HCNO H2CrO4/H2Cr2O7 H2CO3 H2CS3 HF HFΟ HI HIO HIO2 HIO3 HIO4 HMnO4 H2MoO4 HNC NaHCO3 HNCO HNO HNO2 HNO3 H2N2O2 HNO5S H3NSO3 H2O H2O2 H2O3 H3PO2 H3PO3 H3PO4 H4P2O7 H5P3O10 H2PtCl6 H2S H2S2 H2Se H2SeO3 H2SeO4 H4SiO4 H2SiF6 HSCN HNSC H2SO3 H2SO4 H2SO5 H2S2O3 H2S2O6 H2S2O7 H2S2O8 CF3SO3H H2Te H2TeO3 H6TeO6 H4TiO4 H2Po HCo(CO)4

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Silver
compounds

Silver
Silver
nitrate

Alcohols

Propanol (propyl alcohol) Isopropanol (isopropyl alcohol) Ethanol
Ethanol
(ethyl alcohol)#

Other

Potassium permanganate Sodium hypochlorite Hydrogen
Hydrogen
peroxide Eosin Tosylchloramide Octenidine dihydrochloride

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

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Stomatological
Stomatological
preparations (A01)

Caries
Caries
prophylaxis

Dectaflur Olaflur Sodium fluoride Sodium monofluorophosphate Stannous fluoride

Infection
Infection
and antiseptics

Amphotericin B Benzoxonium chloride Chlorhexidine Chlortetracycline Clotrimazole Cetylpyridinium chloride Domiphen bromide Doxycycline Eugenol Hexetidine Hydrogen
Hydrogen
peroxide Mepartricin Metronidazole Miconazole Minocycline Natamycin Neomycin Oxyquinoline Polynoxylin Sodium perborate Tetracycline Tibezonium iodide

Corticosteroids (Glucocorticoids)

Dexamethasone Hydrocortisone Triamcinolone

Other

Amlexanox Acetylsalicylic acid Becaplermin Benzydamine Epinephrine/Adrenalone

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Drugs used for diseases of the ear (S02)

Infection

Acetic acid Aluminium acetotartrate Aluminium triacetate
Aluminium triacetate
(Burow's solution) Boric acid Chloramphenicol Chlorhexidine Ciprofloxacin Clioquinol Gentamicin Hydrogen
Hydrogen
peroxide Miconazole Neomycin Nitrofurazone Ofloxacin Polymyxin B Rifamycin Tetracycline

Corticosteroids

Betamethasone Dexamethasone Fluocinolone acetonide Hydrocortisone Prednisolone

Analgesics and anesthetics

Lidocaine Cocaine Phenazone

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Human hair color

Hair
Hair
color

Black Blond Brown (varieties: Chestnut • Auburn) Red (varieties: Auburn • Titian) White/Grey

Hair
Hair
coloring

Blue rinse Grecian Formula Hair
Hair
dye stripping Hair
Hair
highlighting Henna Hydrogen
Hydrogen
peroxide Blue hair

Other

Disappearing blonde gene Fischer–Saller scale Fischer scale Melanocortin 1 receptor

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Molecules detected in outer space

Molecules

Diatomic

Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argonium Carbon
Carbon
monophosphide Carbon
Carbon
monosulfide Carbon
Carbon
monoxide Carborundum Cyanogen
Cyanogen
radical Diatomic carbon Fluoromethylidynium Hydrogen
Hydrogen
chloride Hydrogen
Hydrogen
fluoride Hydrogen
Hydrogen
(molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen
Nitrogen
(molecular) Nitrogen
Nitrogen
monohydride Nitrogen
Nitrogen
sulfide Oxygen
Oxygen
(molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur
Sulfur
monohydride Sulfur
Sulfur
monoxide Titanium oxide

Triatomic

Aluminium hydroxide Aluminium isocyanide Amino radical Carbon
Carbon
dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen
Hydrogen
cyanide (HCN) Hydrogen
Hydrogen
isocyanide (HNC) Hydrogen
Hydrogen
sulfide Hydroperoxyl Iron
Iron
cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N2H+ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide Silicon naphthalocyanine Sulfur
Sulfur
dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water

Four atoms

Acetylene Ammonia Cyanic acid Cyanoethynyl Cyclopropynylidyne Formaldehyde Fulminic acid HCCN Hydrogen
Hydrogen
peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon
Tricarbon
monoxide Tricarbon
Tricarbon
sulfide Thiocyanic acid

Five atoms

Ammonium
Ammonium
ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy
Methoxy
radical Methylenimine Propadienylidene Protonated formaldehyde Protonated formaldehyde Silane Silicon-carbide cluster

Six atoms

Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene

Seven atoms

Acetaldehyde Acrylonitrile

Vinyl cyanide

Cyanodiacetylene Ethylene
Ethylene
oxide Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol

Eight atoms

Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal

Nine atoms

Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile

Ten atoms or more

Acetone Benzene Benzonitrile Buckminsterfullerene
Buckminsterfullerene
(C60 fullerene, buckyball) C70 fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene
Ethylene
glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine

Deuterated molecules

Ammonia Ammonium
Ammonium
ion Formaldehyde Formyl radical Heavy water Hydrogen
Hydrogen
cyanide Hydrogen
Hydrogen
deuteride Hydrogen
Hydrogen
isocyanide Methylacetylene N2D+ Trihydrogen cation

Unconfirmed

Anthracene Dihydroxyacetone Ethyl methyl ether Glycine Graphene H2NCO+ Linear C5 Naphthalene
Naphthalene
cation Phosphine Pyrene Silylidine

Related

Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion Homochirality Intergalactic dust Interplanetary medium Interstellar medium Photodissociation region Iron–sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Panspermia Polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon
(PAH) RNA world hypothesis Spectroscopy Tholin

Book:Chemistry Category:Astrochemistry Category:Molecules Portal:Astrobiology Portal:Astronomy Portal:Chemistry

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Oxygen
Oxygen
compounds

AgO Al2O3 AmO2 Am2O3 As2O3 As2O5 Au2O3 B2O3 BaO BeO Bi2O3 BiO2 Bi2O5 BrO2 Br2O3 Br2O5 CO CO2 C2O3 CaO CaO2 CdO CeO2 Ce3O4 Ce2O3 ClO2 Cl2O Cl2O3 Cl2O4 Cl2O6 Cl2O7 CoO Co2O3 Co3O4 CrO3 Cr2O3 Cr2O5 Cr5O12 CsO2 Cs2O3 CuO D2O Dy2O3 Er2O3 Eu2O3 F2O F2O2 F2O4 FeO Fe2O3 Fe3O4 Ga2O Ga2O3 GeO GeO2 H2O H218O H2O2 HfO2 HgO Hg2O Ho2O3 I2O4 I2O5 I2O6 I4O9 In2O3 IrO2 KO2 K2O2 La2O3 Li2O Li2O2 Lu2O3 MgO Mg2O3 MnO MnO2 Mn2O3 Mn2O7 MoO2 MoO3 Mo2O3 NO NO2 N2O N2O3 N2O4 N2O5 NaO2 Na2O Na2O2 NbO NbO2 Nd2O3

Chemical formulas

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TRP channel modulators

TRPA

Activators

4-Hydroxynonenal 4-Oxo-2-nonenal 4,5-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandin J2 α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Acrolein Allicin
Allicin
(garlic) Allyl isothiocyanate
Allyl isothiocyanate
(mustard, radish, horseradish, wasabi) AM404 Bradykinin Cannabichromene
Cannabichromene
(cannabis) Cannabidiol
Cannabidiol
(cannabis) Cannabigerol
Cannabigerol
(cannabis) Cinnamaldehyde
Cinnamaldehyde
(cinnamon) CR gas
CR gas
(dibenzoxazepine; DBO) CS gas
CS gas
(2-chlorobenzal malononitrile) Curcumin
Curcumin
(turmeric) Dehydroligustilide (celery) Diallyl disulfide Dicentrine
Dicentrine
( Lindera
Lindera
spp.) Farnesyl thiosalicylic acid Formalin Gingerols (ginger) Hepoxilin A3 Hepoxilin B3 Hydrogen
Hydrogen
peroxide Icilin Isothiocyanate Ligustilide (celery, Angelica acutiloba) Linalool
Linalool
(Sichuan pepper, thyme) Methylglyoxal Methyl salicylate
Methyl salicylate
(wintergreen) N-Methylmaleimide Nicotine
Nicotine
(tobacco) Oleocanthal
Oleocanthal
(olive oil) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) PF-4840154 Phenacyl chloride Polygodial
Polygodial
(Dorrigo pepper) Shogaols (ginger, Sichuan and melegueta peppers) Tear gases Tetrahydrocannabinol
Tetrahydrocannabinol
(cannabis) Thiopropanal S-oxide
Thiopropanal S-oxide
(onion) Umbellulone
Umbellulone
(Umbellularia californica) WIN 55,212-2

Blockers

Dehydroligustilide (celery) Nicotine
Nicotine
(tobacco) Ruthenium red

TRPC

Activators

Adhyperforin
Adhyperforin
(St John's wort) Diacyl glycerol GSK1702934A Hyperforin
Hyperforin
(St John's wort) Substance P

Blockers

DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators

ADP-ribose BCTC Calcium
Calcium
(intracellular) Cold Coolact P Cooling Agent 10 CPS-369 Eucalyptol
Eucalyptol
(eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol
Menthol
(mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g., stevioside) (Stevia rebaudiana) Sweet tastants (e.g., glucose, fructose, sucrose; indirectly) Thio-BCTC WS-3 WS-12 WS-23

Blockers

Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-amylcinnamoyl)anthranilic acid Nicotine
Nicotine
(tobacco) Niflumic acid Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO

TRPML

Activators

MK6-83 PI(3,5)P2 SF-22

TRPP

Activators

Triptolide
Triptolide
(Tripterygium wilfordii)

Blockers

Ruthenium red

TRPV

Activators

2-APB 5',6'-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Allicin
Allicin
(garlic) AM404 Anandamide Bisandrographolide (Andrographis paniculata) Camphor
Camphor
(camphor laurel, rosemary, camphorweed, African blue basil, camphor basil) Cannabidiol
Cannabidiol
(cannabis) Cannabidivarin
Cannabidivarin
(cannabis) Capsaicin
Capsaicin
(chili pepper) Carvacrol
Carvacrol
(oregano, thyme, pepperwort, wild bergamot, others) DHEA Diacyl glycerol Dihydrocapsaicin
Dihydrocapsaicin
(chili pepper) Estradiol Eugenol
Eugenol
(basil, clove) Evodiamine
Evodiamine
(Euodia ruticarpa) Gingerols (ginger) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin
Homocapsaicin
(chili pepper) Homodihydrocapsaicin
Homodihydrocapsaicin
(chili pepper) Incensole
Incensole
(incense) Lysophosphatidic acid Low pH (acidic conditions) Menthol
Menthol
(mint) N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide
Nonivamide
(PAVA) (PAVA spray) Nordihydrocapsaicin
Nordihydrocapsaicin
(chili pepper) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) Phorbol esters
Phorbol esters
(e.g., 4α-PDD) Piperine
Piperine
(black pepper, long pepper) Polygodial
Polygodial
(Dorrigo pepper) Probenecid Protons RhTx Rutamarin (Ruta graveolens) Resiniferatoxin
Resiniferatoxin
(RTX) (Euphorbia resinifera/pooissonii) Shogaols (ginger, Sichuan and melegueta peppers) Tetrahydrocannabivarin
Tetrahydrocannabivarin
(cannabis) Thymol
Thymol
(thyme, oregano) Tinyatoxin
Tinyatoxin
(Euphorbia resinifera/pooissonii) Tramadol Vanillin
Vanillin
(vanilla) Zucapsaicin

Blockers

α- Spinasterol
Spinasterol
( Vernonia
Vernonia
tweediana) AMG-517 Asivatrep BCTC Cannabigerol
Cannabigerol
(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol
Cannabinol
(cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047 Lanthanum Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid NGD-8243 Niflumic acid Pregnenolone sulfate RN-1734 RN-9893 Ruthenium red SB-705498 Tivanisiran Tolfenamic acid

See also: Receptor/signaling modulators • Ion channel modulators

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