Furan-2-ylmethanethiol
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Furan-2-ylmethanethiol
Furan-2-ylmethanethiol (2-Furanmethanethiol) is an organic compound containing a furan substituted with a sulfanylmethyl group. It is a clear colourless liquid when pure, but it becomes yellow coloured upon prolonged standing. It possesses a strong odour of roasted coffee and a bitter taste. It is a key component of the aroma of roasted coffee. It has been identified as a trigger molecule for parosmia following COVID-19 infection. Synthesis Furan-2-ylmethanethiol is easily prepared by reacting furfuryl alcohol with thiourea in hydrochloric acid via an intermediate isothiouronium salt which is hydrolized to the thiol by heating with sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali .... References {{Heterocyclic-stub Flavors Thiols 2-Furyl compounds
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Furfuryl Alcohol
Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents. Synthesis Furfuryl alcohol is manufactured industrially by hydrogenation of furfural, which is itself typically produced from waste bio-mass such as corncobs or sugar cane bagasse. As such furfuryl alcohol may be considered a green chemical. One-pot systems have been investigated to produce furfuryl alcohol directly from xylose using solid acid catalysts. Reactions It undergoes many reactions including Diels-Alder additions to electrophilic alkenes and alkynes. Hydroxymethylation gives 1,5-bis(hydroxymethyl)furan. Hydrolysis gives levulinic acid. Upon treatment with acids, heat and/or catalysts, furfuryl alcohol can be made to polymerize into a resin, poly(furfuryl alcohol). H ...
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Thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "''thio-''" with "alcohol". Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans () or mercapto compounds, a term introduced in 1832 by William Christopher Zeise and is derived from the Latin ('capturing mercury')''Oxford American Dictionaries'' ( Mac OS X Leopard). because the thiolate group () bonds very str ...
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Thiols
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "''thio-''" with "alcohol". Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans () or mercapto compounds, a term introduced in 1832 by William Christopher Zeise and is derived from the Latin ('capturing mercury')''Oxford American Dictionaries'' (Mac OS X Leopard). because the thiolate group () bonds very strongly ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Livin ...
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Furan
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water. Its odor is "strong, ethereal; chloroform-like". It is toxic and may be carcinogenic in humans. Furan is used as a starting point for other speciality chemicals. History The name "furan" comes from the Latin ''furfur'', which means bran. (Furfural is produced from bran.) The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele in 1780. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Limp ...
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Parosmia
Parosmia (from the Greek παρά ''pará'' and ὀσμή ''osmḗ'' "smell") is a dysfunctional smell detection characterized by the inability of the brain to correctly identify an odor's "natural" smell. Instead, the natural odor is usually transformed into an unpleasant aroma, typically a "burned", "rotting", "fecal", or "chemical" smell. There can also be rare instances of a pleasant odor called euosmia. The condition was rare and little-researched until it became relatively more widespread since 2020 as a side effect of COVID-19. Causes There are numerous diseases with which parosmia is associated. In a case study, Frasnelli ''et al.'' examined five patients that endured parosmia or phantosmia, most as a result of upper respiratory tract infections (URTIs). It is hypothesized that URTIs can result in parosmia because of damage to olfactory receptor neurons (ORNs). The condition has been linked to coronavirus disease 2019 as a rare side effect. Common triggers in COVID-19 rel ...
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COVID-19
Coronavirus disease 2019 (COVID-19) is a contagious disease caused by a virus, the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The first known case was identified in Wuhan, China, in December 2019. The disease quickly spread worldwide, resulting in the COVID-19 pandemic. The symptoms of COVID‑19 are variable but often include fever, cough, headache, fatigue, breathing difficulties, loss of smell, and loss of taste. Symptoms may begin one to fourteen days after exposure to the virus. At least a third of people who are infected do not develop noticeable symptoms. Of those who develop symptoms noticeable enough to be classified as patients, most (81%) develop mild to moderate symptoms (up to mild pneumonia), while 14% develop severe symptoms ( dyspnea, hypoxia, or more than 50% lung involvement on imaging), and 5% develop critical symptoms ( respiratory failure, shock, or multiorgan dysfunction). Older people are at a higher risk of developing ...
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Thiourea
Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), except that the oxygen atom is replaced by a sulfur atom (as implied by the '' thio-'' prefix); however, the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. " Thioureas" refer to a broad class of compounds with the general structure . Thioureas are related to thioamides, e.g. , where R is methyl, ethyl, etc. Structure and bonding Thiourea is a planar molecule. The C=S bond distance is 1.71 Å. The C-N distances average 1.33 Å. The weakening of the C-S bond by C-N pi-bonding is indicated by the short C=S bond in thiobenzophenone, which is 1.63 Å. Thiourea occurs in two tautomeric forms, of which the thione form predominates in aqueous solutions. The equilibrium constant has been calculated as ''K''eq is . The thiol form, which is also known as an isothiourea, can be encountered in substituted compounds ...
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Hydrochloric Acid
Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid. It is a component of the gastric acid in the digestive systems of most animal species, including humans. Hydrochloric acid is an important laboratory reagent and industrial chemical. History In the early tenth century, the Persian physician and alchemist Abu Bakr al-Razi ( 865–925, Latin: Rhazes) conducted experiments with sal ammoniac ( ammonium chloride) and vitriol (hydrated sulfates of various metals), which he distilled together, thus producing the gas hydrogen chloride. In doing so, al-Razi may have stumbled upon a primitive method for producing hydrochloric acid, as perhaps manifested in the following recipe from his ("The Book of Secrets"): However, it appears that in most of his experiments al-Razi disregarded the gaseous products, concentrating instead on the color c ...
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Isothiouronium
In organic chemistry, isothiouronium is a functional group with the formula SC(NH2)2sup>+ (R = alkyl, aryl) and is the acid salt of isothiourea. The H centres can also be replaced by alkyl and aryl. Structurally, these cations resemble guanidinium cations. The CN2S core is planar and the C–N bonds are short. Synthesis Salts comprising these cations are typically prepared by alkylation of thiourea: :SC(NH2)2 + RX → SC(NH2)2sup>+X− Reactions Hydrolysis of isothiouronium salts gives thiols. : SC(NH2)2sup>+X− + NaOH → RSH + OC(NH2)2 + NaX Isothiouronium salts in which the sulfur has been alkylated, such as ''S''-methylisothiourea hemisulfate (CAS number: 867-44-7), will convert amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent su ...s into guanidinium groups. This ...
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Hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the substance and water molecule to split into two parts. I ...
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Sodium Hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali that decomposes proteins at ordinary ambient temperatures and may cause severe chemical burns. It is highly soluble in water, and readily absorbs moisture and carbon dioxide from the air. It forms a series of hydrates . The monohydrate crystallizes from water solutions between 12.3 and 61.8 °C. The commercially available "sodium hydroxide" is often this monohydrate, and published data may refer to it instead of the anhydrous compound. As one of the simplest hydroxides, sodium hydroxide is frequently used alongside neutral water and acidic hydrochloric acid to demonstrate the pH scale to chemistry students. Sodium hydroxide is used in many industries: in the manufacture of pulp and paper, textiles, drinking water, soaps and de ...
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