Sulfites or sulphites are
compounds that contain the sulfite
ion
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...
(or the sulfate(IV) ion, from its correct systematic name), . The sulfite ion is the
conjugate base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...
of
bisulfite
The bisulfite ion (IUPAC-recommended nomenclature: hydrogensulfite) is the ion . Salts containing the ion are also known as "sulfite lyes". Sodium bisulfite is used interchangeably with sodium metabisulfite (Na2S2O5). Sodium metabisulfite disso ...
. Although its acid (
sulfurous acid) is elusive,
its salts are widely used.
Sulfites are substances that naturally occur in some foods and the human body. They are also used as regulated food additives.
When in food or drink, sulfites are often lumped together with
sulfur dioxide.
[Se]
REGULATION (EU) No 1169/2011 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL
/ref>
Structure
The structure of the sulfite anion can be described with three equivalent resonance structures
In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or ''forms'', also variously known as ''resonance structures'' or '' ...
. In each resonance structure, the sulfur atom is double-bonded to one oxygen atom with a formal charge of zero (neutral), and sulfur is singly bonded to the other two oxygen atoms, which each carry a formal charge of −1, together accounting for the −2 charge on the anion. There is also a non-bonded lone pair on the sulfur, so the structure predicted by VSEPR theory
Valence shell electron pair repulsion (VSEPR) theory ( , ), is a model used in chemistry to predict the geometry of individual molecules from the number of electron pairs surrounding their central atoms. It is also named the Gillespie-Nyholm the ...
is trigonal pyramidal, as in ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...
(NH3). In the hybrid resonance structure, the S−O bonds are equivalently of bond order one and one-third.
Evidence from 17O NMR spectroscopic data suggests that protonation of the sulfite ion gives a mixture of isomers:
Commercial uses
Sulfites are used as a food preservative
A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...
or enhancer. They may come in various forms, such as:
* Sulfur dioxide, which is not a sulfite, but a closely related chemical oxide
* Potassium bisulfite
Potassium bisulfite (or potassium hydrogen sulfite) is a chemical mixture with the approximate chemical formula KHSO3. Potassium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of ...
or potassium metabisulfite
Potassium metabisulfite, K2S2O5, also known as potassium pyrosulfite, is a white crystalline powder with a pungent odour. It is mainly used as an antioxidant or chemical sterilant. As a disulfite, it is chemically very similar to sodium metabi ...
* Sodium bisulfite
Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions ...
, sodium metabisulfite
Sodium metabisulfite or sodium pyrosulfite (IUPAC spelling; Br. E. sodium metabisulphite or sodium pyrosulphite) is an inorganic compound of chemical formula Na2S2O5. The substance is sometimes referred to as disodium metabisulfite. It is used a ...
or sodium sulfite
Sodium sulfite (sodium sulphite) is the inorganic compound with the chemical formula Na2 SO3. A white, water-soluble solid, it is used commercially as an antioxidant and preservative. A heptahydrate is also known but it is less useful because of ...
Wine
Sulfites occur naturally in all wine
Wine is an alcoholic drink typically made from fermented grapes. Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different varieties of grapes and strains of yeasts are m ...
s to some extent. Sulfites are commonly introduced to arrest fermentation at a desired time, and may also be added to wine as preservative
A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...
s to prevent spoilage and oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
at several stages of the winemaking
Winemaking or vinification is the production of wine, starting with the selection of the fruit, its fermentation into alcohol, and the bottling of the finished liquid. The history of wine-making stretches over millennia. The science of wine and ...
. Sulfur dioxide (SO2) protects wine not only from oxidation, but also from bacteria.
Organic wines are not necessarily sulfite-free, but generally have lower amounts and regulations stipulate lower maximum sulfite contents for these wines. In general, white wines contain more sulfites than red wines and sweeter wines contain more sulfites than drier ones.
In the United States, wines bottled after mid-1987 must have a label stating that they contain sulfites if they contain more than 10 parts per million (ppm).
In the European Union
The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...
an equivalent regulation came into force in November 2005. This includes sulfur dioxide, and the limit is on the milligrams per kilogram or per litre of sulfur dioxide equivalent.[ In 2012, a new regulation for organic wines came into force. In the United Kingdom, similar laws apply. Bottles of wine that contain over 10 mg/L (ppm) of "sulfites" (or sulfur dioxide) are required to bear "contains sulphites" on the label. This does not differ if sulfites are naturally occurring or added in the winemaking process.
]
Other foods
Sulfites are often used as preservative
A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...
s in dried fruit
Dried fruit is fruit from which the majority of the original water content has been removed either naturally, through sun drying, or through the use of specialized dryers or dehydrators. Dried fruit has a long tradition of use dating back to th ...
s, preserved radish
The radish (''Raphanus raphanistrum'' subsp. ''sativus'') is an edible root vegetable of the family Brassicaceae that was domesticated in Asia prior to Roman times.
Radishes are grown and consumed throughout the world, being mostly eaten raw ...
, and dried potato
The potato is a starchy food, a tuber of the plant ''Solanum tuberosum'' and is a root vegetable native to the Americas. The plant is a perennial in the nightshade family Solanaceae.
Wild potato species can be found from the southern Unit ...
products.
Most beer
Beer is one of the oldest and the most widely consumed type of alcoholic drink in the world, and the third most popular drink overall after water and tea. It is produced by the brewing and fermentation of starches, mainly derived from ce ...
s no longer contain sulfites, although some alcoholic ciders contain them. Although shrimp are sometimes treated with sulfites on fishing vessels, the chemical may not appear on the label. In 1986, the Food and Drug Administration
The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
in the United States banned the addition of sulfites to all fresh fruit and vegetables that are eaten raw.
E numbers
E numbers
E numbers ("E" stands for "Europe") are codes for substances used as food additives, including those found naturally in many foods such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly f ...
for sulfites as food additives
Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (sal ...
are:
Health effects
Allergic reactions to sulfites appear to be very rare in the general population, but more common in hyperallergic individuals.
Sulfites are counted among the top nine food allergens, but a reaction to sulfite is not a true allergy. Some people have positive skin allergy tests to sulfites indicating true (IgE
Immunoglobulin E (IgE) is a type of antibody (or immunoglobulin (Ig) " isotype") that has been found only in mammals. IgE is synthesised by plasma cells. Monomers of IgE consist of two heavy chains (ε chain) and two light chains, with the ε c ...
-mediated) allergy. Chronic skin conditions in the hands, perineum
The perineum in humans is the space between the anus and scrotum in the male, or between the anus and the vulva in the female. The perineum is the region of the body between the pubic symphysis (pubic arch) and the coccyx (tail bone), includi ...
, and face have been reported in individuals that regularly use cosmetics or medications containing sulfites. Occupational exposure to sulfites has been reported to cause persistent skin symptoms.
It may cause breathing difficulty within minutes after eating a food containing it. Asthma
Asthma is a long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wheezing, co ...
tics and possibly people with salicylate sensitivity
Salicylate sensitivity is any adverse effect that occurs when a usual amount of salicylate is ingested. People with salicylate intolerance are unable to consume a normal amount of salicylate without adverse effects.
Salicylate sensitivity diffe ...
(or aspirin
Aspirin, also known as acetylsalicylic acid (ASA), is a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and/or inflammation, and as an antithrombotic. Specific inflammatory conditions which aspirin is used to treat inc ...
sensitivity) are at an elevated risk for reaction to sulfites. Anaphylaxis
Anaphylaxis is a serious, potentially fatal allergic reaction and medical emergency that is rapid in onset and requires immediate medical attention regardless of use of emergency medication on site. It typically causes more than one of the foll ...
and life-threatening reactions are rare. Other potential symptoms include sneezing
A sneeze (also known as sternutation) is a semi-autonomous, convulsive expulsion of air from the lungs through the nose and mouth, usually caused by foreign particles irritating the nasal mucosa. A sneeze expels air forcibly from the mouth and ...
, swelling of the throat
In vertebrate anatomy, the throat is the front part of the neck, internally positioned in front of the vertebrae. It contains the pharynx and larynx. An important section of it is the epiglottis, separating the esophagus from the trachea (windpip ...
, hives, and migraine.
A 2017 study has shown negative impacts of sulfites on bacteria found in the human microbiome
A microbiome () is the community of microorganisms that can usually be found living together in any given habitat. It was defined more precisely in 1988 by Whipps ''et al.'' as "a characteristic microbial community occupying a reasonably wel ...
.
Use and labeling regulations
In 1986, the U.S. Food and Drug Administration banned the use of sulfites as preservatives on foods intended to be eaten fresh (such as salad ingredients). This has contributed to the increased use of erythorbic acid
Erythorbic acid (isoascorbic acid, D-araboascorbic acid) is a stereoisomer of ascorbic acid (vitamin C). It is synthesized by a reaction between methyl 2-keto-D-gluconate and sodium methoxide. It can also be synthesized from sucrose or by strains ...
and its salts
In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...
as preservatives.
They also cannot be added to foods high in vitamin B1
Thiamine, also known as thiamin and vitamin B1, is a vitamin, an essential micronutrient, that cannot be made in the body. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thia ...
such as meats because sulfites can destroy vitamin B1 from foods
Generally, U.S. labeling regulations do not require products to indicate the presence of sulfites in foods unless it is added specifically as a preservative; still, many companies voluntarily label sulfite-containing foods. Sulfites used in food processing (but not as a preservative) are required to be listed if they are not incidental additives (21 CFR 101.100(a)(3)), and if there are more than 10 ppm in the finished product (21 CFR 101.100(a)(4))
Sulfites that are allowed to be added in food in the US are sulfur dioxide, sodium sulfite
Sodium sulfite (sodium sulphite) is the inorganic compound with the chemical formula Na2 SO3. A white, water-soluble solid, it is used commercially as an antioxidant and preservative. A heptahydrate is also known but it is less useful because of ...
, sodium bisulfite
Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions ...
, potassium bisulfite
Potassium bisulfite (or potassium hydrogen sulfite) is a chemical mixture with the approximate chemical formula KHSO3. Potassium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of ...
, sodium metabisulfite
Sodium metabisulfite or sodium pyrosulfite (IUPAC spelling; Br. E. sodium metabisulphite or sodium pyrosulphite) is an inorganic compound of chemical formula Na2S2O5. The substance is sometimes referred to as disodium metabisulfite. It is used a ...
, and potassium metabisulfite
Potassium metabisulfite, K2S2O5, also known as potassium pyrosulfite, is a white crystalline powder with a pungent odour. It is mainly used as an antioxidant or chemical sterilant. As a disulfite, it is chemically very similar to sodium metabi ...
.
Products likely to contain sulfites at less than 10 ppm (fruits and alcoholic beverages) do not require ingredients labels, and the presence of sulfites usually is undisclosed.
In Australia and New Zealand, sulfites must be declared in the statement of ingredients when present in packaged foods in concentrations of 10 mg/kg (ppm) or more as an ingredient; or as an ingredient of a compound ingredient; or as a food additive or component of a food additive; or as a processing aid or component of a processing aid.
Sulfites that can be added to foods in Canada are potassium bisulfite, potassium metabisulfite, sodium bisulfite, sodium dithionite
Sodium dithionite (also known as sodium hydrosulfite) is a white crystalline powder with a sulfurous odor. Although it is stable in dry air, it decomposes in hot water and in acid solutions.
Structure
The structure has been examined by Raman s ...
, sodium metabisulfite, sodium sulfite, sulfur dioxide and sulfurous acid. These can also be declared using the common names sulfites, sulfates, sulfiting agents.
In the European Union
The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...
, "EU law requires food labels to indicate “contains sulfites” (when exceeding 10 milligrams per kilogram or per litre) without specifying the amount".
Metabolic diseases
High sulfite content in the blood and urine of babies can be caused by molybdenum cofactor deficiency
Molybdenum cofactor deficiency is a rare human disease in which the absence of molybdopterin – and consequently its molybdenum complex, commonly called molybdenum cofactor – leads to accumulation of toxic levels of sulphite and neurological da ...
disease which leads to neurological damage and early death unless treated. Treatment, requiring daily injections, became available in 2009.
See also
*HSO bisulfite
The bisulfite ion (IUPAC-recommended nomenclature: hydrogensulfite) is the ion . Salts containing the ion are also known as "sulfite lyes". Sodium bisulfite is used interchangeably with sodium metabisulfite (Na2S2O5). Sodium metabisulfite disso ...
ion
*S2O metabisulfite
A disulfite, commonly known as metabisulfite or pyrosulfite, is a chemical compound containing the ion . It is a colorless dianion that is primarily marketed in the form of sodium metabisulfite or potassium metabisulfite. When dissolved in wat ...
ion
*H2SO3 sulfurous acid
*SO persulfate ion
*SO sulfate
The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
ion
*SO hyposulfite ion
*S2O thiosulfate
Thiosulfate ( IUPAC-recommended spelling; sometimes thiosulphate in British English) is an oxyanion of sulfur with the chemical formula . Thiosulfate also refers to the compounds containing this anion, which are the salts of thiosulfuric acid, ...
ion
*SO2 sulfur dioxide
*SO3 sulfur trioxide (a sulfate
The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
precursor)
* Sulfites for a list of sulfites.
*''Grant v The Australian Knitting Mills
''Grant v Australian Knitting Mills'',; . is a landmark case in consumer and negligence law from 1935, holding that where a manufacturer knows that a consumer may be injured if the manufacturer does not take reasonable care, the manufacturer ...
''
References
{{Reflist
*
Sulfur oxyanions
"Allergies: Sulfite Sensitivity". WebMD., 1 February 2007. What Is Sulfite Sensitivity? Foods and Ingredients To Avoid (webmd.com)