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Names | |
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IUPAC name D-erythro-Hex-2-enosono-1,4-lactone | |
Preferred IUPAC name (5R)-5-[(1R)-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one | |
Other names D-Araboascorbic acid, Erythorbate, Isoascorbic acid. | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.001.753 |
E number | E315 (antioxidants, ...) |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H8O6 | |
Molar mass | 176.124 g·mol−1 |
Density | 0.704 g/cm3 |
Melting point | 164 to 172 °C (327 to 342 °F; 437 to 445 K) (decomposes) |
Acidity (pKa) | 2.1 |
Hazards | |
NFPA 704 (fire diamond) | |
Related compounds | |
Other cations | Calcium erythorbate, sodium erythorbate, potassium erythorbate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Erythorbic acid (isoascorbic acid, D-araboascorbic acid) is a stereoisomer of ascorbic acid (vitamin C). [1] 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 of Penicillium that have been selected for this feature. [2] It is denoted by E number E315, and is widely used as an antioxidant in processed foods. [3]
Clinical trials have been conducted to investigate aspects of the nutritional value of erythorbic acid. One such trial investigated the effects of erythorbic acid on vitamin C metabolism in young women; no effect on vitamin C uptake or clearance from the body was found. [4] A later study found that erythorbic acid is a potent enhancer of nonheme-iron absorption. [5]
Since the U.S. Food and Drug Administration banned the use of sulfites as a preservative in foods intended to be eaten fresh (such as salad bar ingredients), the use of erythorbic acid as a food preservative has increased.
It is also used as a preservative in cured meats and frozen vegetables. [6]
It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt. [7] [8]
The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt ; this is sometimes referred to as a Pinner salt. The reaction is named after Adolf Pinner, who first described it in 1877. Pinner salts are themselves reactive and undergo additional nucleophilic additions to give various useful products:
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.
Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Furfural is only derived from lignocellulosic biomass, i.e., its origin is non-food or non-coal/oil based. Aside from ethanol, acetic acid, and sugar, it is one of the oldest renewable chemicals. It is also found in many processed foods and beverages.
Skatole or 3-methylindole is an organic compound belonging to the indole family. It occurs naturally in the feces of mammals and birds and is the primary contributor to fecal odor. In low concentrations, it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana.
The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. The reaction was discovered in 1883 by Emil Fischer. Today antimigraine drugs of the triptan class are often synthesized by this method.
The Japp–Klingemann reaction is a chemical reaction used to synthesize hydrazones from β-keto-acids and aryl diazonium salts. The reaction is named after the chemists Francis Robert Japp and Felix Klingemann.
The Reed reaction is a chemical reaction that utilizes light to oxidize hydrocarbons to alkylsulfonyl chlorides. This reaction is employed in modifying polyethylene to give chlorosulfonated polyethylene (CSPE), which noted for its toughness.
The Rosenmund reduction is a hydrogenation process in which an acyl chloride is selectively reduced to an aldehyde. The reaction was named after Karl Wilhelm Rosenmund, who first reported it in 1918.
Elemicin is a phenylpropene, a natural organic compound, and is a constituent of several plant species' essential oils.
Organomercury refers to the group of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.
Hans von Pechmann was a German chemist, renowned for his discovery of diazomethane in 1894. Pechmann condensation and Pechmann pyrazole synthesis. He also first prepared 1,2-diketones, acetonedicarboxylic acid, methylglyoxal and diphenyltriketone; established the symmetrical structure of anthraquinone.
Fischer glycosidation refers to the formation of a glycoside by the reaction of an aldose or ketose with an alcohol in the presence of an acid catalyst. The reaction is named after the German chemist, Emil Fischer, winner of the Nobel Prize in chemistry, 1902, who developed this method between 1893 and 1895.
Chlorobutanol (trichloro-2-methyl-2-propanol) is a preservative, sedative, hypnotic and weak local anesthetic similar in nature to chloral hydrate. It has antibacterial and antifungal properties. Chlorobutanol is typically used at a concentration of 0.5% where it lends long term stability to multi-ingredient formulations. However, it retains antimicrobial activity at 0.05% in water. Chlorobutanol has been used in anesthesia and euthanasia of invertebrates and fishes. It is a white, volatile solid with a camphor-like odor.
Phenylarsonic acid is the chemical compound with the formula C6H5AsO(OH)2, commonly abbreviated PhAsO3H2. This colourless solid is an organic derivative of arsenic acid, AsO(OH)3, where one OH group has been replaced by a phenyl group. The compound is a buffering agent and a precursor to other organoarsenic compounds, some of which are used in animal nutrition, e.g. 4-hydroxy-3-nitrobenzenearsonic acid.
The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides:
Carl Theodore Liebermann was a German chemist and student of Adolf von Baeyer.
The Hoesch reaction or Houben–Hoesch reaction is an organic reaction in which a nitrile reacts with an arene compound to form an aryl ketone. The reaction is a type of Friedel-Crafts acylation with hydrogen chloride and a Lewis acid catalyst.
Oskar Piloty was a German chemist.
Conhydrine is a poisonous alkaloid found in poison hemlock in small quantities.
Roland Heinrich Scholl was a Swiss chemist who taught at various European universities. Among his most notable achievements are the synthesis of coronene, the co-development of the Bally-Scholl synthesis, and various discoveries about polycyclic aromatic hydrocarbons.