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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443733958 |
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| verifiedrevid = 443736114 |
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| Name = Erythorbic acid |
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| ImageFile = Erythorbic acid.png |
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| Name = Erythorbic acid |
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| ImageFile = D-Erythorbic acid.svg |
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| ImageSize = 150px |
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| ImageName = |
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| ImageSize = |
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| ImageFile1 = Erythorbic-acid-3D-balls.png |
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| ImageName = |
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| ImageFile1 = Erythorbic-acid-3D-balls.png |
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| ImageSize1 = 200px |
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| ImageSize1 = |
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| IUPACName = <small>D</small>-''erythro''-Hex-2-enono-1,4-lactone |
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| IUPACName = (5R)-5--3,4-dihydroxyfuran-2(5H)-one |
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| SystematicName = (5''R'')-5--3,4-dihydroxyfuran-2(5''H'')-one |
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| OtherNames=<small>D</small>-Araboascorbic acid, Erythorbate, Isoascorbic acid, E315 |
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| OtherNames = <small>D</small>-Araboascorbic acid, Erythorbate, Isoascorbic acid. |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 16736142 |
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| ChemSpiderID = 16736142 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 89-65-6 |
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| CASNo = 89-65-6 |
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| PubChem = 6981 |
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| PubChem = 6981 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 51438 |
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| ChEBI = 51438 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES = OC=1(OC(=O)C=1O)(O)CO |
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| SMILES = OC=1(OC(=O)C=1O)(O)CO |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=6 | H=8 | O=6 |
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| Formula = C<sub>6</sub>H<sub>8</sub>O<sub>6</sub> |
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| MolarMass = 176.13 g/mol |
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| Density = 0.704 g/cm<sup>3</sup> |
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| MeltingPtC = 164 to 172 |
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| Density = 0.704 g/cm<sup>3</sup> |
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| MeltingPt = 164-172 °C (decomposes) |
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| MeltingPt_notes = (decomposes) |
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| pKa = 2.1 |
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| pKa = 2.1 |
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}} |
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| Section3 = {{Chembox Hazards |
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| NFPA-H = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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}} |
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| Section6 = {{Chembox Related |
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| OtherCations = ], ], ] |
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'''Erythorbic acid''', formerly known as isoascorbic acid and <small>D</small>-araboascorbic acid, is a ] of ] (]).<ref> Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.</ref> It is a vegetable-derived food additive produced from ]. It is denoted by ] E315, and is widely used as an ] in processed foods.<ref>, Food Standards Agency</ref> |
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'''Erythorbic acid''' ('''isoascorbic acid''', '''<small>D</small>-araboascorbic acid''') is a ] of ] (]).<ref> Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.</ref> It is synthesized by a reaction between methyl 2-keto-<small>D</small>-gluconate and ]. It can also be synthesized from ] or by strains of '']'' that have been selected for this feature.<ref>{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Erythorbic_acid#section=Industry-Uses |title = Erythorbic acid}}</ref> It is denoted by ] E315, and is widely used as an ] in processed foods.<ref>, Food Standards Agency</ref> |
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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.<ref>{{cite journal | title = Effects of erythorbic acid on vitamin C metabolism in young women | last = Sauberlich | first = HE | coauthors = Tamura T, Craig CB, Freeberg LE, Liu T | journal = American Journal of Clinical Nutrition | month = September | year = 1996 | volume = 64 | issue = 3 | pages = pp. 336–46 | pmid = 8780343}}</ref> A later study found that erythorbic acid is a potent enhancer of nonheme-iron ].<ref>{{cite journal | title = Erythorbic acid is a potent enhancer of nonheme-iron absorption | last = Fidler | first = MC | coauthors = Davidsson L, Zeder C, Hurrell RF | journal = American Journal of Clinical Nutrition | month = January | year = 2004 | volume = 79 | issue = 1 | pmid = 14684404 | pages = pp. 99–102}}</ref> |
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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.<ref>{{cite journal | title = Effects of erythorbic acid on vitamin C metabolism in young women | last = Sauberlich | first = HE |author2=Tamura T |author3=Craig CB |author4=Freeberg LE |author5=Liu T | journal = American Journal of Clinical Nutrition |date=September 1996 | volume = 64 | issue = 3 | pages = 336–46 | doi = 10.1093/ajcn/64.3.336 | pmid = 8780343| doi-access = free }}</ref> A later study found that erythorbic acid is a potent enhancer of nonheme-iron ].<ref>{{cite journal | title = Erythorbic acid is a potent enhancer of nonheme-iron absorption | last = Fidler | first = MC |author2=Davidsson L |author3=Zeder C |author4=Hurrell RF | journal = American Journal of Clinical Nutrition |date=January 2004 | volume = 79 | issue = 1 | pmid = 14684404 | pages = 99–102 | doi=10.1093/ajcn/79.1.99| doi-access = free }}</ref> |
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Since the U.S. Food and Drug Administration banned the use of ] as a ] 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.<ref>Hui YH. Handbook of Food Science, Technology and Engineering. CRC Press, 2006, ISBN 0849398487, p. 83-32 </ref> |
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Since the U.S. Food and Drug Administration banned the use of ] as a ] in foods intended to be eaten fresh (such as salad bar ingredients), the use of erythorbic acid as a food preservative has increased. |
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It is also used as a preservative in cured meats and frozen vegetables.<ref>{{cite book | author = Hui YH | title = Handbook of Food Science, Technology and Engineering | publisher = CRC Press | year = 2006 | isbn = 0-8493-9848-7 | pages = 83–32 }}<!--page numbers don't make sense--></ref> |
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==See also == |
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* ] |
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It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.<ref>See: |
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* {{cite journal | last1 = Maurer | first1 = Kurt | last2 = Schiedt | first2 = Bruno | date = August 2, 1933 | title = "Die Darstellung einer Säure C<sub>6</sub>H<sub>8</sub>O<sub>6</sub> aus Glucose, die in ihrer Reduktionskraft der Ascorbinsäure gleicht (Vorläuf. Mitteil.)" (The preparation of an acid C<sub>6</sub>H<sub>8</sub>O<sub>6</sub> from glucose, which equals ascorbic acid in its reducing power (preliminary report)) | url = | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 66 | issue = 8| pages = 1054–1057 | doi = 10.1002/cber.19330660807 }} |
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* {{cite journal | last1 = Maurer | first1 = Kurt | last2 = Schiedt | first2 = Bruno | date = July 4, 1934 | title = "Zur Darstellung des Iso-Vitamins C (''d''-Arabo-ascorbinsäure) (II. Mitteil.)" (On the preparation of iso-vitamin C (''d''-arabo-ascorbic acid) (2nd report)) | url = | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 67 | issue = 7| pages = 1239–1241 | doi = 10.1002/cber.19340670724 }}</ref><ref>See also: |
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* {{cite journal | last1 = Ohle | first1 = Heinz | last2 = Erlbach | first2 = Heinz | last3 = Carls | first3 = Herbert | date = February 7, 1934 | title = "''d''-Gluco-saccharosonsäure, ein Isomeres der Ascorbinsäure, I. Mitteil.: Darstellung und Eigenschaften" (''d''-Gluco-saccharosonic acid, an isomer of ascorbic acid, 1st report: preparation and properties) | url = | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 67 | issue = 2| pages = 324–332 | doi = 10.1002/cber.19340670235 }} |
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* {{cite journal | last1 = Baird | first1 = D. K. | last2 = Haworth | first2 = W. N. | last3 = Herbert | first3 = R. W. | last4 = Hirst | first4 = E. L. | last5 = Smith | first5 = F. | last6 = Stacey | first6 = M. | year = 1934 | title = Ascorbic acid and synthetic analogues | url = | journal = Journal of the Chemical Society | volume = | issue = | pages = 63–67 | doi = 10.1039/JR9340000062 }} |
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* {{cite journal | last1 = Reichstein | first1 = T. | last2 = Grüssner | first2 = A. | last3 = Oppenauer | first3 = R. | year = 1934 | title = "Synthese der Ascorbinsäure und verwandter Verbindungen nach der Oson-Blausäure-Methode"(Synthesis of ascorbic acid and related compounds via the ozone-hydrogen cyanide method) | url = | journal = Helvetica Chimica Acta | volume = 17 | issue = | pages = 510–520 | doi = 10.1002/hlca.19340170157 }}</ref> |
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==References== |
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