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{{chembox
{{chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 443736114
| verifiedrevid = 443736114
| Name = Erythorbic acid
| Name = Erythorbic acid
| ImageFile = D-Erythorbic acid.svg
| ImageFile = D-Erythorbic acid.svg
| ImageSize =
| ImageSize =
| ImageName =
| ImageName =
| ImageFile1 = Erythorbic-acid-3D-balls.png
| ImageFile1 = Erythorbic-acid-3D-balls.png
| ImageSize1 =
| ImageSize1 =
| IUPACName = (5''R'')-5-[(1''R'')-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5''H'')-one
| IUPACName = <small>D</small>-''erythro''-Hex-2-enono-1,4-lactone
| SystematicName = (5''R'')-5-[(1''R'')-1,2-Dihydroxyethyl]-3,4-dihydroxyfuran-2(5''H'')-one
| OtherNames =<small>D</small>-Araboascorbic acid, Erythorbate, Isoascorbic acid, E315
| OtherNames = <small>D</small>-Araboascorbic acid, Erythorbate, Isoascorbic acid.
|Section1={{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736142
| ChemSpiderID = 16736142
Line 28: Line 29:
| SMILES = OC=1[C@H](OC(=O)C=1O)[C@H](O)CO
| SMILES = OC=1[C@H](OC(=O)C=1O)[C@H](O)CO
}}
}}
|Section2={{Chembox Properties
| Section2 = {{Chembox Properties
| C =6|H=8|O=6
| C=6 | H=8 | O=6
| Density = 0.704 g/cm<sup>3</sup>
| Density = 0.704 g/cm<sup>3</sup>
| MeltingPtC = 164 to 172
| MeltingPtC = 164 to 172
| Melting_notes = (decomposes)
| MeltingPt_notes = (decomposes)
| pKa = 2.1
| pKa = 2.1
}}
}}
|Section3={{Chembox Hazards
| Section3 = {{Chembox Hazards
| NFPA-H = 1
| NFPA-H = 1
| NFPA-F = 1
| NFPA-F = 1
| NFPA-R = 0
| NFPA-R = 0
}}
}}
| Section6 = {{Chembox Related
| OtherCations = [[Calcium erythorbate]], [[sodium erythorbate]], [[potassium erythorbate]]
}}
}}
}}


'''Erythorbic acid''' (isoascorbic acid, <small>D</small>-araboascorbic acid) is a [[stereoisomer]] of [[ascorbic acid]] ([[vitamin C]]).<ref>[http://www.inchem.org/documents/jecfa/jecmono/v28je03.htm Erythorbic acid and its sodium salt] Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.</ref> It is a [[natural product]], a vegetable-derived food additive produced from [[sucrose]]. It is denoted by [[E number]] E315, and is widely used as an [[antioxidant]] in processed foods.<ref>[http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist Current EU approved additives and their E Numbers], Food Standards Agency</ref>
'''Erythorbic acid''' ('''isoascorbic acid''', '''<small>D</small>-araboascorbic acid''') is a [[stereoisomer]] of [[ascorbic acid]] ([[vitamin C]]).<ref>[http://www.inchem.org/documents/jecfa/jecmono/v28je03.htm Erythorbic acid and its sodium salt] 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 [[sodium methoxide]]. It can also be synthesized from [[sucrose]] or by strains of ''[[Penicillium]]'' 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 [[E number]] E315, and is widely used as an [[antioxidant]] in processed foods.<ref>[http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist Current EU approved additives and their E Numbers], Food Standards Agency</ref>


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 = pp.&nbsp;336–46 | pmid = 8780343}}</ref> A later study found that erythorbic acid is a potent enhancer of nonheme-iron [[absorption (pharmacokinetics)|absorption]].<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}}</ref>
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 [[absorption (pharmacokinetics)|absorption]].<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>


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.
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.<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>
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>


It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.<ref>See:
It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.<ref>See:
* Kurt Maurer and Bruno Schiedt (August 2, 1933) "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)), ''Berichte der deutschen chemischen Gesellschaft'', '''66''' (8): 1054-1057.
* {{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 }}
* Kurt Maurer and Bruno Schiedt (July 4, 1934) "Zur Darstellung des Iso-Vitamins C (d-Arabo-ascorbinsäure) (II. Mitteil.)" (On the preparation of iso-vitamin C (d-arabo-ascorbic acid) (2nd report)), ''Berichte der deutschen chemischen Gesellschaft'', '''67''' (7) : 1239–1241.</ref>
* {{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:
* {{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 }}

* {{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 }}
==See also==
* {{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>
* [[Sodium erythorbate]]

==References==
==References==
{{reflist}}
{{reflist}}


[[Category:Food antioxidants]]
[[Category:Food antioxidants]]
[[Category:E-number additives]]
[[Category:Substances discovered in the 1930s]]

Latest revision as of 01:59, 7 May 2023

Erythorbic acid
Names
IUPAC name
D-erythro-Hex-2-enono-1,4-lactone
Systematic 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 Edit this at Wikidata
E number E315 (antioxidants, ...)
UNII
  • InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1 checkY
    Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N checkY
  • InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1
    Key: CIWBSHSKHKDKBQ-DUZGATOHBV
  • OC=1[C@H](OC(=O)C=1O)[C@H](O)CO
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
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).
checkY verify (what is checkY☒N ?)

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]

References[edit]

  1. ^ Erythorbic acid and its sodium salt Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.
  2. ^ "Erythorbic acid".
  3. ^ Current EU approved additives and their E Numbers, Food Standards Agency
  4. ^ Sauberlich, HE; Tamura T; Craig CB; Freeberg LE; Liu T (September 1996). "Effects of erythorbic acid on vitamin C metabolism in young women". American Journal of Clinical Nutrition. 64 (3): 336–46. doi:10.1093/ajcn/64.3.336. PMID 8780343.
  5. ^ Fidler, MC; Davidsson L; Zeder C; Hurrell RF (January 2004). "Erythorbic acid is a potent enhancer of nonheme-iron absorption". American Journal of Clinical Nutrition. 79 (1): 99–102. doi:10.1093/ajcn/79.1.99. PMID 14684404.
  6. ^ Hui YH (2006). Handbook of Food Science, Technology and Engineering. CRC Press. pp. 83–32. ISBN 0-8493-9848-7.
  7. ^ See:
    • Maurer, Kurt; Schiedt, Bruno (August 2, 1933). ""Die Darstellung einer Säure C6H8O6 aus Glucose, die in ihrer Reduktionskraft der Ascorbinsäure gleicht (Vorläuf. Mitteil.)" (The preparation of an acid C6H8O6 from glucose, which equals ascorbic acid in its reducing power (preliminary report))". Berichte der Deutschen Chemischen Gesellschaft. 66 (8): 1054–1057. doi:10.1002/cber.19330660807.
    • Maurer, Kurt; Schiedt, Bruno (July 4, 1934). ""Zur Darstellung des Iso-Vitamins C (d-Arabo-ascorbinsäure) (II. Mitteil.)" (On the preparation of iso-vitamin C (d-arabo-ascorbic acid) (2nd report))". Berichte der Deutschen Chemischen Gesellschaft. 67 (7): 1239–1241. doi:10.1002/cber.19340670724.
  8. ^ See also:
    • Ohle, Heinz; Erlbach, Heinz; Carls, Herbert (February 7, 1934). ""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)". Berichte der Deutschen Chemischen Gesellschaft. 67 (2): 324–332. doi:10.1002/cber.19340670235.
    • Baird, D. K.; Haworth, W. N.; Herbert, R. W.; Hirst, E. L.; Smith, F.; Stacey, M. (1934). "Ascorbic acid and synthetic analogues". Journal of the Chemical Society: 63–67. doi:10.1039/JR9340000062.
    • Reichstein, T.; Grüssner, A.; Oppenauer, R. (1934). ""Synthese der Ascorbinsäure und verwandter Verbindungen nach der Oson-Blausäure-Methode"(Synthesis of ascorbic acid and related compounds via the ozone-hydrogen cyanide method)". Helvetica Chimica Acta. 17: 510–520. doi:10.1002/hlca.19340170157.
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