Erythorbic acid

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
CAS Number	89-65-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:51438 ;
ChemSpider	16736142 ;
ECHA InfoCard	100.001.753
E number	E315 (antioxidants, ...)
PubChem CID	6981;
UNII	311332OII1 ;
CompTox Dashboard (EPA)	DTXSID6026537 ;
	InChI 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 Key: CIWBSHSKHKDKBQ-DUZGATOHSA-N ; 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;
	SMILES OC=1[C@H](OC(=O)C=1O)[C@H](O)CO;
Properties
Chemical formula	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)	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). verify (what is ?) Infobox references

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

^ Erythorbic acid and its sodium salt Dr R. Walker, Professor of Food Science, Department of Biochemistry, University of Surrey, England.
^ "Erythorbic acid".
^ Current EU approved additives and their E Numbers, Food Standards Agency
^ 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.
^ 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.
^ Hui YH (2006). Handbook of Food Science, Technology and Engineering. CRC Press. pp. 83–32. ISBN 0-8493-9848-7.
^
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.19330660807.6H₈O₆ 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))&rft.volume=66&rft.issue=8&rft.pages=1054-1057&rft.date=1933-08-02&rft_id=info:doi/10.1002/cber.19330660807&rft.aulast=Maurer&rft.aufirst=Kurt&rft.au=Schiedt, Bruno&rfr_id=info:sid/en.wikipedia.org:Erythorbic acid" class="Z3988">
- 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.
^
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.

[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.19330660807.6H₈O₆ 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))&rft.volume=66&rft.issue=8&rft.pages=1054-1057&rft.date=1933-08-02&rft_id=info:doi/10.1002/cber.19330660807&rft.aulast=Maurer&rft.aufirst=Kurt&rft.au=Schiedt, Bruno&rfr_id=info:sid/en.wikipedia.org:Erythorbic acid" class="Z3988">

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] 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.19330660807.6H₈O₆ 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))&rft.volume=66&rft.issue=8&rft.pages=1054-1057&rft.date=1933-08-02&rft_id=info:doi/10.1002/cber.19330660807&rft.aulast=Maurer&rft.aufirst=Kurt&rft.au=Schiedt, Bruno&rfr_id=info:sid/en.wikipedia.org:Erythorbic acid" class="Z3988">

[9] 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.

[11] 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.

[12] 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.

[13] 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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