erythorbic acid

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.{{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 }}

A later study found that erythorbic acid is a potent enhancer of nonheme-iron absorption, just like ascorbate. This is thought to be due to it exerting the same iron-reducing and iron-chelating activity as ascorbic acid. Neither of these reactions is mediated by an enzyme, which would confer some chiral selectivity.{{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 }} It is twice as effective as ascorbic acid in enhancing non-heme iron absorption. Americans are estimated to ingest 200 mg of erythorbic acid per day, making it a very important factor in understanding iron absorption.{{cite journal |last1=Hurrell |first1=Richard |last2=Egli |first2=Ines |title=Iron bioavailability and dietary reference values |journal=The American Journal of Clinical Nutrition |date=May 2010 |volume=91 |issue=5 |pages=1461S–1467S |doi=10.3945/ajcn.2010.28674F}}

{{See also|Sodium erythorbate}}

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.{{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 }} Much like ascorbic acid, it increases nitrosylation of the central iron atom of muscle myoglobin, resulting in the formation of reddish-brown nitrosomyoglobin and the characteristic pink color of nitrosohemochrome or nitrosyl-heme upon cooking. Again like ascorbic acid, it reduces the formation of nitrosamines.{{cite journal |last1=Herrmann |first1=S.S. |last2=Granby |first2=K. |last3=Duedahl-Olesen |first3=L. |title=Formation and mitigation of N-nitrosamines in nitrite preserved cooked sausages |journal=Food Chemistry |date=May 2015 |volume=174 |pages=516–526 |doi=10.1016/j.foodchem.2014.11.101|doi-access=free }}

It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.See:

• {{cite journal | last1 = Maurer | first1 = Kurt | last2 = Schiedt | first2 = Bruno | date = August 2, 1933 | title = "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)) | url = | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 66 | issue = 8| pages = 1054–1057 | doi = 10.1002/cber.19330660807 }}
• {{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 }}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 }}
• {{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 }}

Erythorbic acid is very easily produced by fermentation, being obtainable in just one step compared to ascorbic acid's two. A number of Penicillium naturally produce this chemical from glucose. This is the original process developed in the 1960s, but it has low volumetric efficiency and glucose yield compared to the modern method.{{cite journal |last1=Pappenberger |first1=Günter |last2=Hohmann |first2=Hans-Peter |title=Industrial Production of l-Ascorbic Acid (Vitamin C) and d-Isoascorbic Acid |journal=Biotechnology of Food and Feed Additives |date=2013 |volume=143 |pages=143–188 |doi=10.1007/10_2013_243}}

Today the industrial process is quite similar to the Reichstein process used for ascorbic acid, only chirally flipped. Microbial fermentation first produces a 2-keto-sugar acid, e.g. by Pseudomonas fluorescens AR4 converting glucose to 2-keto-D-gluconate. Then chemical rearrangement produces the product.

Like ascorbic acid, the production of erythorbic acid is concentrated in China. Its price is less volatile than that of ascorbic acid, making it an attractive alternative in non-nutritive uses in times of high ascorbic acid prices.

The structurally similar C5 sugar acid, D-erythroascorbic acid, is made by baker's yeast and other fungi, acting as an antioxidant in their own cells. It is made by and has some antioxidant activity in Manduca sexta.{{cite journal |last1=Shao |first1=Yi Yuan. |last2=Seib |first2=Paul A. |last3=Kramer |first3=Karl J. |last4=Van Galen |first4=Dean A. |title=Synthesis and properties of D-erythroascorbic acid and its vitamin C activity in the tobacco hornworm (Manduca sexta) |journal=Journal of Agricultural and Food Chemistry |date=1 September 1993 |volume=41 |issue=9 |pages=1391–1396 |doi=10.1021/jf00033a009}} It has no industrial use, however.

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Category:Food antioxidants

Category:E-number additives

Category:Substances discovered in the 1930s