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Erythorbic acid: Difference between revisions - Wikipedia

Erythorbic acid: Difference between revisions

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{{chembox
| Watchedfields = changed
| verifiedrevid = 443736114
| Name Name = Erythorbic acid
| ImageFile ImageFile = D-Erythorbic acid.pngsvg
| ImageSize ImageSize = 150px
| ImageName ImageName =
| ImageFile1 ImageFile1 = Erythorbic-acid-3D-balls.png
| ImageSize1 ImageSize1 = 200px
| IUPACName = <small>D</small>-''erythro''-Hex-2-enono-1,4-lactone
| IUPACNameSystematicName = (5R5''R'')-5-[(1R1''R'')-1,2-dihydroxyethylDihydroxyethyl]-3,4-dihydroxyfuran-2(5H5''H'')-one
| OtherNames OtherNames= <small>D</small>-Araboascorbic acid, Erythorbate, Isoascorbic acid, E315.
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736142
| UNII_Ref = {{fdacite|correct|FDA}}
Line 19 ⟶ 20:
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 89-65-6
| PubChem = 6981
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51438
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 28 ⟶ 29:
| SMILES = OC=1[C@H](OC(=O)C=1O)[C@H](O)CO
}}
| Section2 = {{Chembox Properties
| C=6 | H=8 | O=6
| Formula = C<sub>6</sub>H<sub>8</sub>O<sub>6</sub>
| MolarMassDensity = 1760.13704 g/molcm<sup>3</sup>
| MeltingPtC = 164 to 172
| Density = 0.704 g/cm<sup>3</sup>
| MeltingPtMeltingPt_notes = 164–172&nbsp;°C (decomposes)
| pKa = 2.1
}}
| Section3 = {{Chembox Hazards
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
}}
| Section6 = {{Chembox Related
| OtherCations = [[Calcium erythorbate]], [[sodium erythorbate]], [[potassium erythorbate]]
}}
}}
 
'''Erythorbic acid''', formerly known as ('''isoascorbic acid''', and '''<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 vegetablereaction between methyl 2-keto-<small>D</small>-derivedgluconate foodand additive[[sodium producedmethoxide]]. 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 | coauthors author2= Tamura T, |author3=Craig CB, |author4=Freeberg LE, |author5=Liu T | journal = American Journal of Clinical Nutrition | month date= September | year = 1996 | volume = 64 | issue = 3 | pages = pp336–46 | doi = 10.1093/ajcn/64.3.&nbsp;336&ndash;46 | 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 | coauthors author2= Davidsson L, |author3=Zeder C, |author4=Hurrell RF | journal = American Journal of Clinical Nutrition | month date= January | year = 2004 | volume = 79 | issue = 1 | pmid = 14684404 | pages = pp99–102 | doi=10.1093/ajcn/79.1.&nbsp;99&ndash;102| 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. 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>
 
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>
==See also ==
* [[Sodium erythorbate]]
 
It was first synthesized in 1933 by the German chemists Kurt Maurer and Bruno Schiedt.<ref>See:
* {{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 }}
* {{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 }}
* {{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>
==References==
{{reflist}}
 
[[Category:Food antioxidants]]
[[Category:E-number additives]]
 
[[Category:Substances discovered in the 1930s]]
[[ca:Àcid eritòrbic]]
[[lt:Eritorbo rūgštis]]
[[hu:Eritroaszkorbinsav]]
[[nl:Erythorbinezuur]]
[[ja:エリソルビンさん]]
[[pt:Ácido eritórbico]]
[[fi:Erytorbiinihappo]]
[[sv:Isoaskorbinsyra]]