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2D Structure
Also known as: Isoascorbic acid, D-isoascorbic acid, 89-65-6, D-araboascorbic acid, Araboascorbic acid, D-erythorbic acid
Molecular Formula
C6H8O6
Molecular Weight
176.12  g/mol
InChI Key
CIWBSHSKHKDKBQ-DUZGATOHSA-N
FDA UNII
311332OII1

erythorbic acid is a natural product found in Flammulina velutipes, Hypsizygus marmoreus, and other organisms with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
2.1.2 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
2.1.3 InChI Key
CIWBSHSKHKDKBQ-DUZGATOHSA-N
2.1.4 Canonical SMILES
C(C(C1C(=C(C(=O)O1)O)O)O)O
2.1.5 Isomeric SMILES
C([C@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
311332OII1
2.3 Synonyms
2.3.1 MeSH Synonyms

1. D-araboascorbic Acid

2. Erythroascorbic Acid

3. Isoascorbic Acid

4. Isoascorbic Acid, Disodium Salt

5. Isoascorbic Acid, Monosodium Salt

6. Isoascorbic Acid, Sodium Salt

7. Sodium Erythorbate

2.3.2 Depositor-Supplied Synonyms

1. Isoascorbic Acid

2. D-isoascorbic Acid

3. 89-65-6

4. D-araboascorbic Acid

5. Araboascorbic Acid

6. D-erythorbic Acid

7. Isovitamin C

8. D-(-)-isoascorbic Acid

9. Saccharosonic Acid

10. Glucosaccharonic Acid

11. 2,3-didehydro-d-erythro-hexono-1,4-lactone

12. Fema No. 2410

13. Erycorbin

14. Neo-cebicure

15. D-erythro-hex-2-enonic Acid, .gamma.-lactone

16. (5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one

17. (r)-5-((r)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5h)-one

18. D-erythro-hex-2-enonic Acid Gamma-lactone

19. Chebi:51438

20. (2r)-2-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one

21. D-ascorbic Acid, Iso

22. D-erythro-hex-2-enono-1,4-lactone

23. 311332oii1

24. D(-)-isoascorbic Acid (erythorbic Acid)

25. Mercate 5

26. Erythroascorbic Acid, D-

27. Mfcd00005378

28. Fema Number: 2410

29. Ccris 6568

30. Hsdb 584

31. Erythorbic Acid [nf]

32. Nsc 8117

33. D-erythro-3-oxohexonic Acid Lactone

34. Einecs 201-928-0

35. D-erythro-3-ketohexonic Acid Lactone

36. 3-oxohexonic Acid Lactone, D-erythro-

37. Brn 0084271

38. Nsc-8117

39. 3-keto-d-erythro-hexonic Acid Gamma-lactone

40. Hex-2-enonic Acid Gamma-lactone, D-erythro-

41. (5r)-5-((1r)-1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5h)-one

42. Unii-311332oii1

43. D-iso-ascorbic Acid

44. Erythorbate

45. Isoascorbic-acid

46. 1f9g

47. E315

48. D-erythro-hex-2-enonic Acid, Gamma-lactone,

49. Dsstox_cid_6537

50. Ec 201-928-0

51. Dsstox_rid_78143

52. Dsstox_gsid_26537

53. Schembl18678

54. Erythorbic Acid [ii]

55. 5-18-05-00026 (beilstein Handbook Reference)

56. Erythorbic Acid [fcc]

57. Isoascorbic Acid [mi]

58. Erythorbic Acid [fhfi]

59. Erythorbic Acid [hsdb]

60. Erythorbic Acid [inci]

61. Chembl486293

62. Ins No.315

63. Schembl3700961

64. Dtxsid6026537

65. Erythorbic Acid [mart.]

66. Erythorbic Acid [usp-rs]

67. Ins-315

68. D-(-)-isoascorbic Acid, 98%

69. Hy-n7079

70. Tox21_201111

71. Ac8021

72. Akos015856346

73. D-erythro-hex-2-enoic Acid ?-lactone

74. Zinc100006772

75. Zinc100057602

76. Cas-89-65-6

77. D-erythro-hex-2-enonic Acid, G-lactone

78. Ncgc00258663-01

79. D-erythro-hex-2-enoic Acid Gamma-lactone

80. D-isoascorbic Acid, >=99%, Fcc, Fg

81. A0520

82. Cs-0014152

83. E-315

84. C20364

85. A843272

86. Q424531

87. D-isoascorbic Acid 1000 Microg/ml In Acetonitrile

88. J-506944

89. 7179c406-7ccf-4c07-9125-aa71e28fb983

90. Erythorbic Acid, United States Pharmacopeia (usp) Reference Standard

91. (5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one (d-isoascorbic Acid)

92. (5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5h)-one (non-preferred Name)

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 176.12 g/mol
Molecular Formula C6H8O6
XLogP3-1.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass176.03208797 g/mol
Monoisotopic Mass176.03208797 g/mol
Topological Polar Surface Area107 Ų
Heavy Atom Count12
Formal Charge0
Complexity232
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Erythorbic acid is a stereoisomer of l-ascorbic acid, and is used as an antioxidant in foods and oral pharmaceutical formulations. It has approximately 5% of the vitamin C activity of l-ascorbic acid.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 250


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


5.2 Absorption, Distribution and Excretion

Erythorbic acid is readily absorbed and metabolized. Following an oral dose of 500 mg of erythorbic acid to human subjects the blood level curves for ascorbic acid and erythorbic acid showed a similar rise. In five human subjects, an oral dose of 300 mg was shown to have no effect on urinary excretion of ascorbic acid.

WHO; Food Additives Series 28 (1991). Available from, as of August 6, 2010: https://www.inchem.org/documents/jecfa/jecmono/v28je03.htm


In hamster, rat and rabbit, for which ascorbate is not an essential vitamin, intestinal absorption of L-ascorbic acid is low and takes place by passive diffusion; conversely, in guinea pig and human, ascorbate absorption is mediated by a saturable, sodium- dependent, active transport mechanism. It follows that the former species are not suitable models for human absorption. Since the active transport system is saturable but since passive diffusion might also be significant at high dose levels, the absorption of ascorbic acid is dose dependent. Erythorbic acid appears to be another but much poorer substrate for the same transport system and may thus act as a weak competitive inhibitor of L-ascorbate uptake. In studies using isolated brush border vesicles from guinea pig ileum, the K1 has variously been estimated at about 11 mM and around 20 mM; this compares with an apparent Km for ascorbate uptake of about 0.3 mM in the same system.

WHO; Food Additives Series 28 (1991). Available from, as of August 6, 2010: https://www.inchem.org/documents/jecfa/jecmono/v28je03.htm


The reason for lack of a stronger antiscorbutic action of erythorbic acid is probably the incapacity of the tissues to retain it in the quantities that ascorbic acid is stored.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1577


The absorption of erythorbic acid through the human buccal mucosa was studied in healthy adult subjects. Absorption of a solution of 10 mM erythorbic acid, buffered to pH 6, was 13.0 +/- 0.74 umol/5 minutes. No statistical difference was found between the absorptions of Erythorbic Acid and L-ascorbic acid.

Cosmetic Ingredient Expert Review Panel; Final Report on the Safety Assessment of Ascorbyl Palmitate, Ascorbyl Dipalmitate, Ascorbyl Stearate, Erythorbic Acid, and Sodium Erythorbate; International Journal of Toxicology 18 ( Suppl 3): 1-26 (1999).


For more Absorption, Distribution and Excretion (Complete) data for Erythorbic acid (13 total), please visit the HSDB record page.


5.3 Biological Half-Life

In dogs, this resulted in a half-life of approximately 30 minutes for erythorbic acid in the plasma.

Cosmetic Ingredient Expert Review Panel; Final Report on the Safety Assessment of Ascorbyl Palmitate, Ascorbyl Dipalmitate, Ascorbyl Stearate, Erythorbic Acid, and Sodium Erythorbate; International Journal of Toxicology 18 ( Suppl 3): 1-26 (1999).