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2D Structure
Also known as: 134-03-2, Sodium l-ascorbate, L-ascorbic acid sodium salt, Vitamin c sodium, Ascorbic acid sodium salt, Monosodium l-ascorbate
Molecular Formula
C6H7NaO6
Molecular Weight
198.11  g/mol
InChI Key
PPASLZSBLFJQEF-RXSVEWSESA-M
FDA UNII
S033EH8359

A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2H-furan-3-olate
2.1.2 InChI
InChI=1S/C6H8O6.Na/c7-1-2(8)5-3(9)4(10)6(11)12-5;/h2,5,7-10H,1H2;/q;+1/p-1/t2-,5+;/m0./s1
2.1.3 InChI Key
PPASLZSBLFJQEF-RXSVEWSESA-M
2.1.4 Canonical SMILES
C(C(C1C(=C(C(=O)O1)O)[O-])O)O.[Na+]
2.1.5 Isomeric SMILES
C([C@@H]([C@@H]1C(=C(C(=O)O1)O)[O-])O)O.[Na+]
2.2 Other Identifiers
2.2.1 UNII
S033EH8359
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Ascorbic

2. Acid, L-ascorbic

3. Ascorbate, Ferrous

4. Ascorbate, Magnesium

5. Ascorbate, Sodium

6. Ascorbic Acid

7. Ascorbic Acid, Monosodium Salt

8. Di-l-ascorbate, Magnesium

9. Ferrous Ascorbate

10. Hybrin

11. L Ascorbic Acid

12. L-ascorbic Acid

13. Magnesium Ascorbate

14. Magnesium Ascorbicum

15. Magnesium Di L Ascorbate

16. Magnesium Di-l-ascorbate

17. Magnorbin

18. Vitamin C

2.3.2 Depositor-Supplied Synonyms

1. 134-03-2

2. Sodium L-ascorbate

3. L-ascorbic Acid Sodium Salt

4. Vitamin C Sodium

5. Ascorbic Acid Sodium Salt

6. Monosodium L-ascorbate

7. Vitamin C Sodium Salt

8. Ascorbicin

9. Sodascorbate

10. (+)-sodium L-ascorbate

11. L-ascorbic Acid, Monosodium Salt

12. Natrii Ascorbas

13. Vitamin C, Sodium Salt

14. Ascorbate

15. Ascorbate De Sodium

16. Ascorbin

17. Cevalin

18. L-ascorbic Acid Sodium

19. Ins No.301

20. L-ascorbic Acid (sodium Salt)

21. Ins-301

22. L-ascorbate, Sodium

23. Sodium (r)-2-((s)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate

24. S033eh8359

25. Cebitate

26. Aminofenitrooxon

27. E-301

28. Sodium (2r)-2-[(1s)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2h-furan-3-olate

29. Iskia-c

30. Natri-c

31. Sodium (l)-ascorbate

32. Sodiumascorbate

33. Ascorbato Sodico

34. Ascorbato Sodico [dcit]

35. Sodium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2h-furan-3-olate

36. Mfcd00082340

37. Natrii Ascorbas [inn-latin]

38. Ascorbic Acid Sodium Derivative

39. Ccris 3291

40. Hsdb 694

41. 3-oxo-l-gulofuranolactone Sodium

42. Hbl 508

43. Ascorbate De Sodium [inn-french]

44. Einecs 205-126-1

45. Tianafacacid

46. Sodium Ascorbate [usp:inn]

47. Unii-s033eh8359

48. Sodium Derivative Of 3-oxo-l-gulofuranolactone

49. Ascorbic Acid Sodium

50. E301

51. Sodium L-ascorbate Salt

52. Dsstox_cid_105

53. Ec 205-126-1

54. Schembl3745

55. Dsstox_rid_75369

56. Dsstox_gsid_20105

57. Sodium Ascorbate [ii]

58. L(+)ascorbic Acid Sodium Salt

59. Sodium Ascorbate [fcc]

60. Sodium Ascorbate [inn]

61. Chembl591665

62. Sodium Ascorbate [hsdb]

63. Sodium Ascorbate [inci]

64. Dtxsid0020105

65. Sodium Ascorbate [vandf]

66. Hy-b0166a

67. Sodium Ascorbate [mart.]

68. Chebi:113451

69. Sodium Ascorbate [usp-rs]

70. Sodium Ascorbate [who-dd]

71. L-ascorbic Acid Sodium Salt,(s)

72. L-ascorbic Acid - Monosodium Salt

73. Tox21_300556

74. Akos015895058

75. L-ascorbic Acid, Sodium Salt (1:1)

76. Sodium Ascorbate [orange Book]

77. Ascorbic Acid Sodium Salt [mi]

78. Cs-6063

79. Db14482

80. Sodium Ascorbate [ep Monograph]

81. Sodium (2r)-2-[(1s)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate

82. Sodium Ascorbate [usp Monograph]

83. Ncgc00254355-01

84. Bp-30077

85. Cas-134-03-2

86. A0539

87. B1834

88. E80761

89. A806721

90. Q424551

91. J-006471

92. Sodium (2r)-2-[(1s)-1,2-bis(oxidanyl)ethyl]-4-oxidanyl-5-oxidanylidene-2h-furan-3-olate

93. Sodium(r)-2-((s)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 198.11 g/mol
Molecular Formula C6H7NaO6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass198.01403222 g/mol
Monoisotopic Mass198.01403222 g/mol
Topological Polar Surface Area110 Ų
Heavy Atom Count13
Formal Charge0
Complexity237
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Antioxidants; Free Radical Scavengers

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Ascorbic acid and calcium and sodium ascorbates are used as antoxidants in pharmaceutical manufacturing and in the food industry.

Sweetman SC (ed), Martindale: The Complete Drug Reference. London: Pharmaceutical Press (2009), p.1985.


In 20 patients in acute asthmatic crisis, 16 recovered promptly after receiving 6 g sodium ascorbate iv. Chronic oral treatment (0.6-1 g/day/60 days) with Na ascorbate prevented asthmatic symptoms in 18/25 asthmatic patients.

Miyares C et al; Rev Cubana Med 10 (5): 469 (1971)


8 patients with hyphema were treated with iv glycerin in combination with sodium ascorbate. The results showed that glycerol in combination with sodium ascorbate diminished the hemorrhage in eye within 12-24 hr.

PMID:7272018 Latinovic S et al; Boll Chim Farm 120: 156-8 (1981)


For more Therapeutic Uses (Complete) data for Sodium ascorbate (6 total), please visit the HSDB record page.


4.2 Drug Warning

Each gram of sodium ascorbate contains approximately 5 mEq of sodium; this should be considered when the drug is used in patients on salt-restricted diets.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


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.)


Vitamins

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body. (See all compounds classified as Vitamins.)


5.2 Absorption, Distribution and Excretion

Ascorbic acid, the reduced form of vitamin C, functions as a potent antioxidant as well as in cell differentiation. Ascorbate is taken up by mammalian cells through the specific sodium/ascorbate co-transporters SVCT1 and SVCT2. Although skeletal muscle contains about 50% of the whole-body vitamin C, the expression of SVCT transporters has not been clearly addressed in this tissue. ... This work ... analyzed the expression pattern of SVCT2 during embryonic myogenesis using the chick as model system. ... Immunohistochemical analyses showed that SVCT2 is preferentially expressed by type I slow-twitch muscle fibers throughout chick myogenesis as well as in post-natal skeletal muscles of several species, including human...

Low M et al; Histochem Cell Biol 131 (5): 565-74 (2009). Available from, as of March 15, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=19125272


Humans use two sodium-ascorbate cotransporters (hSVCT1 and hSVCT2) for transporting the dietary essential micronutrient ascorbic acid, the reduced and active form of vitamin C. Although the human liver plays a pivotal role in regulating and maintaining vitamin C homeostasis, vitamin C transport physiology and regulation of the hSVCT systems in this organ have not been well defined. Thus, this research used a human hepatic cell line (HepG2), confirming certain results with primary human hepatocytes and determined the initial rate of ascorbic acid uptake to be Na(+) gradient, pH dependent, and saturable as a function of concentration over low and high micromolar ranges. Additionally, hSVCT2 protein and mRNA are expressed at higher levels in HepG2 cells and native human liver, and the cloned hSVCT2 promoter has more activity in HepG2 cells. Results using short interfering RNA suggest that in HepG2 cells, decreasing hSVCT2 message levels reduces the overall ascorbic acid uptake process more than decreasing hSVCT1 message levels. Activation of PKC intracellular regulatory pathways caused a downregulation in ascorbic acid uptake not mediated by a single predicted PKC-specific amino acid phosphorylation site in hSVCT1 or hSVCT2. However, PKC activation causes internalization of hSVCT1 but not hSVCT2. Examination of other intracellular regulatory pathways on ascorbic acid uptake determined that regulation also potentially occurs by PKA, PTK, and Ca(2+)/calmodulin, but not by nitric oxide-dependent pathways...

Reidling JC et al; Am J Physiol. Gastrointest Liver Physiol 295 (6): 1217-27 (2008). Available from, as of March 15, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=18845575


5.3 Metabolism/Metabolites

... Adrenal cortex is closely associated with ascorbate metabolism ... Hydrocortisone was reported ... to stimulate synthesis of ascorbate from gluconolactone, but deoxycorticosterone or aldosterone caused ... increase in ascorbate excretion in normal or adrenalectomized rats...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 607


5.4 Mechanism of Action

Mechanism of action of ascorbate is a superoxide radical scavenger.

Amdur, M.O., J. Doull, C.D. Klaasen (eds). Casarett and Doull's Toxicology. 4th ed. New York, NY: Pergamon Press, 1991., p. 524


... Sodium ascorbate decreases cellular iron uptake by melanoma cells in a dose- and time-dependent fashion, indicating that intracellular iron levels may be a critical factor in sodium ascorbate-induced apoptosis. Indeed, sodium ascorbate-induced apoptosis is enhanced by the iron chelator, desferrioxamine (DFO) while it is inhibited by the iron donor, ferric ammonium citrate (FAC). Moreover, the inhibitory effects of sodium ascorbate on intracellular iron levels are blocked by addition of transferrin, suggesting that transferrin receptor (TfR) dependent pathway of iron uptake may be regulated by sodium ascorbate. Cells exposed to sodium ascorbate demonstrated down-regulation of TfR expression and this precedes sodium ascorbate-induced apoptosis. Taken together, sodium ascorbate-mediated apoptosis appears to be initiated by a reduction of TfR expression, resulting in a down-regulation of iron uptake followed by an induction of apoptosis...

Kang JS et al; J Cell Physiol 204 (1): 192-7 (2005). Available from, as of March 15, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15672419


Humans use two sodium-ascorbate cotransporters (hSVCT1 and hSVCT2) for transporting the dietary essential micronutrient ascorbic acid, the reduced and active form of vitamin C. Although the human liver plays a pivotal role in regulating and maintaining vitamin C homeostasis, vitamin C transport physiology and regulation of the hSVCT systems in this organ have not been well defined. Thus, this research used a human hepatic cell line (HepG2), confirming certain results with primary human hepatocytes and determined the initial rate of ascorbic acid uptake to be Na(+) gradient, pH dependent, and saturable as a function of concentration over low and high micromolar ranges. Additionally, hSVCT2 protein and mRNA are expressed at higher levels in HepG2 cells and native human liver, and the cloned hSVCT2 promoter has more activity in HepG2 cells. Results using short interfering RNA suggest that in HepG2 cells, decreasing hSVCT2 message levels reduces the overall ascorbic acid uptake process more than decreasing hSVCT1 message levels. Activation of PKC intracellular regulatory pathways caused a downregulation in ascorbic acid uptake not mediated by a single predicted PKC-specific amino acid phosphorylation site in hSVCT1 or hSVCT2. However, PKC activation causes internalization of hSVCT1 but not hSVCT2. Examination of other intracellular regulatory pathways on ascorbic acid uptake determined that regulation also potentially occurs by PKA, PTK, and Ca(2+)/calmodulin, but not by nitric oxide-dependent pathways...

Reidling JC et al; Am J Physiol. Gastrointest Liver Physiol 295 (6): 1217-27 (2008). Available from, as of March 15, 2010: https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=18845575