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    Chemistry

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    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
    Sodium Ascorbate
    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

    Sodium Ascorbate

    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

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    19-Jan-2021
    30-Oct-2024
    KGS
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