Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:37 UTC
HMDB IDHMDB00044
Secondary Accession Numbers
  • HMDB14273
  • HMDB29945
Metabolite Identification
Common NameAscorbic acid
DescriptionAscorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. [PubChem] Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants. (PMID: 10799361 ).
Structure
Thumb
Synonyms
  1. (+)-ascorbate
  2. (+)-ascorbic acid
  3. (+)-Sodium L-ascorbate
  4. 3-Keto-L-gulofuranolactone
  5. 3-Oxo-L-gulofuranolactone
  6. Adenex
  7. Allercorb
  8. Antiscorbic vitamin
  9. Antiscorbutic vitamin
  10. Arco-cee
  11. Ascoltin
  12. Ascor-B.I.D.
  13. Ascorb
  14. Ascorbajen
  15. Ascorbate
  16. Ascorbic acid
  17. Ascorbicab
  18. Ascorbicap
  19. Ascorbicin
  20. Ascorbin
  21. Ascorbutina
  22. Ascorin
  23. Ascorteal
  24. Ascorvit
  25. C-Level
  26. C-Long
  27. C-Quin
  28. C-Span
  29. C-Vimin
  30. Cantan
  31. Cantaxin
  32. Catavin C
  33. Ce lent
  34. Ce-mi-lin
  35. Ce-vi-sol
  36. Cebicure
  37. Cebid
  38. Cebion
  39. Cebione
  40. Cecon
  41. Cee-caps TD
  42. Cee-vite
  43. Cegiolan
  44. Ceglion
  45. Ceklin
  46. Celaskon
  47. Celin
  48. Cell C
  49. Cemagyl
  50. Cemill
  51. Cenetone
  52. Cenolate
  53. Cereon
  54. Cergona
  55. Cescorbat
  56. Cetamid
  57. Cetane
  58. Cetane-caps TC
  59. Cetane-caps TD
  60. Cetebe
  61. Cetemican
  62. Cevalin
  63. Cevatine
  64. Cevex
  65. Cevi-bid
  66. Cevimin
  67. Cevital
  68. Cevitamate
  69. Cevitamic acid
  70. Cevitamin
  71. Cevitan
  72. Cevitex
  73. Cewin
  74. Chewcee
  75. Ciamin
  76. Cipca
  77. Citriscorb
  78. Citrovit
  79. Colascor
  80. Concemin
  81. Davitamon C
  82. Dora-C-500
  83. Duoscorb
  84. Ferrous ascorbate
  85. gamma-Lactone L-threo-Hex-2-enonate
  86. gamma-Lactone L-threo-Hex-2-enonic acid
  87. HiCee
  88. Hybrin
  89. Ido-C
  90. Juvamine
  91. Kangbingfeng
  92. Kyselina askorbova
  93. L(+)-Ascorbate
  94. L(+)-Ascorbic acid
  95. L-(+)-Ascorbate
  96. L-(+)-Ascorbic acid
  97. L-3-Ketothreohexuronic acid lactone
  98. L-Ascorbate
  99. L-Ascorbic acid
  100. L-Lyxoascorbate
  101. L-Lyxoascorbic acid
  102. L-Threo-ascorbic acid
  103. L-Xyloascorbate
  104. L-Xyloascorbic acid
  105. Laroscorbine
  106. Lemascorb
  107. Liqui-cee
  108. Meri-c
  109. Natrascorb
  110. Natrascorb injectable
  111. Planavit C
  112. Proscorbin
  113. Redoxon
  114. Ribena
  115. Ronotec 100
  116. Rontex 100
  117. Roscorbic
  118. Rovimix C
  119. Scorbacid
  120. Scorbu C
  121. Scorbu-C
  122. Secorbate
  123. Sodascorbate
  124. Suncoat VC 40
  125. Testascorbic
  126. VASC
  127. Vicelat
  128. Vicin
  129. Vicomin C
  130. Viforcit
  131. Viscorin
  132. Viscorin 100M
  133. Vitace
  134. Vitacee
  135. Vitacimin
  136. Vitacin
  137. Vitamin C
  138. Vitamisin
  139. Vitascorbol
  140. Xitix
Chemical FormulaC6H8O6
Average Molecular Weight176.1241
Monoisotopic Molecular Weight176.032087988
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
Traditional IUPAC Namevitamin C
CAS Registry Number50-81-7
SMILES
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
InChI KeyCIWBSHSKHKDKBQ-JLAZNSOCSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Heteromonocyclic Compounds
ClassDihydrofurans
Sub ClassFuranones
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
Substituents
  • 1,2 Diol
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentButenolides
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Anti-oxidant
  • Component of Tyrosine metabolism
  • Enzyme co-factor
  • Essential vitamins
  • Free Radical Scavengers
  • Nutrient
  • Vitamins
  • Vitamins (Vitamin C)
Application
  • Dye / Coloring Agent
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point191 °CPhysProp
Boiling PointNot AvailableNot Available
Water Solubility400 mg/mL at 40 °CMERCK INDEX (1996)
LogP-1.85AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
water solubility245 g/LALOGPS
logP-1.6ALOGPS
logP-1.9ChemAxon
logS0.14ALOGPS
pKa (strongest acidic)4.36ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count4ChemAxon
polar surface area107.22ChemAxon
rotatable bond count2ChemAxon
refractivity37.03ChemAxon
polarizability14.94ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Amniotic Fluid
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Erythrocyte
  • Eye Lens
  • Fibroblasts
  • Gonads
  • Heart
  • Intestine
  • Liver
  • Lung
  • Lymphocyte
  • Most Tissues
  • Muscle
  • Myelin
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Amniotic FluidDetected and Quantified20.4 +/- 12.21 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified88.6 (21.0 - 171.0) uMChildren (1-13 year old)Not SpecifiedNormal
  • Geigy Scient...
BloodDetected and Quantified60.8 +/- 15.9 uMAdult (>18 years old)Not SpecifiedNormal
  • Geigy Scient...
BloodDetected and Quantified51.0 (11.0 - 125.0) uMNewborn (0-30 days old)Not SpecifiedNormal
  • Geigy Scient...
BloodDetected and Quantified36.0 +/- 18.0 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified63.0 (11.0-114.0) uMAdult (>18 years old)BothNormal
  • The Merck Ma...
BloodDetected and Quantified22.2 (14.0-40.0) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified27.0 (11.1-49.7) uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
BloodDetected and Quantified50.9 (35.4-80.1) uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
Cellular CytoplasmDetected and Quantified68.0 +/- 43.0 uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified68.0 (17.0-119.0) uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified163.8 +/- 21 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified133 +/- 58.8 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified164.0 (143.0-185.0) uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified144.0 (36.2-251.0) uMAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified32.5 (4.6-78) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified1.70-22.72 umol/mmol creatinineAdult (>18 years old)BothNormal
  • David F. Put...
UrineDetected and Quantified17.0 +/- 2.5 umol/mmol creatinineNewborn (0-30 days old)BothNormal
  • Geigy Scient...
UrineDetected and Quantified63.6 +/-142.9 umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified0.512 +/-0.058 umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified39.0 +/- 92.7 uMAdult (>18 years old)BothCommentHyperoxalemia
BloodDetected and Quantified6.5 +/- 18.6 uMAdult (>18 years old)BothCommentHyperoxalemia
BloodDetected and Quantified82.57 +/- 36.71 uMAdult (>18 years old)BothCanavan disease
Cerebrospinal Fluid (CSF)Detected and Quantified53.8 (45.8-61.8) uMChildren (1-13 year old)BothCommentBrain injury
Cerebrospinal Fluid (CSF)Detected and Quantified11.9 (0.0-24) uMAdult (>18 years old)BothCommentMeningitis
Associated Disorders and Diseases
Disease References
Traumatic brain injury
  • Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8. Pubmed: 11978879
Canavan disease
  • Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. Pubmed: 16139832
Hyperoxalemia
  • Ogawa Y, Machida N, Jahana M, Gakiya M, Chinen Y, Oda M, Morozumi M, Sugaya K: Major factors modulating the serum oxalic acid level in hemodialysis patients. Front Biosci. 2004 Sep 1;9:2901-8. Pubmed: 15353324
Meningitis
  • Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. Pubmed: 11805243
Associated OMIM IDs
DrugBank IDDB00126
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001224
KNApSAcK IDC00001179
Chemspider ID10189562
KEGG Compound IDC00072
BioCyc IDASCORBATE
BiGG ID33747
Wikipedia LinkAscorbic acid
NuGOwiki LinkHMDB00044
Metagene LinkHMDB00044
METLIN ID3753
PubChem Compound54670067
PDB ID1E71
ChEBI ID17208
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  3. Jacobsson L, Lindgarde F, Manthorpe R, Akesson B: Fatty acid composition of adipose tissue and serum micronutrients in relation to common rheumatic complaints in Swedish adults 50-70 years old. Scand J Rheumatol. 1992;21(4):171-7. Pubmed: 1529283
  4. Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8. Pubmed: 11978879
  5. Luck MR, Jeyaseelan I, Scholes RA: Ascorbic acid and fertility. Biol Reprod. 1995 Feb;52(2):262-6. Pubmed: 7711198
  6. Sotiriou S, Gispert S, Cheng J, Wang Y, Chen A, Hoogstraten-Miller S, Miller GF, Kwon O, Levine M, Guttentag SH, Nussbaum RL: Ascorbic-acid transporter Slc23a1 is essential for vitamin C transport into the brain and for perinatal survival. Nat Med. 2002 May;8(5):514-7. Pubmed: 11984597
  7. Wolters M, Hickstein M, Flintermann A, Tewes U, Hahn A: Cognitive performance in relation to vitamin status in healthy elderly German women-the effect of 6-month multivitamin supplementation. Prev Med. 2005 Jul;41(1):253-9. Epub 2005 Jan 6. Pubmed: 15917019
  8. Chiplonkar SA, Agte VV, Tarwadi KV, Paknikar KM, Diwate UP: Micronutrient deficiencies as predisposing factors for hypertension in lacto-vegetarian Indian adults. J Am Coll Nutr. 2004 Jun;23(3):239-47. Pubmed: 15190049
  9. Dudek H, Farbiszewski R, Rydzewska M, Michno T, Kozlowski A: [Concentration of glutathione (GSH), ascorbic acid (vitamin C) and substances reacting with thiobarbituric acid (TBA-rs) in single human brain metastases] Wiad Lek. 2005;58(7-8):379-81. Pubmed: 16425787
  10. Berndt SI, Carter HB, Landis PK, Hallfrisch J, Rohrmann S, Metter EJ, Platz EA: Prediagnostic plasma vitamin C levels and the subsequent risk of prostate cancer. Nutrition. 2005 Jun;21(6):686-90. Pubmed: 15925292
  11. Atanasova BD, Li AC, Bjarnason I, Tzatchev KN, Simpson RJ: Duodenal ascorbate and ferric reductase in human iron deficiency. Am J Clin Nutr. 2005 Jan;81(1):130-3. Pubmed: 15640471
  12. Huang J, May JM: Ascorbic acid protects SH-SY5Y neuroblastoma cells from apoptosis and death induced by beta-amyloid. Brain Res. 2006 Jun 30;1097(1):52-8. Epub 2006 May 24. Pubmed: 16725131
  13. Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. Pubmed: 11805243
  14. Hino K, Murakami Y, Nagai A, Kitase A, Hara Y, Furutani T, Ren F, Yamaguchi Y, Yutoku K, Yamashita S, Okuda M, Okita M, Okita K: Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients. J Gastroenterol Hepatol. 2006 Aug;21(8):1269-75. Pubmed: 16872308
  15. Kodama M, Inoue F, Kodama T, Kodama M: Intraperitoneal administration of ascorbic acid delays the turnover of 3H-labelled cortisol in the plasma of an ODS rat, but not in the Wistar rat. Evidence in support of the cardinal role of vitamin C in the progression of glucocorticoid synthesis. In Vivo. 1996 Jan-Feb;10(1):97-102. Pubmed: 8726814
  16. Trommer H, Bottcher R, Poppl A, Hoentsch J, Wartewig S, Neubert RH: Role of ascorbic acid in stratum corneum lipid models exposed to UV irradiation. Pharm Res. 2002 Jul;19(7):982-90. Pubmed: 12180551
  17. Grunewald RA: Ascorbic acid in the brain. Brain Res Brain Res Rev. 1993 Jan-Apr;18(1):123-33. Pubmed: 8467348
  18. Close GL, Ashton T, Cable T, Doran D, Holloway C, McArdle F, MacLaren DP: Ascorbic acid supplementation does not attenuate post-exercise muscle soreness following muscle-damaging exercise but may delay the recovery process. Br J Nutr. 2006 May;95(5):976-81. Pubmed: 16611389
  19. Li C, Chen Y, Wang Q: [Whole bladder wall laser irradiation to prevent bladder cancer recurrence with intravesical HpD and ascorbic acid] Zhonghua Zhong Liu Za Zhi. 1997 Nov;19(6):463-5. Pubmed: 10920885
  20. Wannamethee SG, Lowe GD, Rumley A, Bruckdorfer KR, Whincup PH: Associations of vitamin C status, fruit and vegetable intakes, and markers of inflammation and hemostasis. Am J Clin Nutr. 2006 Mar;83(3):567-74; quiz 726-7. Pubmed: 16522902
  21. Padayatty SJ, Levine M: Vitamin C and myocardial infarction: the heart of the matter. Am J Clin Nutr. 2000 May;71(5):1027-8. Pubmed: 10799361
  22. Englard S, Seifter S: The biochemical functions of ascorbic acid. Annu Rev Nutr. 1986;6:365-406. Pubmed: 3015170
  23. Proctor P: Similar functions of uric acid and ascorbate in man? Nature. 1970 Nov 28;228(5274):868. Pubmed: 5477017
  24. Meister A: Glutathione-ascorbic acid antioxidant system in animals. J Biol Chem. 1994 Apr 1;269(13):9397-400. Pubmed: 8144521
  25. Banhegyi G, Mandl J: The hepatic glycogenoreticular system. Pathol Oncol Res. 2001;7(2):107-10. Pubmed: 11458272
  26. Padayatty SJ, Katz A, Wang Y, Eck P, Kwon O, Lee JH, Chen S, Corpe C, Dutta A, Dutta SK, Levine M: Vitamin C as an antioxidant: evaluation of its role in disease prevention. J Am Coll Nutr. 2003 Feb;22(1):18-35. Pubmed: 12569111
  27. Korcok J, Dixon SJ, Lo TC, Wilson JX: Differential effects of glucose on dehydroascorbic acid transport and intracellular ascorbate accumulation in astrocytes and skeletal myocytes. Brain Res. 2003 Dec 12;993(1-2):201-7. Pubmed: 14642847

Enzymes

Gene Name:
PAM
Uniprot ID:
P19021
Reactions
Peptidylglycine + Ascorbic acid + Oxygen unknown peptidyl(2-hydroxyglycine) + Dehydroascorbic acid + Waterdetails
Gene Name:
DBH
Uniprot ID:
P09172
Reactions
Dopamine + Ascorbic acid + Oxygen unknown xi-Norepinephrine + Dehydroascorbic acid + Waterdetails
Dopamine + Ascorbic acid + Oxygen unknown Norepinephrine + Dehydroascorbic acid + Waterdetails
Gene Name:
P4HA2
Uniprot ID:
O15460
Gene Name:
P4HA1
Uniprot ID:
P13674
Gene Name:
LCT
Uniprot ID:
P09848
Gene Name:
BBOX1
Uniprot ID:
O75936
Gene Name:
GSTO1
Uniprot ID:
P78417
Reactions
Glutathione + Dehydroascorbic acid unknown Oxidized glutathione + Ascorbic aciddetails
Gene Name:
GSTO2
Uniprot ID:
Q9H4Y5
Reactions
Glutathione + Dehydroascorbic acid unknown Oxidized glutathione + Ascorbic aciddetails
Gene Name:
P4HB
Uniprot ID:
P07237
Gene Name:
SLC23A1
Uniprot ID:
Q9UHI7
Gene Name:
SLC23A2
Uniprot ID:
Q9UGH3
Gene Name:
LEPRE1
Uniprot ID:
Q32P28
Gene Name:
LEPREL1
Uniprot ID:
Q8IVL5
Gene Name:
LEPREL2
Uniprot ID:
Q8IVL6
Gene Name:
SLC23A3
Uniprot ID:
Q6PIS1
Gene Name:
P4HA3
Uniprot ID:
Q7Z4N8
Gene Name:
EGLN1
Uniprot ID:
Q9GZT9
Gene Name:
EGLN2
Uniprot ID:
Q96KS0
Gene Name:
EGLN3
Uniprot ID:
Q9H6Z9
Gene Name:
P4HTM
Uniprot ID:
Q9NXG6