| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-04-02 20:27:22 -0600 |
| HMDB ID |
HMDB00044 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
| Common Name |
Ascorbic acid |
| Description |
Ascorbic 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (+)-ascorbate
- (+)-ascorbic acid
- (+)-Sodium L-ascorbate
- 3-Keto-L-gulofuranolactone
- 3-Oxo-L-gulofuranolactone
- Adenex
- Allercorb
- Antiscorbic vitamin
- Antiscorbutic vitamin
- Arco-cee
- Ascoltin
- Ascor-B.I.D.
- Ascorb
- Ascorbajen
- Ascorbate
- Ascorbic acid
- Ascorbicab
- Ascorbicap
- Ascorbicin
- Ascorbin
- Ascorbutina
- Ascorin
- Ascorteal
- Ascorvit
- C-Level
- C-Long
- C-Quin
- C-Span
- C-Vimin
- Cantan
- Cantaxin
- Catavin C
- Ce lent
- Ce-mi-lin
- Ce-vi-sol
- Cebicure
- Cebid
- Cebion
- Cebione
- Cecon
- Cee-caps TD
- Cee-vite
- Cegiolan
- Ceglion
- Ceklin
- Celaskon
- Celin
- Cell C
- Cemagyl
- Cemill
- Cenetone
- Cenolate
- Cereon
- Cergona
- Cescorbat
- Cetamid
- Cetane
- Cetane-caps TC
- Cetane-caps TD
- Cetebe
- Cetemican
- Cevalin
- Cevatine
- Cevex
- Cevi-bid
- Cevimin
- Cevital
- Cevitamate
- Cevitamic acid
- Cevitamin
- Cevitan
- Cevitex
- Cewin
- Chewcee
- Ciamin
- Cipca
- Citriscorb
- Citrovit
- Colascor
- Concemin
- Davitamon C
- Dora-C-500
- Duoscorb
- Ferrous ascorbate
- gamma-Lactone L-threo-Hex-2-enonate
- gamma-Lactone L-threo-Hex-2-enonic acid
- HiCee
- Hybrin
- Ido-C
- Juvamine
- Kangbingfeng
- Kyselina askorbova
- L(+)-Ascorbate
- L(+)-Ascorbic acid
- L-(+)-Ascorbate
- L-(+)-Ascorbic acid
- L-3-Ketothreohexuronic acid lactone
- L-Ascorbate
- L-Ascorbic acid
- L-Lyxoascorbate
- L-Lyxoascorbic acid
- L-Threo-ascorbic acid
- L-Xyloascorbate
- L-Xyloascorbic acid
- Laroscorbine
- Lemascorb
- Liqui-cee
- Meri-c
- Natrascorb
- Natrascorb injectable
- Planavit C
- Proscorbin
- Redoxon
- Ribena
- Ronotec 100
- Rontex 100
- Roscorbic
- Rovimix C
- Scorbacid
- Scorbu C
- Scorbu-C
- Secorbate
- Sodascorbate
- Suncoat VC 40
- Testascorbic
- VASC
- Vicelat
- Vicin
- Vicomin C
- Viforcit
- Viscorin
- Viscorin 100M
- Vitace
- Vitacee
- Vitacimin
- Vitacin
- Vitamin C
- Vitamisin
- Vitascorbol
- Xitix
|
| Chemical Formula |
C6H8O6 |
| Average Molecular Weight |
176.1241 |
| Monoisotopic Molecular Weight |
176.032087988 |
| IUPAC Name |
(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one |
| Traditional IUPAC Name |
vitamin C |
| CAS Registry Number |
50-81-7 |
| 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 Key |
CIWBSHSKHKDKBQ-JLAZNSOCSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Aliphatic Heteromonocyclic Compounds |
| Class |
Dihydrofurans |
| Sub Class |
Furanones |
| Other Descriptors |
- Aliphatic Heteromonocyclic Compounds
|
| Substituents |
- 1,2 Diol
- Ketone
- Primary Alcohol
- Secondary Alcohol
|
| Direct Parent |
Butenolides |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| 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 |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
191 °C |
PhysProp |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
400 mg/mL at 40 °C |
MERCK INDEX (1996) |
| LogP |
-1.85 |
AVDEEF,A (1997) |
|
| Predicted Properties |
|
| Spectra |
|
Not Available
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
- Amniotic Fluid
- Blood
- Cellular Cytoplasm
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Bladder
- Fibroblasts
- Intestine
- Lymphocyte
- Most Tissues
- Neuron
- Placenta
- Erythrocyte
- Liver
- Epidermis
- Brain
- Myelin
- Prostate
- Adipose Tissue
- Adrenal Cortex
- Adrenal Medulla
- Lung
- Platelet
- Gonads
- Spleen
- Eye Lens
- Heart
|
| Pathways |
|
| Normal Concentrations |
|
| Amniotic Fluid |
Detected and Quantified |
|
20.4 +/- 12.21 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
88.6 (21.0 - 171.0) uM |
Children (1-13 year old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
60.8 +/- 15.9 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
51.0 (11.0 - 125.0) uM |
Newborn (0-30 days old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
36.0 +/- 18.0 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
63.0 (11.0-114.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
22.2 (14.0-40.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
27.0 (11.1-49.7) uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
50.9 (35.4-80.1) uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Cellular Cytoplasm |
Detected and Quantified |
|
68.0 +/- 43.0 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
68.0 (17.0-119.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
163.8 +/- 21 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
133 +/- 58.8 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
164.0 (143.0-185.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
144.0 (36.2-251.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Urine compound detected by GC-MS
|
| Urine |
Detected and Quantified |
|
32.5 (4.6-78) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
1.70-22.72 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
17.0 +/- 2.5 umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
63.6 +/-142.9 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.512 +/-0.058 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
39.0 +/- 92.7 uM |
Adult (>18 years old) |
Both |
Hyperoxalemia |
Patients with long-term hyperoxalemia (before...
|
| Blood |
Detected and Quantified |
|
6.5 +/- 18.6 uM |
Adult (>18 years old) |
Both |
Hyperoxalemia |
Patients with long-term hyperoxalemia (after...
|
| Blood |
Detected and Quantified |
|
82.57 +/- 36.71 uM |
Adult (>18 years old) |
Both |
Canavan disease |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
53.8 (45.8-61.8) uM |
Children (1-13 year old) |
Both |
Brain injury |
Pediatric traumatic brain injury
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
11.9 (0.0-24) uM |
Adult (>18 years old) |
Both |
Meningitis |
Bacterial
|
|
| 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
|
| 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
|
| 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
|
| 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
|
|
| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
DB00126  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB001224 |
| KNApSAcK ID |
C00001179  |
| Chemspider ID |
10189562  |
| KEGG Compound ID |
C00072  |
| BioCyc ID |
ASCORBATE  |
| BiGG ID |
33747  |
| Wikipedia Link |
Ascorbic acid  |
| NuGOwiki Link |
HMDB00044  |
| Metagene Link |
HMDB00044  |
| METLIN ID |
3753  |
| PubChem Compound |
54670067  |
| PDB ID |
1E71  |
| ChEBI ID |
17208  |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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
- 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
- Luck MR, Jeyaseelan I, Scholes RA: Ascorbic acid and fertility. Biol Reprod. 1995 Feb;52(2):262-6.
Pubmed: 7711198
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Grunewald RA: Ascorbic acid in the brain. Brain Res Brain Res Rev. 1993 Jan-Apr;18(1):123-33.
Pubmed: 8467348
- 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
- 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
- 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
- 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
|
| Enzymes |
|
|
| Name: |
Dopamine beta-hydroxylase
|
| Reactions: |
- 3,4-dihydroxyphenethylamine + ascorbate + O2 = noradrenaline + dehydroascorbate + H2O [RN:R02535]
|
| Gene Name: |
DBH |
| Uniprot ID: |
P09172  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Gamma-butyrobetaine dioxygenase
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| Reactions: |
- 4-trimethylammoniobutanoate + 2-oxoglutarate + O2 = 3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2 [RN:R02397]
|
| Gene Name: |
BBOX1 |
| Uniprot ID: |
O75936  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Prolyl 3-hydroxylase 1
|
| Reactions: |
- procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
|
| Gene Name: |
LEPRE1 |
| Uniprot ID: |
Q32P28  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Prolyl 3-hydroxylase 2
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| Reactions: |
- procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
|
| Gene Name: |
LEPREL1 |
| Uniprot ID: |
Q8IVL5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Prolyl 3-hydroxylase 3
|
| Reactions: |
- procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
|
| Gene Name: |
LEPREL2 |
| Uniprot ID: |
Q8IVL6  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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