U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H8O6
Molecular Weight 176.1244
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASCORBIC ACID

SMILES

C([C@@]([H])([C@]1([H])C(=C(C(=O)O1)O)O)O)O

InChI

InChIKey=CIWBSHSKHKDKBQ-JLAZNSOCSA-N
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

HIDE SMILES / InChI

Molecular Formula C6H8O6
Molecular Weight 176.1244
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Ascorbic acid (vitamin C) is a water-soluble vitamin. It occurs as a white or slightly yellow crystal or powder with a slight acidic taste. Ascorbic acid is an electron donor, and this property accounts for all its known functions. As an electron donor, ascorbic acid is a potent water-soluble antioxidant in humans. Ascorbic acid acts as an antioxidant under physiologic conditions exhibiting a cross over role as a pro-oxidant in pathological conditions. Oxidized ascorbic acid (dehydroascorbic acid (DHA) directly inhibits IkappaBalpha kinase beta (IKKbeta) and IKKalpha enzymatic activity in vitro, whereas ascorbic acid did not have this effect. These findings define a function for vitamin C in signal transduction other than as an antioxidant and mechanistically illuminate how vitamin C down-modulates NF-kappaB signaling. Vitamin C is recommended for the prevention and treatment of scurvy. Its parenteral administration is desirable for patients with an acute deficiency or for those whose absorption of orally ingested ascorbic acid (vitamin c) is uncertain. Symptoms of mild deficiency may include faulty bone and tooth development, gingivitis, bleeding gums, and loosened teeth. Febrile states, chronic illness, and infection (pneumonia, whooping cough, tuberculosis, diphtheria, sinusitis, rheumatic fever, etc.) increase the need for ascorbic acid (vitamin c). Hemovascular disorders, burns, delayed fracture and wound healing are indications for an increase in the daily intake.

CNS Activity

Curator's Comment:: Ascorbic acid readily crosses the blood-brain barrier. Ascorbate (vitamin C) is a vital antioxidant molecule in the brain. Neurodegenerative diseases typically involve high levels of oxidative stress and thus ascorbate has been posited to have potential therapeutic roles against ischemic stroke, Alzheimer's disease, Parkinson's disease, and Huntington's disease.

Originator

Curator's Comment:: In 1928, Albert Szent-Györgyi isolated a substance from adrenal glands that he called 'hexuronic acid'. Four years later, Charles Glen King isolated vitamin C in his laboratory and concluded that it was the same as 'hexuronic acid'. Norman Haworth deduced the chemical structure of vitamin C in 1933.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Vitamin C

Approved Use

Vitamin C is recommended for the prevention and treatment of scurvy. Its parenteral administration is desirable for patients with an acute deficiency or for those whose absorption of orally ingested ascorbic acid (vitamin c) is uncertain. Symptoms of mild deficiency may include faulty bone and tooth development, gingivitis, bleeding gums, and loosened teeth. Febrile states, chronic illness, and infection (pneumonia, whooping cough, tuberculosis, diphtheria, sinusitis, rheumatic fever, etc.) increase the need for ascorbic acid (vitamin c) . Hemovascular disorders, burns, delayed fracture and wound healing are indications for an increase in the daily intake
Preventing
Vitamin C

Approved Use

Vitamin C is recommended for the prevention and treatment of scurvy. Its parenteral administration is desirable for patients with an acute deficiency or for those whose absorption of orally ingested ascorbic acid (vitamin c) is uncertain. Symptoms of mild deficiency may include faulty bone and tooth development, gingivitis, bleeding gums, and loosened teeth. Febrile states, chronic illness, and infection (pneumonia, whooping cough, tuberculosis, diphtheria, sinusitis, rheumatic fever, etc.) increase the need for ascorbic acid (vitamin c) . Hemovascular disorders, burns, delayed fracture and wound healing are indications for an increase in the daily intake
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
33 mM
50 g/m² 1 times / day multiple, intravenous
dose: 50 g/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ASCORBIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
124 mM × h
50 g/m² 1 times / day multiple, intravenous
dose: 50 g/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ASCORBIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.8 h
50 g/m² 1 times / day multiple, intravenous
dose: 50 g/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ASCORBIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
moderate
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Vanadium and ascorbate effects on 3-hydroxy-3-methylglutaryl coenzyme A reductase, cholesterol and tissue minerals in guinea pigs fed low-chromium diets.
1991-1992
Mutagenicity of food-derived carcinogens and the effect of antioxidant vitamins.
2002
Effect of antioxidants (vitamin C, E and turmeric extract) on methimazole induced hypothyroidism in rats.
2002 Jun
Activation of Rac1 and the p38 mitogen-activated protein kinase pathway in response to arsenic trioxide.
2002 Nov 22
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Ascorbic acid enhances differentiation of embryonic stem cells into cardiac myocytes.
2003 Apr 15
L-ascorbic acid stimulates expression of smooth muscle-specific markers in smooth muscle cells both in vitro and in vivo.
2003 Dec
Vitamin C as an antioxidant: evaluation of its role in disease prevention.
2003 Feb
Ascorbic acid induces collagenase-1 in human periodontal ligament cells but not in MC3T3-E1 osteoblast-like cells: potential association between collagenase expression and changes in alkaline phosphatase phenotype.
2003 Jan
Arsenic trioxide induces apoptosis in cells of MOLT-4 and its daunorubicin-resistant cell line via depletion of intracellular glutathione, disruption of mitochondrial membrane potential and activation of caspase-3.
2003 Jul
Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.
2003 Jun
Lead-induced downregulation of soluble guanylate cyclase in isolated rat aortic segments mediated by reactive oxygen species and cyclooxygenase-2.
2003 Jun
Bisphenol A induces reactive oxygen species generation in the liver of male rats.
2003 Jun 30
Modulation of TNF-alpha-induced ICAM-1 expression, NO and H2O2 production by alginate, allicin and ascorbic acid in human endothelial cells.
2003 Mar
Up-regulation and polarized expression of the sodium-ascorbic acid transporter SVCT1 in post-confluent differentiated CaCo-2 cells.
2003 Mar 14
Effects of supplementation with vitamins A, C, and E, selenium, and zinc on immune function in a murine sensitization model.
2003 Nov-Dec
Toluene diisocyanate exposure induces laryngo-tracheal eosinophilia, which can be ameliorated by supplementation with antioxidant vitamins in guinea pigs.
2003 Oct
Incorporation of an oxygen from water into troglitazone quinone by cytochrome P450 and myeloperoxidase.
2004 Apr
Ascorbic acid responsive genes during neuronal differentiation of embryonic stem cells.
2004 Aug 26
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Nelfinavir induces necrosis of 3T3F44-2A adipocytes by oxidative stress.
2004 Dec 15
[Ascorbic acid inhibits the formation and function of osteoclasts from RAW264.7 cells induced by receptor activated nuclear factor kappaB ligand in vitro].
2004 Dec 17
Vitamin C and vitamin E protect the rat testes from cadmium-induced reactive oxygen species.
2004 Feb 29
Alteration of cellular phenotype and responses to oxidative stress by manganese superoxide dismutase and a superoxide dismutase mimic in RWPE-2 human prostate adenocarcinoma cells.
2004 Jun
Norepinephrine induces apoptosis in neonatal rat cardiomyocytes through a reactive oxygen species-TNF alpha-caspase signaling pathway.
2004 Jun 1
Platelet activating factor receptor binding plays a critical role in jet fuel-induced immune suppression.
2004 Mar 15
Effect of antioxidant flavanone, naringenin, from Citrus junoson neuroprotection.
2004 Mar 24
Copper ions and hypochlorite are mainly responsible for oxidative inactivation of paraoxon-hydrolyzing activity in human high density lipoprotein.
2004 Mar 7
Does supplemental vitamin C increase cardiovascular disease risk in women with diabetes?
2004 Nov
Cytoprotection by bcl-2 gene transfer against ischemic liver injuries together with repressed lipid peroxidation and increased ascorbic acid in livers and serum.
2004 Nov 15
Changes of gene expression profiles during neuronal differentiation of central nervous system precursors treated with ascorbic acid.
2004 Oct 1
Effects of various antioxidants on endotoxin-induced lung injury and gene expression: mRNA expressions of MnSOD, interleukin-1beta and iNOS.
2004 Sep 30
Anti-angiogenesis efficacy of the garlic ingredient alliin and antioxidants: role of nitric oxide and p53.
2005
The amyloid precursor protein (APP) of Alzheimer disease and its paralog, APLP2, modulate the Cu/Zn-Nitric Oxide-catalyzed degradation of glypican-1 heparan sulfate in vivo.
2005 Apr 8
Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia.
2005 Aug
[Effect of compound salvia injection on nitrate ester tolerance].
2005 Jan
[The role of reactive oxygen species in N-[4-hydroxyphenyl] retinamide induced apoptosis in bladder cancer cell lineT24].
2005 Jun
Ascorbic acid inhibits osteoclastogenesis of RAW264.7 cells induced by receptor activated nuclear factor kappaB ligand (RANKL) in vitro.
2005 Mar
Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]).
2005 May
Mismatch repair proteins are activators of toxic responses to chromium-DNA damage.
2005 May
Studies on the protective role of vitamin C and E against polychlorinated biphenyl (Aroclor 1254)--induced oxidative damage in Leydig cells.
2005 Nov
Relationship of bone morphogenetic protein expression during osteoblast differentiation to wild type p53.
2005 Nov
Iron-ascorbic acid-induced oxidant stress and its quenching by paraoxonase 1 in HDL and the liver: comparison between humans and rats.
2005 Oct 1
Inhibition of iNOS gene expression by quercetin is mediated by the inhibition of IkappaB kinase, nuclear factor-kappa B and STAT1, and depends on heme oxygenase-1 induction in mouse BV-2 microglia.
2005 Oct 3
Ascorbate depletion mediates up-regulation of hypoxia-associated proteins by cell density and nickel.
2006 Apr 1
Ascorbic acid deficiency stimulates hepatic expression of inflammatory chemokine, cytokine-induced neutrophil chemoattractant-1, in scurvy-prone ODS rats.
2006 Feb
Morphology and DNA degeneration during autoschizic cell death in bladder carcinoma T24 cells induced by ascorbate and menadione treatment.
2006 Jan
Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification.
2006 Jul
Antioxidant effect of ascorbic acid on PCB (Aroclor 1254) induced oxidative stress in hypothalamus of albino rats.
2006 Mar
Attenuation of abnormalities in the lipid metabolism during experimental myocardial infarction induced by isoproterenol in rats: beneficial effect of ferulic acid and ascorbic acid.
2006 May
Patents

Sample Use Guides

Ascorbic acid (vitamin c) is usually administered orally. When oral administration is not feasible or when malabsorption is suspected, the drug may be administered IM, IV, or subcutaneously. When given parenterally, utilization of the vitamin reportedly is best after IM administration and that is the preferred parenteral route.
Route of Administration: Other
cell-derived decellularized extracellular matrix (dECM) with 250 µM of L-ascorbic acid phosphate (AA) treatment for 10 d had better rejuvenation in chondrogenic capacity if the deposited cells were from passage 2 rather than passage 5, despite no significant difference in matrix stiffness. In the dose regimen study, we found that dECMs deposited by varied concentrations of AA yielded expanded cells with higher proliferation capacity despite lower expression levels of stem cell related surface markers. Compared to cells expanded on tissue culture polystyrene, those on dECM exhibited greater chondrogenic potential, particularly for the dECMs with 50 µM and 250 µM of AA treatment. With the supplementation of ethyl-3,4-dihydroxybenzoate (EDHB), an inhibitor targeting procollagen synthesis, the dECM with 50 µM of AA treatment exhibited a dramatic decrease in the rejuvenation effect of expanded cell chondrogenic potential at both mRNA and protein levels despite no significant difference in matrix stiffness.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:15:56 UTC 2021
Edited
by admin
on Fri Jun 25 21:15:56 UTC 2021
Record UNII
PQ6CK8PD0R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASCORBIC ACID
EP   FCC   FHFI   HSDB   II   INCI   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   INCI  
Official Name English
ASCORBICUM ACIDUM
Common Name English
ASCORBATE
Common Name English
E-300
Code English
3-KETO-L-GULOFURANOLACTONE
Common Name English
ASCORBIC ACID [WHO-IP]
Common Name English
ASCORBICAP
Brand Name English
ASCORBIC ACID [JAN]
Common Name English
ASCOLTIN
Brand Name English
L-ASCORBIC ACID
Common Name English
VITAMIN C [VANDF]
Common Name English
ASCORBIC ACID [MI]
Common Name English
ASCORBIC ACID, L-
Common Name English
ASCORBIC ACID [HSDB]
Common Name English
NSC-218455
Code English
ACIDUM ASCORBICUM [WHO-IP LATIN]
Common Name English
INS-300
Code English
ASCORBIC ACID [FCC]
Common Name English
ASCORBIC ACID [ORANGE BOOK]
Common Name English
INS NO.300
Code English
ASCORBIC ACID [INCI]
Common Name English
ASCORBIC ACID [FHFI]
Common Name English
ASCORBIC ACID [USP]
Common Name English
ASCORBIC ACID [II]
Common Name English
ASCORBIC ACID [MART.]
Common Name English
ASCORBIC ACID [USP-RS]
Common Name English
L-ASCORBATE
Common Name English
2,3-DEHYDRO-L-THREO-HEXONO-1,4-LACTONE
Common Name English
VITAMIN C
VANDF  
Systematic Name English
ASCORBIC ACID [VANDF]
Common Name English
FEMA NO. 2109
Code English
NSC-33832
Code English
ASCORBIC ACID [EP MONOGRAPH]
Common Name English
ASCORBIC ACID [WHO-DD]
Common Name English
(5R)-5-((1S)-1,2-DIHYDROXYETHYL)-3,4-DIHYDROXYFURAN-2(5H)-ONE
Systematic Name English
ASCOR
Brand Name English
VITAMIN C (AS ASCORBIC ACID)
Common Name English
ASCORBIC ACID [INN]
Common Name English
Classification Tree Code System Code
LOINC 54351-2
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
LOINC 34246-9
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WHO-ATC S01XA15
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WHO-VATC QG01AD03
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LOINC 1905-9
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LOINC 54350-4
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WHO-ATC G01AD03
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DSLD 10 (Number of products:9521)
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LOINC 12482-6
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LOINC 14622-5
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LOINC 56779-2
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LOINC 1902-6
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WHO-ATC A11GA01
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NCI_THESAURUS C275
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DSLD 3135 (Number of products:3731)
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WHO-ESSENTIAL MEDICINES LIST 27
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NDF-RT N0000193618
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JECFA EVALUATION INS-300
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FDA ORPHAN DRUG 280909
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LOINC 1903-4
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DSLD 3428 (Number of products:24)
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EU-Orphan Drug EU/3/17/1832
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CFR 21 CFR 862.1095
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WHO-ATC A11GB01
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DSLD 2644 (Number of products:145)
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FDA ORPHAN DRUG 678719
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NCI_THESAURUS C68507
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WHO-VATC QA11GB01
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FDA ORPHAN DRUG 645618
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LOINC 16408-7
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LOINC 15033-4
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WHO-VATC QS01XA15
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FDA ORPHAN DRUG 243707
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CFR 21 CFR 101.78
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LOINC 6686-0
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CFR 21 CFR 310.727
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DSLD 2886 (Number of products:101)
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DSLD 3376 (Number of products:376)
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LOINC 59398-8
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LIVERTOX 65
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CODEX ALIMENTARIUS (GSFA) INS-300
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LOINC 34248-5
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LOINC 54385-0
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LOINC 34247-7
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WHO-VATC QA11GA01
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LOINC 1904-2
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Code System Code Type Description
INN
372
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
FDA UNII
PQ6CK8PD0R
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-066-2
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
CAS
50-81-7
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PRIMARY
EVMPD
SUB05579MIG
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PRIMARY
EPA CompTox
50-81-7
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PRIMARY
EVMPD
SUB127188
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
WIKIPEDIA
VITAMIN C
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
USP_CATALOG
1043003
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PRIMARY USP-RS
HSDB
818
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PRIMARY
MESH
D001205
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PRIMARY
DRUG BANK
DB00126
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PRIMARY
ChEMBL
CHEMBL196
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PRIMARY
MERCK INDEX
M2089
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY Merck Index
RXCUI
1151
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY RxNorm
LACTMED
Vitamin C
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
NCI_THESAURUS
C285
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ASCORBIC ACID
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY Description: Colourless crystals or a white or almost white, crystalline powder; odourless or almost odourless. Solubility: Freely soluble in water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Antiscorbutic. Storage: Ascorbic acid should be kept in a tightly closed, non-metallic container, protected from light. Additional information: Ascorbic acid in solution deteriorates rapidly in contact with air; it has an acid taste. Even in the absenceof light, Ascorbic acid is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Ascorbic acid contains not less than 99.0% and not more than 100.5% of C6H8O6.
RXCUI
1370460
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
ALTERNATIVE
PUBCHEM
54670067
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-300
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
DRUG CENTRAL
4072
Created by admin on Fri Jun 25 21:15:56 UTC 2021 , Edited by admin on Fri Jun 25 21:15:56 UTC 2021
PRIMARY
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http://apps.who.int/phint/pdf/b/Jb.6.1.35.pdf