Common NameL-ascorbate
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 ). Moreover, ascorbic acid is found to be associated with hyperoxalemia, which is an inborn error of metabolism. Ascorbic acid is also a microbial metabolite produced by Ketogulonicigenium (PMID: 15785002 ).
Structure
Molecular FormulaC6H8O6
Average Mass176.12410
Monoisotopic Mass176.03209
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
Traditional NameVitamin c
CAS Registry Number50-81-7
SMILESO=C1O[C@H]([C@@H](O)CO)C([O-])=C1O
InChI IdentifierInChI=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
CHEBI IDCHEBI:38290
HMDB IDHMDB0000044
Pathways
NameSMPDB/PathBank
Tyrosine metabolism
Tyrosine metabolism
Oxidation of Branched Chain Fatty Acids
Alkaptonuria
Aromatic L-Aminoacid Decarboxylase Deficiency
Hawkinsinuria
Tyrosinemia Type I
Disulfiram Action Pathway
Phytanic Acid Peroxisomal Oxidation
Refsum Disease
Carnitine Synthesis
Tyrosinemia, transient, of the newborn
Tyrosine hydroxylase deficiency
Dopamine beta-hydroxylase deficiency
Monoamine oxidase-a deficiency (MAO-A)
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
StateSolid
Water Solubility2.45e+02 g/l
logP-1.58
logS0.14
pKa (Strongest Acidic)4.36
pKa (Strongest Basic)-2.98
Hydrogen Acceptor Count5
Hydrogen Donor Count4
Polar Surface Area107.22 Ų
Rotatable Bond Count2
Physiological Charge-1
Formal Charge0
Refractivity37.03 m³·mol⁻¹
Polarizability14.94

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