Dehydroascorbic acid
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Dehydroascorbic acid
structure -
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CAS No:
490-83-5
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Formula:
C6H6O6
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Chemical Name:
Dehydroascorbic acid
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Synonyms:
L-threo-2,3-Hexodiulosonic acid,γ-lactone;Dehydroascorbic acid,L-;DHAA;Oxidized ascorbic acid;L-Ascorbic acid,dehydro-;L-Dehydroascorbic acid;Dehydroascorbic acid;L-threo-Dehydroascorbic acid;Dehydro-L-ascorbic acid;L-Ascorbic acid,oxidized;Oxidized vitamin C;2365-07-3;19455-06-2;21090-23-3;882741-16-4
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CAS No:
Description
Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke.
Solid
L-dehydroascorbic acid is dehydroascorbic acid having the L-configuration. It has a role as a coenzyme and a mouse metabolite. It is a vitamin C and a dehydroascorbic acid. It derives from a L-ascorbic acid. It is a conjugate acid of a L-dehydroascorbate.|Dehydroascorbic acid is made from the oxidation of ascorbic acid. This reaction is reversible, but dehydroascorbic acid can instead undergo irreversible hydrolysis to 2,3-diketogulonic acid. Dehydroascorbic acid as well as ascorbic acid are both termed Vitamin C, but the latter is the main form found in humans. In the body, both dehydroascorbic acid and ascorbic acid have similar biological activity as antivirals but dehydroascorbic acid also has neuroprotective effects. Currently dehydroascorbic acid is an experimental drug with no known approved indications.|The reversibly oxidized form of ascorbic acid. It is the lactone of 2,3-DIKETOGULONIC ACID and has antiscorbutic activity in man on oral ingestion.
Characteristics
100.90000
-2.32
Solid
1.7±0.1 g/cm3
204-205 °C (decomp)
389.3±38.0 °C at 760 mmHg
170.0±20.3 °C
1.570
Soluble in water at 60°C
−20°C
D20 +56°
3.9None
3.90
169.7 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|127.8 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|128.2 Ų [M-H]-
Drug Information
There is no approved indication for dehydroascorbic acid, but it has potential therapeutic use in patients with certain viruses and ischemic stroke.
Dehydroascorbic acid has similar biological activity as ascorbic acid. Both compounds have been shown to have antiviral effects against herpes simplex virus type 1, influenza virus type A and poliovirus type 1 with dehydroascorbic acid having the stronger effect. In addition, unlike ascorbic acid, dehydroascorbic acid can cross the blood brain barrier and is then converted to ascorbic acid to enable retention in the brain. This is important because one study has found that after an ischemic stroke, dehydroascorbic acid has neuroprotective effects by reducing infarct volume, neurological deficits, and mortality.
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.)
Even though dehydroascorbic acid and ascorbic acid have similar effects, their mechanism of action seems to be different. The exact mechanism of action is still being investigated, but some have been elucidated. Concerning dehydroascorbic acid's antiviral effect against herpes simplex virus type 1, it is suggested that dehydroascorbic acid acts after replication of viral DNA and prevents the assembly of progeny virus particles.
Acid, Dehydroascorbic
Computed Properties
Molecular Weight:174.11
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:174.01643791
Monoisotopic Mass:174.01643791
Topological Polar Surface Area:101
Heavy Atom Count:12
Complexity:244
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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