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L-Dehydroascorbic acid

Names

[ CAS No. ]:
490-83-5

[ Name ]:
L-Dehydroascorbic acid

[Synonym ]:
L-threo-2,3-Hexodiulosonic Acid g-Lactone
(5R)-5-[(1S)-1,2-Dihydroxyethyl]-2,3,4(5H)-furantrion
MFCD00066467
(5R)-5-[(1S)-1,2-Dihydroxyethyl]-2,3,4(5H)-furantrione
L-Dehydro Ascorbic Acid
DEHYDROASCORBIC ACID
EINECS 207-720-6
L-Dehydroascorbic acid
L-threo-2,3-Hexodiulosonic acid γ-lactone
(5R)-5-[(1S)-1,2-Dihydroxyéthyl]-2,3,4(5H)-furanetrione
(5R)-5-[(1S)-1,2-Dihydroxyethyl]furan-2,3,4(5H)-trione (non-preferred name)

Biological Activity

[Description]:

Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke.

[Related Catalog]:

Natural Products >> Acids and Aldehydes
Research Areas >> Neurological Disease

[Target]

Human Endogenous Metabolite


[In Vitro]

Neuronal injury in ischemic stroke is partly mediated by cytotoxic reactive oxygen species. Although the antioxidant ascorbic acid (AA) or vitamin C does not penetrate the blood-brain barrier (BBB), its oxidized form, dehydroascorbic acid (DHA), enters the brain by means of facilitative transport[1].

[References]

[1]. Huang J, et al. Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potentcerebroprotection in experimental stroke. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11720-4.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
389.3±38.0 °C at 760 mmHg

[ Melting Point ]:
228 °C (dec.)(lit.)

[ Molecular Formula ]:
C6H6O6

[ Molecular Weight ]:
174.108

[ Flash Point ]:
170.0±20.3 °C

[ Exact Mass ]:
174.016434

[ PSA ]:
100.90000

[ LogP ]:
-2.32

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.570

[ Storage condition ]:
−20°C

MSDS

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Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ WGK Germany ]:
3

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds