Dehydroascorbic acid
Systematic name	Dehydroascorbic acid
Chemical formula	C6H6O6
Molecular mass	174.13 g/mol
Density	x.xxx g/cm³
Melting point	xx.x °C
Boiling point	xx.x °C
CAS number	[xx-xx-xx]
SMILES	xxxxx
Disclaimer and references

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Chemistry

Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid. It is actively imported into the endoplasmic reticulum of cells and generates the oxidative potential found there. Protein disulfide isomerases are known to reduce DHA back to ascorbic acid, oxidizing their disulfide bonds in the process. Therefore L-dehydroascorbic acid is a vitamin C compound much like L-ascorbic acid. Oxidized forms of esterified ascorbic acids can be numbered at C(5) or C(6) atoms and the (free) chemical radical semi-dehydroascorbate or semidehydro ascorbic acid (SDA) to the group of dehydroascorbic acids. This article deals with the molecular aspects of ascorbic acid. ... The endoplasmic reticulum (endoplasmic meaning within the cytoplasm, reticulum meaning little net in Latin) or ER is an organelle found in all eukaryotic cells that is an interconnected network of tubules, vesicles and cisternae that is responsible for several specialized functions: Protein translation, folding, and transport of proteins (e. ... Protein disulfide isomerase or PDI (EC 5. ... In chemistry, radicals (often referred to as free radicals) are atomic or molecular species with unpaired electrons on an otherwise open shell configuration. ...

Physiological Significance

Top: ascorbic acid
(reduced form of Vitamin C)
Bottom: dehydroascorbic acid
(oxidized form of Vitamin C)

Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... This article deals with the molecular aspects of ascorbic acid. ... A reducing agent (also called a reductant or reducer) is the element or a compound in a redox (reduction-oxidation) reaction (see electrochemistry) that reduces another species. ... This article is about the nutrient. ... European Union Chemical hazard symbol for oxidizing agents Dangerous goods label for oxidising agents An oxidizing agent (also called an oxidant or oxidizer) is referred to as A chemical compound that readily transfers oxygen atoms or A substance that gains electrons in a redox chemical reaction. ... This article is about the nutrient. ...

General significance

Although there exists a transporter for Vitamin C, it is mainly present in specialized cells, whereas the glucose transporters, most notably GLUT1, ensure in most cells of the body the transport of vitamin C (it its oxidized form, DHA)^[1] where it is required as an enzyme cofactor and an intracellular antioxidant, after it is recycled back to ascorbic acid (see Transport to mitochondria). This article is about the nutrient. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... GLUT1 was the first glucose transporter to be characterized (Mueckler et al. ...

Transport to mitochondria

Vitamin C accumulates in mitochondria, where most of the free radicals are produced, by entering through the glucose transporters, GLUT1. It is the oxidized form (dehydroascorbic acid) that is transported by GLUT1, not the reduced form (ascorbic acid). Ascorbic acid protects the mitochondrial genome and membrane[1].^[1] In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... In chemistry free radicals are uncharged atomic or molecular species with unpaired electrons or an otherwise open shell configuration. ... The mitochondrial genome is the genetic material of the mitochondria. ...

Transport to the brain

Vitamin C does not enter the brain. However, the brain is one of the organs which has the greatest concentrations of vitamin C. It is dehydroascorbate that is tranported through the blood-brain barrier via de GLUT1 transporters. Administration of dehydroascorbic acid confers protection from neuronal injury following stroke (ischemic stroke). In animals, the brain, or encephalon (Greek for in the head), is the control center of the central nervous system. ... Freeze-fracture morphology of the blood-brain barrier of a rat The blood-brain barrier (abbreviated BBB, not to be confused with the blood-cerebrospinal fluid barrier, a function of the choroid plexus) is a membrane that controls the passage of substances from the blood into the central nervous system. ... A stroke, also known as cerebrovascular accident (CVA),[1] is an acute neurological injury in which the blood supply to a part of the brain is interrupted. ...

The lack of increased intracerebral hemorrhage (ICH) after the delayed administration of DHA after ischemia confers two significant advantages to this agent, which could lead to its utility at clinically relevant time points. As a well-tolerated agent, it could be given safely in the field before arrival in the hospital and the definitive diagnosis of stroke. Furthermore, its low risk of increasing ICH when administered after stroke obviates the expenditure of valuable time within the therapeutic window by eliminating the prerequisite radiographic imaging studies. Taken together, a pharmacological strategy to increase cerebral levels of ascorbate in stroke has tremendous potential to represent the timely translation of basic research into a relevant therapy for thromboembolic stroke in humans.^[2] ...

References

External links

• Links to external chemical sources