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Dehydroascorbic acid (DHA) is an oxidized form of
ascorbic acid Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical 'serum' ingredient to treat melasma (dark pigment spots) ...
(vitamin C). It is actively imported into the
endoplasmic reticulum The endoplasmic reticulum (ER) is, in essence, the transportation system of the eukaryotic cell, and has many other important functions such as protein folding. It is a type of organelle made up of two subunits – rough endoplasmic reticulum ...
of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by
glutathione Glutathione (GSH, ) is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, pe ...
and other
thiols In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...
. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids.


Structure and physiology

Top:
ascorbic acid Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical 'serum' ingredient to treat melasma (dark pigment spots) ...

(
reduced form In statistics, and particularly in econometrics, the reduced form of a system of equations is the result of solving the system for the endogenous variables. This gives the latter as functions of the exogenous variables, if any. In econometrics, the ...
of
vitamin C Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical 'serum' ingredient to treat melasma (dark pigment spots) ...
)
Bottom: dehydroascorbic acid
( nominal oxidized form of vitamin C)
Although a sodium-dependent transporter for
vitamin C Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical 'serum' ingredient to treat melasma (dark pigment spots) ...
exists, it is present mainly in specialized cells, whereas the glucose transporters, the most notable being
GLUT1 Glucose transporter 1 (or GLUT1), also known as solute carrier family 2, facilitated glucose transporter member 1 (SLC2A1), is a uniporter protein that in humans is encoded by the ''SLC2A1'' gene. GLUT1 facilitates the transport of glucose across ...
, transport Vitamin C (in its oxidized form, DHA) in most cells, where recycling back to ascorbate generates the necessary enzyme cofactor and intracellular antioxidant, (see Transport to mitochondria). The structure shown here for DHA is the commonly shown textbook structure. This 1,2,3-tricarbonyl is too electrophilic to survive more than a few milliseconds in aqueous solution, however. The actual structure shown by spectroscopic studies is the result of rapid
hemiketal A hemiacetal or a hemiketal has the general formula R1R2C(OH)OR, where R1 or R2 is hydrogen or an organic substituent. They generally result from the addition of an alcohol to an aldehyde or a ketone, although the latter are sometimes called hemike ...
formation between the 6-OH and the 3-carbonyl groups. Hydration of the 2-carbonyl is also observed. The lifetime of the stabilized species is commonly said to be about 6 minutes under biological conditions. Destruction results from irreversible hydrolysis of the ester bond, with additional degradation reactions following. Crystallization of solutions of DHA gives a pentacyclic dimer structure of indefinite stability. Recycling of ascorbate via active transport of DHA into cells, followed by reduction and reuse, mitigates the inability of humans to synthesize it from glucose.


Transport to mitochondria

Vitamin C accumulates in
mitochondria A mitochondrion (; ) is an organelle found in the cells of most Eukaryotes, such as animals, plants and fungi. Mitochondria have a double membrane structure and use aerobic respiration to generate adenosine triphosphate (ATP), which is used ...
, where most of the
free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Ailments of unknown cause Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabo ...
s are produced, by entering as DHA through the glucose transporter GLUT10. Ascorbic acid protects the mitochondrial genome and
membrane A membrane is a selective barrier; it allows some things to pass through but stops others. Such things may be molecules, ions, or other small particles. Membranes can be generally classified into synthetic membranes and biological membranes. ...
.


Transport to the brain

Vitamin C does not pass from the bloodstream into the
brain A brain is an organ (biology), organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It is located in the head, usually close to the sensory organs for senses such as Visual perception, vision. I ...
, although the brain is one of the organs that have the greatest concentration of vitamin C. Instead, DHA is transported through the
blood–brain barrier The blood–brain barrier (BBB) is a highly selective semipermeable border of endothelial cells that prevents solutes in the circulating blood from ''non-selectively'' crossing into the extracellular fluid of the central nervous system where ne ...
via GLUT1 transporters, and then converted back to ascorbate.


Use

Dehydroascorbic acid has been used as a vitamin C dietary supplement. As a cosmetic ingredient, dehydroascorbic acid is used to enhance the appearance of the skin. It may be used in a process for permanent waving of hairUS Patent 6,506,373
(issued January 14, 2003)
and in a process for
sunless tanning Sunless tanning, also known as UV filled tanning, self tanning, spray tanning (when applied topically), or fake tanning, refers to the effect of a suntan without exposure to the Sun. Sunless tanning involves the use of oral agents (carotenids) ...
of skin.U.S. Patent Application No. 10/685,073
Publication No. 20100221203 (published September 2, 2010)
In a
cell culture Cell culture or tissue culture is the process by which cells are grown under controlled conditions, generally outside of their natural environment. The term "tissue culture" was coined by American pathologist Montrose Thomas Burrows. This tec ...
growth medium A growth medium or culture medium is a solid, liquid, or semi-solid designed to support the growth of a population of microorganisms or cells via the process of cell proliferation or small plants like the moss ''Physcomitrella patens''. Differen ...
, dehydroascorbic acid has been used to assure the uptake of vitamin C into cell types that do not contain ascorbic acid transporters. As a pharmaceutical agent, some research has suggested that administration of dehydroascorbic acid may confer protection from neuronal injury following an
ischemic stroke A stroke is a medical condition in which poor blood flow to the brain causes cell death. There are two main types of stroke: ischemic, due to lack of blood flow, and hemorrhagic, due to bleeding. Both cause parts of the brain to stop funct ...
. The literature contains many reports on the antiviral effects of vitamin C, and one study suggests dehydroascorbic acid has stronger antiviral effects and a different mechanism of action than ascorbic acid. Solutions in water containing ascorbic acid and copper ions and/or peroxide, resulting in rapid oxidation of ascorbic acid to dehydroascorbic acid, have been shown to possess powerful but short-lived antimicrobial, antifungal, and antiviral properties, and have been used to treat gingivitis, periodontal disease, and dental plaque.Ericsson, Sten et al. "Anti Infectant Topical Preparations." U.S. Patent 3,065,139, filed November 9, 1954 and issued November 20, 1962
/ref>Fine, Daniel. "Gel composition for reduction of gingival inflammation and retardation of dental plaque." U.S Patent 5,298,237, filed Jan.24, 1992 and issued March 29, 1994
/ref> A pharmaceutical product named Ascoxal is an example of such a solution used as a mouth rinse as an oral mucolytic and prophylactic agent against gingivitis. Ascoxal solution has also been tested with positive results as a treatment for recurrent mucocutaneous herpes, and as a mucolytic agent in acute and chronic pulmonary disease such as emphysema, bronchitis, and asthma by aerosol inhalation.


References


Further reading

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External links

* {{Vitamin Organic acids Vitamin C Diketones de:Ascorbinsäure#Dehydroascorbinsäure