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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/01 17:58:13」(JST)

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Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid (vitamin C). It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols.^[1] The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids.

Structure and Physiology[edit]

Top: ascorbic acid

(reduced form of vitamin C)
Bottom: dehydroascorbic acid

(nominal oxidized form of vitamin C)

Although there exists a sodium-dependent transporter for vitamin C, it is mainly present in specialized cells, whereas the glucose transporters, most notably GLUT1, transport Vitamin C (in its oxidized form, DHA)^[2] 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 hemiacetal formation between the 6-OH and the 3-carbonyl groups. Hydration of the 2-carbonyl is also observed.^[3] The lifetime of the stabilized species is commonly said to be about 6 minutes under biological conditions.^[4] Destruction results from irreversible hydrolysis of the ester bond, with additional degradation reactions following.^[5] 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.^[6]

Hydration equilibria of DHA - the hemiacetal structure (center) is the predominant one.

Transport to mitochondria[edit]

Vitamin C accumulates in mitochondria, where most of the free radicals are produced, by entering as DHA through the glucose transporters, GLUT1. Ascorbic acid protects the mitochondrial genome and membrane.^[2]

Transport to the brain[edit]

Vitamin C does not pass from the blood stream into the brain, although the brain is one of the organs which has the greatest concentration of vitamin C. Instead, DHA is transported through the blood–brain barrier via GLUT1 transporters, and then converted back to ascorbate.^[7]

Use[edit]

Dehydroascorbic acid has been used as a vitamin C dietary supplement.^[8]

As a cosmetic ingredient, dehydroascorbic acid is used to enhance the appearance of the skin.^[9] It may be used in a process for permanent waving of hair^[10] and in a process for sunless tanning of skin.^[11]

In a cell culture growth medium, dehydroascorbic acid has been used to assure the uptake of vitamin C into cell types that do not contain ascorbic acid transporters.^[12]

As a pharmaceutical agent, some research has suggested that administration of dehydroascorbic acid may confer protection from neuronal injury following an ischemic stroke.^[7] The literature contains many reports on the antiviral effects of vitamin C,^[13] and one study suggests dehydroascorbic acid has stronger antiviral effects and a different mechanism of action than ascorbic acid.^[14] 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.^[15]^[16] 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.^[16]^[17] Ascoxal solution has also been tested with positive results as a treatment for recurrent mucocutaneous herpes,^[17] and as a mucolytic agent in acute and chronic pulmonary disease such as emphysema, bronchitis and asthma by aerosol inhalation.^[18]

References[edit]

^ Welch, R.W.; Wang, Y.; Crossman, A., Jr.; Park, J.B.; Kirk, K.L.; Levine, M.; "Accumulation of Vitamin C (Ascorbate) and Its Oxidized Metabolite Dehydroascorbic Acid Occurs by Separate Mechanisms," J. Biol. Chem. 1995 270 12584-92.
^ ^a ^b KC S, Carcamo JM, Golde DW (2005). "Vitamin C enters mitochondria via facilitative glucose transporter 1 (Glut1) and confers mitochondrial protection against oxidative injury". FASEB J 19 (12): 1657–67. doi:10.1096/fj.05-4107com. PMID 16195374.
^ Kerber, R.C.; "'As Simple as Possible, but not Simpler' -- The Case of Dehydroascorbic Acid," J. Chem. Ed. 85 (2008) 1237-1242.
^ May, J.M.; "Ascorbate Function and Metabolism in the Human Erythrocyte," Frontiers in Bioscience, 3 (1981) d1-10.
^ Kimoto, E.; Tanaka, H.; Ohmoto, T.; Choami, M.; "Analysis of the Transformation Products of Dehydro-L-Ascorbic Acid by Ion-Pairing High-Performance Liquid Chromatography," Anal. Biochem. 214 (1993) 38-44.
^ Montel-Hagen, A.; Kinet, S.; Manel, N.; Mongellaz, C.; Prohaska,R.; Battini, J.L.; Delaunay,J.; Sitbon, M.; Taylor, N.; "Erythrocyte GLUT1 triggers Dehydroascorbic Acid Uptake in Mammals unable to Synthesize Vitamin C," Cell 132 (2008) 1039-48.
^ ^a ^b Huang J, Agus DB, Winfree CJ, Kiss S, Mack WJ, McTaggart RA, Choudhri TF, Kim LJ, Mocco J, Pinsky DJ, Fox WD, Israel RJ, Boyd TA, Golde DW, Connolly ES Jr. (2001). "Dehydroascorbic acid, a blood–brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke". Proceedings of the National Academy of Sciences 98 (20): 11720–11724. doi:10.1073/pnas.171325998. PMC 58796. PMID 11573006.
^ Higdon, Jane (May, 2001). "The Bioavailability of Different Forms of Vitamin C". The Linus Pauling Institute. Retrieved 2010-11-10. Check date values in: |date= (help)
^ Kitt, D.Q. (2012), Topical Dehydroascorbic Acid (Oxidized Vitamin C) Permeates Stratum Corneum More Rapidly Than Ascorbic Acid, retrieved 2012-07-31
^ US Patent 6,506,373 (issued Jan. 14, 2003)
^ U.S. Patent Application No. 10/685,073 Publication No. 20100221203 (published Sept. 2, 2010)
^ Heaney ML, Gardner JR, Karasavvas N, Golde DW, Scheinberg DA, Smith EA, O'Conner OA (2008). "Vitamin C antagonizes the cytotoxic effects of antineoplastic drugs". Cancer Research 68 (19): 8031–8038. doi:10.1158/0008-5472.CAN-08-1490. PMID 18829561.
^ Jariwalla, R.J. & Harakeh S. (1997). Mechanisms underlying the action of vitamin C in viral and immunodeficiency disease. In L. Packer & J. Fuchs (Eds.), Vitamin C in health and disease (pp. 309-322). New York:Marcell Dekker, Inc.
^ Furuya A, Uozaki M, Yamasaki H, Arakawa T, Arita M, Koyama AH (2008). "Antiviral effects of ascorbic and dehydroascorbic acids in vitro". International Journal of Molecular Medicine 22 (4): 541–545. doi:10.3892/ijmm_00000053. PMID 18813862.
^ Ericsson, Sten et al. “Anti Infectant Topical Preparations.” U.S. Patent 3,065,139, filed Nov. 9, 1954 and issued Nov. 20, 1962
^ ^a ^b 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
^ ^a ^b Hovi T, et al. Topical treatment of recurrent mucocutaneous herpes with ascorbic acid-containing solution. Antiviral Research 27 (1995) 263-270
^ Fisher AJ and Ten Pas RH. Clinical evaluation of Ascoxal: a new mucolytic agent. Anesthesia and Analgesia 45(5) 531-534 (1966)

UpToDate Contents

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English Journal

Metabolic profiling of a range of peach fruit varieties reveals high metabolic diversity and commonalities and differences during ripening.

Monti LL1, Bustamante CA1, Osorio S2, Gabilondo J3, Borsani J1, Lauxmann MA1, Maulión E1, Valentini G3, Budde CO3, Fernie AR2, Lara MV1, Drincovich MF4.
Food chemistry.Food Chem.2016 Jan 1;190:879-88. doi: 10.1016/j.foodchem.2015.06.043. Epub 2015 Jun 16.
Peach (Prunus persica) fruits from different varieties display differential organoleptic and nutritional properties, characteristics related to their chemical composition. Here, chemical biodiversity of peach fruits from fifteen varieties, at harvest and after post-harvest ripening, was explored by
PMID 26213052

Reductive dechlorination of carbon tetrachloride using buffered alkaline ascorbic acid.

Lin YT1, Liang C2.
Chemosphere.Chemosphere.2015 Oct;136:27-31. doi: 10.1016/j.chemosphere.2015.04.007. Epub 2015 Apr 26.
Alkaline ascorbic acid (AA) was recently discovered as a novel in-situ chemical reduction (ISCR) reagent for remediating chlorinated solvents in the subsurface. For this ISCR process, the maintenance of an alkaline pH is essential. This study investigated the possibility of the reduction of carbon t
PMID 25912910

Deficit irrigation strategies combined with controlled atmosphere preserve quality in early peaches.

Falagán N1, Artés F1, Gómez PA2, Artés-Hernández F1, Conejero W3, Aguayo E4.
Food science and technology international = Ciencia y tecnología de los alimentos internacional.Food Sci Technol Int.2015 Oct;21(7):547-56. doi: 10.1177/1082013214553997. Epub 2014 Oct 3.
Due to the water scarcity in the Mediterranean countries, irrigation must be optimized while keeping fruit quality. The effect of deficit irrigation strategies on changes in quality parameters of the early "Flordastar" peaches was studied. The deficit irrigation was programmed according to signal in
PMID 25280939

Japanese Journal

Suppressive Effects of Natural Compounds on Methionine Auxotrophy of a Cu,Zn-Superoxide Dismutase-Deficient Mutant of Saccharomyces cerevisiae

Ikeda Shogo,Senoo Takanori,Kawano Shinji,Tamura Sayaka,Shinozuka Yuki,Sugishita Shihori
Food Science and Technology Research 21(1), 137-143, 2015
… Ascorbic acid (1 to 50 mM) restored sod1Δ growth, indicating that the action of this antioxidant could improve Met biosynthesis. … However, ascorbic acid derivatives, ascorbic acid 2-glucoside and dehydroascorbic acid, did not show any activity. …
NAID 130005061945

L-Ascorbic Acid- and L-Ascorbic Acid 2-Glucoside Accelerate in Vivo Liver Regeneration and Lower Serum Alanine Aminotransaminase Activity in 70% Partially Hepatectomized Rats

木村光利,茂木肇,内田昌希,夏目秀視,荻原政彦
Biological and Pharmaceutical Bulletin 37(4), 597-603, 2014-04
… The effects of L-ascorbic acid and its stable analogue L-ascorbic acid 2-glucoside on the restoration of liver mass and recovery of liver function after 70% partial hepatectomy (PH), were compared with other natural vitamin C analogues in rats in vivo. …
NAID 120005520954

ヒトのビタミンCとグルタチオン-S-トランスフェラーゼ遺伝子多型:―経口負荷後の経時的ビタミンC血中濃度および尿中排泄―

辻村卓
日本食生活学会誌 25(2), 131-135, 2014
… We provided a low-vitamin C (C) diet to 17 healthy females ( age, 21.0±1.1 y ) for three days before the experimental day and the orally administered 1 mmol ascorbic acid crystal ( 1 mmol 176 mg ) or dehydroascorbic acid ( 1 mmol 174 mg ). …
NAID 130004701695

Related Pictures

★リンクテーブル★

リンク元	「酸化型ビタミンC」「デヒドロアスコルビン酸」「dehydroascorbate」

「酸化型ビタミンC」

Dehydroascorbic acid
	IUPAC name (5R)-5-[(1S)-1,2-dihydroxyethyl]furan-2,3,4(5H)-trione
Identifiers
CAS number	490-83-5
PubChem	440667
ChemSpider	389547
ChEBI	CHEBI:27956
Jmol-3D images	Image 1
	SMILES O=C1C(=O)C(=O)O[C@@H]1[C@@H](O)CO ;
	InChI InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1 ; Key: SBJKKFFYIZUCET-JLAZNSOCSA-N InChI=1/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1; Key: SBJKKFFYIZUCET-JLAZNSOCBE ;
Properties
Molecular formula	C6H6O6
Molar mass	174.11 g mol−1
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references