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261556

Sigma-Aldrich

(L)-Dehydroascorbic acid

Synonym(s):

DHAA, Dehydro-L-ascorbate, Dehydro-L-ascorbic acid, L-threo-Dehydroascorbic acid, oxidized ascorbic acid, oxidized vitamin C

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About This Item

Empirical Formula (Hill Notation):
C6H6O6
CAS Number:
490-83-5
Molecular Weight:
174.11
EC Number:
207-720-6
MDL number:
MFCD00066467
UNSPSC Code:
12352205
PubChem Substance ID:
24855820
NACRES:
NA.22

form

powder

mp

228 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

OC[C@H](O)[C@H]1OC(=O)C(=O)C1=O

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

InChI key

SBJKKFFYIZUCET-JLAZNSOCSA-N

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General description

(L)-Dehydroascorbic acid (DHA) is a potent glycation agent that is produced by the oxidation of ascorbic acid (vitamin C). In vitro studies revealed that DHA is significantly more reactive than glucose and fructose in the glycation of lens proteins. Thus, DHA could be a critical precursor for the in vivo formation of advanced glycation end products (AGEs).
DHA is a dimer when it is solid, but when it is dissolved in a solution, it becomes a monomer.

Application

(L)-Dehydroascorbic acid can be used as a starting material to synthesize:
  • Pyrano[3,4-b]indole derivatives by reacting with 2-hydroxymethylindole.
  • (−)-ascorbyl phloroglucinol via stereoselective C-C bond formation reaction with phloroglucinol.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jens Lykkesfeldt
Nutrition research (New York, N.Y.), 32(1), 66-69 (2012-01-21)
Ascorbate and dehydroascorbic acid are frequently used as biomarkers of oxidative stress, but their lack of stability ex vivo and rapid postsampling interconversion continue to result in erroneous reference values. One problem is the large variety of vacutainer devices used
A biomimetic synthesis of (-)-ascorbyl phloroglucinol and studies toward the construction of ascorbyl-modified catechin natural products and analogues
Belapure SA, et al.
Tetrahedron, 67(48), 9265-9272 (2011)
Oliver Reihl et al.
Carbohydrate research, 339(3), 483-491 (2004-03-12)
Covalently cross-linked proteins are among the major modifications caused by the advanced Maillard reaction. So far, the chemical nature of these aggregates is largely unknown. L-dehydroascorbic acid (DHA, 5), the oxidation product of L-ascorbic acid (vitamin C), is known as
Scheling Wibowo et al.
Food chemistry, 187, 140-151 (2015-05-16)
In view of understanding colour instability of pasteurised orange juice during storage, to the best of our knowledge, this study reports for the first time in a systematic and quantitative way on a range of changes in specific quality parameters
John M Benjamin et al.
Antimicrobial agents and chemotherapy, 59(7), 4260-4271 (2015-05-13)
The tolerability, safety, and disposition of dihydroartemisinin (DHA) and piperaquine (PQ) were assessed in 32 pregnant (second/third trimester) and 33 nonpregnant Papua New Guinean women randomized to adult treatment courses of DHA-PQ (three daily doses) or sulfadoxine-pyrimethamine (SP)-PQ (three daily
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Articles

Determination of Ascorbic Acid and Dehydroascorbic Acid in Different Food Products and Supplements - A Simple HPTLC Based Approach

Simultaneous analysis of ascorbic acid and dehydroascorbic acid in various food samples by High Performance Thin Layer Chromatography (HPTLC).

Determination of Ascorbic Acid and Dehydroascorbic Acid in Different Food Products and Supplements - A Simple HPTLC Based Approach

Simultaneous analysis of ascorbic acid and dehydroascorbic acid in various food samples by High Performance Thin Layer Chromatography (HPTLC).

Determination of Ascorbic Acid and Dehydroascorbic Acid in Different Food Products and Supplements - A Simple HPTLC Based Approach

Simultaneous analysis of ascorbic acid and dehydroascorbic acid in various food samples by High Performance Thin Layer Chromatography (HPTLC).

Determination of Ascorbic Acid and Dehydroascorbic Acid in Different Food Products and Supplements - A Simple HPTLC Based Approach

Simultaneous analysis of ascorbic acid and dehydroascorbic acid in various food samples by High Performance Thin Layer Chromatography (HPTLC).

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