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D8132

Sigma-Aldrich

Dehydro-L-(+)-ascorbic acid dimer

≥80% (enzymatic)

Synonym(s):

Bis(dehydro-L-ascorbic acid), Bis-DHA, DHA

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About This Item

Empirical Formula (Hill Notation):
C12H12O12
CAS Number:
72691-25-9
Molecular Weight:
348.22
Beilstein/REAXYS Number:
84277
MDL number:
MFCD00066467
UNSPSC Code:
12352205
PubChem Substance ID:
24894191
NACRES:
NA.79

biological source

synthetic

Quality Level

200

assay

≥80% (enzymatic)

form

powder

color

faint beige to beige
faint brown to light brown
 white to yellow

shipped in

dry ice

storage temp.

−20°C

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

Dehydro-L-(+)-ascorbic acid dimer is a water soluble molecule, which is produced by vitamin C in the lumen of gastrointestinal tract.

Application

Dehydro-L-(+)-ascorbic acid dimer has been used to study its transformation and stability under the influence of pH, concentration and temperature.

Biochem/physiol Actions

Dehydro-L-(+)-ascorbic acid dimer is used to regenerate ascorbic acid(AA). AA oxidation to dehydroascorbic acid (DHA) takes place in extracellular fluid and cells. AA acts as an antioxidant and enzyme cofactor. It is used in a wide variety of applications, including cell culture. It also acts as a reducing agent, that helps reduce oxidative stress. L-Ascorbate can be regenerated from dehydroascorbic acid (DHA) by biological systems.

Other Notes

Dimer in crystalline form; hydrated monomer in aqueous solution

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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The physiological role of dehydroascorbic acid
Wilson JX
Febs Letters, 527(1-3), 5-9 (2002)
Stability and transformation of products formed from dimeric dehydroascorbic acid at low pH
Wechtersbach L, et al.
Food Chemistry, 129(3), 965-973 (2011)
Vitamin C (2017)
Sarah E Bohndiek et al.
Journal of the American Chemical Society, 133(30), 11795-11801 (2011-06-23)
Dynamic nuclear polarization (DNP) of (13)C-labeled metabolic substrates in vitro and their subsequent intravenous administration allow both the location of the hyperpolarized substrate and the dynamics of its subsequent conversion into other metabolic products to be detected in vivo. We
Gisele Monteiro et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(12), 4886-4891 (2007-03-16)
Peroxiredoxins (Prx) are widely distributed peroxidases that can be divided into 1-Cys and 2-Cys Prx groups based on the number of conserved cysteine residues that participate in their catalytical cycle. Prx have been described to be strictly dependent on thiols
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