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D8132

Sigma-Aldrich

Dehydro-L-(+)-ascorbic acid dimer

≥80% (enzymatic)

Synonym(s):
Bis-DHA, DHA, Bis(dehydro-L-ascorbic acid)
Empirical Formula (Hill Notation):
C12H12O12
CAS Number:
Molecular Weight:
348.22
Beilstein:
84277
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic

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
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D8132.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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...
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...
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...

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