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261556

(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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Size/SKUAvailabilityPrice
250 mg
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$104.00
1 g
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$189.00
5 g
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$475.00

About This Item

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

$104.00


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form

powder

Quality Segment

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

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.


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≥80% (enzymatic)

description

powder, BioReagent, suitable for cell culture

Quality Level

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Quality Level

200

Quality Level

200

form

powder

form

-

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

mp

228 °C (dec.) (lit.)

mp

228 °C (dec.) (lit.)

mp

-

mp

220 °C (dec.) (lit.)


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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2



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Questions

1–4 of 4 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. Is the product stable in aqueous buffer solutions and how long at RT? Could this be used for the DHAR activity assay in a 1 ml reaction mixture containing 50 mm potassium phosphate (pH 7.0), 0.1 mm EDTA, 0.5 mm DHA, 2.5 mm GSH?

    1 answer
    1. The stability information for this product in aqueous buffer solutions is not available, and it has not been specifically tested in the conditions of 50 mM potassium phosphate, pH 7.0, 0.1 mM EDTA, 0.5 mM DHA, 2.5 mM GSH.

      Helpful?

  3. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  4. What is the solubility of dehydroascorbic acid

    1 answer
    1. This product has not been tested for solubility. However, external sources state that dehydroascorbic acid is soluble in DMSO at 10 mg/ml, and water at 50 mg/mL. This information has not been validated.

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