(5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

• ChemBase ID: 126883
• Molecular Formular: C6H6O6
• Molecular Mass: 174.10824
• Monoisotopic Mass: 174.01643791
• SMILES: O=C1C(=O)C(=O)O[C@@H]1[C@@H](O)CO
• Canonical SMILES: OC[C@@H]([C@H]1OC(=O)C(=O)C1=O)O
• 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
• InChIKey: SBJKKFFYIZUCET-JLAZNSOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
• IUPAC Traditional name: DHAA
• Synonyms: Dehydroascorbic acid; Dehydroascorbic acid; Bis(dehydro-L-ascorbic acid); Bis-DHA; DHA; Dehydro-L-(+)-ascorbic acid dimer; 脱氢抗坏血酸

Database IDs

• CAS Number: 72691-25-9; 490-83-5
• EC Number: 207-720-6
• MDL Number: MFCD00066467
• Beilstein Number: 84277
• PubChem SID: 24894191; 24855820; 162221209
• PubChem CID: 440667
• CHEBI ID: 27956
• Chemspider ID: 389547
• Wikipedia Title: Dehydroascorbic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.5571897
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.748775
• LogD (pH = 7.4): -3.8112833
• Log P: -0.67283064
• Molar Refractivity: 33.5458 cm^3
• Polarizability: 13.592451 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 228 °C (dec.)(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (enzymatic)
• Shipped in: dry ice; wet ice
• Empirical Formula (Hill Notation): C12H12O12; C6H6O6

DETAILS

Sigma Aldrich - D8132

Other Notes
Dimer in crystalline form; dihydrate in 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.
Biochem/physiol Actions
L-Ascorbic acid (Vitamin C) is a water soluble molecule use in a wide variety of applications, including cell culture, as a reducing agent that helps reduce oxidative stress. L-Ascorbate can be regenerated from dehydroascorbic acid (DHA) by biological systems.

Sigma Aldrich - 261556

Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 261556.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 30790

Other Notes
Review1