(L)-Dehydroascorbic acid - Moligand™, used for (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 form

CAS: 490-83-5 Cat. No.: L303806 Formule: C₆H₆O₆ Poids moléculaire: 174.11 Numéro CE: 207-720-6

GRADE & PURITY Moligand™

Synonyms

L-Dehydro Ascorbic Acid | Dehydroascorbic acid | L-threo-2,3-Hexodiulosonic acid γ-lactone | DHAA

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

(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.

Specifications

Synonymes

L-Dehydro Ascorbic Acid | Dehydroascorbic acid | L-threo-2,3-Hexodiulosonic acid γ-lactone | DHAA

Spécifications et pureté

Moligand™

Mécanismes biochimiques et physiologiques

Oxidized form ofL-Ascorbic acid. Transported into cells through GLUT1. Selectively induces cell death inKRASandBRAFmutant cellsin vitro.

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.

Conditions de stockage de stockage

Protected from light,Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Grade

Moligand™

Noms et identifiants

Pubchem Sid

488189766

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488189766

Sourires canoniques

C(C(C1C(=O)C(=O)C(=O)O1)O)O

IUPAC Name

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

InChIKey

SBJKKFFYIZUCET-JLAZNSOCSA-N

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

Isomères SMILES

C([C@@H]([C@@H]1C(=O)C(=O)C(=O)O1)O)O

WGK Allemagne

3

Poids moléculaire

174.11

Reaxy-Rn

1345285

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1345285&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Lactones
      • Subclass Gamma butyrolactones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Lactones
• Subclass: Gamma butyrolactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Gamma butyrolactones
• Alternative Parents: Furanones Tetrahydrofurans Secondary alcohols Cyclic ketones Carboxylic acid esters 1,2-diols Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 3-furanone - Gamma butyrolactone - Tetrahydrofuran - 1,2-diol - Carboxylic acid ester - Cyclic ketone - Secondary alcohol - Ketone - Carboxylic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Primary alcohol - Organooxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
• External Descriptors: dehydroascorbic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propriétés chimiques et physiques

• Solubilité: Solvent:water, Max Conc. mg/mL: 1.74, Max Conc. mM: 10 with gentle warming; Solvent:DMSO, Max Conc. mg/mL: 17.41, Max Conc. mM: 100
• Sensibilité: Light sensitive
• Point de fusion (°C): 228 °C (dec.) (lit.)
• Poids moléculaire: 174.110 g/mol
• XLogP3: -1.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 174.016 Da
• Monoisotopic Mass: 174.016 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 244.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1