(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 分子式: C₆H₆O₆ 分子量: 174.11 EC番号: 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

概要

(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

同義語

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

仕様と純度

Moligand™

生化学的・生理学的メカニズム

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

申し込み

(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.

保管条件

Protected from light,Store at -20°C

入荷

Ice chest + Ice pads

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

名前と識別子

パブケム・シド

488189766

パブケム・シド・ウル

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

カノニカル・スマイル

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

異性体SMILES

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

WGKドイツ

3

分子量

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
    • 分類 Lactones
      • Subclass Gamma butyrolactones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 分類: 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
• 説明: 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

化学的性質と物理的性質

• 溶解度: 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
• 感度: Light sensitive
• 融点（°C）: 228 °C (dec.) (lit.)
• 分子量: 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