(L)-Dehydroascorbic acid - Moligand™, 10mM in DMSO , CAS No.490-83-5

CAS: 490-83-5 Cat. No.: L424249 Molecular Weight: 174.11 EC Number: 207-720-6

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

(5R)-5-[(1S)-1,2-dihydroxyethyl]furan-2,3,4(5H)-trione (non-preferred name) | L-threo-2,3-Hexodiulosonic acid, g-lactone | MFCD00066467 | procollagen L-erythro-5-hydroxy-L-lysine | BS-28662 | Q3116723 | SBJKKFFYIZUCET-JLAZNSOCSA-N | (L)-Dehydroascorbic ac

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

(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

Synonyms

(5R)-5-[(1S)-1, 2-dihydroxyethyl]furan-2, 3, 4(5H)-trione (non-preferred name) | L-threo-2, 3-Hexodiulosonic acid, g-lactone | MFCD00066467 | procollagen L-erythro-5-hydroxy-L-lysine | BS-28662 | Q3116723 | SBJKKFFYIZUCET-JLAZNSOCSA-N | (L)-Dehydroascorbic ac

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

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

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: 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
• Isomeric SMILES: C([C@@H]([C@@H]1C(=O)C(=O)C(=O)O1)O)O
• WGK Germany: 3
• Molecular Weight: 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
    • Class Lactones
      • Subclass Gamma butyrolactones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: 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

Chemical and Physical Properties

• Melt Point(°C): 228 °C (dec.) (lit.)
• Molecular Weight: 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

References

1. Hao Lin Zou, Ling Yun Qin, Hong Qun Luo, Bang Lin Li, Nian Bing Li.  (2021)  High-valence Mo(VI) derived from in-situ oxidized MoS2 nanosheets enables enhanced electrochemical responses for nitrite measurements.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2021.129812]

2. Zhipeng Zhang, Qi Liu, Kecen Chen, Xiaoxing Li, Ruili Li, Xiaoqing Chen.  (2024)  Hydrogen Bonding-Induced Aggregation of Chiral Functionalized AuNS@Ag NPs for Photothermal Enantioanalysis.  ANALYTICAL CHEMISTRY,      [PMID:38597814] [10.1021/acs.analchem.3c05751]

3. Wang Yong, Liu Li-Na, Wei Shang-Hua, Wang Wei, Liu Cong-Jun, Gao Song, Yu Shu-Ping, Yao Ning, Wang Yu-Fei.  (2025)  Synthesis of Dehydroabietic Acid Derivatives with 1,2,3-Triazole Substituents and Their Antiproliferative Activity against HeLa, MCF-7, and HEK-293T Cells.  RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY,  51  (6): (2582-2592).  [PMID:] [10.1134/S1068162025600448]