(±)12,13-DiHOME - ≥98%, ~100ug/ml in methyl acetate , CAS No.263399-35-5

CAS: 263399-35-5 Cat. No.: D351350 Molecular Weight: 314.46

GRADE & PURITY ≥98%, ~100ug/ml in methyl acetate

Synonyms

9-Octadecenoic acid, 12,13-dihydroxy-, (9Z)- | HY-116003 | (??)12(13)-DiHOME | (9Z)-12,13-Dihydroxy-9-octadecenoic acid | 12,13-DiHOME | (9Z)-12,13-Dihydroxyoctadec-9-enoic acid | SCHEMBL2228623 | LMFA02000230 | Q27140059 | (+/-)12,13-Dihome | J-016390 |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

(±)12,13-DiHOME is the diol resulting from the soluble epoxide hydrolase opening of (±)12,13-EpOME. The mixture of the methyl ester of this diol and the 9,10 isomer are more cytotoxic than the methyl ester epoxides in renal proximal tubular cells.However, in renal cortical mitochondria, the conversion of the epoxide to 12,13-DiHOME appears to be part of the detoxification pathway that prevents mitochondrial dysfunction. This diol and the 9,10 isomer can be glucuronidated by human liver and intestinal microsomes as well as recombinant UGT2B7 through a hydroxyl group. High levels of LA-diol glucuronides have been found in the urine of humans with peroxisomal diseases. A mixture of the diols stimulates breast cancer cell proliferation in vitro and disrupts reproductive function in rats at relatively low concentrations.

(±)12,13-DiHOME is supplied as a solution in methyl acetate. To change the solvent, simply evaporate the methyl acetate under a gentle stream of nitrogen and immediately add the solvent of choice. Solvents such as ethanol, DMSO, and dimethyl formamide purged with an inert gas can be used. The solubility of (±)12,13-DiHOME in these solvents is approximately 20 mg/ml.

Specifications

Synonyms

9-Octadecenoic acid, 12, 13-dihydroxy-, (9Z)- | HY-116003 | (??)12(13)-DiHOME | (9Z)-12, 13-Dihydroxy-9-octadecenoic acid | 12, 13-DiHOME | (9Z)-12, 13-Dihydroxyoctadec-9-enoic acid | SCHEMBL2228623 | LMFA02000230 | Q27140059 | (+/-)12, 13-Dihome | J-016390 |

Specifications & Purity

≥98%, ~100ug/ml in methyl acetate

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCC(C(CC=CCCCCCCCC(=O)O)O)O
• IUPAC Name: (Z)-12,13-dihydroxyoctadec-9-enoic acid
• InChIKey: CQSLTKIXAJTQGA-FLIBITNWSA-N
• INCHI: 1S/C18H34O4/c1-2-3-10-13-16(19)17(20)14-11-8-6-4-5-7-9-12-15-18(21)22/h8,11,16-17,19-20H,2-7,9-10,12-15H2,1H3,(H,21,22)/b11-8-
• Isomeric SMILES: CCCCCC(C(C/C=C\CCCCCCCC(=O)O)O)O
• Molecular Weight: 314.46
• Reaxy-Rn: 23821611
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=23821611&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Long-chain fatty acids
• Alternative Parents: Hydroxy fatty acids Unsaturated fatty acids Secondary alcohols 1,2-diols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Long-chain fatty acid - Hydroxy fatty acid - Unsaturated fatty acid - Secondary alcohol - 1,2-diol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
• External Descriptors: Other Octadecanoids

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

• Solubility: DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 20 mg/ml,PBS (pH 7.2): 10 µ g/ml
• Boil Point(°C): 57° C
• Molecular Weight: 314.500 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 314.246 Da
• Monoisotopic Mass: 314.246 Da
• Topological Polar Surface Area: 77.800 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 289.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1