9,10-dihydroxyoctadecanoic acid

• ChemBase ID: 167876
• Molecular Formular: C18H36O4
• Molecular Mass: 316.47604
• Monoisotopic Mass: 316.26135963
• SMILES: C(CCCCCCC(C(CCCCCCCC(=O)O)O)O)C
• Canonical SMILES: CCCCCCCCC(C(CCCCCCCC(=O)O)O)O
• InChI: InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)
• InChIKey: VACHUYIREGFMSP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9,10-dihydroxyoctadecanoic acid
• IUPAC Traditional name: 9,10-dihydroxystearic acid
• Synonyms: (9R,10R)-rel-9,10-Dihydroxyoctadecanoic Acid; trans-9,10-Dihydroxystearic Acid; rac threo-9,10-Dihydroxystearic Acid

Database IDs

• CAS Number: 2391-05-1
• PubChem SID: 162262009
• PubChem CID: 89377

CALCULATED PROPERTIES

• Acid pKa: 4.6153255
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.7471685
• LogD (pH = 7.4): 1.9705827
• Log P: 4.684098
• Molar Refractivity: 89.3166 cm^3
• Polarizability: 35.6328 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 92-94°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D454750

A compound having PPAR ligand activity containing hydroxy fatty acids. A metabolite of oleic acid.

REFERENCES

• Lecka-Czernik, B., et al.: Endocrinology, 143, 2376 (2002)
• LI, Q., et al.: J. Biol. Chem., 279, 11570 (2002)
• Velasco, J., et al.: J. Agr. Food Chem., 52(2002)
• 4438 (2002)