3-[(1E,3Z,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

• ChemBase ID: 172110
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C1CC(=O)C(=C(C1(C)C)/C=C/C(=C\C=C\C(=C\CO)\C)/C)C
• Canonical SMILES: OC/C=C(/C=C/C=C(\C=C\C1=C(C)C(=O)CCC1(C)C)/C)\C
• InChI: InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7-,16-12+
• InChIKey: PLIUCYCUYQIBDZ-NXTBRRCASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1E,3Z,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
• IUPAC Traditional name: 3-[(1E,3Z,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
• Synonyms: 9-cis-4-Oxo-retinol; 9-(2,6,6-Trimethyl-3-keto-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraen-1-ol; 9-cis-4-Ketoretinol

Database IDs

• PubChem SID: 164228020
• PubChem CID: 29982682

CALCULATED PROPERTIES

• Acid pKa: 16.435617
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.0268097
• LogD (pH = 7.4): 4.0268097
• Log P: 4.0268097
• Molar Refractivity: 98.6166 cm^3
• Polarizability: 36.363087 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Yellow Semi-Solid

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - K205005

These compounds activate gene expression through binding to nuclear receptor proteins. They are useful for treating leukemia, lymphoma, squamous cell carcinoma, deep (cystic) acne, psoriasis, and photodamaged or aging skin.