(3E,5E,7E)-3,7-dimethyl-9-[(1Z)-2,6,6-trimethylcyclohex-2-en-1-ylidene]nona-3,5,7-trien-1-ol

• ChemBase ID: 177474
• Molecular Formular: C20H30O
• Molecular Mass: 286.4516
• Monoisotopic Mass: 286.22966558
• SMILES: C1CC=C(/C(=C\C=C(\C=C\C=C(\CCO)/C)/C)/C1(C)C)C
• Canonical SMILES: OCC/C(=C/C=C/C(=C/C=C/1\C(=CCCC1(C)C)C)/C)/C
• InChI: InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-12,21H,7,13-15H2,1-5H3/b8-6+,16-11+,17-9+,19-12+
• InChIKey: LWSSYLJSLZBNKE-YIAYGWAFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E,5E,7E)-3,7-dimethyl-9-[(1Z)-2,6,6-trimethylcyclohex-2-en-1-ylidene]nona-3,5,7-trien-1-ol
• IUPAC Traditional name: (3E,5E,7E)-3,7-dimethyl-9-[(1Z)-2,6,6-trimethylcyclohex-2-en-1-ylidene]nona-3,5,7-trien-1-ol
• Synonyms: 4,14-retro-Retinol; retro-Vitamin A; Retroretinol; all-trans-Retroretinol; all-trans-retro-Vitamin A; all-trans-Retro Retinol

Database IDs

• CAS Number: 16729-22-9
• PubChem SID: 164233384
• PubChem CID: 5378255

CALCULATED PROPERTIES

• Acid pKa: 17.10772
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.5381856
• LogD (pH = 7.4): 4.5381856
• Log P: 4.5381856
• Molar Refractivity: 98.0774 cm^3
• Polarizability: 36.345623 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R277500

A degradation product of Vitamin A (R252000). Vitamin A impurity.

REFERENCES

• Schreckenbach, T., et al.: Biochemistry, 17, 5353 (1978)