(2E,4Z,6E,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal

• ChemBase ID: 171270
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C1(=C(CC(CC1(C)C)O)C)/C=C/C(=C/C=C\C(=C\C=O)\C)/C
• Canonical SMILES: O=C/C=C(/C=C\C=C(\C=C\C1=C(C)CC(CC1(C)C)O)/C)\C
• InChI: InChI=1S/C20H28O2/c1-15(7-6-8-16(2)11-12-21)9-10-19-17(3)13-18(22)14-20(19,4)5/h6-12,18,22H,13-14H2,1-5H3/b8-6-,10-9+,15-7+,16-11+
• InChIKey: QPRQNCDEPWLQRO-SKVGZCNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4Z,6E,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal
• IUPAC Traditional name: (2E,4Z,6E,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal
• Synonyms: 11-cis-3-Hydroxyretinal; Retinal3; 3-Hydroxy-11-cis-retinal; rac 11-cis-3-Hydroxy Retinal

Database IDs

• CAS Number: 102918-00-3
• PubChem SID: 164227180
• PubChem CID: 14015972

CALCULATED PROPERTIES

• Acid pKa: 18.907213
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4690328
• LogD (pH = 7.4): 3.469033
• Log P: 3.469033
• Molar Refractivity: 98.5349 cm^3
• Polarizability: 36.363087 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953320

11-cis-3-Hydroxyretinal is a hydroxylated 11-cis-Retinal (R239860) derivative. 11-cis-3-Hydroxyretinal is formed in the cytosol of butterfly eye and that of other insects via a light dependant metaboli pathway.

REFERENCES

• Shimazaki, Y. et al.: Vision Res., 33, 155 (1993)
• Shimazaki, Y. et al.: J. Comp. Physiol. Sens. Neural Behav. Physiol., 176, 661 (1993)
• Seki, T. et al.: Vision Res., 26, 255 (1993)