1,3,3-trimethyl-2-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene

• ChemBase ID: 163826
• Molecular Formular: C40H56
• Molecular Mass: 536.87264
• Monoisotopic Mass: 536.43820179
• SMILES: C1CC(C(=C(C1)C)/C=C/C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C)/C)\C)/C)(C)C
• Canonical SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)CCCC1(C)C)/C)/C)/C=C/C=C(\C=C\C1=C(C)CCCC1(C)C)/C
• InChI: InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21-,34-22+
• InChIKey: OENHQHLEOONYIE-BVZAMQQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,3-trimethyl-2-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
• IUPAC Traditional name: 1,3,3-trimethyl-2-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
• Synonyms: Neo-β-carotene U; neo U-β-Carotene; (9Z)-β,β-Carotene; (9Z)-β-Carotene; 9-cis-β,β-Carotene; 9-cis-β-Carotene

Database IDs

• CAS Number: 13312-52-2
• PubChem SID: 162257961
• PubChem CID: 9828626

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 11.124081
• LogD (pH = 7.4): 11.124081
• Log P: 11.124081
• Molar Refractivity: 191.6118 cm^3
• Polarizability: 70.62342 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C184230

The 9-cis isomer of β-Caroten (C184250). Carrots are one of the highest dietary sources of β-carotene and are naturally high in the (all-E)-β-carotene isomer, which has higher bioavailability, provitamin A activity, and antioxidant capacity compared to Z

REFERENCES

• Chen, B., et al.: J. Agric. Food Chem., 43, 1912 (1995)
• During, A., et al.: J. Lipid Res., 43, 1086 (1995)
• Marx, M., et al.: Food Chem. 83, 609 (1995)