2,2,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-one

• ChemBase ID: 163607
• Molecular Formular: C40H52O2
• Molecular Mass: 564.83968
• Monoisotopic Mass: 564.3967309
• SMILES: C1(=C(CCC(=O)C1(C)C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(CCC(=O)C1(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)CCC(=O)C1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCC(=O)C1(C)C)\C
• InChI: InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-25-35-33(5)23-27-37(41)39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-26-36-34(6)24-28-38(42)40(36,9)10/h11-22,25-26H,23-24,27-28H2,1-10H3/b12-11+,17-13+,18-14+,25-21+,26-22+,29-15+,30-16+,31-19+,32-20+
• InChIKey: KDBGSEPFLRHEKZ-RIRRTMASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-one
• IUPAC Traditional name: 2,2,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-one
• Synonyms: 4,4'-Diketo-β-carotene; 4,4'-Dioxo-β-carotene; Canthaxanthin; Canthaxanthine; all-trans-β-Carotene-4,4'-dione; NSC 374110; all-trans-Canthaxanthin

Database IDs

• CAS Number: 514-78-3
• PubChem SID: 162257742
• PubChem CID: 14523227

CALCULATED PROPERTIES

• Acid pKa: 19.537237
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 9.789515
• LogD (pH = 7.4): 9.789515
• Log P: 9.789515
• Molar Refractivity: 192.9982 cm^3
• Polarizability: 70.61036 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate; Methanol

Safety Information

• Storage Condition: -86?C Freezer

DETAILS

Toronto Research Chemicals - C175735

Oral suntanning agent

REFERENCES

• Butler, M., et al.: Arch. Biochem. Biophys., 504, 154 (2010)
• Wenzel, M., et al.: Food Chem., 124, 1343 (2010)
• de la Fuente, J., et al.: J. Biotechnol., 148, 144 (2010)