(1S)-3,5,5-trimethyl-4-[(1E,3E,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-3-en-1-ol

• ChemBase ID: 165045
• Molecular Formular: C40H56O
• Molecular Mass: 552.87204
• Monoisotopic Mass: 552.43311641
• SMILES: C1(=C(C[C@@H](CC1(C)C)O)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
• Canonical SMILES: O[C@H]1CC(=C(C(C1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)/C)/C)C
• InChI: InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m0/s1
• InChIKey: DMASLKHVQRHNES-GMKWGACXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-3,5,5-trimethyl-4-[(1E,3E,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-3-en-1-ol
• IUPAC Traditional name: (1S)-3,5,5-trimethyl-4-[(1E,3E,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-3-en-1-ol
• Synonyms: (3S)-β,β-Caroten-3-ol; ent-β-Cryptoxanthin; (3S)-β-Cryptoxanthin

Database IDs

• CAS Number: 1200446-88-3
• PubChem SID: 162259178
• PubChem CID: 44554791

CALCULATED PROPERTIES

• Acid pKa: 18.907213
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 9.737363
• LogD (pH = 7.4): 9.737363
• Log P: 9.737363
• Molar Refractivity: 193.2813 cm^3
• Polarizability: 71.1635 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C827505

The R-enatiomer of (3S)-β-Cryptoxanthin (C827500), a natural caratenoid pigment that is an antioxidant which helps prevent free radical damage to cells and DNA as well as being a potential chemopreventative agent against lung cancer.

REFERENCES

• Lorenzo, Y. et al.: Carcinogen., 30, 308 (2008)
• Lian, F. et al.: Int. J. Cancer, 119, 2084 (2008)
• Fu. H. et al.: Food Chem., 122, 602 (2008)