[(1S,4S,5R,6R)-6-(hydroxymethyl)-2,5-dimethyl-4-[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl]-5-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]cyclohex-2-en-1-yl]methanol

• ChemBase ID: 172137
• Molecular Formular: C40H60O2
• Molecular Mass: 572.9032
• Monoisotopic Mass: 572.45933116
• SMILES: C1=C([C@H]([C@H]([C@@]([C@H]1/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)C)CO)CO)C
• Canonical SMILES: OC[C@@H]1C(=C[C@@H]([C@@]([C@@H]1CO)(C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)C
• InChI: InChI=1S/C40H60O2/c1-28(17-19-35-30(3)15-12-21-38(35,6)7)14-11-23-40(10)33(25-32(5)34(26-41)37(40)27-42)24-29(2)18-20-36-31(4)16-13-22-39(36,8)9/h11,14,17-20,23-25,33-34,37,41-42H,12-13,15-16,21-22,26-27H2,1-10H3/b19-17+,20-18+,23-11+,28-14+,29-24+/t33-,34+,37+,40+/m0/s1
• InChIKey: NTTHYVALAYBGDV-WHFXJCNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,4S,5R,6R)-6-(hydroxymethyl)-2,5-dimethyl-4-[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl]-5-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]cyclohex-2-en-1-yl]methanol
• IUPAC Traditional name: [(1S,4S,5R,6R)-6-(hydroxymethyl)-2,5-dimethyl-4-[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl]-5-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]cyclohex-2-en-1-yl]methanol
• Synonyms: (1R,2S,5S,6R)-rel-3,6-Dimethyl-5-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-butadienyl]-6-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatrienyl]-3-cyclohexene-1,2-dimethanol; [1α,2α,5α(1E,3E),6β(1E,3E,5E)]-3,6-Dimethyl-5-[2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-butadienyl]-6-[4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatrienyl]-3-cyclohexene-1,2-dimethanol; Kitol A; Kitol

Database IDs

• CAS Number: 4626-00-0
• PubChem SID: 164228047
• PubChem CID: 6441296

CALCULATED PROPERTIES

• Acid pKa: 15.114155
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 8.455158
• LogD (pH = 7.4): 8.455158
• Log P: 8.455158
• Molar Refractivity: 190.1467 cm^3
• Polarizability: 71.66658 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - K570500

Kitol is a natural retinol dimer obtained from mammalian liver oil. It is a provitamin A which can be converted to vitamin A.

REFERENCES

• Runge, F. et al.: J. Agric. Food Chem., 48, 47 (2000)
• Tsukida, K. et al.: Nip. Suis. Gak., 46, 1391 (2000)