(2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol

• ChemBase ID: 179771
• Molecular Formular: C15H26O
• Molecular Mass: 222.36634
• Monoisotopic Mass: 222.19836545
• SMILES: C1=C(CC[C@@H]([C@](O)(CCC=C(C)C)C)C1)C
• Canonical SMILES: CC(=CCC[C@]([C@@H]1CCC(=CC1)C)(O)C)C
• InChI: InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m0/s1
• InChIKey: RGZSQWQPBWRIAQ-LSDHHAIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
• IUPAC Traditional name: (2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
• Synonyms: 2,10-Bisaboladien-7-ol; Bisabolol

Database IDs

• CAS Number: 23178-88-3
• PubChem SID: 164235681
• PubChem CID: 1549992

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.9119651
• LogD (pH = 7.4): 3.9119656
• Log P: 3.9119656
• Molar Refractivity: 72.1875 cm^3
• Polarizability: 27.80676 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Biological Source: Isol. from essential oil of Matricaria chamomilla (chamomile oil). Also from Vanillosmopsis erythropappa
• Application(s): Anti-inflammator; Anti-irritant; Anti-microbial

REFERENCES

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• O'Brien, K.G. et al., Aust. J. Chem., 1953, 6, 166; 1954, 7, 298, (Anymol)
• Yakovlev, V. et al., Arzneim.-Forsch., 1969, 19, 615, (pharmacol, tox)
• Sampath, V. et al., Indian J. Chem., 1969, 7, 1060, (isol)
• Kergomard, A. et al., Tetrahedron, 1977, 33, 2215, (synth)
• Schwartz, M.A. et al., J.O.C., 1979, 44, 953, (synth, abs config)
• Babin, D. et al., Tetrahedron, Suppl., No. 1, 1981, 1, (synth, abs config)
• Khan, V.A. et al., Khim. Prir. Soedin., 1985, 21, 575; Chem. Nat. Compd. (Engl. Transl.), 1985, 21, 575, (isol, cmr)
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• Titova, T.F. et al., Khim. Prir. Soedin., 1987, 23, 460; Chem. Nat. Compd. (Engl. Transl.), 1987, 23, 386, (isol)
• O'Donnell, G.W. et al., Aust. J. Chem., 1989, 42, 2021, (bibl, isol, deriv)
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• Wu, C.-L. et al., Phytochemistry, 1992, 31, 4213, (pmr, cmr)
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• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1383
• Nemoto, H. et al., Tet. Lett., 1993, 34, 4939, (synth)
• Roth, L. et al., Roth Collection of Natural Product Data, VCH, Weinheim, 1995
• Hashidoko, Y. et al., Biosci., Biotechnol., Biochem., 2000, 64, 907-910, (isol, pmr, cmr)