2-[(5S)-5-methyl-5-[(1S)-4-methylcyclohex-3-en-1-yl]oxolan-2-yl]propan-2-ol

• ChemBase ID: 162136
• Molecular Formular: C15H26O2
• Molecular Mass: 238.36574
• Monoisotopic Mass: 238.19328007
• SMILES: [C@@H]1(CCC(=CC1)C)[C@]1(OC(CC1)C(O)(C)C)C
• Canonical SMILES: CC1=CC[C@H](CC1)[C@]1(C)CCC(O1)C(O)(C)C
• InChI: InChI=1S/C15H26O2/c1-11-5-7-12(8-6-11)15(4)10-9-13(17-15)14(2,3)16/h5,12-13,16H,6-10H2,1-4H3/t12-,13?,15+/m1/s1
• InChIKey: RKBAYVATPNYHLW-JHIQODARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5S)-5-methyl-5-[(1S)-4-methylcyclohex-3-en-1-yl]oxolan-2-yl]propan-2-ol
• IUPAC Traditional name: 2-[(5S)-5-methyl-5-[(1S)-4-methylcyclohex-3-en-1-yl]oxolan-2-yl]propan-2-ol
• Synonyms: Tetrahydro-α,α,5-trimethyl-5-(4-methyl-3-cyclohexen-1-yl)-2-furanmethanol; Bisabolol Oxide B(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162256271
• PubChem CID: 71314017

CALCULATED PROPERTIES

• Acid pKa: 14.325329
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.9332302
• LogD (pH = 7.4): 2.9332302
• Log P: 2.9332302
• Molar Refractivity: 71.025 cm^3
• Polarizability: 27.971695 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B399800

Bisabolol Oxide B is a metabolite of (-)-α-Bisabolol. In the metabolic pathway was used Glomerella Cingulata, a pathogenic fungus. Bisabolol Oxide A and B are in the composition of chamomile flower.

REFERENCES

• Hoelzl, J., et al.: J. Biosci., 30, 853 (1975)
• Gibson, S.E., et al.: Org. Biomol. Chem., 1, 676 (1975)