(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol

• ChemBase ID: 138092
• Molecular Formular: C10H18O
• Molecular Mass: 154.24932
• Monoisotopic Mass: 154.1357652
• SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(=C)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(=C)C
• InChI: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
• InChIKey: ZYTMANIQRDEHIO-KXUCPTDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
• IUPAC Traditional name: (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
• Synonyms: (1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanol; (1R,3R,4S)-p-Menth-8-en-3-ol; (-)-Isopulegol; 8,9-Menthen-3-ol; p-Menth-8-en-3-ol; FEMA 2962; Isopulegol; (1R,2S,5R)-2-异丙烯基-5-甲基环己醇; (1R,3R,4S)-对薄荷-8-烯-3-醇; (-)-异蒲勒醇

Database IDs

• CAS Number: 7786-67-6; 89-79-2
• EC Number: 201-940-6
• MDL Number: MFCD00134655
• Beilstein Number: 1906573
• PubChem SID: 24881712; 24867323; 24901421; 162232350; 24901422
• PubChem CID: 170833
• FEMA ID: 2962
• Council of Europe Number: 2033
• Flavis Number: 2.067

CALCULATED PROPERTIES

• Acid pKa: 19.465338
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.3166273
• LogD (pH = 7.4): 2.3166273
• Log P: 2.3166273
• Molar Refractivity: 47.2228 cm^3
• Polarizability: 18.809866 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 212 °C(lit.)
• Flash Point: 172.4 °F; 78 °C
• Density: 0.912 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.471(lit.); n20/D 1.472
• Optical Rotation: [α]20/D -21°, neat; [α]20/D -22±0.5°, neat; [α]20/D -22°, neat; [α]22/D -7 to 0°, neat
• Organoleptic: minty

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Regulation Compliance: FCC

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥95%; ≥98%; ≥99.0% (sum of enantiomers, GC); 99%
• Grade: analytical standard, for terpene analysis; Halal
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (GC)
• Description: Stereoisomers
• Biological Source: Isol. from Ceratocystis coerulescens (fungus), also in Mentha pulegium and other essential oils. Constit. of Leptospermum liversidgei
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Flavouring agent
• Empirical Formula (Hill Notation): C10H18O

DETAILS

Sigma Aldrich - 439061

Packaging
1 mL in glass bottle

Sigma Aldrich - W296236

Packaging
1 kg in glass bottle
1 sample in glass bottle
9, 20 kg in poly drum

Sigma Aldrich - 59770

Other Notes
Monoterpenoid chiral building block, hydroboration to a 1,4-diol1,2,3,4

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 244C, (nmr)
• Barbier, P. et al., C. R. Hebd. Seances Acad. Sci., 1897, 124, 1309, (synth)
• Grignard, V. et al., C. R. Hebd. Seances Acad. Sci., 1928, 187, 270-273, (synth)
• Shishibori, T., Bull. Chem. Soc. Jpn., 1968, 41, 1170-1174, (synth, ir)
• Chabudzinski, Z. et al., Pol. J. Chem. (Rocz. Chem.), 1968, 42, 283-287, (synth)
• Nishimura, H. et al., Agric. Biol. Chem., 1982, 46, 319-320; 2601-2604, (isol)
• Clark, B.C. et al., J.O.C., 1984, 49, 4557-4559, (synth)
• Nishimura, H., Fragrance J., 1985, 13, 160-162, (rev, isol, props)
• Asakawa, Y. et al., Phytochemistry, 1988, 27, 3861-3869, (synth, ir, pmr, cmr)
• Chen, F. et al., CA, 1992, 116, 67006p, (isol)
• Kocovsky, P. et al., J.O.C., 1999, 64, 2765-2775, (synth)
• Yuasa, Y. et al., Org. Process Res. Dev., 2000, 4, 159-161, (isomers, synth, ir, pmr, cmr, ms)