(5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one

• ChemBase ID: 119045
• Molecular Formular: C10H16O
• Molecular Mass: 152.23344
• Monoisotopic Mass: 152.12011513
• SMILES: C1(=C(C)C)C(=O)C[C@@H](CC1)C
• Canonical SMILES: C[C@@H]1CCC(=C(C)C)C(=O)C1
• InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
• InChIKey: NZGWDASTMWDZIW-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
• IUPAC Traditional name: (+)-pulegone
• Synonyms: (R)-5-methyl-2-(propan-2-ylidene)cyclohexanone; p-Menth-4(8)-en-3-oneδ-4(8)-p-menthen-3-one(R)-2-Isopropylidene-5-methylcyclohexanone(R)-p-Menth-4(8)-en-3-one(R)-(+)-Pulegone; Pulegone; (+)-Pulegone; (+)-Pulegone; (R)-p-Menth-4(8)-en-3-one; (R)-2-Isopropylidene-5-methylcyclohexanone; p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone; (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone; (R)-(+)-p-Menth-4(8)-en-3-one; Pulegon; Pulegone; d-Pulegone; NSC 15334; (R)-Pulegone; (+)-蒲勒酮; (+)-蒲勒酮; (R)-(+)-长叶薄荷酮; (R)-2-异亚丙基-5-甲基环己酮; 长叶薄荷酮; (R)-(+)-蒲勒酮

Database IDs

• CAS Number: 89-82-7
• EC Number: 201-943-2
• MDL Number: MFCD00063000
• Beilstein Number: 2040703
• PubChem SID: 24901423; 24898670; 24863438; 24887985; 162102837
• PubChem CID: 442495
• CHEBI ID: 35596
• Chemspider ID: 390923
• FEMA ID: 2963
• Unique Ingredient Identifier: 4LF2673R3G
• Wikipedia Title: Pulegone
• Council of Europe Number: 2050c

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.8565173
• LogD (pH = 7.4): 2.8565173
• Log P: 2.8565173
• Molar Refractivity: 47.1294 cm^3
• Polarizability: 18.259748 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water; Miscible in Ethanol; Ether; Chloroform
• Apperance: Colorless oil
• Boiling Point: 223-224 °C(lit.); 224 °C(lit.); 224°C
• Flash Point: 179.6 °F; 82 °C
• Density: 0.9346 g/cm^3; 0.935 g/mL at 20 °C(lit.); 0.937 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.486; n20/D 1.486(lit.); n20/D 1.487; n20/D 1.488
• Vapor Pressure: 138 mmHg ( 25 °C)
• Optical Rotation: [α]20/D +22°, neat; [α]20/D +23.5±1°, neat; [α]20/D +23.5°, neat; [α]20/D +23±1.5°, neat
• Organoleptic: cinnamon; lime; minty; fruity; herbaceous; vanilla; spicy

Safety Information

• RTECS: OT0261000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 23-24/25; R
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~85% (sum of enantiomers, GC); ≥85%; ≥95.0% (sum of enantiomers, GC); ≥98.5% (sum of enantiomers, GC); 85%; 97%
• Grade: analytical standard, for terpene analysis; NI; purum; technical; technical grade
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H16O
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - P55708

Packaging
100 mL in poly bottle
5 mL in glass bottle

Sigma Aldrich - 376388

Packaging
100 g in poly bottle
5 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 376388.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - W296309

Biochem/physiol Actions
Taste at 20 ppm
Other Notes
Natural occurrence: Buchu oil, native spearmint, pennyroyal, peppermint, scotch spearmint and thyme.
Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in poly drum

Sigma Aldrich - 82570

Other Notes
Chiral building block1,2 Synthesis of (-)-8-phenylmenthol 3,4

Toronto Research Chemicals - P840140

A monoterpene, commonly found in the essential oils of Nepeta cataria (Catnip).

REFERENCES

• Sonboli, A., et al.: Chem. Biodivers., 7, 1784 (2010)
• Ntalli, N., et al.: J. Agric. Food Chem., 58, 7856 (2010)
• Chun, M., et al.: Microchem. J., 95, 25 (2010)