(2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one

• ChemBase ID: 112597
• Molecular Formular: C10H18O
• Molecular Mass: 154.24932
• Monoisotopic Mass: 154.1357652
• SMILES: CC(C)[C@@H]1CC[C@@H](C)CC1=O
• Canonical SMILES: C[C@@H]1CC[C@H](C(=O)C1)C(C)C
• InChI: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
• InChIKey: NFLGAXVYCFJBMK-BDAKNGLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-one
• IUPAC Traditional name: (-)-menthone
• Synonyms: L-MENTHONE; (2S,5R)-2-isopropyl-5-methylcyclohexanone; (-)-Menthone; (1R,4S)-p-Menthan-3-one; (2S,5R)-2-Isopropyl-5-methylcyclohexanone; L-Menthone; l-Menthone; Menthone; (-)-Menthone; (-)-薄荷酮; (1R,4S)-对-薄荷烷-3-酮; (2S,5R)-2-异丙基-5-甲基环己酮; L-薄荷酮; (-)-薄荷酮

Database IDs

• CAS Number: 14073-97-3
• EC Number: 237-926-1
• MDL Number: MFCD00001634
• Beilstein Number: 3648743; 2041368
• Merck Index: 145838
• PubChem SID: 162097474; 24853053; 24882806; 24882804; 24901231
• PubChem CID: 26447
• CHEBI ID: 15410
• CHEMBL: 276311
• Chemspider ID: 24636
• FEMA ID: 2667
• Wikipedia Title: Menthone
• Council of Europe Number: 2035

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.0497873
• LogD (pH = 7.4): 3.0497873
• Log P: 3.0497873
• Molar Refractivity: 46.5201 cm^3
• Polarizability: 18.4969 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -6 °C
• Boiling Point: 207 °C; 207°C; 207-210 °C(lit.); 208-210°C
• Flash Point: 163.4 °F; 72°C(162°F); 73 °C
• Density: 0.893; 0.893 g/mL at 20 °C(lit.); 0.895 g/cm3
• Refractive Index: 1.4500; n20/D 1.45(lit.); n20/D 1.451
• Vapor Pressure: 0.5 mmHg ( 20 °C)
• Optical Rotation: [α]20/D -20°, neat; [α]20/D -29±1°, neat; -25 (neat)
• Organoleptic: berry; minty; fruity; peach; raspberry; sweet; herbaceous; camphoraceous; woody

Safety Information

• RTECS: OS9542200
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H319-H227
• GHS Precautionary statements: P210-P280-P305+P351+P338-P337+P313-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C
• Regulation Compliance: FCC

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥90% (sum of enantiomers, GC); ≥96%; ≥99.0% (sum of enantiomers, GC); 90%; 97%
• Grade: analytical standard, for terpene analysis; Halal; Kosher; NI; technical
• Optical Purity: enantiomeric ratio: ≥99:1 (GC)
• Impurities: 5% isomenthone
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H18O
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05224811

MP Biomedicals Rare Chemical collection

Sigma Aldrich - W266701

Biochem/physiol Actions
Taste at 50 ppm
Other Notes
Natural occurrence: Mentha species.
Packaging
1 kg in poly bottle
1 sample in glass bottle
9, 20 kg in poly drum

Sigma Aldrich - 218235

Packaging
25, 100 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 218235.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 63677

Other Notes
Highly purified (-)-menthone. Resolving agent for diols via acetalization 1; Menthone-derived spirocyclic 1,3-dioxane-4,6-diones are used in asymmetric Diels-Alder and (2+2) cycloadditions 2