(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one

• ChemBase ID: 119729
• Molecular Formular: C10H14O
• Molecular Mass: 150.21756
• Monoisotopic Mass: 150.10446507
• SMILES: C1(=O)C(=CC[C@H](C1)C(=C)C)C
• Canonical SMILES: CC(=C)[C@@H]1CC=C(C(=O)C1)C
• InChI: InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
• InChIKey: ULDHMXUKGWMISQ-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
• IUPAC Traditional name: (-)-carvone
• Synonyms: (R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone; Δ^6:8(9)-p-menthadien-2-one; 1-methyl-4-isopropenyl-; Δ^6-cyclohexen-2-one; carvol (obsolete); Carvone; (R)-(-)-Carvone; (-)-Carvone; (R)-(-)-Carvone; (R)-5-Isopropenyl-2-methyl-2-cyclohexenone; p-Mentha-6,8-dien-2-one; Carvol; L-Carvone; (-)-Carvone; (R)-(-)-香芹酮; (-)-香芹酮; (R)-(-)-香芹酮; (R)-5-异丙烯基-2-甲基-2-环己烯酮; 葛缕醇; 香芹酮; 左旋香芹酮; (-)-香芹酮

Database IDs

• CAS Number: 99-49-0; 6485-40-1
• EC Number: 229-352-5
• MDL Number: MFCD00001578
• Beilstein Number: 2206714
• PubChem SID: 162102840; 24853179; 24900948; 24847635; 24853181
• PubChem CID: 439570
• CHEBI ID: 38265
• CHEMBL: 15676
• Chemspider ID: 21106424
• FEMA ID: 2249
• KEGG ID: C01767
• Unique Ingredient Identifier: 75GK9XIA8I
• Wikipedia Title: Carvone
• Flavis Number: 7.147

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.5525293
• LogD (pH = 7.4): 2.5525293
• Log P: 2.5525293
• Molar Refractivity: 47.1735 cm^3
• Polarizability: 18.023672 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Insoluble (cold); Slightly soluble (hot)/soluble in trace amounts
• Apperance: Clear, colorless liquid
• Melting Point: 25.2 °C
• Boiling Point: 227-230 °C(lit.); 228-230 °C(lit.); 231 °C; 91 °C (@ 5 mmHg)
• Flash Point: 201.2 °F; 94 °C
• Density: 0.959 g/mL at 25 °C(lit.); 0.96 g/cm^3; 0.960 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.497(lit.); n20/D 1.498
• Vapor Pressure: 0.4 mmHg ( 20 °C)
• Vapor Density: 5.2 (vs air)
• Optical Rotation: [α]20/D -61.5±2°, neat; [α]20/D -61°, neat; -61° (R)-Carvone; 61° (S)-Carvone
• Organoleptic: minty; herbaceous

Safety Information

• RTECS: OS8650000; OS8650000 (R); OS8670000 (S)
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22; R22
• Safety Statements: S36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Main Hazard: inflammable
• NFPA704:
  

  2

  1

  0
• 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
• Regulation Compliance: FCC

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥97%; ≥99.0% (sum of enantiomers, GC); 98%
• Grade: analytical standard, for terpene analysis; Halal; Kosher; NI; puriss.
• Optical Purity: ee: 98% (GLC)
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H14O
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 124931

Packaging
100, 500 mL in poly bottle
5 mL in glass bottle
Application
Chiral starting material.1,2

Sigma Aldrich - W224901

Packaging
1 kg in glass bottle
1 sample in glass bottle
5, 10 kg in poly drum

Sigma Aldrich - 22057

Other Notes
Uses as chiral building block 1,2,3