218251

(1S)-(−)-Verbenone

94%

• Synonym(s): (1S,5S)-2-Pinen-4-one, (1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one
• Empirical Formula (Hill Notation): C₁₀H₁₄O
• CAS Number: 1196-01-6
• Molecular Weight: 150.22
• Beilstein: 1907623
• EC Number: 214-807-2
• MDL number: MFCD00065445
• UNSPSC Code: 85151701
• PubChem Substance ID: 24853055
• NACRES: NA.22

Properties

• Assay: 94%
• form: liquid
• optical activity: [α]25/D −130°, c = 10 in ethanol
• refractive index: n20/D 1.496 (lit.)
• bp: 227-228 °C (lit.)
• density: 0.975 g/mL at 20 °C (lit.)
• SMILES string: CC1=CC(=O)[C@H]2C[C@@H]1C2(C)C
• InChI: 1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m0/s1
• InChI key: DCSCXTJOXBUFGB-JGVFFNPUSA-N

Description

General description

(1S)-(-)-Verbenone is one of the main components of the essential oil of Suregada zanzibariensis leaves. It can be prepared by the biotransformation of (-)-α-pinene. (1S)-(-)-Verbenone acts as an antiaggregation pheromone towards the aggregation pheromone released by western pine beetle (WPB).

Application

(1S)-(−)-Verbenone can be used along with (1R)-(+)-nopinone for the stereoselective synthesis of chiral annulated indene derivatives via acid-catalyzed electrocyclic reaction. It can also be employed as a starting material in the preparation of verbenone derivatives containing a 4-styryl scaffold with potent anti-ischemic property.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 185.0 °F - closed cup
• Flash Point(C): 85 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves