218251

(−)-Verbenone

94%

• Synonyme(s) : (1S,5S)-2-pinène-4-one, (1S,5S)-4,6,6-triméthylbicyclo[3.1.1]hept-3-en-2-one
• Formule empirique (notation de Hill): C₁₀H₁₄O
• Numéro CAS: 1196-01-6
• Poids moléculaire : 150.22
• Beilstein: 1907623
• Numéro CE : 214-807-2
• Numéro MDL: MFCD00065445
• Code UNSPSC : 85151701
• ID de substance PubChem : 24853055
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 100
• Essai: 94%
• Forme: liquid
• Activité optique: [α]25/D −130°, c = 10 in ethanol
• Indice de réfraction: n20/D 1.496 (lit.)
• pb: 227-228 °C (lit.)
• Densité: 0.975 g/mL at 20 °C (lit.)
• Groupe fonctionnel: ketone
• Chaîne SMILES: 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
• Clé InChI: DCSCXTJOXBUFGB-JGVFFNPUSA-N

Description

Description générale

(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.

Informations sur la sécurité

• Code de la classe de stockage: 10 - Combustible liquids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 185.0 °F - closed cup
• Point d'éclair (°C): 85 °C - closed cup
• Équipement de protection individuelle: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)