218251

(1S)-(−)-Verbenone

94%

• Sinônimo(s): (1S,5S)-2-Pinen-4-one, (1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one
• Fórmula empírica (Notação de Hill): C₁₀H₁₄O
• Número CAS: 1196-01-6
• Peso molecular: 150.22
• Beilstein: 1907623
• Número CE: 214-807-2
• Número MDL: MFCD00065445
• Código UNSPSC: 85151701
• ID de substância PubChem: 24853055
• NACRES: NA.22

Propriedades

• Ensaio: 94%
• Formulário: liquid
• atividade óptica: [α]25/D −130°, c = 10 in ethanol
• índice de refração: n20/D 1.496 (lit.)
• p.e.: 227-228 °C (lit.)
• densidade: 0.975 g/mL at 20 °C (lit.)
• grupo funcional: ketone
• cadeia de caracteres 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
• chave InChI: DCSCXTJOXBUFGB-JGVFFNPUSA-N

Descrição

Descrição geral

(1S)-(-)-Verbenone is one of the main components of the essential oil of Suregada zanzibariensis leaves.[1] It can be prepared by the biotransformation of (-)-α-pinene.[2] (1S)-(-)-Verbenone acts as an antiaggregation pheromone towards the aggregation pheromone released by western pine beetle (WPB).[3]

Aplicação

(1S)-(−)-Verbenone can be used along with (1R)-(+)-nopinone for the stereoselective synthesis of chiral annulated indene derivatives via acid-catalyzed electrocyclic reaction.[4] 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.[5]

Informações de segurança

• Código de classe de armazenamento: 10 - Combustible liquids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): 185.0 °F - closed cup
• Ponto de fulgor (°C): 85 °C - closed cup
• Equipamento de proteção individual: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)