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
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About This Item
Empirical Formula (Hill Notation):
C10H14O
CAS Number:
Molecular Weight:
150.22
UNSPSC Code:
85151701
NACRES:
NA.22
PubChem Substance ID:
EC Number:
214-807-2
Beilstein/REAXYS Number:
1907623
MDL number:
Assay:
94%
Form:
liquid
Quality Level
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.)
functional group
ketone
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
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.
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Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
185.0 °F - closed cup
flash_point_c
85 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus brevicomis LeConte (Coleoptera: Scolytidae).
Journal of Chemical Ecology, 33(4), 817-817 (2007)
Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae ss.
Innocent E, et al.
Journal of Insect Science, 10(1), 57-57 (2010)
Bioconversion of (+)-and (-)-alpha-pinene to (+)-and (-)-verbenone by plant cell cultures of Psychotria brachyceras and Rauvolfia sellowii.
Limberger RP, et al.
Electronic journal of Biotechnology, 10(4), 500-507 (2007)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 218251-10G | 04061838775412 |
| 218251-50G | 04061837392351 |