Skip to Content
MilliporeSigma
All Photos(1)

Documents

218251

Sigma-Aldrich

(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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
1196-01-6
Molecular Weight:
150.22
Beilstein/REAXYS Number:
1907623
EC Number:
214-807-2
MDL number:
MFCD00065445
UNSPSC Code:
85151701
PubChem Substance ID:
24853055
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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.

Storage Class

10 - Combustible liquids

wgk_germany

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
Chung Ju et al.
Bioorganic & medicinal chemistry letters, 23(19), 5421-5425 (2013-08-21)
A series of novel (1S)-(-)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen-glucose deprivation-induced neuronal injury and N-methyl-D-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore
Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus brevicomis LeConte (Coleoptera: Scolytidae).
Journal of Chemical Ecology, 33(4), 817-817 (2007)
Synthesis of (1R)-(+)-nopinone-and (1S)-(-)-verbenone-derived chiral annulated indenes via electrocyclic reactions.
Liu C and Sowa JR.
Tetrahedron Letters, 37(40), 7241-7244 (1996)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service