Verbenone

Structural formula
	Structural formula without representation of the stereochemistry
General
Surname	Verbenone
other names	4,6,6-trimethyl-bicyclo [3.1.1] hept-3-en-2-one; 2-pinene-4-one;
Molecular formula	C 10 H 14 O
Brief description	light yellow liquid
External identifiers / databases
EC number	201-292-4
ECHA InfoCard	100.001.176
PubChem	29025
ChemSpider	27001
Wikidata	Q421151
properties
Molar mass	150.21 g mol −1
Physical state	liquid
density	0.98 g cm −3
Melting point	9.8 ° C
boiling point	227-228 ° C
solubility	practically insoluble in water
Refractive index	1.4993 (18 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Verbenone refers to the two enantiomers (+) - verbenone and (-) - verbenone.

There are colorless liquids with the empirical formula C ₁₀ H ₁₄ O belonging to the monoterpene - ketones count. Both have a minty odor that increases when heated.

Isomers

Isomers of verbenone
Surname	(+) - Verbenone	(-) - Verbenone
other names	D -Vbenone (1 R , 5 R ) -4,6,6-trimethyl-bicyclo [3.1.1] hept-3-en-2-one	L -Vbenone (1 S , 5 S ) -4,6,6-trimethyl-bicyclo [3.1.1] hept-3-en-2-one levoverbenone
Structural formula
CAS number	18309-32-5	1196-01-6
	80-57-9 (undefined)
EC number	242-195-7	214-807-2
	201-292-4 (undefined)
ECHA info card	100.038.344	100.013.461
	100.001.176 (undefined)
PubChem	65724	92874
	29025 (undefined)
Wikidata	Q55929359	Q6535827
	Q421151 (undefined)

Occurrence and representation

rosemary

Verbenone occurs in the essential oils of rosemary ( Rosmarinus officinalis ) and the lemon bush (also scent verbena, lemon verbena, Aloysia triphylla ). It is together with the verbenol pheromone of the bark beetle . The attractant Verbenol leads to the "gathering" of the beetles on a tree; Finally, Verbenon drives the bark beetles to other trees that have not yet been infested. The ketone can be artificially made from pinene .

properties

Verbenone is flammable, the flash point is around 85 ° C. The substance is readily soluble in ethanol and other organic solvents, but almost not in water.

use

Verbenone serves as a fragrance and is also used as a remedy for the printer's bark beetle , where it acts as a repellent that repels the beetles.

Individual evidence

↑ ^a ^b Data sheet (1S) - (-) - Verbenone at Acros, accessed on February 20, 2010.
↑ ^a ^b Ingredients of essential oils: Verbenone .
↑ ^a ^b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-518.
↑ Data sheet (1S) - (-) - Verbenone at Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).
↑ Gabriela Lobinger: Development of new strategies in bark beetle management. ( Memento from September 27, 2007 in the Internet Archive ) In: Forstschutz aktuell No. 37, 2006, pp. 11-13.

[acros-1] Data sheet (1S) - (-) - Verbenone at Acros, accessed on February 20, 2010.

[ChemLex-2] Ingredients of essential oils: Verbenone .

[CRC90_3_518-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-518.

[Sigma-4] Data sheet (1S) - (-) - Verbenone at Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).

[5] Gabriela Lobinger: Development of new strategies in bark beetle management. ( Memento from September 27, 2007 in the Internet Archive ) In: Forstschutz aktuell No. 37, 2006, pp. 11-13.