Verbenols

The verbenols (stress on the third syllable: verbs o le , also 2-pinene-4-ole ) form a group of substances of bicyclic monoterpenes - alcohols .

Representative

Various isomeric forms of verbenols are known. In the cis isomer , the two methyl groups (-CH ₃ ) are on the same side of the carbon ring as the hydroxyl group (-OH), in the trans isomer on opposite sides. In turn , there are enantiomers of each form that have optical activity , i.e. when light passes through, they rotate the position of the plane of linearly polarized light . All verbenols are monohydric, secondary alcohols, since the carbon atom that carries the hydroxyl group is bonded to two other carbon atoms.

Verbenols
Surname	(+) - trans -Vbenol	(-) - trans -Vbenol	(+) - cis -Vbenol	(-) - cis -Vbenol
Structural formula
other names	(1 R , 2 S , 5 R ) -4,7,7-trimethyl bicyclo [3.1.1] hept-3-en-2-ol	(1 S , 2 R , 5 S ) -4,7,7-trimethyl bicyclo [3.1.1] hept-3-en-2-ol	(1 S , 2 S , 5 S ) -4,7,7-trimethyl bicyclo [3.1.1] hept-3-en-2-ol	(1 R , 2 R , 5 R ) -4,7,7-trimethyl bicyclo [3.1.1] hept-3-en-2-ol
CAS number	22339-08-8	19890-02-9	18881-04-4	13040-03-4
PubChem	89664	88298	87839	164888
Molecular formula	C 10 H 16 O
Molar mass	152.24 g mol −1
Physical state	liquid
Brief description	clear, colorless liquids with an oily consistency and a peculiar smell
boiling point	88 ° C at 1.199 kilopascals
GHS labeling	no classification available	no classification available	Caution	no classification available
H and P phrases	see above	see above	315-319-335	see above
	see above	see above	no EUH phrases	see above
	see above	see above	261-305 + 351 + 338	see above

Occurrence, properties and use

Verbenols are found in turpentine and incense . Together with myrcene , verbenone and ipsdienol, they are aggregation pheromones of the bark beetle .

Because of the high price, verbenols are not used as pure substances in perfumery, but only as a mixture in the form of essential oils . Because of the pheromone properties, they are used in insect traps, for example . Verbenole can be part of pesticides to be. There is no approval for this in the EU countries, but plant protection products with ( S ) - cis -beneol as an active ingredient are available in Switzerland .

literature

• Jean Pierre Vité, Wittko Francke: Forest protection against bark beetles: From the catch tree to the trap , in: Chemistry in our time , 19 (1), 11-21, (1985); doi : 10.1002 / ciuz.19850190103 .
• Chemical Abstracts (37, 361 (1943); 57, 16772 (1962)): Verbenol representation

Individual evidence

1. ↑ Data sheet (S) -cis-Verbenol from Sigma-Aldrich , accessed on May 11, 2011 ( PDF ).
2. ↑ General Directorate Health and Food Safety of the European Commission: Entry on 4,6,6-trimethyl-bicyclo [3.1.1] hept-3-en-ol, ((S) -cis-verbenol) in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 7, 2019.