Olivetol

Structural formula
General
Surname	Olivetol
other names	5-pentylbenzene-1,3-diol; 5-pentylresorcinol;
Molecular formula	C 11 H 16 O 2
Brief description	white to yellowish white powder
External identifiers / databases
EC number	207-908-8
ECHA InfoCard	100.007.190
PubChem	10377
Wikidata	Q3881822
properties
Molar mass	180.24 g mol −1
Physical state	firmly
Melting point	46-48 ° C
boiling point	162–164 ° C (7 hPa)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Olivetol ( 5-Pentylresorcin ) is a natural substance and the pentyl - derivative of resorcinol .

Occurrence and extraction

Bladder lichen ( Hypogymnia physodes )

Olivetol occurs with a share of up to 2.6% in the bladder lichen ( Hypogymnia physodes ). It is also found as a pheromone in various insect species.

Chemical properties

Since olivetol is weakly acidic due to the phenolic hydroxyl groups , it can be dissolved in basic solvents.

use

Olivetol is used in various perfumes by using the lichen extract.

By condensation of pulegone and olivetol can be tetrahydrocannabinol synthesize. Olivetolic acid (the carboxylic acid derivative of olivetol) occurs in the biosynthesis of hexahydrocannabinol.

Individual evidence

^ Robert Turkington: Chemicals Used for Illegal Purposes . John Wiley & Sons, 2009, ISBN 978-0-470-18780-7 , pp. 436 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d data sheet Olivetol, 95% from Sigma-Aldrich , accessed on June 21, 2015 ( PDF ).
^ Igor Stojanovic, Niko Radulovic, Tatjana Mitrovic, Slavisa Stamenkovic, Gordana Stojanovic: Volatile constituents of selected Parmeliaceae lichens . In: Journal of the Serbian Chemical Society . tape 76 , no. 7 , 2011, p. 987 , doi : 10.2298 / JSC101004087S .
↑ U. Claussen, P. Mummenhoff, F. Korte: Haschisch — XVIII . In: Tetrahedron . tape 24 , no. January 7 , 1968, p. 2897 , doi : 10.1016 / s0040-4020 (01) 98697-1 .

^ Raj K. Razdan: Total Synthesis of Natural Products . Ed .: John ApSimon. John Wiley & Sons, 1981, ISBN 978-0-470-12967-8 , The Total Synthesis of Cannabinoids, pp. 185–262 , doi : 10.1002 / 9780470129678.ch2 ( PDF ). PDF ( Memento of the original from June 21, 2015 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2

[Robert_Turkington-1] Robert Turkington: Chemicals Used for Illegal Purposes . John Wiley & Sons, 2009, ISBN 978-0-470-18780-7 , pp. 436 ( limited preview in Google Book search).

[Sigma-2] ta sheet Olivetol, 95% from Sigma-Aldrich , accessed on June 21, 2015 ( PDF ).

[3] Igor Stojanovic, Niko Radulovic, Tatjana Mitrovic, Slavisa Stamenkovic, Gordana Stojanovic: Volatile constituents of selected Parmeliaceae lichens . In: Journal of the Serbian Chemical Society . tape 76 , no. 7 , 2011, p. 987 , doi : 10.2298 / JSC101004087S .

[4] U. Claussen, P. Mummenhoff, F. Korte: Haschisch — XVIII . In: Tetrahedron . tape 24 , no. January 7 , 1968, p. 2897 , doi : 10.1016 / s0040-4020 (01) 98697-1 .

[5] Raj K. Razdan: Total Synthesis of Natural Products . Ed .: John ApSimon. John Wiley & Sons, 1981, ISBN 978-0-470-12967-8 , The Total Synthesis of Cannabinoids, pp. 185–262 , doi : 10.1002 / 9780470129678.ch2 ( PDF ). PDF ( Memento of the original from June 21, 2015 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2