Cubebol

Structural formula
General
Surname	Cubebol
other names	(-) - Cubebol; Cubebe camphor; (-) - (1 R , 4 S , 5 R , 6 R , 7 S , 10 R ) -7-Isopropyl-4,10-dimethyl-tricyclo [4.4.0.0 1,5 ] decan-4-ol; FEMA 4497 ;
Molecular formula	C 15 H 26 O
Brief description	colorless solid
External identifiers / databases
PubChem	11276107
ChemSpider	9451107
Wikidata	Q726875
properties
Molar mass	222.37 g mol −1
Physical state	firmly
Melting point	61 to 62 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cubebol is a sesquiterpene and is the main component of the essential oil of cubeb pepper ( Piper cubeba ).

Occurrence

Cubeb pepper

Extraction and synthesis

This was already distilled from cubeb oil before the 1950s. Cubebol can be obtained from cubeb oil. Alternatively, it can be made synthetically. A. Yohshikoshi succeeded in the first total synthesis of Cubebol.

use

The essential oil with the main component Cubebol can only be used for a few areas of application due to its bitter taste. The purified Cubebol, on the other hand, has a cooling stimulus effect that is effective for up to 30 minutes and starts approx. 2 minutes after consumption. Because it has been included in the GRAS list and has a low smell or taste, it can be used in numerous areas. Some possible application examples would be soft drinks, dental hygiene or confectionery. The patent rights for use as a flavoring substance in Europe and the USA have been with Firmenich since 2000 and 2001 respectively .

Individual evidence

^ Entry on FEMA 4497 in the database of the Flavor and Extract Manufacturers Association of the United States .
↑ entry Cubebol at The Good Scents Company , accessed on November 7 2017th
↑ George Gerald Henderson , John Monteath Robertson: CCCLXXIII. — The chemistry of cadinene. Part II. Compounds related to cadinene. In: J. Chem. Soc. 129, 1926, pp. 2811-2816, doi: 10.1039 / JR9262902811 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Hodgson, DM; Salik, S .; Fox, DJ: Stereocontrolled Syntheses of (-) - Cubebol and (-) - 10-Epicubebol Involving Intramolecular Cyclopropanation of α-Lithiated Epoxides. In: The Journal of Organic Chemistry. , Volume 75, No. 7, 2010, pp. 2157-2168.
^ E. Guenther: The Constituents of Essentials Oils. , D. Van Nostrand Company Inc., Volume 2, 1949, pp. 287ff.
↑ ^a ^b Patent EP1040765 : Use of Cubebol as a flavoring substance. Published on April 10, 2000 , inventor: Velazco Maria Ines Wuensche Laurent Deladoey Patrice. ‌
↑ J. Heck, B. König & R. Winter (eds.): Fragrances, between stink and scent . Wolfgang Legrum, Springer Spektrum, Marburg 2013, ISBN 978-3-658-07310-7 , e-book, p. 20.

[FEMA4497-1] Entry on FEMA 4497 in the database of the Flavor and Extract Manufacturers Association of the United States .

[2] try Cubebol at The Good Scents Company , accessed on November 7 2017th

[Henderson-3] George Gerald Henderson , John Monteath Robertson: CCCLXXIII. — The chemistry of cadinene. Part II. Compounds related to cadinene. In: J. Chem. Soc. 129, 1926, pp. 2811-2816, doi: 10.1039 / JR9262902811 .

[NV-4] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Hodgson-5] Hodgson, DM; Salik, S .; Fox, DJ: Stereocontrolled Syntheses of (-) - Cubebol and (-) - 10-Epicubebol Involving Intramolecular Cyclopropanation of α-Lithiated Epoxides. In: The Journal of Organic Chemistry. , Volume 75, No. 7, 2010, pp. 2157-2168.

[Guenther-6] E. Guenther: The Constituents of Essentials Oils. , D. Van Nostrand Company Inc., Volume 2, 1949, pp. 287ff.

[DE-Patent1-7] Patent EP1040765 : Use of Cubebol as a flavoring substance. Published on April 10, 2000 , inventor: Velazco Maria Ines Wuensche Laurent Deladoey Patrice. ‌

[Heck-8] J. Heck, B. König & R. Winter (eds.): Fragrances, between stink and scent . Wolfgang Legrum, Springer Spektrum, Marburg 2013, ISBN 978-3-658-07310-7 , e-book, p. 20.