(-) - α-bisabolol

Structural formula
	(-) - α-bisabolol
General
Surname	(-) - α-bisabolol
other names	(2 S ) -6-Methyl-2 - [(1 S ) -4-methylcyclohex-3-en-1-yl] hept-5-en-2-ol; Levomenol ( INN ); BISABOLOL ( INCI ) ;
Molecular formula	C 15 H 26 O
Brief description	light yellow liquid
External identifiers / databases
EC number	245-423-3
ECHA InfoCard	100.041.279
PubChem	442343
DrugBank	DB13153
Wikidata	Q179896
properties
Molar mass	222.37 g · mol -1
Physical state	liquid
density	0.929 g cm −3
solubility	soluble in ethanol , insoluble in water
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 .

(-) - α-Bisabolol (synonym: Levomenol ) describes a chemical compound from the series of isomeric bisabolols . There is a monocyclic sesquiterpene - alcohol .

Natural occurrence

Roman chamomile ( Chamaemelum nobile )

(-) - α-Bisabolol is the main component of chamomile oil , which is obtained from the real chamomile ( Matricaria chamomilla ), which is traditionally used as a medicinal plant .

Originally from Spain coming Manzana chamomile , a cultivated form, contains particularly large quantities of Bisabolol (up to 45% of the essential oil) and is therefore now also in countries such as France , Germany and the United States cultivated.

Propolis made by bees can also contain considerable amounts of bisabolol - up to approx. 20% in Chinese / Mongolian propolis.

synthesis

Enantiomerically pure (-) - α-bisabolol is usually obtained from natural sources, although synthetic routes to (-) - α-bisabolol are known; these are often based on nerolidol .

Racemic α-bisabolol, which is also used, is mostly of synthetic origin.

Analytics

For reliable qualitative and quantitative determination of (-) - α-bisabolol, the coupling of gas chromatography with mass spectrometry can be used after adequate sample preparation . Using headspace analysis , these methods are also suitable for detection in various body fluids such as B. blood, urine or tissue samples and faeces .

properties

(-) - α-Bisabolol is a colorless to slightly yellowish, viscous liquid that is insoluble in water, but easily soluble in alcohols and oils. Their smell is described as slightly flowery-sweet.

Effect and use

Bisabolol has an anti-inflammatory effect on the skin and mucous membranes, it is used for skin regeneration and wound healing, for example after burns or sunburn.

These effects have been described both for the enantiomerically pure natural product and for the synthetically accessible racemate.

Web links

Entry for bisabolols in the Consumer Product Information Database

Individual evidence

↑ Entry on BISABOLOL in the CosIng database of the EU Commission, accessed on December 28, 2019.
↑ ^a ^b ^c ^d data sheet (-) - α-bisabolol from Sigma-Aldrich , accessed on July 17, 2016 ( PDF ).
↑ ^a ^b ^c ^d ^e Entry on (-) - α-bisabolol. In: Römpp Online . Georg Thieme Verlag, accessed on July 17, 2016.
^ Rolf Franke, Heinz Schilcher (ed.): Chamomile. Industrial Profiles (= Medicinal and aromatic Plants - Industrial Profiles. Volume 42). CRC Press, New York NY et al. 2005, ISBN 0-415-33463-2 .
↑ Yu-Xin Fu, Yuan-Jun Xu, Bin Chen, Yan Li, Li-Ping Luo: Analysis of Volatile Components from Inner Mongolia Propolis by Gas Chromatography-Mass Spectrometry. In: Chinese Journal of Analytical Chemistry. 37 (5), 2009, pp. 745-748.
↑ Patent DE10246038 : Process for the production of alpha-bisabolol from nerolidol. Published on April 15, 2004 , inventor: Wilhelm Dr. Pickenhagen, Dietmar Schatkowski. ‌
↑ M. Ghasemi, N. Babaeian Jelodar, M. Modarresi, N. Bagheri, A. Jamali: Increase of Chamazulene and α-Bisabolol Contents of the Essential Oil of German Chamomile (Matricaria chamomilla L.) Using Salicylic Acid Treatments under Normal and Heat Stress Conditions. In: Foods. 5 (3), Aug 27, 2016. PMID 28231151
↑ ES Chernetsova, AN Shikov, EA Crawford, S. Grashorn, I. Laakso, ON Pozharitskaya, VG Makarov, R. Hiltunen, B. Galambosi, GE Morlock: Characterization of volatile and semi-volatile compounds in green and fermented leaves of Bergenia crassifolia L. by gas chromatography-mass spectrometry and ID-CUBE direct analysis in real time-high resolution mass spectrometry. In: Eur J Mass Spectrom (Chichester). 20 (2), 2014, pp. 199-205. PMID 24895781
↑ L. Perbellini, R. Gottardo, A. Caprini, F. Bortolotti, S. Mariotto, F. Tagliaro: Determination of alpha-bisabolol in human blood by micro-HPLC-ion trap MS and head space-GC-MS methods. In: J Chromatogr B Analyt Technol Biomed Life Sci. 812 (1-2), Dec 5, 2004, pp. 373-377. PMID 15556509
↑ Ernst Luppold: Matricaria chamomilla - an old and new medicinal plant. In: Pharmacy in our time. 13, 1984, p. 65, doi: 10.1002 / pauz.19840130301 .

[CosIng-1] Entry on BISABOLOL in the CosIng database of the EU Commission, accessed on December 28, 2019.

[sigma-2] ta sheet (-) - α-bisabolol from Sigma-Aldrich , accessed on July 17, 2016 ( PDF ).

[Römpp-3] Entry on (-) - α-bisabolol. In: Römpp Online . Georg Thieme Verlag, accessed on July 17, 2016.

[franke-4] Rolf Franke, Heinz Schilcher (ed.): Chamomile. Industrial Profiles (= Medicinal and aromatic Plants - Industrial Profiles. Volume 42). CRC Press, New York NY et al. 2005, ISBN 0-415-33463-2 .

[5] Yu-Xin Fu, Yuan-Jun Xu, Bin Chen, Yan Li, Li-Ping Luo: Analysis of Volatile Components from Inner Mongolia Propolis by Gas Chromatography-Mass Spectrometry. In: Chinese Journal of Analytical Chemistry. 37 (5), 2009, pp. 745-748.

[6] Patent DE10246038 : Process for the production of alpha-bisabolol from nerolidol. Published on April 15, 2004 , inventor: Wilhelm Dr. Pickenhagen, Dietmar Schatkowski. ‌

[7] M. Ghasemi, N. Babaeian Jelodar, M. Modarresi, N. Bagheri, A. Jamali: Increase of Chamazulene and α-Bisabolol Contents of the Essential Oil of German Chamomile (Matricaria chamomilla L.) Using Salicylic Acid Treatments under Normal and Heat Stress Conditions. In: Foods. 5 (3), Aug 27, 2016. PMID 28231151

[8] ES Chernetsova, AN Shikov, EA Crawford, S. Grashorn, I. Laakso, ON Pozharitskaya, VG Makarov, R. Hiltunen, B. Galambosi, GE Morlock: Characterization of volatile and semi-volatile compounds in green and fermented leaves of Bergenia crassifolia L. by gas chromatography-mass spectrometry and ID-CUBE direct analysis in real time-high resolution mass spectrometry. In: Eur J Mass Spectrom (Chichester). 20 (2), 2014, pp. 199-205. PMID 24895781

[9] L. Perbellini, R. Gottardo, A. Caprini, F. Bortolotti, S. Mariotto, F. Tagliaro: Determination of alpha-bisabolol in human blood by micro-HPLC-ion trap MS and head space-GC-MS methods. In: J Chromatogr B Analyt Technol Biomed Life Sci. 812 (1-2), Dec 5, 2004, pp. 373-377. PMID 15556509

[10] Ernst Luppold: Matricaria chamomilla - an old and new medicinal plant. In: Pharmacy in our time. 13, 1984, p. 65, doi: 10.1002 / pauz.19840130301 .