Incensol

Structural formula
General
Surname	Incensol
other names	(1 R , 2 S , 5 E , 9 E , 12 S ) -1,5,9-trimethyl-12-propan-2-yl-15-oxabicyclo [10.2.1] pentadeca-5,9-diene-2 -ol ( IUPAC )
Molecular formula	C 20 H 34 O 2
External identifiers / databases
PubChem	44583885
ChemSpider	24708200
Wikidata	Q1660941
properties
Molar mass	306.48 g mol −1
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 .

Incensol is like his O -acetyliertes derivative Incensolacetat a Cembranoid - diterpene with antidepressant and anxiolytic effect.

Occurrence

Resin escaping from Boswellia sacra

Incensol is contained in the resin of Boswellia sacra known as frankincense to an average of 2.7%.

In the incense resin of the species Boswellia papyrifera , the incensol and its acetate can even make up a total content of up to 10% and more. According to the current state of knowledge, incensol acetate, the actually bioactive derivative, seems to be produced biosynthetically in significant quantities by this species. Other species such as Boswellia serrata , Boswellia carterii and the Arabic variant of it, Boswellia sacra , have incensol, but its acetate could not be found in these varieties.

In a traditional resin from the monastic republic of Mount Athos , incensol and incensol acetate as well as incensol oxide and incensol oxide acetate were detected, which allowed the identification of Boswellia papyrifera as the starting material.

Effects

The anxiolysis is based on the pro-GABAergic effect of the cembranoids on the GABA _A receptor.

Incensol acetate is an agonist of the TRPV3 receptor , which is responsible for the sensation of warmth in the skin. The effect in the brain, in which these receptors are also present, has not yet been clarified. At least on wild mice it has an effect similar to that of antidepressants and anxiolytics. There was no effect in genetically modified mice without a TRPV3 receptor.

It is believed that the psychoactive effects of Incensol and its derivatives one of the reasons for the different religions widespread cult is using.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Hager's Handbook of Pharmaceutical Practice. ( limited preview in Google Book search)
^ M. Paul, J. Jauch: Efficient preparation of incensole and incensole acetate, and quantification of these bioactive diterpenes in Boswellia papyrifera by a RP-DAD-HPLC method. In: Nat Prod Commun. 7 (3), Mar 2012, pp. 283-288, PMID 22545396 .
^ M. Paul: Chemotaxonomic Investigations on Resins of the Frankincense Species Boswellia papyrifera, Boswellia serrata and Boswellia sacra, respectively, Boswellia carterii: A Qualitative and Quantitative Approach by Chromatographic and Spectroscopic Methodology. (PDF; 3.5 MB) Dissertation . Saarland University, 2012.
↑ M. Paul, G. Brüning, J. Bergmann, J. Jauch: A thin-layer chromatography method for the identification of three different olibanum resins (Boswellia serrata, Boswellia papyrifera and Boswellia carterii, respectively, Boswellia sacra). In: Phytochem Anal . 23 (2), Mar-Apr 2012, pp. 184-189, doi: 10.1002 / pca.1341 , PMID 21858880 .
^ Maria Perla Colombini, Francesca Modugno: Organic Mass Spectrometry in Art and Archeology. Wiley 2009, ISBN 978-0-470-51703-1 . ( limited preview in Google Book search).
↑ Al-Harrasi A, Khan A, Rehman NU, Al-Shidhani S, Karim N, Khan I, Halim SA, Al-Rawahi A, Hussain J, Csuk R: Evidence for the involvement of a GABAergic mechanism in the effectiveness of natural and synthetically modified incensole derivatives in neuropharmacological disorders: A computational and pharmacological approach . In: Phytochemistry . 163, 2019, pp. 58-74. doi : 10.1016 / j.phytochem.2019.04.007 . PMID 31015070 .
^ A. Moussaieff et al .: Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain. In: The Federation of American Societies for Experimental Biology Journal. No. 22 (8), 2008, pp. 3024-3034, PMID 18492727 .
↑ F. Rötzer: Frankincense is a psychoactive drug. In: Telepolis . May 23, 2008.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] Hager's Handbook of Pharmaceutical Practice. ( limited preview in Google Book search)

[3] M. Paul, J. Jauch: Efficient preparation of incensole and incensole acetate, and quantification of these bioactive diterpenes in Boswellia papyrifera by a RP-DAD-HPLC method. In: Nat Prod Commun. 7 (3), Mar 2012, pp. 283-288, PMID 22545396 .

[4] M. Paul: Chemotaxonomic Investigations on Resins of the Frankincense Species Boswellia papyrifera, Boswellia serrata and Boswellia sacra, respectively, Boswellia carterii: A Qualitative and Quantitative Approach by Chromatographic and Spectroscopic Methodology. (PDF; 3.5 MB) Dissertation . Saarland University, 2012.

[5] M. Paul, G. Brüning, J. Bergmann, J. Jauch: A thin-layer chromatography method for the identification of three different olibanum resins (Boswellia serrata, Boswellia papyrifera and Boswellia carterii, respectively, Boswellia sacra). In: Phytochem Anal . 23 (2), Mar-Apr 2012, pp. 184-189, doi: 10.1002 / pca.1341 , PMID 21858880 .

[6] Maria Perla Colombini, Francesca Modugno: Organic Mass Spectrometry in Art and Archeology. Wiley 2009, ISBN 978-0-470-51703-1 . ( limited preview in Google Book search).

[pmid31015070-7] Al-Harrasi A, Khan A, Rehman NU, Al-Shidhani S, Karim N, Khan I, Halim SA, Al-Rawahi A, Hussain J, Csuk R: Evidence for the involvement of a GABAergic mechanism in the effectiveness of natural and synthetically modified incensole derivatives in neuropharmacological disorders: A computational and pharmacological approach . In: Phytochemistry . 163, 2019, pp. 58-74. doi : 10.1016 / j.phytochem.2019.04.007 . PMID 31015070 .

[8] A. Moussaieff et al .: Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain. In: The Federation of American Societies for Experimental Biology Journal. No. 22 (8), 2008, pp. 3024-3034, PMID 18492727 .

[9] F. Rötzer: Frankincense is a psychoactive drug. In: Telepolis . May 23, 2008.