Incensole

Incensole
Names
	IUPAC name (1R,2R,5E,9Z)-1,5,9-trimethyl-12-propan-2-yl-15-oxabicyclo[10.2.1]pentadeca-5,9-dien-2-ol
Identifiers
CAS Number	22419-74-5;
3D model (JSmol)	Interactive image;
ChemSpider	57579845;
PubChem CID	102004667;
	InChI InChI=1S/C20H34O2/c1-15(2)20-12-11-17(4)8-6-7-16(3)9-10-18(21)19(5,22-20)13-14-20/h7,11,15,18,21H,6,8-10,12-14H2,1-5H3/b16-7+,17-11-/t18-,19-,20?/m1/s1 Key: SSBZLMMXFQMHDP-AWBFOCMTSA-N;
	SMILES CC1=CCCC(=CCC2(CCC(O2)(C(CC1)O)C)C(C)C)C;
Properties
Chemical formula	C20H34O2
Molar mass	306.490 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Insensole is an organic compound that is naturally found as its acetate ester in some frankincense. It is a diterpene alcohol, with an oily appearance.[1] This compound can be synthetically prepared from cembrene.[2]

The formula of insensole is C₂₀H₃₄O₂[3]

Incensole acetate is the O-acetyl derivative.[4] It acts as a TRPV3 agonist.[5] Its effects on animals have been studied.[6]

References

Corsano S, Nicoletti R (January 1967). "The structure of incensole". Tetrahedron. 23 (4): 1977–1984. doi:10.1016/S0040-4020(01)82601-6.
Strappaghetti G, Proietti G, Corsano S, Grgurina I (March 1982). "Synthesis of incensole". Bioorganic Chemistry. 11 (1): 1–3. doi:10.1016/0045-2068(82)90042-6. ISSN 0045-2068.
"Insensole". PubChem.
"Incensole acetate". NIST.
Moussaieff A, Rimmerman N, Bregman T, Straiker A, Felder CC, Shoham S, et al. (August 2008). "Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain". FASEB Journal. 22 (8): 3024–34. doi:10.1096/fj.07-101865. PMC 2493463. PMID 18492727.
Moussaieff A, Gross M, Nesher E, Tikhonov T, Yadid G, Pinhasov A (December 2012). "Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals". Journal of Psychopharmacology. 26 (12): 1584–93. doi:10.1177/0269881112458729. PMID 23015543.

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[1] Corsano S, Nicoletti R (January 1967). "The structure of incensole". Tetrahedron. 23 (4): 1977–1984. doi:10.1016/S0040-4020(01)82601-6.

[StrappaghettiProietti1982-2] Strappaghetti G, Proietti G, Corsano S, Grgurina I (March 1982). "Synthesis of incensole". Bioorganic Chemistry. 11 (1): 1–3. doi:10.1016/0045-2068(82)90042-6. ISSN 0045-2068.

[PCh-3] "Insensole". PubChem.

[NIST-4] "Incensole acetate". NIST.

[pmid18492727-5] Moussaieff A, Rimmerman N, Bregman T, Straiker A, Felder CC, Shoham S, et al. (August 2008). "Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain". FASEB Journal. 22 (8): 3024–34. doi:10.1096/fj.07-101865. PMC 2493463. PMID 18492727.

[6] Moussaieff A, Gross M, Nesher E, Tikhonov T, Yadid G, Pinhasov A (December 2012). "Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals". Journal of Psychopharmacology. 26 (12): 1584–93. doi:10.1177/0269881112458729. PMID 23015543.