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;
CompTox Dashboard (EPA)	DTXSID401318606 ;
	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] Its effects on animals have been studied.^[5]

References

^ Corsano, S.; Nicoletti, R. (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. (1982). "Synthesis of incensole". Bioorganic Chemistry. 11 (1): 1–3. doi:10.1016/0045-2068(82)90042-6. ISSN 0045-2068.
^ Insensole (at PubChem)
^ Incensole acetate (@NIST)
^ Moussaieff, A; Gross, M; Nesher, E; Tikhonov, T; Yadid, G; Pinhasov, A (2012). "Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals". J. Psychopharmacol. 26 (12): 1584–93. doi:10.1177/0269881112458729. PMID 23015543.

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[1] Corsano, S.; Nicoletti, R. (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. (1982). "Synthesis of incensole". Bioorganic Chemistry. 11 (1): 1–3. doi:10.1016/0045-2068(82)90042-6. ISSN 0045-2068.

[PCh-3] Insensole (at PubChem)

[NIST-4] Incensole acetate (@NIST)

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

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