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
3D model (JSmol)
ChemSpider
  • 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
  • CC1=CCCC(=CCC2(CCC(O2)(C(CC1)O)C)C(C)C)C
Properties
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

  1. ^ Corsano S, Nicoletti R (January 1967). "The structure of incensole". Tetrahedron. 23 (4): 1977–1984. doi:10.1016/S0040-4020(01)82601-6.
  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.
  3. ^ "Insensole". PubChem.
  4. ^ "Incensole acetate". NIST.
  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.