Incensole: Difference between revisions

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

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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.{{cite journal}}: CS1 maint: year (link)
^ 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.{{cite journal}}: CS1 maint: year (link)
^ "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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ 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.{{cite journal}}: CS1 maint: year (link)

[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.{{cite journal}}: CS1 maint: year (link)

[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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[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.

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-'''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.<ref>{{cite journal| doi=10.1016/S0040-4020(01)82601-6 | volume=23 | issue=4 | title=The structure of incensole | year=1967 | journal=Tetrahedron | pages=1977–1984 | last1 = Corsano | first1 = S. | last2 = Nicoletti | first2 = R.}}</ref> This compound can be synthetically prepared from [[cembrene]].<ref name="StrappaghettiProietti1982">{{cite journal|last1=Strappaghetti|first1=G.|last2=Proietti|first2=G.|last3=Corsano|first3=S.|last4=Grgurina|first4=I.|title=Synthesis of incensole|journal=Bioorganic Chemistry|volume=11|issue=1|year=1982|pages=1–3|issn=00452068|doi=10.1016/0045-2068(82)90042-6}}</ref>
+'''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.<ref>{{cite journal | vauthors = Corsano S, Nicoletti R | doi=10.1016/S0040-4020(01)82601-6 | volume=23 | issue=4 | title=The structure of incensole | year = January 1967 | journal=Tetrahedron | pages=1977–1984 }}</ref> This compound can be synthetically prepared from [[cembrene]].<ref name="StrappaghettiProietti1982">{{cite journal| vauthors = Strappaghetti G, Proietti G, Corsano S, Grgurina I |title=Synthesis of incensole|journal=Bioorganic Chemistry|volume=11|issue=1|year= March 1982 |pages=1–3|issn=00452068|doi=10.1016/0045-2068(82)90042-6}}</ref>
-The formula of insensole is C<sub>20</sub>H<sub>34</sub>O<sub>2</sub><ref name=PCh>[https://pubchem.ncbi.nlm.nih.gov/compound/102004667 Insensole (at PubChem)]</ref>
+The formula of insensole is C<sub>20</sub>H<sub>34</sub>O<sub>2</sub><ref name=PCh>{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/compound/102004667 | title = Insensole | work = PubChem }}</ref>
-'''Incensole acetate''' is the O-[[acetyl]] derivative.<ref name=NIST>[http://webbook.nist.gov/cgi/inchi?ID=C34701536&Mask=2000 Incensole acetate (@NIST)]</ref> It acts as a [[TRPV3]] agonist.<ref>Moussaieff A, Rimmerman N, Bregman T, Straiker A, Felder CC, Shoham S, Kashman Y, Huang SM, Lee H, Shohami E, Mackie K, Caterina MJ, Walker JM, Fride E, Mechoulam R. Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain. ''FASEB J''. 2008 Aug;22(8):3024-34. {{doi|10.1096/fj.07-101865}} {{pmid|18492727}}</ref> Its effects on animals have been studied.<ref>{{cite journal |doi=10.1177/0269881112458729 |title=Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals |year=2012 |last1=Moussaieff |first1=A |last2=Gross |first2=M |last3=Nesher |first3=E |last4=Tikhonov |first4=T |last5=Yadid |first5=G |last6=Pinhasov |first6=A |journal=J. Psychopharmacol. |volume=26 |issue=12 |pmid=23015543 |pages=1584–93}}</ref>
+'''Incensole acetate''' is the O-[[acetyl]] derivative.<ref name=NIST>{{cite web | url = http://webbook.nist.gov/cgi/inchi?ID=C34701536&Mask=2000 | title = Incensole acetate | work = NIST }}</ref> It acts as a [[TRPV3]] agonist.<ref name="pmid18492727">{{cite journal | vauthors = Moussaieff A, Rimmerman N, Bregman T, Straiker A, Felder CC, Shoham S, Kashman Y, Huang SM, Lee H, Shohami E, Mackie K, Caterina MJ, Walker JM, Fride E, Mechoulam R | display-authors = 6 | title = Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain | journal = FASEB Journal | volume = 22 | issue = 8 | pages = 3024–34 | date = August 2008 | pmid = 18492727 | pmc = 2493463 | doi = 10.1096/fj.07-101865 }}</ref> Its effects on animals have been studied.<ref>{{cite journal | vauthors = Moussaieff A, Gross M, Nesher E, Tikhonov T, Yadid G, Pinhasov A | title = Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals | journal = Journal of Psychopharmacology | volume = 26 | issue = 12 | pages = 1584–93 | date = December 2012 | pmid = 23015543 | doi = 10.1177/0269881112458729 }}</ref>
-==References==
+== References ==
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 [[Category:Oxygen heterocycles]]
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