Perrottetinene

Perrottetinene

Systematic (IUPAC) name
(6aS,10aR)- 6,6,9-trimethyl- 3-(2-phenylethyl)- 6a,7,8,10a-tetrahydrobenzo[c]chromen- 1-ol
Identifiers
CAS Number	160041-34-9
ATC code	none
PubChem	CID 24766094
ChemSpider	28284856
Chemical data
Formula	C24H28O2
Molar mass	348.477 g/mol
SMILES CC1=C[C@H]2c3c(cc(cc3OC([C@H]2CC1)(C)C)CCc4ccccc4)O
InChI InChI=1S/C24H28O2/c1-16-9-12-20-19(13-16)23-21(25)14-18(15-22(23)26-24(20,2)3)11-10-17-7-5-4-6-8-17/h4-8,13-15,19-20,25H,9-12H2,1-3H3/t19-,20+/m1/s1 Key:DYHMKBLKWFFFSZ-UXHICEINSA-N
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Perrottetinene is a naturally occurring cannabinoid compound found in the New Zealand liverwort plant Radula marginata and other species from the Radula genus,^[1] along with a number of similar compounds. Its chemical structure closely resembles that of THC, the main active component of marijuana, and it is thought that perrottetinene may also be an active cannabinoid agonist although detailed pharmacological investigation of the compound has yet to be reported.^[2][3] Stereoselective synthesis of perrottinene has also been carried out to investigate the activity of its different enantiomers.^[4]

References

1. Cullmann F, Becker H. Prenylated bibenzyls from the liverwort Radula laxiramea. Zeitschrift für Naturforschung. 1999; 54(3-4): 147-150. ISSN 0939-5075
2. Toyota, Masao; Kinugawa, Tomohide; Asakawa, Yoshinoiu (1994). "Bibenzyl cannabinoid and bisbibenzyl derivative from the liverwort Radula perrottetii". Phytochemistry 37 (3): 859. doi:10.1016/S0031-9422(00)90371-6.
3. Toyota, Masao; Shimamura, Takuji; Ishii, Hikari; Renner, Matt; Braggins, John; Asakawa, Yoshinori (2002). "New Bibenzyl Cannabinoid from the New Zealand Liverwort Radula marginata". Chemical & Pharmaceutical Bulletin 50 (10): 1390. doi:10.1248/cpb.50.1390.
4. Song, Yanling; Hwang, Soonho; Gong, Ping; Kim, Deukjoon; Kim, Sanghee (2008). "Stereoselective Total Synthesis of (−)-Perrottetinene and Assignment of Its Absolute Configuration". Organic Letters 10 (2): 269. doi:10.1021/ol702692q. PMID 18085788.