Lagochilin

Lagochilin
Names

IUPAC name (6S,2R)-2,12-bis(hydroxymethyl)-12-(2-hydroxyethyl)-2,6,8-trimethylspiro[bicyc lo[4.4.0]decane-7,5'-oxolane]-3-ol
Identifiers
CAS Registry Number	23554-81-6^Y
ChemSpider	5417062^N
InChI InChI=1S/C20H36O5/c1-14-4-5-15-17(2,12-22)16(24)6-7-18(15,3)20(14)9-8-19(13-23,25-20)10-11-21/h14-16,21-24H,4-13H2,1-3H3/t14-,15+,16+,17+,18+,19+,20-/m1/s1^N Key: XYPPDQHBNJURHU-IPOQXWOTSA-N^N InChI=1/C20H36O5/c1-14-4-5-15-17(2,12-22)16(24)6-7-18(15,3)20(14)9-8-19(13-23,25-20)10-11-21/h14-16,21-24H,4-13H2,1-3H3/t14-,15+,16+,17+,18+,19+,20-/m1/s1 Key: XYPPDQHBNJURHU-IPOQXWOTBH
Jmol-3D images	Image
PubChem	7061097
SMILES C[C@@]1(CO)[C@@H](O)CC[C@@]2(C)[C@]([H])1CC[C@@H](C)[C@]32O[C@](CO)(CCO)CC3
Properties
Chemical formula	C₂₀H₃₆O₅
Molar mass	356.495 g/mol
Appearance	Light grey crystalline solid
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Lagochilin is a bitter diterpene that forms a grey crystalline solid. It is found in various plants from the genus Lagochilus, most notably Lagochilus inebrians, and is thought to be responsible for the sedative, hypotensive and hemostatic effects of this plant.^[1]^[2]^[3]^[4]

References

↑ Pulatova, TP; Khazanovich, RL (1962). "On the alkaloid content of some Lagochilus species and on the nature of lagochiline". Aptechnoe delo 6: 29–32. PMID 13972488.
↑ Mavlyankulova ZI, Zainutdinov UN, Mukhamedkhanov SI, Leont'ev VD, Aslanov Kh.A, Khimiya Prirodnykh Soedinenii. 1980;1:46.
↑ Chizhov, O. S.; Kessenikh, A. V.; Yakovlev, I. P.; Zolotarev, B. M.; Petukhov, V. A.; Zelinskii, N. D. (1969). "Structure of lagochilin". Tetrahedron Letters 10 (17): 1361–1364. doi:10.1016/S0040-4039(01)87886-2.
↑ Chizhov, O. S.; Kessenikh, A. V.; Yakovlev, I. P.; Zolotarev, B. M.; Petukhov, V. A. (1970). "The structure of lagochilin". Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 19 (9): 1866–1972. doi:10.1007/BF00849762.