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 Number	23554-81-6
3D model (Jmol)	Interactive image
ChemSpider	5417062
PubChem	7061097
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 Key: XYPPDQHBNJURHU-IPOQXWOTSA-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
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

1. 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.
2. Mavlyankulova ZI, Zainutdinov UN, Mukhamedkhanov SI, Leont'ev VD, Aslanov Kh.A, Khimiya Prirodnykh Soedinenii. 1980;1:46.
3. 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.
4. 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.