Lagochilin

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]

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 (JSmol)	Interactive image
ChemSpider	5417062
PubChem CID	7061097
CompTox Dashboard (EPA)	DTXSID30392905
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

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 KA (1980). "Investigation of the Lagochiline Acetylation Reaction". Khimiya Prirodnykh Soedinenii. 1: 46–9.
3. Chizhov OS, Kessenikh AV, Yakovlev IP, Zolotarev BM, Petukhov VA, Zelinsky ND (January 1969). "Structure of lagochilin". Tetrahedron Letters. 10 (17): 1361–1364. doi:10.1016/S0040-4039(01)87886-2.
4. Chizhov OS, Kessenikh AV, Yakovlev IP, Zolotarev BM, Petukhov VA (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.