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
(13S)-9α,13-Epoxy-8α-labdane-3β,15,16,18-tetrol
Systematic IUPAC name
(1R,2R,4aS,5R,5′S,6S)-5′-(2-Hydroxyethyl)-5,5′-bis(hydroxymethyl)-2,5,8a-trimethyloctahydro-2H-spiro[naphthalene-1,2′-oxolan]-6-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • C[C@@]1(CO)[C@@H](O)CC[C@@]2(C)[C@]([H])1CC[C@@H](C)[C@]32O[C@](CO)(CCO)CC3
Properties
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.
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