Lagochilin

Last updated
Lagochilin
Lagochilin.png
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
PubChem CID
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 X mark.svgN
    Key: XYPPDQHBNJURHU-IPOQXWOTSA-N X mark.svgN
  • 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
AppearanceLight grey crystalline solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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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.