Lactucin

Chemical compound From Wikipedia, the free encyclopedia

Lactucin is a bitter substance that forms a white crystalline solid and belongs to the group of sesquiterpene lactones. It is found in some varieties of lettuce and is an ingredient of lactucarium. It is also found in dandelion coffee. It has been shown to have analgesic and sedative properties,[1] which are speculated to occur via modulation of the GABAA receptor,[2] as well as antimalarial activity.[3]

Quick facts Names, Identifiers ...
Lactucin
Names
Preferred IUPAC name
(3aR,4S,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.440.674 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12-,13+,14+/m1/s1 ☒N
    Key: VJQAFLAZRVKAKM-QQUHWDOBSA-N ☒N
  • InChI=1/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12-,13+,14+/m1/s1
    Key: VJQAFLAZRVKAKM-QQUHWDOBBA
  • CC1=C2[C@@H]([C@@H]3[C@@H]([C@@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)CO
Properties
C15H16O5
Molar mass 276.28 g/mol
Appearance White 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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