Lactucin

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
CAS Number
  • 1891-29-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:6358 ☒N
ChemSpider
  • 717609 ☒N
KEGG
  • C09489 ☒N
PubChem CID
  • 821383
UNII
  • R6E2918904 checkY
CompTox Dashboard (EPA)
  • DTXSID70894751 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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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Infobox references
Chemical compound

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 has been shown to have analgesic and sedative properties[1] which are speculated to occur via modulation of the GABAA receptor.[2] It has also shown some antimalarial effects.[3] It is also found in dandelion coffee.

See also

References

  1. ^ Wesołowska A, Nikiforuk A, Michalska K, Kisiel W, Chojnacka-Wójcik E (2006). "Analgesic and Sedative Activities of Lactucin and some Lactucin-Like Guaianolides in Mice". Journal of Ethnopharmacology. 107 (2): 254–258. doi:10.1016/j.jep.2006.03.003. PMID 16621374.
  2. ^ Kim H, Suh H, Choi H, Hong K, Jo K (2019). "Effectiveness of the Sleep Enhancement by Green Romaine Lettuce (Lactuca sativa) in a Rodent Model". Biol Pharm Bull. 42 (10): 1726–1732. doi:10.1248/bpb.b19-00454. PMID 31582660.
  3. ^ Bischoff TA, Kelley CJ, Karchesy Y, Laurantos M, Nguyen-Dinh P, Arefi AG (2004). "Antimalarial Activity of Lactucin and Lactucopicrin: Sesquiterpene Lactones Isolated from Cichorium intybus L.". Journal of Ethnopharmacology. 95 (2–3): 455–457. doi:10.1016/j.jep.2004.06.031. PMID 15507374.
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