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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6358 ;
ChemSpider	717609 ;
KEGG	C09489 ;
PubChem CID	821383;
UNII	R6E2918904 ;
CompTox Dashboard (EPA)	DTXSID70894751 ;
	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 Key: VJQAFLAZRVKAKM-QQUHWDOBSA-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;
	SMILES 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). verify (what is ?) Infobox references

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.

References

^ 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.
^ 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.
^ 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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[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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See also

References