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  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6358  N
ChemSpider	717609  N
ECHA InfoCard	100.440.674
KEGG	C09489  N
PubChem CID	821383
UNII	R6E2918904  Y
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 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
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). N  verify  (what is  YN ?) 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 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 GABA_A receptor, ^[2] as well as antimalarial activity. ^[3]

See also

• Lactucopicrin

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.