Lactucin

Lactucin

Names
IUPAC name (3aR,4R,9aS,9bR)-4-Hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-4,5,9a,9b-tetrahydro-3aH-azuleno[5,4-d]furan-2,7-dione
Identifiers
CAS Registry Number	1891-29-8 Y
ChemSpider	717609 N
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
Jmol-3D images	Image
KEGG	C09489 N
PubChem	821383
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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] It has also shown some antimalarial effects.^[2] It is also found in dandelion coffee.

It acts as adenosine receptor agonist.

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. ↑ 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.