Lactucin

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.

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 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).
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Infobox references

It acts as an adenosine receptor agonist.[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. 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.
3. Qasem, Jamal R (2015-04-01). "Prospects of wild medicinal and industrial plants of saline habitats in the Jordan Valley". Pakistan Journal of Botany. 47 (2). ISSN 0556-3321.