4-Caffeoyl-1,5-quinide

4-Caffeoyl-1,5-quinide
Names

Other names 4-Caffeoylquinic-1,5-lactone; 4-CQL
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	30776763
InChI InChI=1S/C16H16O8/c17-9-3-1-8(5-10(9)18)2-4-13(20)24-14-11(19)6-16(22)7-12(14)23-15(16)21/h1-5,11-12,14,17-19,22H,6-7H2/b4-2+/t11-,12-,14-,16+/m1/s1 Key: BMSNCTFPYHTXGU-JUHZACGLSA-N
SMILES c1cc(c(cc1/C=C/C(=O)O[C@@H]2[C@@H](C[C@@]3(C[C@H]2OC3=O)O)O)O)O
Properties
Chemical formula	C₁₆H₁₆O₈
Molar mass	336.30 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-Caffeoyl-1,5-quinide (4-caffeoylquinic-1,5-lactone or 4-CQL) is found in roasted coffee beans. It is formed by lactonization of 4-O-caffeoylquinic acid during the roasting process.^[1]

Lactonization of 4-O-caffeoylquinic acid during roasting to form of 4-CQL

It is reported to possess opioid antagonist properties in mice.^[2]

References

↑ Alan Crozier; Mike N. Clifford; Hiroshi Ashihara, eds. (2006). Plant Secondary Metabolites: Occurrence, Structure and Role in the Human Diet. Blackwell Publishing Ltd. p. 275.
↑ de Paulis, Tomas; Commers, Patricia; Farah, Adriana; Zhao, Jiali; McDonald, Michael P.; Galici, Ruggero; Martin, Peter R. (2004). "4-Caffeoyl-1,5-quinide in roasted coffee inhibits [³H]naloxone binding and reverses anti-nociceptive effects of morphine in mice" (PDF). Psychopharmacology. 176: 146–153. PMID 15088081. doi:10.1007/s00213-004-1876-9. Retrieved 2013-05-29.

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