4-Caffeoyl-1,5-quinide

4-Caffeoyl-1,5-quinide
Names
	Other names 4-Caffeoylquinic-1,5-lactone; 4-CQL
Identifiers
Properties
Chemical formula	C16H16O8
Molar mass	336.296 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. doi:10.1007/s00213-004-1876-9. Retrieved 2013-05-29.

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[1] 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.

[2] 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. doi:10.1007/s00213-004-1876-9. Retrieved 2013-05-29.

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