4-Caffeoyl-1,5-quinide

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4-Caffeoyl-1,5-quinide
4-Caffeoyl-1,5-quinide.svg
Names
Other names
4-Caffeoylquinic-1,5-lactone; 4-CQL
Identifiers
3D model (JSmol)
ChemSpider
Properties
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[edit]

  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. ^ 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.