Chemistry:4-Caffeoyl-1,5-quinide

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4-Caffeoyl-1,5-quinide
4-Caffeoyl-1,5-quinide.svg
Names
Preferred IUPAC name
(1S,3R,4R,5R)-1,3-Dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Other names
4-Caffeoylquinic-1,5-lactone; 4-CQL
Identifiers
3D model (JSmol)
ChemSpider
Properties
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

  1. Plant Secondary Metabolites: Occurrence, Structure and Role in the Human Diet. Blackwell Publishing Ltd. 2006. p. 275. https://archive.org/details/plantsecondaryme00croz_308. 
  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 [3Hnaloxone binding and reverses anti-nociceptive effects of morphine in mice"]. Psychopharmacology 176 (2): 146–153. doi:10.1007/s00213-004-1876-9. PMID 15088081. http://vanderbilt.edu/ics/Files/QUINIDE_opioids.pdf. Retrieved 2013-05-29.