4-Caffeoyl-1,5-quinide
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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 | |
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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 |
Chemical compound
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]
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 (2): 146–153. doi:10.1007/s00213-004-1876-9. PMID 15088081. S2CID 10181204. Archived from the original (PDF) on 2016-03-04. Retrieved 2013-05-29.
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