4-Caffeoyl-1,5-quinide

4-Caffeoyl-1,5-quinide
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)
ChEBI
ChemSpider
  • 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
  • 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
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).

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. ^ 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 (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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