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4-Caffeoyl-1,5-quinide

From Wikipedia, the free encyclopedia
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 mass336.296 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

4-Caffeoyl-1,5-quinide (4-caffeoylquinic-1,5-lactone or4-CQL) is found in roastedcoffee beans. It is formed bylactonization 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 possessopioid antagonist properties inmice.[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 (2):146–153.doi:10.1007/s00213-004-1876-9.PMID 15088081.S2CID 10181204. Archived fromthe original(PDF) on 2016-03-04. Retrieved2013-05-29.
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others

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