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4-Caffeoyl-1,5-quinide






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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

CAS Number

3D model (JSmol)
ChEBI
ChemSpider

PubChem CID

  • 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

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

4-Caffeoyl-1,5-quinide (4-caffeoylquinic-1,5-lactoneor4-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.
  • ^ 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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    • Retrieved from "https://en.wikipedia.org/w/index.php?title=4-Caffeoyl-1,5-quinide&oldid=1196531002"
    Categories: 
    ●Lactones
     ●Coffee chemistry
     ●Mu-opioid receptor antagonists
     ●Hydroxycinnamic acid esters
     ●Heterocyclic compounds with 2 rings
     ●Organic compound stubs
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