4-Caffeoyl-1,5-quinide

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| ImageFile = 4-Caffeoyl-1,5-quinide.svg

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| PIN = (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

| OtherNames = 4-Caffeoylquinic-1,5-lactone; 4-CQL

|Section1={{Chembox Identifiers

| CASNo = 1188414-37-0

| ChEBI = 175265

| ChemSpiderID = 30776763

| PubChem = 102210471

| SMILES = 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

| StdInChI = 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

| StdInChIKey = BMSNCTFPYHTXGU-JUHZACGLSA-N }}

|Section2={{Chembox Properties

| C=16 | H=16 | O=8

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|Section3={{Chembox Hazards

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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.{{cite book | title = Plant Secondary Metabolites: Occurrence, Structure and Role in the Human Diet | url = https://archive.org/details/plantsecondaryme00croz_308 | url-access = limited |editor1=Alan Crozier |editor2=Mike N. Clifford |editor3=Hiroshi Ashihara | year = 2006 | publisher = Blackwell Publishing Ltd | page = [https://archive.org/details/plantsecondaryme00croz_308/page/n286 275]}}

:File:4-caffeoyl-1-5-quinide.png{{clear left}}

It is reported to possess opioid antagonist properties in mice.{{cite journal |journal= Psychopharmacology |year= 2004 |volume= 176 |pages= 146–153 |doi= 10.1007/s00213-004-1876-9 |first1= Tomas |last1= de Paulis |first2= Patricia |last2= Commers |first3= Adriana |last3= Farah |first4= Jiali |last4= Zhao |first5= Michael P. |last5= McDonald |first6= Ruggero |last6= Galici |first7= Peter R. |last7= Martin |url= http://vanderbilt.edu/ics/Files/QUINIDE_opioids.pdf |title= 4-Caffeoyl-1,5-quinide in roasted coffee inhibits [³H]naloxone binding and reverses anti-nociceptive effects of morphine in mice |issue= 2 |access-date= 2013-05-29 |pmid= 15088081 |s2cid= 10181204 |archive-url= https://web.archive.org/web/20160304084651/http://vanderbilt.edu/ics/Files/QUINIDE_opioids.pdf |archive-date= 2016-03-04 |url-status= dead }}