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4-Caffeoyl-1,5-quinide

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.

Column 1	Column 2

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
CAS Number	.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}1188414-37-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:175265
ChemSpider	30776763
PubChem CID	102210471
InChI
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/s1Key: BMSNCTFPYHTXGU-JUHZACGLSA-N
SMILES
c1cc(c(cc1/C=C/C(=O)O[C@@H]2C@@HO)O)O
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-lactone or 4-CQL) is found in roasted coffee beans. It is formed by lactonization of 4-O-caffeoylquinic acid during the roasting process.

Lactonization of 4-O-caffeoylquinic acid during roasting to form of 4-CQL

It is reported to possess opioid antagonist properties in mice.

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