FComEx: Chlorogenic acid (PC001180)

Record Information

Version

1.0

Creation date

2018-05-02 12:09:31 UTC

Update date

2018-05-04 14:25:18 UTC

FoodComEx ID

PC001180

FoodDB Record

FDB002582

Chemical Information

Name

Chlorogenic acid

Description

Chlorogenic acid, also known as chlorogenate or 3-caffeoylquinate, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Chlorogenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Chlorogenic acid has been detected, but not quantified in, several different foods, such as limes, cocoa beans, celery leaves, caraway, and epazotes. This could make chlorogenic acid a potential biomarker for the consumption of these foods.

CAS Number

327-97-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	Generator
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	ChEBI
[1S-(1α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	Generator
3-(3,4-Dihydroxycinnamoyl)quinate	Generator
3-(3,4-Dihydroxycinnamoyl)quinic acid	db_source
3-Caffeoylquinate	Generator
3-Caffeoylquinic acid	manual
3-O-Caffeoylquinate	Generator
3-O-Caffeoylquinic acid	ChEBI
3-trans-Caffeoylquinic acid	HMDB
5-Caffeoylquinic acid?	manual
5-O-(3,4-Dihydroxycinnamoyl)-L-quinate	Generator
5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid	ChEBI
5-O-Caffeoylquinic acid?	manual
Caffeoyl quinate	Generator
Caffeoyl quinic acid	ChEBI
Caffetannic acid	db_source
Chlorogenate	ChEBI
Chlorogenic acid	db_source
Helianthic acid	db_source
Heriguard	HMDB
Hlorogenate	HMDB
Hlorogenic acid	HMDB
trans-5-O-Caffeoyl-D-quinate	ChEBI
trans-5-O-Caffeoyl-D-quinic acid	Generator

Chemical Formula

C16H18O9

IUPAC name

(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

InChI Key

CWVRJTMFETXNAD-JUHZACGLSA-N

Isomeric SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents