5-P-COUMAROYLQUINIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18O8
Molecular Weight	338.3093
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BMRSEYFENKXDIS-OTCYKTEZSA-N

InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H18O8
Molecular Weight	338.3093
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26457815 | https://www.ncbi.nlm.nih.gov/pubmed/24228586 | https://www.ncbi.nlm.nih.gov/pubmed/17520524

5-P-Coumaroylquinic acid is a cinnamate ester formed by condensation of the carboxyl group of 4-coumaric acid with the 5-hydroxy group of (-)-quinic acid. It is a naturally occuring compound in coffee, Ixeris sonchifolia and Aloe barbadensis. 5-P Coumaroylquinic acid and related compounds are reported to have antioxidant properties.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Characterization by LC-MS(n) of four new classes of p-coumaric acid-containing diacyl chlorogenic acids in green coffee beans.	2006 Jun 14	16756331
Profiling the chlorogenic acids of aster by HPLC-MS(n).	2006 Nov-Dec	17144245

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:22:08 UTC 2023` Edited by `admin` on `Sat Dec 16 11:22:08 UTC 2023`
Record UNII	4C4BU5688G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5-P-COUMAROYLQUINIC ACID

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 1,3,4-TRIHYDROXY-5-(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (1S,3R,4R,5R)-

Systematic Name

English

5-P-TRANS-COUMAROYLQUINIC ACID

Common Name

English

TRANS-P-COUMARIC ACID 5-O-D-QUINATE

Common Name

English

21600YP321

Common Name

English

5-P-COUMAROYLQUINIC ACID, (E)-

Common Name

English

CINNAMIC ACID, P-HYDROXY-, 5-ESTER WITH 1,3,4,5-TETRAHYDROXYCYCLOHEXANECARBOXYLIC ACID, (E)-

Systematic Name

English

5-P-COQA

Common Name

English

2-COUMAROYLQUINIC ACID

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 1,3,4-TRIHYDROXY-5-(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (1S,3R,4R,5R)-

Systematic Name

English

CYCLOHEXANECARBOXYLIC ACID, 1,3,4-TRIHYDROXY-5-((3-(4-HYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (1S-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.(E)))-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID201312826