CRYPTOCHLOROGENIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18O9
Molecular Weight	354.3087
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](O)[C@H]1OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)=O

InChI

InChIKey=GYFFKZTYYAFCTR-JUHZACGLSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H18O9
Molecular Weight	354.3087
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/20862961 | http://www.hmdb.ca/metabolites/HMDB30653 | https://www.ncbi.nlm.nih.gov/pubmed/26213025 | http://pubs.acs.org/doi/pdf/10.1021/jf960900s | https://www.ncbi.nlm.nih.gov/pubmed/25743191 | https://www.ncbi.nlm.nih.gov/pubmed/25219603 | https://www.ncbi.nlm.nih.gov/pubmed/11087511 | https://www.ncbi.nlm.nih.gov/pubmed/26657159

Cryptochlorogenic acid is a structural isomer of chlorogenic acid; it is a cinnamate ester formed by the condensation of the carboxy group of trans-caffeic acid with the 4-hydroxy group of quinic acid. It can be isolated from several plant sources including apples, coffee, sunflowers, potatoes, and Hibiscus sabdariffa. Cryptochlorogenic acid mixed with related compounds has demonstrated potential anti-oxidant and anti-inflammatory properties and shown inhibitory activity against HBV DNA replication.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L. ).	2000 Nov	11087511
Simultaneous Determination of Crypto-Chlorogenic Acid, Isoquercetin, and Astragalin Contents in Moringa oleifera Leaf Extracts by TLC-Densitometric Method.	2013	23533530
Simultaneous determination of 5 phenolic acids in fried Fructus xanthii from different production sites and its dispensing granules by using ultra-pressure liquid chromatography.	2013 Apr	23772104
Caffeic acid derivatives from Bupleurum chinense.	2014 Sep-Oct	25657804
Quantitative comparison of caffeoylquinic acids and flavonoids in Chrysanthemum morifolium flowers and their sulfur-fumigated products by three-channel liquid chromatography with electrochemical detection.	2015	25743191
Antioxidant Activity and Induction of mRNA Expressions of Antioxidant Enzymes in HEK-293 Cells of Moringa oleifera Leaf Extract.	2015 Aug	26166137
[Degradation kinetics of chlorogenic acid, cryptochlorogenic acid, and neochlorogenic acid at neutral and alkaline pH values].	2016 Jan	27405173

Patents

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 01:12:20 GMT 2023` Edited by `admin` on `Sat Dec 16 01:12:20 GMT 2023`
Record UNII	F23DJ84IZ9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CRYPTOCHLOROGENIC ACID

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 4-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-

Systematic Name

English

QUINIC ACID 4-O-CAFFEATE

Common Name

English

4-O-CAFFEOYL QUINIC ACID

Common Name

English

4-CQA

Common Name

English

4-CAFFEOYLQUINIC ACID

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 4-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-

Systematic Name

English

Code System Code Type Description

CHEBI

75491