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

InChI

InChIKey=CWVRJTMFETXNAD-NXLLHMKUSA-N

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

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: http://phenol-explorer.eu/compounds/519 | https://www.ncbi.nlm.nih.gov/pubmed/20405920 | https://www.ncbi.nlm.nih.gov/pubmed/21899864 | https://www.ncbi.nlm.nih.gov/pubmed/27591562http://www.scielo.cl/pdf/chiljar/v71n3/at16.pdf | https://www.ncbi.nlm.nih.gov/pubmed/19530711 | https://www.ncbi.nlm.nih.gov/pubmed/11401245 | https://www.ncbi.nlm.nih.gov/pubmed/26152332

Neochlorogenic acid is a natural polyphenolic compound which can be found in a variety of plant sources and especially some types of dried fruit. It is an epimer of chlorogenic acid. Neochlorogenic has been investigated as a chemopreventative dietary compound for breast cancer and collorectal cancer. It has in-vitro anti-inflammatory properties, and may be responsible for the laxative effect fo prunes. Research surrounding neochlorgenic acid has often involved various plant extracts, rather than pure preparations of the compound.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19530711	Preventing	Basic research	Unknown Approved Use Unknown
Constipation 112 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11401245	Primary	Natural Metabolite	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26152332	Primary	Natural Metabolite	Unknown Approved Use Unknown
Unknown 2578

PubMed

Title	Date	PubMed
Profiling and characterization by LC-MSn of the chlorogenic acids and hydroxycinnamoylshikimate esters in maté (Ilex paraguariensis).	2010 May 12	20405920
High chlorogenic and neochlorogenic acid levels in immature peaches reduce Monilinia laxa infection by interfering with fungal melanin biosynthesis.	2011 Apr 13	21370882
Isolation, identification and quantitation of hydroxycinnamic acid conjugates, potential platform chemicals, in the leaves and stems of Miscanthus × giganteus using LC-ESI-MSn.	2011 Dec	21899864
Variation in the contents of neochlorogenic acid, chlorogenic acid and three quercetin glycosides in leaves and fruits of Rowan (Sorbus) species and varieties from collections in Lithuania.	2013 Aug	24079179
Simultaneous determination of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and geniposide in rat plasma by UPLC-MS/MS and its application to a pharmacokinetic study after administration of Reduning injection.	2015 Jan	24842397
Neochlorogenic Acid Inhibits Lipopolysaccharide-Induced Activation and Pro-inflammatory Responses in BV2 Microglial Cells.	2015 Sep	26152332
Plum polyphenols inhibit colorectal aberrant crypt foci formation in rats: potential role of the miR-143/protein kinase B/mammalian target of rapamycin axis.	2016 Oct	27865352
Anticarcinogenic Effect of Spices Due to Phenolic and Flavonoid Compounds-In Vitro Evaluation on Prostate Cells.	2017 Sep 28	28956846

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 `Fri Dec 15 22:08:29 GMT 2023` Edited by `admin` on `Fri Dec 15 22:08:29 GMT 2023`
Record UNII	O4601UER1Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NEOCHLOROGENIC ACID

Common Name

English

NEOCHLOROGENIC ACID (CONSTITUENT OF ST. JOHN'S WORT) [DSC]

Common Name

English

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

Common Name

English

(1R-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.))-3-((3-(3,4-DIHYDROXYPHENYL)-1-OXOALLYL)OXY)-1,4,5-TRIHYDROXYCYCLOHEXANECARBOXYLIC ACID

Common Name

English

(E)-NEOCHLOROGENIC ACID

Common Name

English

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

Systematic Name

English

3-CQA

Common Name

English

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

Common Name

English

3-O-(E)-CAFFEOYLQUINIC ACID

Common Name

English

Code System Code Type Description

CAS

342811-68-1