U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of NEOCHLOROGENIC ACID

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

(Z)-Neochlorogenic acid is an isomer of neochlorogenic acid incorporating cis-cafeic acid instead of trans-cafeic acid. It is a naturally occurring compound which can be found in plants such as Ilex paraguariensis, Miscanthus giganteus, Nicotiana tabacum.

Approval Year

Unknown
127998
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Basic research
Unknown

Approved Use

Unknown
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Profiling and characterization by LC-MSn of the chlorogenic acids and hydroxycinnamoylshikimate esters in maté (Ilex paraguariensis).
2010 May 12
High chlorogenic and neochlorogenic acid levels in immature peaches reduce Monilinia laxa infection by interfering with fungal melanin biosynthesis.
2011 Apr 13
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
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
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
Neochlorogenic Acid Inhibits Lipopolysaccharide-Induced Activation and Pro-inflammatory Responses in BV2 Microglial Cells.
2015 Sep
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
Anticarcinogenic Effect of Spices Due to Phenolic and Flavonoid Compounds-In Vitro Evaluation on Prostate Cells.
2017 Sep 28
Patents

Patents

CA2492278A
2
CN104016864
2
EP1524973A
2
US20040006138
4
US20040198807
2
US20070004647
2
US3916028
3
US3924017
2

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 17 07:36:28 UTC 2022
Edited
by admin
on Sat Dec 17 07:36:28 UTC 2022
Record UNII
O4601UER1Z
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
NEOCHLOROGENIC ACID
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
PRIMARY
MESH
C473200
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
PRIMARY
PUBCHEM
5280633
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
PRIMARY
CAS
906-33-2
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
PRIMARY
FDA UNII
O4601UER1Z
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
PRIMARY
ECHA (EC/EINECS)
212-997-1
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
PRIMARY
CHEBI
16384
Created by admin on Sat Dec 17 07:36:29 UTC 2022 , Edited by admin on Sat Dec 17 07:36:29 UTC 2022
PRIMARY
Related Record Type Details
MORINGA OLEIFERA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
The water-soluble fraction was repeatedly chromatographed over MCI gel CHP20P, Sephadex LH-20, and YMC ODSA to yield the compound.
STEVIA REBAUDIUNA LEAF
CONSTITUENT ALWAYS PRESENT -> PARENT
Methanol extracts of stevia dry leaves were directly used for LC-MS analysis. Efficient separation and resolution were achieved with diphenyl packing and acetonitrile/water as solvent in the HPLC method. Negative ion mode was used for all MS measurements.
LONICERA JAPONICA FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966