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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18O9
Molecular Weight 354.3094
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NEOCHLOROGENIC ACID

SMILES

c1cc(c(cc1/C(/[H])=C(\[H])/C(=O)O[C@]2([H])C[C@](C[C@]([H])([C@]2([H])O)O)(C(=O)O)O)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 354.3094
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
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
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
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

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 Jun 26 14:39:22 UTC 2021
Edited
by admin
on Sat Jun 26 14:39:22 UTC 2021
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 Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
NEOCHLOROGENIC ACID
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
MESH
C473200
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
PUBCHEM
5280633
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
CAS
906-33-2
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
FDA UNII
O4601UER1Z
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
ECHA (EC/EINECS)
212-997-1
Created by admin on Sat Jun 26 14:39:22 UTC 2021 , Edited by admin on Sat Jun 26 14:39:22 UTC 2021
PRIMARY
Related Record Type Details
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.
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.
PARENT -> CONSTITUENT ALWAYS PRESENT