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

Details

Stereochemistry ACHIRAL
Molecular Formula C12H10O4
Molecular Weight 218.2054
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CHAVICINIC ACID

SMILES

OC(=O)\C=C/C=C\C1=CC=C2OCOC2=C1

InChI

InChIKey=RHBGITBPARBDPH-CCAGOZQPSA-N
InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2-

HIDE SMILES / InChI

Molecular Formula C12H10O4
Molecular Weight 218.2054
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Piperic Acid is a metabolite of Piperine. Piperic acid is found in herbs and spices. Piperic acid is obtained from black pepper (Piper nigrum), from Minthostachys verticillata, peppermint (Mentha piperita) and others. Piperic acid is an intermediate in the synthesis of other compounds such as piperonal, and as-such may be used to produce fragrances, perfumes flavorants and drugs as well as other useful compounds. The cytotoxic effects of piperic acid in prostate cancer cells (PC-3) and breast cancer cells (MDA-MB-231) were studied. The drug treatment experiments clearly indicated that maximum cytotoxicity was achieved at 48 hours and at 100uM concentration of piperic acid in both the cell lines. It is proposed that piperine might get metabolized into piperonylic acid, piperic acid, and piperonal in human as evidenced in rats. Hence, the three derivatives of piperine presented above shall be of therapeutic significance. Piperic Acid has revealed Lipoxygenase (LOX) inhibitory activity. The possibility of exploiting the higher LOX inhibitory activity and lower IC50 values of piperine derivatives, piperonal, and piperonylic acid, in various ways for therapeutic applications, especially with fermented herbal drugs containing materials with piperine as a constituent has being suggested.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Curcumin conjugates induce apoptosis via a mitochondrion dependent pathway in MCF-7 and MDA-MB-231 cell lines.
2013
Quantitative structure-cytotoxicity relationship of piperic acid amides.
2014 Sep
Derivatives form better lipoxygenase inhibitors than piperine: in vitro and in silico study.
2015 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
MDA-MB231 and PC-3 cell lines were treated with piperic acid in different concentrations (1,10 and100 uM), at different time periods of incubation (24,48,72 hours). 100 uM concentration was optimal to obtain the maximum cytotoxicity in cancer cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:50:06 GMT 2023
Edited
by admin
on Sat Dec 16 04:50:06 GMT 2023
Record UNII
JUO0E351AY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHAVICINIC ACID
Common Name English
PIPERIC ACID (Z,Z)-FORM [MI]
Common Name English
2,4-PENTADIENOIC ACID, 5-(1,3-BENZODIOXOL-5-YL)-, (2Z,4Z)-
Common Name English
2,4-PENTADIENOIC ACID, 5-(1,3-BENZODIOXOL-5-YL)-, (Z,Z)-
Common Name English
5-(1,3-BENZODIOXOL-5-YL)-2,4-PENTADIENOIC ACID, (2Z,4Z)-
Common Name English
PIPERIC ACID, (Z,Z)-
Common Name English
Code System Code Type Description
MERCK INDEX
m8849
Created by admin on Sat Dec 16 04:50:06 GMT 2023 , Edited by admin on Sat Dec 16 04:50:06 GMT 2023
PRIMARY Merck Index
PUBCHEM
5771622
Created by admin on Sat Dec 16 04:50:06 GMT 2023 , Edited by admin on Sat Dec 16 04:50:06 GMT 2023
PRIMARY
FDA UNII
JUO0E351AY
Created by admin on Sat Dec 16 04:50:06 GMT 2023 , Edited by admin on Sat Dec 16 04:50:06 GMT 2023
PRIMARY
CAS
495-89-6
Created by admin on Sat Dec 16 04:50:06 GMT 2023 , Edited by admin on Sat Dec 16 04:50:06 GMT 2023
PRIMARY