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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 PIPERIC ACID

SMILES

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

InChI

InChIKey=RHBGITBPARBDPH-ZPUQHVIOSA-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

Description

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

Primary TargetPharmacologyConditionPotency
45.17 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
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.