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Details

Stereochemistry ACHIRAL
Molecular Formula C8H6O4
Molecular Weight 166.1308
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPERONYLIC ACID

SMILES

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

InChI

InChIKey=VDVJGIYXDVPQLP-UHFFFAOYSA-N
InChI=1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)

HIDE SMILES / InChI

Molecular Formula C8H6O4
Molecular Weight 166.1308
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25520224 | https://www.ncbi.nlm.nih.gov/pubmed/25327968 | https://www.ncbi.nlm.nih.gov/pubmed/17927202

Piperonylic acid is a natural molecule contains in Piper nigrum and bearing a methylenedioxy function that closely mimics the structure of trans-cinnamic acid. Purified piperonylic acid is water-soluble, secure and nontoxic. Recent researchers have verified that piperonylic acid not only inhibited the growth of cancer cells and regulated the immunity, but also improved the lipid metabolism, enhanced endothelial function, and resisted atherosclerotic proliferation. However, related experimental studies are still limited.

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft 22, 2861-3. From: J. Chem. Soc., Abstr. 58, 136 1890

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
43.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Accumulation of p-hydroxybenzoic acid in hairy roots of Daucus carota 2: confirming biosynthetic steps through feeding of inhibitors and precursors.
2009-09-01
Soybean (Glycine max) root lignification induced by ferulic acid. The possible mode of action.
2008-09
High-throughput screening for small-molecule activators of neutrophils: identification of novel N-formyl peptide receptor agonists.
2007-04
8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope.
2006-04-05
Synthesis and evaluation of the antitrypanosomal and antiplasmodial activities of new 4-aminobicyclo[2.2.2]octane derivatives.
2005-09
Study of cis-cinnamic acid in Arabidopsis thaliana.
2005-04-19
Thermodynamic study of sesamol, piperonyl alcohol, piperonylic acid and homopiperonylic acid: a combined experimental and theoretical investigation.
2004-03-21
Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants.
2003-10-09
Chemical inactivation of the cinnamate 4-hydroxylase allows for the accumulation of salicylic acid in elicited cells.
2002-10
Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors.
2001-01
Patents

Sample Use Guides

The rats were intragastrically administered with 3 ml of piperonylic acid (10 g/L) daily
Route of Administration: Oral
VSMCs were inoculated on 96-well culture plates (1×10^6/L), and the culture medium was refreshed after 48 h and then discarded when 90 % of the cells fused, with serum-free DMEM culture medium used instead. The cells were then starved for 48 h to be synchronized in the G0 phase. 50 μl of pH7.4 PBS was added into each well of the control group, 5 % FBS was added into the FBS group, and piperonylic acid solutions (fi nal concentrations: 20, 40, 60, 80 mg/L) were added into each well of each experimental group respectively. 48 h later, 3H-TdR (3.0×105 Bq/L) was added, 48 h after which the cells were collected. Then the cell membrane was broken, and 3 ml of scintillating solution were added. The radiation intensity was measured by liquid scintillation counting.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:04:33 GMT 2025
Edited
by admin
on Mon Mar 31 19:04:33 GMT 2025
Record UNII
QX3V1NO0KH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPERONYLIC ACID
MI  
Systematic Name English
NSC-10072
Preferred Name English
1,3-BENZODIOXOLE-5-CARBOXYLIC ACID
Systematic Name English
3,4-METHYLENEDIOXYBENZOIC ACID
Systematic Name English
PROTOCATECHUIC ACID METHYLENE ETHER
Systematic Name English
PIPERONYLIC ACID [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m8860
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY Merck Index
PUBCHEM
7196
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY
FDA UNII
QX3V1NO0KH
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY
NSC
10072
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-342-8
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY
MESH
C005455
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY
CAS
94-53-1
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID6059104
Created by admin on Mon Mar 31 19:04:33 GMT 2025 , Edited by admin on Mon Mar 31 19:04:33 GMT 2025
PRIMARY