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
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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25520224Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25520224
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25327968 |
43.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25520224
The rats were intragastrically administered with 3 ml of piperonylic acid (10 g/L) daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25520224
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.
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SUBSTANCE RECORD