Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H6O2 |
Molecular Weight | 74.0785 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(O)=O
InChI
InChIKey=XBDQKXXYIPTUBI-UHFFFAOYSA-N
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
Molecular Formula | C3H6O2 |
Molecular Weight | 74.0785 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Propionic acid (PA), also known as propanoic acid, with chemical formula C3H6O2, is an organic acid used as a food additive and found naturally on the skin and in the gastrointestinal tract. It is a byproduct of fermentation reactions and is also produced industrially from ethylene or ethanol and carbon monoxide. Propionic acid is a fungicide and bactericide, registered to controlfungi and bacteria in stored grains, hay, grain storage areas, poultry litter,and drinking water for livestock and poultry. As a food preservative, propionic acid prevents mold in bread and baked goods, and it is used as a flavoring agent in cheese and other packaged goods. The U.S. Environmental Protection Agency considers it safe and therefore, has no limitation on its use. It has been demonstrated that PA lowers fatty acids content in liver and plasma, reduces food intake, exerts immunosuppressive actions and probably improves tissue insulin sensitivity. Thus increased production of PA by the microbiota might be considered beneficial in the context of prevention of obesity and diabetes type 2. The molecular mechanisms by which PA may exert this plethora of physiological effects are slowly being elucidated and include intestinal cyclooxygenase enzyme, the G-protein coupled receptors 41 and 43 and activation of the peroxisome proliferator-activated receptor γ, in turn inhibiting the sentinel transcription factor NF-κB and thus increasing the threshold for inflammatory responses in general. Taken together, PA emerges as a major mediator in the link between nutrition, gut microbiota and physiology. The sodium salt of propionic acid was previously approved in Canada as an active ingredient in Amino-Cerv (used to treat inflammation or injury of the cervix).
Approval Year
PubMed
Title | Date | PubMed |
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Effects of butyrate and propionate on the adhesion, growth, cell cycle kinetics, and protein synthesis of cultured human gingival fibroblasts. | 1999 Dec |
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A circular dichroism and fluorescence quenching study of the interactions between rhodium(II) complexes and human serum albumin. | 1999 May 30 |
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Kinetic modeling of N-[11C]methylpiperidin-4-yl propionate: alternatives for analysis of an irreversible positron emission tomography trace for measurement of acetylcholinesterase activity in human brain. | 1999 Oct |
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Inhibition by chromium and cadmium of anaerobic acidogenesis. | 2001 |
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Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo). | 2001 Apr 13 |
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Solution structure of Methylophilus methylotrophus cytochrome c": insights into the structural basis of haem-ligand detachment. | 2001 Apr 27 |
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Isolation and preliminary characterization of the medium-chain fatty acid:CoA ligase responsible for activation of short- and medium-chain fatty acids in colonic mucosa from swine. | 2001 Feb |
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Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana. | 2001 Feb |
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Quantification of benzoic, phenylacetic, and phenylbutyric acids from filter-paper blood spots by gas chromatography--mass spectrometry with stable isotope dilution. | 2001 Feb |
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Arginine catabolism by Thermanaerovibrio acidaminovorans. | 2001 Feb 20 |
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Cloning and biochemical characterization of Co(2+)-activated bromoperoxidase-esterase (perhydrolase) from Pseudomonas putida IF-3 strain. | 2001 Feb 9 |
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Synthesis and applications of chitosan mercaptanes as heavy metal retention agent. | 2001 Jan 10 |
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Allergic reactions due to ibuprofen in children. | 2001 Jan-Feb |
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New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies. | 2001 Jul |
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Acetate, propionate and butyrate in plasma: determination of the concentration and isotopic enrichment by gas chromatography/mass spectrometry with positive chemical ionization. | 2001 Jul |
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Effect of temperature increase from 55 to 65 degrees C on performance and microbial population dynamics of an anaerobic reactor treating cattle manure. | 2001 Jul |
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Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1). | 2001 Jul-Aug |
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The roles of the multiple CheW and CheA homologues in chemotaxis and in chemoreceptor localization in Rhodobacter sphaeroides. | 2001 Jun |
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Fixed drug eruption due to naproxen; lack of cross-reactivity with other propionic acid derivatives. | 2001 Jun |
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Inhibition of growth of methane-producing bacteria of the ruminant forestomach by hydroxymethylglutaryl-SCoA reductase inhibitors. | 2001 Jun |
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[Ten-year trend of analgesic drug use (1984 to 1995): results of three MONICA-based surveys in Augsburg)]. | 2001 Jun 1 |
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Studies of propionate toxicity in Salmonella enterica identify 2-methylcitrate as a potent inhibitor of cell growth. | 2001 Jun 1 |
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Effect of process configuration and substrate complexity on the performance of anaerobic processes. | 2001 Mar |
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Production of PHA from starchy wastewater via organic acids. | 2001 Mar 30 |
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Preferential utilization of dipeptides by Porphyromonas gingivalis. | 2001 May |
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Carbon-11 acetate as a tracer of myocardial oxygen consumption. | 2001 May |
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One-pot, catalytic, asymmetric synthesis of polypropionates. | 2001 May 17 |
Patents
Sample Use Guides
The maximum safe dietary level of propionic acid for poultry is 10 g/kg complete feed and for pigs 30 g/kg complete feed.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20691280
Propionic acid concentrations equal to or more than 3 mM showed a remarkable
high inhibition of lymphocyte proliferation, whereas 2 mM produced
only a mild reduction in lymphocyte proliferation. 3 mM PA or higher inhibited the production of the
pro-inflammatory cytokine, resistin, by human adipose tissue.
Substance Class |
Chemical
Created
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Record UNII |
JHU490RVYR
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Validated (UNII)
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CFR |
21 CFR 184.1081
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LOINC |
2849-8
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JECFA EVALUATION |
PROPIONIC ACID
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EPA PESTICIDE CODE |
77702
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NCI_THESAURUS |
C802
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DSLD |
4063 (Number of products:1)
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NCI_THESAURUS |
C492
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FDA ORPHAN DRUG |
706219
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FDA ORPHAN DRUG |
515216
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CODEX ALIMENTARIUS (GSFA) |
INS-280
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JECFA EVALUATION |
INS-280
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M9209
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Propionic acid
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1032
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CHEMBL14021
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C029658
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121047
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1192
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INS-280
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201-176-3
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C61911
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17272
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JHU490RVYR
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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ACTIVE MOIETY |