Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H5O2.H4N |
Molecular Weight | 91.1091 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[NH4+].CCC([O-])=O
InChI
InChIKey=XJMWHXZUIGHOBA-UHFFFAOYSA-N
InChI=1S/C3H6O2.H3N/c1-2-3(4)5;/h2H2,1H3,(H,4,5);1H3
Molecular Formula | H3N |
Molecular Weight | 17.0305 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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[Acidemia, propionic]. | 2001 |
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Cytosolic acidification as a signal mediating hyperosmotic stress responses in Dictyostelium discoideum. | 2001 |
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PET reversed mismatch in an experimental model of subacute myocardial infarction. | 2001 Apr |
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The effect of season and monensin sodium on the digestive characteristics of autumn and spring pasture fed to sheep. | 2001 Apr |
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Fluticasone propionate aqueous nasal spray reduces inflammatory cells in unchallenged allergic nasal mucosa: effects of single allergen challenge. | 2001 Apr |
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Influence of anaerobic culture acclimation on the degradation kinetics of various substrates. | 2001 Aug 5 |
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Effect of the liquid upflow velocity on thermophilic sulphate reduction in acidifying granular sludge reactors. | 2001 Feb |
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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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Role of type II thioesterases: evidence for removal of short acyl chains produced by aberrant decarboxylation of chain extender units. | 2001 Feb |
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Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana. | 2001 Feb |
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Effects of corn particle size and source on performance of lactating cows fed direct-cut grass-legume forage. | 2001 Feb |
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In vitro metabolism of citalopram by monoamine oxidase B in human blood. | 2001 Feb |
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Fermentation characteristics and ruminal ciliate protozoal populations in cattle fed medium- or high-concentrate barley-based diets. | 2001 Feb |
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Radiolabeled cholinesterase substrates: in vitro methods for determining structure-activity relationships and identification of a positron emission tomography radiopharmaceutical for in vivo measurement of butyrylcholinesterase activity. | 2001 Feb |
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Uremic concentrations of guanidino compounds inhibit neutrophil superoxide production. | 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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The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones. | 2001 Feb 1 |
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Interaction of hydrophobic anions with the rat skeletal muscle chloride channel ClC-1: effects on permeation and gating. | 2001 Feb 1 |
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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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Laboratory study on the high-temperature capture of HCl gas by dry-injection of calcium-based sorbents. | 2001 Feb-Mar |
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Perturbation of rat renal tubule transport of the organic cation amantadine in recent onset streptozotocin-induced diabetes and in uninephrectomy. | 2001 Jan |
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Modeling the growth boundary of Staphylococcus aureus for risk assessment purposes. | 2001 Jan |
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Synthesis and applications of chitosan mercaptanes as heavy metal retention agent. | 2001 Jan 10 |
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Fluticasone propionate: a rare contact sensitizer. | 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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Influence of carbohydrate source and buffer on rumen fermentation characteristics, milk yield, and milk composition in late-lactation Holstein cows. | 2001 Jul |
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Effects of NutriDense and waxy corn hybrids on the rumen fermentation, digestibility and lactational performance of dairy cows. | 2001 Jul |
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Influence of supplemental chromium on concentrations of liver triglyceride, blood metabolites and rumen VFA profile in steers fed a moderately high fat diet. | 2001 Jul |
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Short-chain fatty acids and human colonic function: roles of resistant starch and nonstarch polysaccharides. | 2001 Jul |
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Identification and quantification of phosphatidylethanolamine-derived glucosylamines and aminoketoses from human erythrocytes--influence of glycation products on lipid peroxidation. | 2001 Jul 15 |
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Factors determining the orientation of axially coordinated imidazoles in heme proteins. | 2001 Jul 3 |
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Functional and structural response of a cellulose-degrading methanogenic microbial community to multiple aeration stress at two different temperatures. | 2001 Jun |
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2-Methylisocitrate lyases from the bacterium Escherichia coli and the filamentous fungus Aspergillus nidulans: characterization and comparison of both enzymes. | 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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Subcritical mineralization of sodium salt of dodecyl benzene sulfonate using sonication-wet oxidation (SONIWO) technique. | 2001 Jun |
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Snapshots of protein folding. A study on the multiple transition state pathway of cytochrome c(551) from Pseudomonas aeruginosa. | 2001 Jun 22 |
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Interannual variations in the lipids of the Antarctic pteropods Clione limacina and Clio pyramidata. | 2001 Mar |
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Molecular characterization, enzyme properties and transcriptional regulation of phosphoenolpyruvate carboxykinase and pyruvate kinase in a ruminal bacterium, Selenomonas ruminantium. | 2001 Mar |
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Crystal structure of the oxidized cytochrome c(2) from Blastochloris viridis. | 2001 Mar 2 |
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Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli. | 2001 Mar 2 |
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Production of PHA from starchy wastewater via organic acids. | 2001 Mar 30 |
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[Directed modification of the pyrrole ring D in natural chlorins]. | 2001 Mar-Apr |
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Preferential utilization of dipeptides by Porphyromonas gingivalis. | 2001 May |
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Study on sludge expansion during treatment of salad oil manufacturing wastewater by yeast. | 2001 May |
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Thin layer chromatographic determination of organic acids for rapid identification of bifidobacteria at genus level. | 2001 May |
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Desensitization of ileal vagal receptors by short-chain fatty acids in pigs. | 2001 May |
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Indolinone tyrosine kinase inhibitors block Kit activation and growth of small cell lung cancer cells. | 2001 May 1 |
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
by
admin
on
Edited
Fri Dec 15 19:09:14 GMT 2023
by
admin
on
Fri Dec 15 19:09:14 GMT 2023
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Record UNII |
V18VR2SK15
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Record Status |
Validated (UNII)
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Record Version |
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17496-08-1
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Ammonium propionate
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300000034785
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |