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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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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[Acidemia, propionic]. | 2001 |
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[Volatile compounds in air and oral saliva in healthy people, and in periodontitis and gingivitis patients]. | 2001 |
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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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SCFA increase intestinal Na absorption by induction of NHE3 in rat colon and human intestinal C2/bbe cells. | 2001 Apr |
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Presynaptic function is altered in snake K+-depolarized motor nerve terminals containing compromised mitochondria. | 2001 Apr 1 |
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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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A biochemical hypothesis explaining the response of enhanced biological phosphorus removal biomass to organic substrates. | 2001 Aug |
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Influence of anaerobic culture acclimation on the degradation kinetics of various substrates. | 2001 Aug 5 |
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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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In vitro metabolism of citalopram by monoamine oxidase B in human blood. | 2001 Feb |
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Effects of short chain fatty acids on colonic Na+ absorption and enzyme activity. | 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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In vitro fermentation characteristics of native and processed cereal grains and potato starch using ileal chyme from dogs. | 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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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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A survey of lipolytic and glycolytic end-products in commercial Cheddar enzyme-modified cheese. | 2001 Jan |
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In vitro mixed ruminal microorganism fermentation of whole cottonseed coated with gelatinized corn starch and urea. | 2001 Jan |
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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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Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms: a highly regio- and stereoselective synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzoxazines and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines. | 2001 Jan 12 |
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Allergic reactions due to ibuprofen in children. | 2001 Jan-Feb |
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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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Sensitivity of acid-adapted and acid-shocked Shigella flexneri to reduced pH achieved with acetic, lactic, and propionic acids. | 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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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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Factors determining the orientation of axially coordinated imidazoles in heme proteins. | 2001 Jul 3 |
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Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1). | 2001 Jul-Aug |
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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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Experimental approach to optimize the use of alpha-Amylases in breadmaking. | 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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Studies of propionate toxicity in Salmonella enterica identify 2-methylcitrate as a potent inhibitor of cell growth. | 2001 Jun 1 |
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Normal and abnormal heme biosynthesis. 3.(1)Synthesis and metabolism of tripropionate analogues of coproporphyrinogen-III: novel probes for the active site of coproporphyrinogen oxidase. | 2001 Jun 1 |
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Comparative gastrointestinal and plasma cholesterol responses of rats fed on cholesterol-free diets supplemented with guar gum and sodium alginate. | 2001 Mar |
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Activation of Na+/H+ exchanger is associated with hyperinsulinemia in borderline hypertensive rats. | 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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Study on sludge expansion during treatment of salad oil manufacturing wastewater by yeast. | 2001 May |
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The effect of Lactobacillus buchneri and other additives on the fermentation and aerobic stability of barley silage. | 2001 May |
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Carbon-11 acetate as a tracer of myocardial oxygen consumption. | 2001 May |
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Human responses to propionic acid. II. Quantification of breathing responses and their relationship to perception. | 2001 May |
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One-pot, catalytic, asymmetric synthesis of polypropionates. | 2001 May 17 |
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The Mycobacterium tuberculosis pks2 gene encodes the synthase for the hepta- and octamethyl-branched fatty acids required for sulfolipid synthesis. | 2001 May 18 |
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Continuous enantioselective esterification of trans-2-phenyl-1-cyclohexanol using a new Candida rugosa lipase in a packed bed bioreactor. | 2001 Nov 17 |
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Fatal propionic acidemia in mice lacking propionyl-CoA carboxylase and its rescue by postnatal, liver-specific supplementation via a transgene. | 2001 Sep 21 |
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
Thu Jul 06 02:17:29 UTC 2023
by
admin
on
Thu Jul 06 02:17:29 UTC 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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V18VR2SK15
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87139
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17496-08-1
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241-503-7
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Ammonium propionate
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DTXSID9066207
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300000034785
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |