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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[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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Cecal volatile fatty acids and broiler chick susceptibility to Salmonella typhimurium colonization as affected by aflatoxins and T-2 toxin. | 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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Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo). | 2001 Apr 13 |
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In vitro conversion of propionate to pyruvate by Salmonella enterica enzymes: 2-methylcitrate dehydratase (PrpD) and aconitase Enzymes catalyze the conversion of 2-methylcitrate to 2-methylisocitrate. | 2001 Apr 17 |
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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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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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Effects of isomalto-oligosaccharides on bowel functions and indicators of nutritional status in constipated elderly men. | 2001 Feb |
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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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[Extracellular protein of propionic acid bacteria inhibits induced mutation in strains of Salmonella typhimurium]. | 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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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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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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The roles of the multiple CheW and CheA homologues in chemotaxis and in chemoreceptor localization in Rhodobacter sphaeroides. | 2001 Jun |
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Effect of an E461G mutation of beta-galactosidase (Escherichia coli, lac Z) on pL rate profiles and solvent deuterium isotope effects. | 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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Effect of administration with the extract of Gymnema sylvestre R. Br leaves on lipid metabolism in rats. | 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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Stable performance of anaerobic digestion in the presence of a high concentration of propionic acid. | 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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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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Artificial cytochrome b: computer modeling and evaluation of redox potentials. | 2001 Jun 27 |
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[Effects of chemical agents on the prevention of fungal contamination during household wheat storage in Cixian county]. | 2001 Mar |
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Dehalogenation of dichloroethene in a contaminated soil: fatty acids and alcohols as electron donors and an apparent requirement for tetrachloroethene. | 2001 Mar |
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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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[Directed modification of the pyrrole ring D in natural chlorins]. | 2001 Mar-Apr |
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Study on sludge expansion during treatment of salad oil manufacturing wastewater by yeast. | 2001 May |
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Comamonas nitrativorans sp. nov., a novel denitrifier isolated from a denitrifying reactor treating landfill leachate. | 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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Anaerobic codigestion of municipal solid waste and biosolids under various mixing conditions--II: Microbial population dynamics. | 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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Indolinone tyrosine kinase inhibitors block Kit activation and growth of small cell lung cancer cells. | 2001 May 1 |
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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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on
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Record UNII |
JHU490RVYR
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Record Status |
Validated (UNII)
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Record Version |
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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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SUB15025MIG
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CHEMBL14021
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C029658
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121047
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1192
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DTXSID8025961
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DB03766
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201-176-3
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JHU490RVYR
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C61911
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17272
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JHU490RVYR
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79-09-4
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Related Record | Type | Details | ||
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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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SALT/SOLVATE -> PARENT | |||
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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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SALT/SOLVATE -> PARENT | |||
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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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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |