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Details

Stereochemistry ACHIRAL
Molecular Formula C3H6O2
Molecular Weight 74.0787
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPIONIC ACID

SMILES

CCC(=O)O

InChI

InChIKey=XBDQKXXYIPTUBI-UHFFFAOYSA-N
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)

HIDE SMILES / InChI

Molecular Formula C3H6O2
Molecular Weight 74.0787
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

PubMed

TitleDatePubMed
[Acidemia, propionic].
2001
Inhibition by chromium and cadmium of anaerobic acidogenesis.
2001
Cytosolic acidification as a signal mediating hyperosmotic stress responses in Dictyostelium discoideum.
2001
PET reversed mismatch in an experimental model of subacute myocardial infarction.
2001 Apr
The effect of season and monensin sodium on the digestive characteristics of autumn and spring pasture fed to sheep.
2001 Apr
Cecal volatile fatty acids and broiler chick susceptibility to Salmonella typhimurium colonization as affected by aflatoxins and T-2 toxin.
2001 Apr
Fluticasone propionate aqueous nasal spray reduces inflammatory cells in unchallenged allergic nasal mucosa: effects of single allergen challenge.
2001 Apr
SCFA increase intestinal Na absorption by induction of NHE3 in rat colon and human intestinal C2/bbe cells.
2001 Apr
Presynaptic function is altered in snake K+-depolarized motor nerve terminals containing compromised mitochondria.
2001 Apr 1
Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo).
2001 Apr 13
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
Solution structure of Methylophilus methylotrophus cytochrome c": insights into the structural basis of haem-ligand detachment.
2001 Apr 27
A biochemical hypothesis explaining the response of enhanced biological phosphorus removal biomass to organic substrates.
2001 Aug
Influence of anaerobic culture acclimation on the degradation kinetics of various substrates.
2001 Aug 5
Effects of isomalto-oligosaccharides on bowel functions and indicators of nutritional status in constipated elderly men.
2001 Feb
Role of type II thioesterases: evidence for removal of short acyl chains produced by aberrant decarboxylation of chain extender units.
2001 Feb
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
[Extracellular protein of propionic acid bacteria inhibits induced mutation in strains of Salmonella typhimurium].
2001 Jan-Feb
New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies.
2001 Jul
Acetate, propionate and butyrate in plasma: determination of the concentration and isotopic enrichment by gas chromatography/mass spectrometry with positive chemical ionization.
2001 Jul
Influence of carbohydrate source and buffer on rumen fermentation characteristics, milk yield, and milk composition in late-lactation Holstein cows.
2001 Jul
Effects of NutriDense and waxy corn hybrids on the rumen fermentation, digestibility and lactational performance of dairy cows.
2001 Jul
Sensitivity of acid-adapted and acid-shocked Shigella flexneri to reduced pH achieved with acetic, lactic, and propionic acids.
2001 Jul
Short-chain fatty acids and human colonic function: roles of resistant starch and nonstarch polysaccharides.
2001 Jul
Identification and quantification of phosphatidylethanolamine-derived glucosylamines and aminoketoses from human erythrocytes--influence of glycation products on lipid peroxidation.
2001 Jul 15
Factors determining the orientation of axially coordinated imidazoles in heme proteins.
2001 Jul 3
Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1).
2001 Jul-Aug
Functional and structural response of a cellulose-degrading methanogenic microbial community to multiple aeration stress at two different temperatures.
2001 Jun
Effect of an E461G mutation of beta-galactosidase (Escherichia coli, lac Z) on pL rate profiles and solvent deuterium isotope effects.
2001 Jun
2-Methylisocitrate lyases from the bacterium Escherichia coli and the filamentous fungus Aspergillus nidulans: characterization and comparison of both enzymes.
2001 Jun
Fixed drug eruption due to naproxen; lack of cross-reactivity with other propionic acid derivatives.
2001 Jun
Inhibition of growth of methane-producing bacteria of the ruminant forestomach by hydroxymethylglutaryl-SCoA reductase inhibitors.
2001 Jun
Effect of administration with the extract of Gymnema sylvestre R. Br leaves on lipid metabolism in rats.
2001 Jun
Experimental approach to optimize the use of alpha-Amylases in breadmaking.
2001 Jun
Stable performance of anaerobic digestion in the presence of a high concentration of propionic acid.
2001 Jun
[Ten-year trend of analgesic drug use (1984 to 1995): results of three MONICA-based surveys in Augsburg)].
2001 Jun 1
Studies of propionate toxicity in Salmonella enterica identify 2-methylcitrate as a potent inhibitor of cell growth.
2001 Jun 1
Artificial cytochrome b: computer modeling and evaluation of redox potentials.
2001 Jun 27
[Effects of chemical agents on the prevention of fungal contamination during household wheat storage in Cixian county].
2001 Mar
Dehalogenation of dichloroethene in a contaminated soil: fatty acids and alcohols as electron donors and an apparent requirement for tetrachloroethene.
2001 Mar
Comparative gastrointestinal and plasma cholesterol responses of rats fed on cholesterol-free diets supplemented with guar gum and sodium alginate.
2001 Mar
Interannual variations in the lipids of the Antarctic pteropods Clione limacina and Clio pyramidata.
2001 Mar
Study on sludge expansion during treatment of salad oil manufacturing wastewater by yeast.
2001 May
Comamonas nitrativorans sp. nov., a novel denitrifier isolated from a denitrifying reactor treating landfill leachate.
2001 May
Carbon-11 acetate as a tracer of myocardial oxygen consumption.
2001 May
Anaerobic codigestion of municipal solid waste and biosolids under various mixing conditions--II: Microbial population dynamics.
2001 May
Thin layer chromatographic determination of organic acids for rapid identification of bifidobacteria at genus level.
2001 May
Desensitization of ileal vagal receptors by short-chain fatty acids in pigs.
2001 May
Indolinone tyrosine kinase inhibitors block Kit activation and growth of small cell lung cancer cells.
2001 May 1
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
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 Sat Jun 26 00:21:48 UTC 2021
Edited
by admin
on Sat Jun 26 00:21:48 UTC 2021
Record UNII
JHU490RVYR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPIONIC ACID
FCC   FHFI   HSDB   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
METACETONIC ACID
Common Name English
PROPIONIC ACID [INCI]
Common Name English
PROPIONIC ACID [FHFI]
Common Name English
ANTISCHIM B
Common Name English
PROPIONIC ACID [VANDF]
Common Name English
PROPANOIC ACID
Common Name English
METHYLACETIC ACID
Systematic Name English
CARBOXYETHANE
Systematic Name English
PROPIONIC ACID [FCC]
Common Name English
LUPROSIL
Common Name English
PROPIONIC ACID [HSDB]
Common Name English
PROPIONATE
Systematic Name English
E-280
Code English
FEMA NO. 2924
Code English
ETHYLFORMIC ACID
Systematic Name English
PROPIONIC ACID [MART.]
Common Name English
INS-280
Code English
PROPIONIC ACID [WHO-DD]
Common Name English
PROPIONIC ACID [MI]
Common Name English
PROPIONIC ACID [USP-RS]
Common Name English
INS NO.280
Code English
Classification Tree Code System Code
CFR 21 CFR 184.1081
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
LOINC 2849-8
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
JECFA EVALUATION PROPIONIC ACID
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
EPA PESTICIDE CODE 77702
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
NCI_THESAURUS C802
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
DSLD 4063 (Number of products:1)
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
NCI_THESAURUS C492
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
FDA ORPHAN DRUG 706219
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
FDA ORPHAN DRUG 515216
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-280
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
JECFA EVALUATION INS-280
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
Code System Code Type Description
MERCK INDEX
M9209
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1572208
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY USP-RS
PUBCHEM
1032
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
EVMPD
SUB15025MIG
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
ChEMBL
CHEMBL14021
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
MESH
C029658
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
RXCUI
121047
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
ALTERNATIVE
HSDB
1192
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-280
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
EPA CompTox
79-09-4
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
DRUG BANK
DB03766
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-176-3
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
NCI_THESAURUS
C61911
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
FDA UNII
JHU490RVYR
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
RXCUI
34658
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
CAS
79-09-4
Created by admin on Sat Jun 26 00:21:48 UTC 2021 , Edited by admin on Sat Jun 26 00:21:48 UTC 2021
PRIMARY
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