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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
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 74.0785
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

PubMed

TitleDatePubMed
Effects of butyrate and propionate on the adhesion, growth, cell cycle kinetics, and protein synthesis of cultured human gingival fibroblasts.
1999 Dec
[Acidemia, propionic].
2001
[Volatile compounds in air and oral saliva in healthy people, and in periodontitis and gingivitis patients].
2001
Release rates for pine sawfly pheromones from two types of dispensers and phenology of Neodiprion sertifer.
2001 Apr
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
In vitro fermentation characteristics of native and processed cereal grains and potato starch using ileal chyme from dogs.
2001 Feb
Uremic concentrations of guanidino compounds inhibit neutrophil superoxide production.
2001 Feb
A survey of lipolytic and glycolytic end-products in commercial Cheddar enzyme-modified cheese.
2001 Jan
In vitro mixed ruminal microorganism fermentation of whole cottonseed coated with gelatinized corn starch and urea.
2001 Jan
Allergic reactions due to ibuprofen in children.
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
Short-chain fatty acids and human colonic function: roles of resistant starch and nonstarch polysaccharides.
2001 Jul
C1-C5 organic acid emissions from an SI engine: influence of fuel and air/fuel equivalence ratio.
2001 Jul 1
Identification and quantification of phosphatidylethanolamine-derived glucosylamines and aminoketoses from human erythrocytes--influence of glycation products on lipid peroxidation.
2001 Jul 15
The roles of the multiple CheW and CheA homologues in chemotaxis and in chemoreceptor localization in Rhodobacter sphaeroides.
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
Effect of administration with the extract of Gymnema sylvestre R. Br leaves on lipid metabolism in rats.
2001 Jun
[Ten-year trend of analgesic drug use (1984 to 1995): results of three MONICA-based surveys in Augsburg)].
2001 Jun 1
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
Dehalogenation of dichloroethene in a contaminated soil: fatty acids and alcohols as electron donors and an apparent requirement for tetrachloroethene.
2001 Mar
Preferential utilization of dipeptides by Porphyromonas gingivalis.
2001 May
Human responses to propionic acid. II. Quantification of breathing responses and their relationship to perception.
2001 May
Anaerobic codigestion of municipal solid waste and biosolids under various mixing conditions--II: Microbial population dynamics.
2001 May
One-pot, catalytic, asymmetric synthesis of polypropionates.
2001 May 17
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 Wed Jul 05 23:28:27 UTC 2023
Edited
by admin
on Wed Jul 05 23:28:27 UTC 2023
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 Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
LOINC 2849-8
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
JECFA EVALUATION PROPIONIC ACID
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
EPA PESTICIDE CODE 77702
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
NCI_THESAURUS C802
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
DSLD 4063 (Number of products:1)
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
NCI_THESAURUS C492
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
FDA ORPHAN DRUG 706219
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
FDA ORPHAN DRUG 515216
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
CODEX ALIMENTARIUS (GSFA) INS-280
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
JECFA EVALUATION INS-280
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
Code System Code Type Description
MERCK INDEX
M9209
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
Propionic acid
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
PUBCHEM
1032
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
CHEBI
30768
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
EVMPD
SUB15025MIG
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL14021
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
MESH
C029658
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
RXCUI
121047
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
ALTERNATIVE
HSDB
1192
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
JECFA MONOGRAPH
INS-280
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID8025961
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
DRUG BANK
DB03766
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
SMS_ID
100000078897
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-176-3
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
DAILYMED
JHU490RVYR
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
NCI_THESAURUS
C61911
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
CHEBI
17272
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
FDA UNII
JHU490RVYR
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
RXCUI
34658
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
RS_ITEM_NUM
1572208
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
CAS
79-09-4
Created by admin on Wed Jul 05 23:28:27 UTC 2023 , Edited by admin on Wed Jul 05 23:28:27 UTC 2023
PRIMARY
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