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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

Description

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

Sample Use Guides

In Vivo Use Guide
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
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.