Propionate

Propionate
Names
	IUPAC name Propionate
	Other names Propanoate, Propanoic acid, ion(1-)
Identifiers
CAS Number	72-03-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	94556;
PubChem CID	104745;
UNII	AKW5EM890C ;
CompTox Dashboard (EPA)	DTXSID90222279 ;
	InChI InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)/p-1 Key: XBDQKXXYIPTUBI-UHFFFAOYSA-M; InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)/p-1 Key: XBDQKXXYIPTUBI-UHFFFAOYSA-M;
	SMILES CCC(=O)[O-];
Properties
Chemical formula	C3H5O2−
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

The propionate /ˈproʊpiəneɪt/, or propanoate ion, is C₂H₅COO⁻ (the conjugate base of propionic acid).

A propionic, or propanoic, compound is a small salt or ester of propionic acid. In these compounds, propionate is often written in shorthand, as CH₃CH₂CO₂ or simply EtCO₂.

Propionates should not be confused with propenoates (commonly known as acrylates), the ions/salts/esters of propenoic acid (also known as 2-propenoic acid or acrylic acid).

Propionate is observed to be among the most common short-chain fatty acids produced by human gut microbiota in response to indigestible carbohydrates (fiber) in the diet.[1] A study in mice suggests that propionate is produced by the bacteria of the genus Bacteroides in the gut, and that it offers some protection against Salmonella there.[2] Another study finds that fatty acid propionate can calm the immune cells that drive up blood pressure, thereby protecting the body from damaging effects of high blood pressure.[3]

Examples

Salts

Sodium propionate NaC₂H₅CO₂
Potassium propionate KC₂H₅CO₂
Calcium propionate Ca(C₂H₅CO₂)₂
Zirconium propionate Zr(C₂H₅CO₂)₄

Esters

Methyl propionate (C₂H₅(CO)OCH₃)
Ethyl propionate (C₂H₅(CO)OC₂H₅)
Propyl propionate (C₂H₅(CO)OC₃H₇)
Pentyl propionate (C₂H₅(CO)OC₅H₁₁)
Fluticasone propionate C₂₅H₃₁F₃O₅S

Bacteriology

The Bacteria species Coprothermobacter platensis produces propionate when fermenting gelatin.[4]

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References

Cani, Patrice D.; Knauf, Claude (27 May 2016). "How gut microbes talk to organs: The role of endocrine and nervous routes". Molecular Metabolism. 5 (9): 743–752. doi:10.1016/j.molmet.2016.05.011. PMC 5004142. PMID 27617197.
http://med.stanford.edu/news/all-news/2018/07/gut-bacteria-byproduct-protects-against-salmonella.html
Ballaschk, Martin. "How dietary fiber and gut bacteria protect the cardiovascular system". Max Delbrück Center for Molecular Medicine. The fatty acid propionate helps defend against the effects of high blood pressure, ... Gut bacteria produce the substance – which calms the immune cells that drive up blood pressure – from natural dietary fiber
Etchebehere, C.; Pavan, M. E.; Zorzópulos, J.; Soubes, M.; Muxí, L. (October 1998). "Coprothermobacter platensis sp. nov., a new anaerobic proteolytic thermophilic bacterium isolated from an anaerobic mesophilic sludge". International Journal of Systematic Bacteriology. 48 Pt 4 (4): 1297–1304. doi:10.1099/00207713-48-4-1297. ISSN 0020-7713. PMID 9828430.

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[1] Cani, Patrice D.; Knauf, Claude (27 May 2016). "How gut microbes talk to organs: The role of endocrine and nervous routes". Molecular Metabolism. 5 (9): 743–752. doi:10.1016/j.molmet.2016.05.011. PMC 5004142. PMID 27617197.

[2] ttp://med.stanford.edu/news/all-news/2018/07/gut-bacteria-byproduct-protects-against-salmonella.html

[3] Ballaschk, Martin. "How dietary fiber and gut bacteria protect the cardiovascular system". Max Delbrück Center for Molecular Medicine. The fatty acid propionate helps defend against the effects of high blood pressure, ... Gut bacteria produce the substance – which calms the immune cells that drive up blood pressure – from natural dietary fiber

[4] Etchebehere, C.; Pavan, M. E.; Zorzópulos, J.; Soubes, M.; Muxí, L. (October 1998). "Coprothermobacter platensis sp. nov., a new anaerobic proteolytic thermophilic bacterium isolated from an anaerobic mesophilic sludge". International Journal of Systematic Bacteriology. 48 Pt 4 (4): 1297–1304. doi:10.1099/00207713-48-4-1297. ISSN 0020-7713. PMID 9828430.