Short-chain fatty acid

Short-chain fatty acids (SCFAs) are fatty acids of two to six carbon atoms. ^[1] The SCFAs' lower limit is interpreted differently, either with one, two, three or four carbon atoms.^{[ citation needed ]} Derived from intestinal microbial fermentation of indigestible foods, SCFAs in human gut are acetic, propionic and butyric acid. Butyrate is the main energy source of colonocytes, making them crucial to gastrointestinal health. ^{[1] [2]} SCFAs all possess varying degrees of water solubility, which distinguishes them from longer chain fatty acids that are immiscible.

List of SCFAs

Lipid number	Name		Salt/Ester Name		Formula		Mass (g/mol)	Diagram
	Common	Systematic	Common	Systematic	Molecular	Structural
C2:0	Acetic acid	Ethanoic acid	Acetate	Ethanoate	C 2 H 4 O 2	CH3COOH	60.05
C3:0	Propionic acid	Propanoic acid	Propionate	Propanoate	C 3 H 6 O 2	CH3CH2COOH	74.08
C4:0	Butyric acid	Butanoic acid	Butyrate	Butanoate	C 4 H 8 O 2	CH3(CH2)2COOH	88.11
C4:0	Isobutyric acid	2-Methylpropanoic acid	Isobutyrate	2-Methylpropanoate	C 4 H 8 O 2	(CH3)2CHCOOH	88.11
C5:0	Valeric acid	Pentanoic acid	Valerate	Pentanoate	C 5 H 10 O 2	CH3(CH2)3COOH	102.13
C5:0	Isovaleric acid	3-Methylbutanoic acid	Isovalerate	3-Methylbutanoate	C 5 H 10 O 2	(CH3)2CHCH2COOH	102.13
C5:0	2-Methylbutyric acid	2-Methylbutanoic acid	2-Methylbutanoate	2-Methylbutanoate	C 5 H 10 O 2	CH3CH2CH(CH3)COOH	102.13

Functions

SCFAs are produced when dietary fiber is fermented in the colon. ^{[1] [3]} Acetate, propionate and butyrate are the three most common SCFAs. ^[3] SCFAs and medium-chain fatty acids are primarily absorbed through the portal vein during lipid digestion, ^[4] while long-chain fatty acids are packed into chylomicrons, enter lymphatic capillaries, then transfer to the blood at the subclavian vein. ^[1]

SCFAs have diverse physiological roles in body functions, affecting the production of lipids, energy, and vitamins. ^{[1] [2] [5]} Butyric acid supports large intestine health as the primary energy source for colonocytes – the epithelial cells of the colon. ^{[1] [2]} The liver can use acetate for energy. ^[6]

See also

• List of carboxylic acids
• Medium-chain fatty acid (MCFA), fatty acid with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides
• Long-chain fatty acid (LCFA), fatty acid with aliphatic tails of 13 to 21 carbons
• Very long chain fatty acid (VLCFA), fatty acid with aliphatic tails of 22 or more carbons
• Odd-chain fatty acid

References

1. Brody T (1999). Nutritional Biochemistry (2nd ed.). Academic Press. p. 320. ISBN   978-0121348366 . Retrieved December 21, 2012.
2. Canfora EE, Jocken JW, Blaak EE (October 2015). "Short-chain fatty acids in control of body weight and insulin sensitivity". Nature Reviews. Endocrinology. 11 (10): 577–591. doi:10.1038/nrendo.2015.128. PMID   26260141. S2CID   1263823.
3. Wong JM, de Souza R, Kendall CW, Emam A, Jenkins DJ (March 2006). "Colonic health: fermentation and short chain fatty acids". Journal of Clinical Gastroenterology. 40 (3): 235–243. doi:10.1097/00004836-200603000-00015. PMID   16633129. S2CID   46228892.
4. Kuksis A (2000). "Biochemistry of Glycerolipids and Formation of Chylomicrons". In Christophe AB, DeVriese S (eds.). Fat Digestion and Absorption. The American Oil Chemists Society. p. 163. ISBN   978-1893997127 . Retrieved December 21, 2012.
5. Byrne CS, Chambers ES, Morrison DJ, Frost G (September 2015). "The role of short chain fatty acids in appetite regulation and energy homeostasis". International Journal of Obesity. 39 (9): 1331–1338. doi:10.1038/ijo.2015.84. PMC   4564526 . PMID   25971927.
6. Roy CC, Kien CL, Bouthillier L, Levy E (August 2006). "Short-chain fatty acids: ready for prime time?". Nutrition in Clinical Practice. 21 (4): 351–366. doi:10.1177/0115426506021004351. PMID   16870803.

Further reading

• A review of the biological properties of SCFA from the Danone Institute via archive.org