Short-chain fatty acid

Short-chain fatty acids (SCFAs), also referred to as volatile fatty acids (VFAs),^[1] are fatty acids with an aliphatic tail of less than six carbon atoms.^[2]

List of SCFAs

Lipid number	Name		Salt/Ester Name		Formula		Mass (g/mol)	Diagram
	Common	Systematic	Common	Systematic	Molecular	Structural
	Formic acid	Methanoic acid	Formate	Methanoate	CH2O2	HCOOH	46.03
C2:0	Acetic acid	Ethanoic acid	Acetate	Ethanoate	C2H4O2	CH3COOH	60.05
C3:0	Propionic acid	Propanoic acid	Propionate	Propanoate	C3H6O2	CH3CH2COOH	74.08
C4:0	Butyric acid	Butanoic acid	Butyrate	Butanoate	C4H8O2	CH3(CH2)2COOH	88.11
	Isobutyric acid	2-Methylpropanoic acid	Isobutyrate	2-Methylpropanoate	C4H8O2	(CH3)2CHCOOH	88.11
C5:0	Valeric acid	Pentanoic acid	Valerate	Pentanoate	C5H10O2	CH3(CH2)3COOH	102.13
	Isovaleric acid	3-Methylbutanoic acid	Isovalerate	3-Methylbutanoate	C5H10O2	(CH3)2CHCH2COOH	102.13

Applications

Dietary relevance

Short-chain fatty acids are produced when dietary fiber is fermented in the colon.^[3]

Short-chain fatty acids 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 and enter lymphatic capillaries, and enter the blood first at the subclavian vein.

Medical relevance

The short-chain fatty acid butyrate is particularly important for colon health because it is the primary energy source for colonic cells and has anti-carcinogenic as well as anti-inflammatory properties^[5] that are important for keeping colon cells healthy.^[6][7] Butyrate inhibits the growth and proliferation of tumor cell lines in vitro, induces differentiation of tumor cells, producing a phenotype similar to that of the normal mature cell,^[8] and induces apoptosis or programmed cell death of human colorectal cancer cells.^[9][10] Butyrate inhibits angiogenesis by inactivating Sp1 transcription factor activity and downregulating VEGF gene expression.^[11]

See also

• List of carboxylic acids

References

1. "Role of Volatile Fatty Acids in Development of the Cecal Microflora in Broiler Chickens during Growth" at asm.org
2. Brody, Tom (1999). Nutritional Biochemistry (2nd ed.). Academic Press. p. 320. ISBN 0121348369. Retrieved December 21, 2012.
3. Wong, Julia M.; de Souza, Russell; Kendall, Cyril W.; Emam, Azadeh; Jenkins, David J. (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. Cite uses deprecated parameter |coauthors= (help)
4. Kuksis, Arnis (2000). "Biochemistry of Glycerolipids and Formation of Chylomicrons". In Christophe, Armand B.; DeVriese, Stephanie. Fat Digestion and Absorption. The American Oil Chemists Society. p. 163. ISBN 189399712X. Retrieved December 21, 2012.
5. Greer JB, O'Keefe SJ (2011). "Microbial induction of immunity, inflammation, and cancer". Front Physiol 1: 168. doi:10.3389/fphys.2010.00168. PMC 3059938. PMID 21423403.
6. Scheppach W (January 1994). "Effects of short chain fatty acids on gut morphology and function". Gut 35 (1 Suppl): S35–8. doi:10.1136/gut.35.1_Suppl.S35. PMC 1378144. PMID 8125387.
7. Andoh A, Tsujikawa T, Fujiyama Y (2003). "Role of dietary fiber and short-chain fatty acids in the colon". Curr. Pharm. Des. 9 (4): 347–58. doi:10.2174/1381612033391973. PMID 12570825.
8. Toscani A, Soprano DR, Soprano KJ (1988). "Molecular analysis of sodium butyrate-induced growth arrest". Oncogene Res. 3 (3): 223–38. PMID 3144695.
9. Wong JM, de Souza R, Kendall CW, Emam A, Jenkins DJ (March 2006). "Colonic health: fermentation and short chain fatty acids". J. Clin. Gastroenterol. 40 (3): 235–43. doi:10.1097/00004836-200603000-00015. PMID 16633129.
10. Scharlau D, Borowicki A, Habermann N, et al. (2009). "Mechanisms of primary cancer prevention by butyrate and other products formed during gut flora-mediated fermentation of dietary fibre". Mutat. Res. 682 (1): 39–53. doi:10.1016/j.mrrev.2009.04.001. PMID 19383551.
11. Prasanna Kumar S, Thippeswamy G, Sheela ML, Prabhakar BT, Salimath BP. Butyrate-induced phosphatase regulates VEGF and angiogenesis via Sp1. Arch Biochem Biophys. 2008 Oct 1;478(1):85-95.

Further reading

• A review of the biological properties of SCFA from the Danone Institute via archive.org
• Besten GD, Bleeker A, Gerding A, van Eunen K, Havinga R, van Dijk TH, Oosterveer MH, Jonker JW, Groen AK, Reijngoud DJ, Bakker BM (2015). "Short-Chain Fatty Acids protect against High-Fat Diet-Induced Obesity via a PPARγ-dependent switch from lipogenesis to fat oxidation". Diabetes 64: 2398–408. doi:10.2337/db14-1213. PMID 25695945. Retrieved 2015-02-22.