Short-chain fatty acid

From Wikipedia, the free encyclopedia

Short-chain fatty acids (SCFAs) are fatty acids with fewer than six carbon atoms.[1] Derived from intestinal microbial fermentation of indigestible foods, SCFAs are 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
C1:0 Formic acid Methanoic acid Formate Methanoate CH2O2 HCOOH 46.03
Ameisensäure Skelett.svg
C2:0 Acetic acid Ethanoic acid Acetate Ethanoate C2H4O2 CH3COOH 60.05
Acetic-acid-2D-skeletal.svg
C3:0 Propionic acid Propanoic acid Propionate Propanoate C3H6O2 CH3CH2COOH 74.08
Propionic acid chemical structure.svg
C4:0 Butyric acid Butanoic acid Butyrate Butanoate C4H8O2 CH3(CH2)2COOH 88.11
Butyric acid acsv.svg
C4:0 Isobutyric acid 2-Methylpropanoic acid Isobutyrate 2-Methylpropanoate C4H8O2 (CH3)2CHCOOH 88.11
Isoutyric-acid.svg
C5:0 Valeric acid Pentanoic acid Valerate Pentanoate C5H10O2 CH3(CH2)3COOH 102.13
Valeric acid acsv.svg
C5:0 Isovaleric acid 3-Methylbutanoic acid Isovalerate 3-Methylbutanoate C5H10O2 (CH3)2CHCH2COOH 102.13
Isovaleric acid structure.png
C5:0 2-Methylbutyric acid 2-Methylbutyric acid 2-Methylbutanoate 2-Methylbutanoate C5H10O2 CH3CH2CH(CH3)COOH 102.13
2-Methylbutanoic acid.png

Functions[]

SCFAs are produced when dietary fiber is fermented in the colon.[1][3] Macronutrient composition (carbohydrate, protein, or fat) of diets affects circulating SCFAs.[4]

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,[5] 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.[1][2] They can affect the production of lipids, energy and vitamins.[6] They can also affect appetite and cardiometabolic health.[4] Butyrate is particularly important for colon health because it is the primary energy source for colonocytes (the epithelial cells of the colon).[1][2] The liver can use acetate for energy.[7]

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

References[]

  1. ^ a b c d e f Brody, Tom (1999). Nutritional Biochemistry (2nd ed.). Academic Press. p. 320. ISBN 978-0121348366. Retrieved December 21, 2012.
  2. ^ a b c Canfora EE, Jocken JW, Blaak EE (2015). "Short-chain fatty acids in control of body weight and insulin sensitivity". Nature Reviews Endocrinology. 11 (10): 577–91. doi:10.1038/nrendo.2015.128. PMID 26260141. S2CID 1263823.
  3. ^ a b Wong, J. M.; De Souza, R; Kendall, C. W.; Emam, A; Jenkins, D. J. (2006). "Colonic health: Fermentation and short chain fatty acids". Journal of Clinical Gastroenterology. 40 (3): 235–43. doi:10.1097/00004836-200603000-00015. PMID 16633129. S2CID 46228892.
  4. ^ a b Mueller, Noel T; Zhang, Mingyu; Juraschek, Stephen P; Miller, Edgar R; Appel, Lawrence J (2020-01-11). "Effects of high-fiber diets enriched with carbohydrate, protein, or unsaturated fat on circulating short chain fatty acids: results from the OmniHeart randomized trial". The American Journal of Clinical Nutrition. 111 (3): 545–554. doi:10.1093/ajcn/nqz322. ISSN 0002-9165. PMC 7049528. PMID 31927581.
  5. ^ Kuksis, Arnis (2000). "Biochemistry of Glycerolipids and Formation of Chylomicrons". In Christophe, Armand B.; DeVriese, Stephanie (eds.). Fat Digestion and Absorption. The American Oil Chemists Society. p. 163. ISBN 978-1893997127. Retrieved December 21, 2012.
  6. ^ Byrne, C. S; Chambers, E. S; Morrison, D. J; Frost, G (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.
  7. ^ Roy, Claude C.; Kien, C. Lawrence; Bouthillier, Lise; Levy, Emile (2006). "Short-chain fatty acids: Ready for prime time?". Nutrition in Clinical Practice. 21 (4): 351–366. doi:10.1177/0115426506021004351. ISSN 0884-5336. PMID 16870803.

Further reading[]

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