Pentadecanoic acid is a 15-carbon saturated fatty acid (15:0) and hence an Odd-Chain Saturated Fatty Acids (OCS-FAs).
Its major dietary source is the butterfat in cow’s milk. It can also be synthesized from propionate.
Most research in fatty acid metabolism has focused on even-chain fatty acids since they represent >99% of total human lipid concentration. For years, it had been concluded that odd chain saturated fatty acids (OCSFAs) were of little significance and used only as internal standards in laboratory methodology. However, there is now a realization that they are, in fact, relevant and important physiologically.
OCS-FAs mainly originate from dairy fat since microbiome fermentation in ruminant animals is a primary source of production. The human body can also synthesize them by elongating propionic acid, a short chain fatty acid formed in the microbiome. New research is showing they may also be formed by shortening VLCFAs by removing carbon molecules using α-oxidation. Metabolism of OCS-FAs is a bit different than even-numbered chained fatty acids. Both odd and even chain fatty acids undergo oxidation, though OCS-FAs produce a molecule of propionyl-CoA and a molecule of acetyl-CoA instead of two acetyl-CoAs. Propionyl-CoA requires a vitamin B12-dependent enzyme to be converted into succinyl-CoA and used in the citric acid cycle. It should be noted that the microbiome is not the only source for the OCS-FA precursor propionate. Endogenous propionate can be produced by the degradation of some amino acids, which can then lead to OCS-FA production.
Several epidemiologic studies show a positive association between OCS-FA and reduced risk for inflammation, cardiometabolic disease, multiple sclerosis, and nonalcoholic steatohepatitis. They are also being studied as adjuvant therapies in cancer due to their cell signaling properties which induce targeted apoptosis. Additionally, it has been found that OCS-FAs increase membrane fluidity more than PUFAs, and they are being studied as a form of treatment for Alzheimer’s disease.
References:
- Jenkins B, West JA, Koulman A. A review of odd-chain fatty acid metabolism and the role of pentadecanoic acid (C15: 0) and heptadecanoic acid (C17: 0) in health and disease. Molecules (Basel, Switzerland). 2015;20(2):2425-2444.
- Pfeuffer M, Jaudszus A. Pentadecanoic and Heptadecanoic Acids: Multifaceted Odd-Chain Fatty Acids. Advances in Nutrition. 2016;7(4):730-734.
- McKee T, McKee J. Biochemistry: The molecular basis of life. 5th. New York: Oxford University Press; 2011.
- To NB, Nguyen YT-K, Moon JY, Ediriweera MK, Cho SK. Pentadecanoic Acid, an Odd-Chain Fatty Acid, Suppresses the Stemness of MCF-7/SC Human Breast Cancer StemLike Cells through JAK2/STAT3 Signaling. Nutrients. 2020;12(6):1663.
- Huang L, Lin J-s, Aris IM, Yang G, Chen W-Q, Li L-J. Circulating saturated fatty acids and incident type 2 diabetes: A systematic review and meta-analysis. Nutrients. 2019;11(5):998.
- Venn-Watson S, Lumpkin R, Dennis EA. Efficacy of dietary odd-chain saturated fatty acid pentadecanoic acid parallels broad associated health benefits in humans: could it be essential? Scientific Reports. 2020;10(1):1-14.
- Weitkunat K, Schumann S, Nickel D, et al. Odd-chain fatty acids as a biomarker for dietary fiber intake: a novel pathway for endogenous production from propionate. The American journal of clinical nutrition. 2017;105(6):1544- 1551.
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High dietary intake of dairy products can increase levels. Because propionate is a precursor for OCS-FAs, high fiber intake can induce the microbiome to produce propionate to be converted to propionyl-CoA.
Because propionylCoA competes with acetyl-CoA, fiber intake can increase OCS-FAs levels at the expense of other saturated fatty acids.
Some studies suggest that OCS-FA levels may act as a biomarker for dietary fiber intake.
Due to the broad health benefits of OCS-FAs, questions are being raised as to whether they should be considered essential nutrients.
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Decreased dietary intake of dairy products and fiber may contribute to low levels. Literature is evolving as to their health benefits, and lower levels have been associated with risk for cardiometabolic diseases, inflammation, Alzheimer’s disease, multiple sclerosis, and nonalcoholic steatohepatitis.
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% Omega-3s, % Omega-6s, % Omega-9s, % Saturated Fats, 1-Methylhistidine, 3-Hydroxyisovaleric Acid, 3-Hydroxyphenylacetic Acid, 3-Hydroxypropionic Acid, 3-Methyl-4-OH-phenylglycol, 3-Methylhistidine, 4-Hydroxyphenylacetic Acid, 5-OH-indoleacetic Acid, 8-OHdG (urine), a-Amino-N-butyric Acid, a-Aminoadipic Acid, a-Hydroxybutyric Acid, a-Hydroxyisobutyric Acid (from MTBE), a-Keto-b-Methylvaleric Acid, a-Ketoadipic Acid, a-Ketoglutaric Acid, a-Ketoisocaproic Acid, a-Ketoisovaleric Acid, a-Ketophenylacetic Acid (from Styrene), a-Linolenic (ALA) 18:3 n3, AA / EPA (20:4 n6 / 20:5 n3), Adipic Acid, Alanine, Aluminum, Anserine (dipeptide), Antimony, Arachidic C20:0, Arachidonic (AA) 20:4 n6, Arginine, Arsenic, Asparagine, Aspartic Acid, b-Alanine, b-Aminoisobutyric Acid, b-OH-b-Methylglutaric Acid, b-OH-Butyric Acid, Barium, Behenic C22:0, Benzoic Acid, Bismuth, Cadmium, Calcium, Carnosine (dipeptide), Cesium, Chromium, cis-Aconitic Acid, Citramalic Acid, Citric Acid, Citrulline, Cobalt, Copper, Creatinine, Creatinine Concentration (Amino Acids FMV), Cystathionine, Cysteine, Cystine, D-Arabinitol, Dihomo-g-linolenic (DGLA) 20:3 n6, Dihydroxyphenylpropionic Acid (DHPPA), Docosahexaenoic (DHA) 22:6 n3, Docosapentaenoic (DPA) 22:5 n3, Docosatetraenoic (DTA) 22:4 n6, Eicosadienoic 20:2 n6, Eicosapentaenoic (EPA) 20:5 n3, Elaidic 18:1 n9t, Ethanolamine, Formiminoglutamic Acid (FIGlu), g-Aminobutyric Acid, g-Linolenic (GLA) 18:3 n6, Gadolinium, Gallium, Glutamic Acid, Glutamine, Glutaric Acid, Glyceric Acid, Glycine, Glycolic Acid, Hippuric Acid, Histidine, Homovanillic Acid, Indoleacetic Acid, Iron, Isocitric Acid, Isoleucine, Isovalerylglycine, Kynurenic / Quinolinic Ratio, Kynurenic Acid, Lactic Acid, Lead, Leucine, Lignoceric C24:0, Linoleic (LA) 18:2 n6, Linoleic / DGLA (18:2 n6 / 20:3 n6), Lipid Peroxides (urine), Lithium, Lysine, Magnesium, Malic Acid, Manganese, Margaric C17:0, Mercury, Methionine, Methylmalonic Acid, Molybdenum, Nervonic 24:1 n9, Nickel, Niobium, Oleic 18:1 n9, Omega-3 Index, Omega-6s /Omega-3s, Ornithine, Orotic Acid, Oxalic Acid, Palmitic C16:0, Palmitoleic 16:1 n7, Pentadecanoic C15:0, Phenylacetic Acid, Phenylalanine, Phosphoethanolamine, Phosphoserine, Platinum, Potassium, Proline, Pyroglutamic Acid, Pyruvic Acid, Quinolinic Acid, Rubidium, Sarcosine, Selenium, Serine, Stearic C18:0, Strontium, Suberic Acid, Succinic Acid, Sulfur, Tartaric Acid, Taurine, Thallium, Thorium, Threonine, Tin, Tricosanoic C23:0, Tryptophan, Tungsten, Tyrosine, Uranium, Urea, Urine Creatinine, Vaccenic 18:1 n7, Valine, Vanadium, Vanilmandelic Acid, Xanthurenic Acid, Zinc
