Lauric acid explained

Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids. It is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and esters of lauric acid are known as laurates.

Occurrence

Lauric acid, as a component of triglycerides, comprises about half of the fatty-acid content in coconut milk, coconut oil, laurel oil, and palm kernel oil (not to be confused with palm oil),^{[1] [2]} Otherwise, it is relatively uncommon. It is also found in human breast milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).

In various plants

• The palm tree Attalea speciosa, a species popularly known in Brazil as babassu – 50% in babassu oil
• Attalea cohune, the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm) – 46.5% in cohune oil
• Astrocaryum murumuru (Arecaceae) a palm native to the Amazon – 47.5% in "murumuru butter"
• Coconut oil 49%
• Pycnanthus kombo (African nutmeg)
• Virola surinamensis (wild nutmeg) 7.8–11.5%
• Peach palm seed 10.4%
• Betel nut 9%
• Date palm seed 0.56–5.4%
• Macadamia nut 0.072–1.1%
• Plum 0.35–0.38%
• Watermelon seed 0.33%
• Viburnum opulus 0.24-0.33%^[3]
• Citrullus lanatus (egusi melon)
• Pumpkin flower 205 ppm, pumpkin seed 472 ppm

Insect

• Black soldier fly Hermetia illucens 30–50 mg/100 mg fat.^[4]

Uses

Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle. It is used mainly for the production of soaps and cosmetics. For these purposes, lauric acid is reacted with sodium hydroxide to give sodium laurate, which is a soap. Most commonly, sodium laurate is obtained by saponification of various oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps.

Lauric acid is a precursor to dilauroyl peroxide, a common initiator of polymerizations.

Nutritional and medical aspects

Although 95% of medium-chain triglycerides are absorbed through the portal vein, only 25–30% of lauric acid is absorbed through it.^{[5] [6]} Lauric acid induces apoptosis in cancer and promotes the proliferation of normal cells by maintaining cellular redox homeostasis. ^[7]

Lauric acid increases total serum lipoproteins more than many other fatty acids, but mostly high-density lipoprotein (HDL). As a result, lauric acid has been characterized as having "a more favorable effect on total HDL than any other fatty acid [examined], either saturated or unsaturated".^[8] In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence.^[9] Nonetheless, an extensive meta-analysis on foods affecting the total LDL/serum lipoprotein ratio found in 2003 that the net effects of lauric acid on coronary artery disease outcomes remained uncertain.^[10] A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence.

Further reading

• Berner, Louise A. (1993). Defining the Role of Milkfat in Balanced Diets. In John E. Kinsella (Ed.) Advances in Food and Nutrition Research – Volume 37. Academic Press. pp. 159–166. .

External links

• Lauric acid MS Spectrum

Notes and References

1. 2001 . Lexicon of lipid nutrition (IUPAC Technical Report) . Pure and Applied Chemistry . 73 . 4 . 685–744 . 10.1351/pac200173040685 . free . Beare-Rogers . J. . Dieffenbacher . A. . Holm . J.V. . 84492006 .
2. David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim.
3. Variation in volatile and fatty acid contents among Viburnum opulus L. Fruits growing different locations . 2019 . Zarifikhosroshahi . Tugba Murathan . Kafkas . Okatan . Scientia Horticulturae . 264 . 109160 . 10.1016/j.scienta.2019.109160. 213568257 .
4. 2019 . Black soldier fly (Hermetia illucens L.): effect on the fat integrity using different approaches to the killing of the prepupae. . Journal of Insects as Food and Feed . 10.3920/JIFF2019.0002 . Montevecchi . G. . Zanasi . L. . Masino . F. . Maistrello . L. . Antonelli . A.. 6 . 2 . 121–131 . 208604432 .
5. Dual Roles of Coconut Oil and Its Major Component Lauric Acid on Redox Nexus: Focus on Cytoprotection and Cancer Cell Death . 2022 . Frontiers in Neuroscience . 16 . 833630 . 10.3389/fnins.2022.833630 . free . Ramya . Venkatesan . Shyam . Karuppiah Prakash . Kowsalya . Eshwaran . Balavigneswaran . Chelladurai Karthikeyan . Kadalmani . Balamuthu . 35360165 . 8963114 .
6. Eyres L, Eyres MF, Chisholm A, Brown RC . Coconut oil consumption and cardiovascular risk factors in humans . . 74 . 4 . 267–280 . 2016 . 10.1093/nutrit/nuw002 . 4892314 . 26946252 .
7. Lauric acid epigenetically regulates lncRNA HOTAIR by remodeling chromatin H3K4 tri-methylation and modulates glucose transport in SH-SY5Y human neuroblastoma cells: Lipid switch in macrophage activation . 2024 . Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids . 1869 . 1 . 159429 . 10.1016/j.bbalip.2023.159429 . Ramya . Venkatesan . Shyam . Karuppiah Prakash . Angelmary . Arulanandu . Kadalmani . Balamuthu .
8. Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials . American Journal of Clinical Nutrition . Mensink RP, Zock PL, Kester AD, Katan MB . 77 . 5 . 1146–1155 . May 2003 . 0002-9165 . 12716665. 10.1093/ajcn/77.5.1146. free .
9. Thijssen, M.A. and R.P. Mensink. (2005). Fatty Acids and Atherosclerotic Risk. In Arnold von Eckardstein (Ed.) Atherosclerosis: Diet and Drugs. Springer. pp. 171–172. .
10. http://ajcn.nutrition.org/content/77/5/1146.full?ijkey=846a72387ebc0d82545acd5442a0c3a9e9fc3566 Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials