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

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

s of lauric acid are known as laurates.

Occurrence

Lauric acid, as a component of

triglyceride A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and ''glyceride''). Triglycerides are the main constituents of body fat in humans and other vertebrates, as ...

s, 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),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. 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 ''Astrocaryum murumuru'' (Portuguese common name: murumuru) is a palm native to Amazon Rainforest vegetation in Brazil, which bears edible fruits. ''Murumuru'' butter, extracted from the seeds of the plant, may be used as a moisturizer.One re ...

'' (Arecaceae) a palm native to the Amazon – 47.5% in "murumuru butter" * Coconut oil 49% *'' Pycnanthus kombo'' (African nutmeg) *''

Virola surinamensis ''Virola surinamensis'', known commonly as baboonwood, ucuuba, ucuhuba and ''chalviande'',Americas Regional Workshop (Conservation & Sustainable Management of Trees, Costa Rica, November 1996). 1998''Virola surinamensis''.The IUCN Red List of Thr ...

'' (wild nutmeg) 7.8–11.5% *

Peach palm ''Bactris gasipaes'' is a species of palm native to the tropical forests of Central and South America. It is well spread in these regions, where it is often cultivated by smallholders in agroforestry systems or more rarely, in monoculture. Comm ...

seed 10.4% *

Betel nut The betel (''Piper betle'') is a vine of the family Piperaceae, which includes pepper and kava. The betel plant is native to Southeast Asia. It is an evergreen, dioecious perennial, with glossy heart-shaped leaves and white catkins. Betel pla ...

9% * Date palm seed 0.56–5.4% * Macadamia nut 0.072–1.1% *

Plum A plum is a fruit of some species in ''Prunus'' subg. ''Prunus'.'' Dried plums are called prunes. History Plums may have been one of the first fruits domesticated by humans. Three of the most abundantly cultivated species are not found ...

0.35–0.38% * Watermelon seed 0.33% *'' Viburnum opulus'' 0.24-0.33% *''

Citrullus lanatus Watermelon (''Citrullus lanatus'') is a flowering plant species of the Cucurbitaceae family and the name of its edible fruit. A scrambling and trailing vine-like plant, it is a highly cultivated fruit worldwide, with more than 1,000 vari ...

'' (egusi melon) * Pumpkin flower 205 ppm, pumpkin seed 472 ppm

In Insects

*Black soldier fly '' Hermetia illucens'' 30–50 mg/100 mg fat.

Uses

Like many other

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, f ...

s, lauric acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle. It is used mainly for the production of

soap Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are us ...

s and

cosmetics Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protec ...

. For these purposes, lauric acid is reacted with sodium hydroxide to give sodium laurate, which is a

. 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

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many f ...

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. Lauric acid increases total serum

lipoprotein A lipoprotein is a biochemical assembly whose primary function is to transport hydrophobic lipid (also known as fat) molecules in water, as in blood plasma or other extracellular fluids. They consist of a triglyceride and cholesterol center, ...

s 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 xamined either saturated or unsaturated". In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence.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. . 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.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
/ref> A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence.

References

External links

Lauric acid MS Spectrum
{{DEFAULTSORT:Lauric Acid Fatty acids Nutrition Palm oil Laurates Alkanoic acids