Lauric acid, systematically dodecanoic acid, is a

saturated fatty acid A saturated fat is a type of fat in which the fatty acid chains have all single bonds. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched c ...

with a 12-carbon atom chain, thus having many properties of

medium-chain fatty acids Medium-chain triglycerides (MCTs) are triglycerides with two or three fatty acids having an aliphatic tail of 6–12 carbon atoms, i.e. medium-chain fatty acids (MCFAs). Rich food sources for commercial extraction of MCTs include palm kernel oil a ...

. It is a bright white, powdery solid with a faint odor of bay oil or soap. The

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...

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 ar ...

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 w ...

s, comprises about half of the fatty-acid content in

coconut milk Coconut milk is an opaque, milky-white liquid extracted from the grated pulp of mature coconuts. The opacity and rich taste of coconut milk are due to its high oil content, most of which is saturated fat. Coconut milk is a traditional food i ...

coconut oil frameless , right , alt = A cracked coconut and a bottle of coconut oil Coconut oil (or coconut butter) is an edible oil derived from the wick, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat; in warmer climates duri ...

, laurel oil, and

palm kernel oil Palm kernel oil is an edible plant oil derived from the kernel of the oil palm tree ''Elaeis guineensis''. It is related to other two edible oils: ''palm oil'', extracted from the fruit pulp of the oil palm, and ''coconut oil'', extracted from ...

(not to be confused with

palm oil Palm oil is an edible vegetable oil derived from the mesocarp (reddish pulp) of the fruit of the oil palms. The oil is used in food manufacturing, in beauty products, and as biofuel. Palm oil accounted for about 33% of global oils produced from ...

),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 Breast milk (sometimes spelled as breastmilk) or mother's milk is milk produced by mammary glands located in the breast of a human female. Breast milk is the primary source of nutrition for newborns, containing fat, protein, carbohydrates ( lacto ...

(6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).

In various plants

*The palm tree ''

Attalea speciosa ''Attalea speciosa'', the babassu, babassu palm, ''babaçu, or cusi'', is a palm native to the Amazon Rainforest region in South America. The babassu palm is the predominant species in the Maranhão Babaçu forests of Maranhão and Piauí state ...

'', a species popularly known in Brazil as ''babassu'' – 50% in ''babassu'' oil *''

Attalea cohune ''Attalea cohune'', commonly known as the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm), is a species of palm tree native to Mexico and parts of Central America. The cohune palm is used in the production of cohune o ...

'', the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm) – 46.5% in

cohune oil Cohune oil is pressed from the seeds of the cohune palm, which is native to Central and South America. Along with other byproducts of the palm, cohune oil is believed to have been used by cultures in southern Mesoamerica since the pre-Columbian ...

*''

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 frameless , right , alt = A cracked coconut and a bottle of coconut oil Coconut oil (or coconut butter) is an edible oil derived from the wick, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat; in warmer climates duri ...

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. Commo ...

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 plan ...

9% *

Date palm ''Phoenix dactylifera'', commonly known as date or date palm, is a flowering plant species in the palm family, Arecaceae, cultivated for its edible sweet fruit called dates. The species is widely cultivated across northern Africa, the Middle Eas ...

seed 0.56–5.4% *

Macadamia nut ''Macadamia'' is a genus of four species of trees in the flowering plant family Proteaceae. They are indigenous to Australia, native to northeastern New South Wales and central and southeastern Queensland specifically. Two species of the genus ...

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 i ...

0.35–0.38% *

Watermelon 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 varieti ...

seed 0.33% *''

Viburnum opulus ''Viburnum opulus'', the guelder-rose or guelder rose () is a species of flowering plant in the family (biology), family Adoxaceae (formerly Caprifoliaceae) native plant, native to Europe, northern Africa and central Asia. Description ''Viburn ...

'' 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 varieti ...

'' (egusi melon) *

Pumpkin A pumpkin is a vernacular term for mature winter squash of species and varieties in the genus ''Cucurbita'' that has culinary and cultural significance but no agreed upon botanical or scientific meaning. The term ''pumpkin'' is sometimes use ...

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, fr ...

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 use ...

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 protect ...

. For these purposes, lauric acid is reacted with

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

to give sodium laurate, which is a

. Most commonly, sodium laurate is obtained by

saponification Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. ...

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 Dilauroyl peroxide is an organic compound with the formula (C11H23CO2)2. A colorless solid, it is often sold as a water-damped solid. It is the symmetrical peroxide of lauric acid Lauric acid, systematically dodecanoic acid, is a saturated fat ...

, a common initiator of

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

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, sur ...

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 Low-density lipoprotein (LDL) is one of the five major groups of lipoprotein that transport all fat molecules around the body in extracellular water. These groups, from least dense to most dense, are chylomicrons (aka ULDL by the overall densit ...

/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 Cardiovascular disease (CVD) is a class of diseases that involve the heart or blood vessels. CVD includes coronary artery diseases (CAD) such as angina and myocardial infarction (commonly known as a heart attack). Other CVDs include stroke, h ...

incidence.

References

External links

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