# Lauric acid

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). Oils with high levels of lauric acid are known as lauric oils. 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%
* Citrullus lanatus (egusi melon)
* Pumpkin flower 205 ppm, pumpkin seed 472 ppm

### Insect

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

## 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 commercial initiator of polymerizations.

## Production and reactions

Lauric acid is mainly isolated from natural sources. Its reactions are representative of those of similar long chain, saturated fatty acids. It can be converted to the symmetrical fatty ketone called laurone (O=C(C$_{11}$H$_{23}$)$_2$). It transesterifies with vinyl acetate. Treatment with sulfur trioxide gives the α-sulfonic acid.

## 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 induces apoptosis in cancer and promotes the proliferation of normal cells by maintaining cellular redox homeostasis.
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". In general, a lower total/HDL serum lipoprotein ratio correlates with a decrease in atherosclerotic incidence. 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. A 2016 review of coconut oil (which is nearly half lauric acid) was similarly inconclusive about the effects on cardiovascular disease incidence.