Tricaprin or tridecanoin is a

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 ...

capric acid Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term ...

and a component of MCT oil. Its formula is .

Occurrence

Tricaprin occurs naturally in the seeds of ''

Umbellularia californica ''Umbellularia californica'' is a large hardwood tree native to coastal forests and the Sierra foothills of California, and to coastal forests extending into Oregon. It is endemic to the California Floristic Province. It is the sole species in th ...

'', a hardwood tree native to North America.

Production

Tricaprin and other

medium-chain triglyceride 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 ...

s (MCTs) are either isolated from natural or

genetically engineered Genetic engineering, also called genetic modification or genetic manipulation, is the modification and manipulation of an organism's genes using technology. It is a set of technologies used to change the genetic makeup of cells, including t ...

sources in the production of MCT oils, or are synthesized on a large scale through the

esterification 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 ...

of medium-chain fatty acids with

glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...

, specifically capric acid in the case of tricaprin. These esterification reactions have been investigated with a focus on

enzyme catalysis Enzyme catalysis is the increase in the rate of a process by a biological molecule, an "enzyme". Most enzymes are proteins, and most such processes are chemical reactions. Within the enzyme, generally catalysis occurs at a localized site, calle ...

as an alternative to traditional manufacturing processes that take place at high temperature and pressure, which result in poorer quality product at low yield. Compared to similar reactions used in the synthesis of other MCTs, tricaprin has a slow conversion rate from capric acid in the presence of

lipozyme Lipozyme, a registered trademark of Novo Nordisk A/S Corp., is a class of industrial enzymes, specifically: lipases. Lipozymes can be differentiated by origin - it can be extracted from ''Mucor miehei'', '' Thermomyces lanuginosus'', ''Candida ant ...

Uses

Tricaprin is used as an additive to

diesel fuel Diesel fuel , also called diesel oil, is any liquid fuel specifically designed for use in a diesel engine, a type of internal combustion engine in which fuel ignition takes place without a spark as a result of compression of the inlet air and t ...

and as part of current and speculative

biodiesel Biodiesel is a form of diesel fuel derived from plants or animals and consisting of long-chain fatty acid esters. It is typically made by chemically reacting lipids such as animal fat (tallow), soybean oil, or some other vegetable oil with ...

Pharmacological

Tricaprin has been indicated as a possible drug to increase the production of

insulin Insulin (, from Latin ''insula'', 'island') is a peptide hormone produced by beta cells of the pancreatic islets encoded in humans by the ''INS'' gene. It is considered to be the main anabolic hormone of the body. It regulates the metabolism o ...

and decrease the production of

androgen An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This inc ...

in the body when taken orally. It, along with other medium-chain triglycerides, has been studied as a treatment option to prevent ruptures of

abdominal aortic aneurysm Abdominal aortic aneurysm (AAA) is a localized enlargement of the abdominal aorta such that the diameter is greater than 3 cm or more than 50% larger than normal. They usually cause no symptoms, except during rupture. Occasionally, abdominal, ...

, and has been specifically studied as a regulator of

membrane A membrane is a selective barrier; it allows some things to pass through but stops others. Such things may be molecules, ions, or other small particles. Membranes can be generally classified into synthetic membranes and biological membranes. B ...

functions and in the

heart The heart is a muscular organ in most animals. This organ pumps blood through the blood vessels of the circulatory system. The pumped blood carries oxygen and nutrients to the body, while carrying metabolic waste such as carbon dioxide t ...

to facilitate

lipolysis Lipolysis is the metabolic pathway through which lipid triglycerides are hydrolyzed into a glycerol and free fatty acids. It is used to mobilize stored energy during fasting or exercise, and usually occurs in fat adipocytes. The most important ...

References

{{Reflist Alkanoic acids Fatty acids Triglycerides

Occurrence

Production

Uses

Pharmacological

See also

References