Tricaprin

Tricaprin or tridecanoin is a triglyceride of capric acid and a component of MCT oil. Its formula is C33H62O6.

Occurrence
Tricaprin occurs naturally in the seeds of Umbellularia californica, a hardwood tree native to North America.

Production
Tricaprin and other medium-chain triglycerides (MCTs) are either isolated from natural or genetically engineered sources in the production of MCT oils, or are synthesized on a large scale through the esterification of medium-chain fatty acids with glycerol, specifically capric acid in the case of tricaprin. These esterification reactions have been investigated with a focus on enzyme catalysis 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.

Uses
Tricaprin is used as an additive to diesel fuel and as part of current and speculative biodiesels.

Pharmacological
Tricaprin has been indicated as a possible drug to increase the production of insulin and decrease the production of androgen 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, and has been specifically studied as a regulator of membrane functions and in the heart to facilitate lipolysis.