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Caprylic acid (), also known under the systematic name octanoic acid or C8 Acid, is a saturated fatty acid, medium-chain fatty acid (MCFA). It has the structural formula , and is a colorless oily liquid that is minimally
soluble In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solub ...
in water with a slightly unpleasant rancid-like smell and taste.
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 ...
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 octanoic acid are known as octanoates or caprylates. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde. Its compounds are found naturally in the
milk Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals (including breastfed human infants) before they are able to digest solid food. Immune factors and immune-modulati ...
of various mammals and as a minor constituent of
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 ...
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 fro ...
. Two other acids are named after
goat The goat or domestic goat (''Capra hircus'') is a domesticated species of goat-antelope typically kept as livestock. It was domesticated from the wild goat (''C. aegagrus'') of Southwest Asia and Eastern Europe. The goat is a member of ...
s via the Latin word '' capra'': caproic acid (C6) and
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 ...
(C10). Together, these three fatty acids comprise 15% of the fatty acids in
goat milk Goat milk is the milk of domestic goats. Goats produce about 2% of the world's total annual milk supply. Some goats are bred specifically for milk. Goat milk naturally has small, well-emulsified fat globules, which means the cream will stay i ...
fat.


Uses

Caprylic acid is used commercially in the production of
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 used in perfumery and also in the manufacture of dyes. Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handling establishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities, schools/colleges, animal care/veterinary facilities, industrial facilities, office buildings, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in nurseries, greenhouses, garden centers, and interiors, and on ornamentation. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids. Caprylic acid plays an important role in the body's regulation of energy input and output, a function which is performed by the hormone
ghrelin Ghrelin (; or lenomorelin, INN) is a hormone produced by enteroendocrine cells of the gastrointestinal tract, especially the stomach, and is often called a "hunger hormone" because it increases the drive to eat. Blood levels of ghrelin are high ...
. The sensation of hunger is a signal that the body requires an input of energy in the form of food consumption. Ghrelin stimulates hunger by triggering receptors in the
hypothalamus The hypothalamus () is a part of the brain that contains a number of small nuclei with a variety of functions. One of the most important functions is to link the nervous system to the endocrine system via the pituitary gland. The hypothalamus ...
. In order to activate these receptors, ghrelin must undergo a process called acylation in which it acquires an - OH group, and caprylic acid provides this by linking at a specific site on ghrelin molecules. 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, ...
s in the same position have similar effects on hunger. The acid chloride of caprylic acid is used in the synthesis of
perfluorooctanoic acid Perfluorooctanoic acid (PFOA; conjugate base perfluorooctanoate; also known colloquially as C8, for its 8 carbon chain structure) is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical processes an ...
.


Dietary uses

Caprylic acid is taken as a
dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in orde ...
. In the body, caprylic acid would be found as octanoate, or unprotonated caprylic acid. Some studies have shown that medium-chain triglycerides (MCTs) can help in the process of excess calorie burning, and thus
weight loss Weight loss, in the context of medicine, health, or physical fitness, refers to a reduction of the total body mass, by a mean loss of fluid, body fat (adipose tissue), or lean mass (namely bone mineral deposits, muscle, tendon, and other con ...
; however, a systematic review of the evidence concluded that the overall results are inconclusive. Also, interest in MCTs has been shown by endurance athletes and the
bodybuilding Bodybuilding is the use of progressive resistance exercise to control and develop one's muscles (muscle building) by muscle hypertrophy for aesthetic purposes. It is distinct from similar activities such as powerlifting because it focuses ...
community, but MCTs have not been found to be beneficial to improved exercise performance.


Medical uses

Caprylic acid has been studied as part of a
ketogenic diet The ketogenic diet is a high- fat, adequate-protein, low-carbohydrate dietary therapy that in conventional medicine is used mainly to treat hard-to-control (refractory) epilepsy in children. The diet forces the body to burn fats rather than ca ...
to treat children with intractable epilepsy. Caprylic acid is currently being researched as a treatment for
essential tremor Essential tremor (ET), also called benign tremor, familial tremor, and idiopathic tremor, is a medical condition characterized by involuntary rhythmic contractions and relaxations ( oscillations or twitching movements) of certain muscle groups in ...
.


See also

* List of saturated fatty acids * List of carboxylic acids


References


External links


Coconut Oil
- Caprylic Acid: Coconut Oil’s Secret
Capryic Acid Benefits
- Caprylic Acid: Benefits & Side Effects {{DEFAULTSORT:Caprylic Acid Antifungals Alkanoic acids Biologically-based therapies Fatty acids Triglycerides