Caprylic acid (), also known under the

systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivi ...

octanoic acid or C8 Acid, is a

saturated fatty acid In chemistry, in particular 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, ...

medium-chain fatty acid In chemistry, in particular 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, f ...

(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 solubi ...

in water with a slightly unpleasant rancid-like smell and taste.

Salts In chemistry, a salt or ionic compound is a chemical compound consisting of an assembly of positively charged ions ( cations) and negatively charged ions (anions), which results in a compound with no net electric charge (electrically neutral). ...

and

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s of octanoic acid are known as octanoates or caprylates. The name of the related

acyl group In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group () or hydrogen in the case of formyl group ( ...

is octanoyl, capryloyl, or caprylyl. 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 lactating mammals. It is the primary source of nutrition for young mammals (including breastfeeding, breastfed human infants) before they are able to digestion, digest solid food. ...

of various mammals and as a minor constituent of

coconut oil Coconut oil (or coconut fat) is an edible oil derived from the kernels, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat below around , and a clear thin liquid oil at higher temperatures. Unrefined varieties have a disti ...

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 two other edible oils: ''palm oil'', extracted from the fruit pulp of the oil palm, and ''coconut oil'', extracted from ...

. Two other acids are named after

goat The goat or domestic goat (''Capra hircus'') is a species of Caprinae, goat-antelope that is mostly kept as livestock. It was domesticated from the wild goat (''C. aegagrus'') of Southwest Asia and Eastern Europe. The goat is a member of the ...

s via the Latin word '' capra'':

caproic acid Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula . It is a colorless oily liquid with a fatty, cheesy, waxy odor resembling that of goats or other barnyard animals. It is a fatty 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 . Salts and esters of decanoic acid are called caprates or decanoates. The term capric aci ...

(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 ...

fat.

Metabolism

Octanoyl-ACP

One of the

products Product may refer to: Business * Product (business), an item that can be offered to a market to satisfy the desire or need of a customer. * Product (project management), a deliverable or set of deliverables that contribute to a business solution ...

of the

mitochondrial fatty acid synthesis In biochemistry, fatty acid synthesis is the creation of fatty acids from acetyl-CoA and NADPH through the action of enzymes. Two '' de novo'' fatty acid syntheses can be distinguished: cytosolic fatty acid synthesis (FAS/FASI) and mitochondrial ...

(mtFAS) pathway is octanoic acid bound to

acyl carrier protein The acyl carrier protein (ACP) is a cofactor of both fatty acid and polyketide biosynthesis machinery. It is one of the most abundant proteins in cells of ''E. coli.'' In both cases, the growing chain is bound to the ACP via a thioester derived fr ...

(ACP), also referred to as octanoyl-ACP. In the absence of a mitochondrial acyl-ACP

thioesterase In biochemistry, thioesterases are enzymes which belong to the esterase family. Esterases, in turn, are one type of the several hydrolases known. Thioesterases exhibit esterase activity (splitting of an ester into an acid and an alcohol, in the ...

—none has been identified in any

animal Animals are multicellular, eukaryotic organisms in the Biology, biological Kingdom (biology), kingdom Animalia (). With few exceptions, animals heterotroph, consume organic material, Cellular respiration#Aerobic respiration, breathe oxygen, ...

species—octanoic acid remains attached to ACP rather than being released as a

free fatty acid In chemistry, in particular 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, f ...

. Octanoyl-ACP serves as the

precursor Precursor or Precursors may refer to: *Precursor (religion), a forerunner, predecessor ** The Precursor, John the Baptist Science and technology * Precursor (bird), hypothesized genus of fossil birds that was composed of fossilized parts of unre ...

for the biosynthesis of

lipoic acid Lipoic acid (LA), also known as α-lipoic acid, alpha-lipoic acid (ALA) and thioctic acid, is an organosulfur compound derived from caprylic acid (octanoic acid). ALA, which is made in animals normally, is essential for aerobic metabolism. It i ...

, a vital cofactor required by several key mitochondrial enzymes complexes, including the

pyruvate dehydrogenase complex Pyruvate dehydrogenase complex (PDC) is a complex of three enzymes that converts pyruvate into acetyl-CoA by a process called pyruvate decarboxylation. Acetyl-CoA may then be used in the citric acid cycle to carry out cellular respiration, and ...

(PDC), the α‑ketoglutarate dehydrogenase complex (OGDC), the 2‑oxoadipate dehydrogenase complex (2‑OADHC), the branched‑chain α‑ketoacid dehydrogenase complex (BCKDC), and the

glycine cleavage system The glycine cleavage system (GCS) is also known as the glycine decarboxylase complex or GDC. The system is a series of enzymes that are triggered in response to high concentrations of the amino acid glycine. The same set of enzymes is sometimes ...

(GCS).

Octanoyl-CoA

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 primarily 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 ghrel ...

. 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 Receptor may refer to: *Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and responds ...

in the

hypothalamus The hypothalamus (: hypothalami; ) is a small part of the vertebrate brain that contains a number of nucleus (neuroanatomy), nuclei with a variety of functions. One of the most important functions is to link the nervous system to the endocrin ...

. In order to activate these receptors, ghrelin must undergo a process called

acylation In chemistry, acylation is a broad class of chemical reactions in which an acyl group () is added to a substrate. The compound providing the acyl group is called the acylating agent. The substrate to be acylated and the product include the foll ...

in which it acquires an

, and caprylic acid provides this by linking at a specific

serine Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α- amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − ...

site on ghrelin molecules. Other

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

s in the same position have similar effects on hunger.

Uses

Industrial and commercial use

Caprylic acid is used commercially in the production of

s used in perfumery and also in the manufacture of dyes. The

acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

of caprylic acid is used in the synthesis of

perfluorooctanoic acid Perfluorooctanoic acid (PFOA; conjugate acid, conjugate base perfluorooctanoate; also known colloquially as C8, from its chemical formula C8HF15O2) is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in ch ...

. 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 and public places. 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.

Dietary uses

Caprylic acid is taken as a

dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...

. 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 conn ...

; 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 practice of Resistance training, progressive resistance exercise to build, control, and develop one's skeletal muscle, muscles via muscle hypertrophy, hypertrophy. An individual who engages in this activity is referred to a ...

community, but MCTs have not been found to be beneficial to 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 diet, 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 b ...

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 i ...

References

External links

Caprylic Acid Benefits
– Caprylic Acid: Benefits & Side Effects {{DEFAULTSORT:Caprylic Acid Antifungals Alkanoic acids Biologically based therapies Fatty acids Triglycerides