Capric acid, also known as decanoic acid or decylic acid, is a
saturated fatty acid
A saturated fat is a type of fat in which the fatty acid chains have all single bonds. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched c ...
,
medium-chain fatty acid
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 ...
(MCFA), and
carboxylic acid. Its formula is CH
3(CH
2)
8COOH.
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 c ...
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 a ...
s of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "''caper / capra''" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
Occurrence
Capric acid occurs naturally in
coconut oil (about 10%) 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 from ...
(about 4%), otherwise it is uncommon in typical seed oils.
[David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2006, Wiley-VCH, Weinheim. ] It is found 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-modula ...
of various mammals and to a lesser extent in other animal fats.
Two other acids are named after goats:
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 an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. It is a f ...
(a C6:0 fatty acid) and
caprylic acid
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 water with a ...
(a C8:0 fatty acid). Along with capric acid, these total 15% in goat milk fat.
Production
Capric acid can be prepared from
oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
of the primary alcohol
decanol
1-Decanol is a straight chain fatty alcohol with ten carbon atoms and the molecular formula C10H21OH. It is a colorless to light yellow viscous liquid that is insoluble in water and has an aromatic odor. The interfacial tension against water at ...
by using
chromium trioxide
Chromium trioxide (also known as chromium(VI) oxide or chromic anhydride) is an inorganic compound with the formula CrO3. It is the acidic anhydride of chromic acid, and is sometimes marketed under the same name.
This compound is a dark-purple s ...
()
oxidant
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxi ...
under acidic conditions.
Neutralization of capric acid or
saponification
Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. ...
of its
triglyceride
A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''wikt:tri-#Prefix, tri-'' and ''glyceride'').
Triglycerides are the main constituents of body fat in humans and other ...
esters with
sodium hydroxide yields sodium caprate, . This
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...
is a component of some types of
soap
Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are use ...
.
Uses
Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.
Pharmaceuticals
Caprate ester
prodrugs of various pharmaceuticals are available. Since capric acid is a fatty acid, forming a salt or ester with a drug will increase its
lipophilicity
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lip ...
and its affinity for
adipose tissue
Adipose tissue, body fat, or simply fat is a loose connective tissue composed mostly of adipocytes. In addition to adipocytes, adipose tissue contains the stromal vascular fraction (SVF) of cells including preadipocytes, fibroblasts, vascular ...
. Since
distribution Distribution may refer to:
Mathematics
*Distribution (mathematics), generalized functions used to formulate solutions of partial differential equations
* Probability distribution, the probability of a particular value or value range of a vari ...
of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a
depot injection
A depot injection is a term for an injection formulation of a medication which releases slowly over time to permit less frequent administration of a medication. They are designed to increase medication adherence and consistency, especially in ...
) by using its caprate form. Some examples of drugs available as a caprate ester include
nandrolone
Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolon ...
,
fluphenazine
Fluphenazine, sold under the brand name Prolixin among others, is a high-potency typical antipsychotic medication. It is used in the treatment of chronic psychoses such as schizophrenia, and appears to be about equal in effectiveness to low-pote ...
,
bromperidol
Bromperidol, sold under the brand names Bromidol and Impromen among others, is a typical antipsychotic of the butyrophenone group which is used in the treatment of schizophrenia. It was discovered at Janssen Pharmaceutica in 1966. An ester prodru ...
, and
haloperidol
Haloperidol, sold under the brand name Haldol among others, is a typical antipsychotic medication. Haloperidol is used in the treatment of schizophrenia, tics in Tourette syndrome, mania in bipolar disorder, delirium, agitation, acute psychosi ...
.
Effects
Capric acid acts as a non-competitive
AMPA receptor antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner, and this is sufficient to explain its antiseizure effects.
This direct inhibition of excitatory neurotransmission by capric acid in the brain contributes to the anticonvulsant effect of the MCT
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 ...
.
[ Decanoic acid and the AMPA receptor antagonist drug ]perampanel
Perampanel, sold under the brand name Fycompa, is an anti-epileptic medication developed by Eisai Co. that is used in addition to other drugs to treat partial seizures and generalized tonic-clonic seizures for people older than twelve years. ...
act at separate sites on the AMPA receptor, and so it is possible that they have a cooperative effect at the AMPA receptor, suggesting that perampanel and the ketogenic diet could be synergistic.[
Capric acid may be responsible for the mitochondrial proliferation associated with the ]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 ...
, and that this may occur via PPARγ receptor agonism and its target genes involved in mitochondrial biogenesis
Mitochondrial biogenesis is the process by which cells increase mitochondrial numbers. It was first described by John Holloszy in the 1960s, when it was discovered that physical endurance training induced higher mitochondrial content levels, leadi ...
.
Complex I
Respiratory complex I, (also known as NADH:ubiquinone oxidoreductase, Type I NADH dehydrogenase and mitochondrial complex I) is the first large protein complex of the respiratory chains of many organisms from bacteria to humans. It catalyzes the ...
activity of the electron transport chain is substantially elevated by decanoic acid treatment.
It should however be noted that orally ingested medium chain fatty acids would be very rapidly degraded by first-pass metabolism by being taken up in the liver via the portal vein, and are quickly metabolized via coenzyme A intermediates through β-oxidation and the citric acid cycle
The citric acid cycle (CAC)—also known as the Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of chemical reactions to release stored energy through the oxidation of acetyl-CoA derived from carbohydrates, fats, and protein ...
to produce carbon dioxide, acetate and ketone bodies. Whether the ketones β-hydroxybutryate and acetone have direct antiseizure activity is unclear.
See also
* List of saturated fatty acids
See also
* List of unsaturated fatty acids
*Carboxylic acid
**List of carboxylic acids
*Dicarboxylic acid
{{DEFAULTSORT:List Of Saturated Fatty Acids
Saturated Fatty Acids
A saturated fat is a type of fat in which the fatty acid chains ...
* List of carboxylic acids
Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature, which ensures systematic and consistent naming of chemicals. Numerous organic compounds have o ...
* Undecylic acid
* Pelargonic acid
Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, ...
, a medium-chain fatty acid, also with antiseizure activity
References
{{Authority control
Alkanoic acids
Fatty acids
Foul-smelling chemicals
Triglycerides