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Decanoic acid is a saturated fatty acid that has been used as a pharmaceutical agent for the treatment of congestive heart failure.
Decanoic acid is also used in the production of glycol ethers and as an intermediate in organic synthesis.
The melting point of decanoic acid is between 30 and 35 degrees Celsius, which is lower than the melting points of caproic acid (40 degress) or lauric acid (45 degrees Celsius).
CAS: 334-48-5
MF: C10H20O2
MW: 172.26
EINECS: 206-376-4
Synonyms
acidedecanoique;Caprinsαure;Caprynic acid;caprynicacid;Decansαure;Decatoicacid;Decoic acid;decoicacid
Decanoic acid has been shown to reduce blood glucose levels in diabetic mice and rats and has also been shown to have antimicrobial activity against c. glabrata, S. aureus, and E. coli.
Decanoic acid may be effective as an adjuvant therapy for melanoma by inducing apoptosis through mitochondrial membrane potential disruption.
Decanoic acid is a saturated fatty acid with a 10-carbon backbone.
Decanoic acid occurs naturally in coconut oils, palm kernel oil, and the milk of cow/goat.
Decanoic acid is most commonly used in the cosmetic and personal care, food/beverage, and pharmaceutical industries.
Decanoic acid is also used as an intermediate in chemical syntheses.
Furthermore, Decanoic acid is used in organic synthesis and in the manufacture of lubricants, greases, rubber, plastics, and dyes.
Decanoic acid, or capric acid, is a saturated fatty acid.
Decanoic acid's formula is CH3(CH2)8COOH.
Salts and esters of decanoic acid are called decanoates or "caprates".
The term capric acid arises from the Latin "capric" which pertains to goats due to their olfactory similarities.
Decanoic acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4 %), otherwise it is uncommon in typical seed oils.
Decanoic acid is found in the milk of various mammals and to a lesser extent in other animal fats.
Two other acids are named after goats: caproic (a C6 fatty acid) and caprylic (a C8 fatty acid).
Along with decanoic acid, these total 15 % in goat milk fat.
Decanoic acid is a C10, straight-chain saturated fatty acid.
Decanoic acid has a role as an antibacterial agent, an anti-inflammatory agent, a human metabolite, a volatile oil component, a plant metabolite and an algal metabolite.
Decanoic acid is a straight-chain saturated fatty acid and a medium-chain fatty acid.
Decanoic acid is a conjugate acid of a decanoate.
Decanoic acid derives from a hydride of a decane.
Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid.
Decanoic acid's formula is CH3(CH2)8COOH.
Salts and esters of decanoic acid are called caprates or decanoates.
The term Decanoic acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
Decanoic acid, also known as capric acid, is a medium-chain fatty acid with a wide range of applications in various industries.
Decanoic acid is recognized for its unique properties, including its ability to act as an effective emulsifier and surfactant.
In the food industry, decanoic acid is utilized as a flavoring agent and preservative, enhancing the taste and shelf life of products.
Its antimicrobial properties make Decanoic acid a valuable ingredient in personal care products, such as soaps and lotions, where it helps to maintain skin health and prevent bacterial growth.
In the realm of research, decanoic acid is being explored for its potential therapeutic effects, particularly in the management of metabolic disorders and as a source of energy in ketogenic diets.
Decanoic acid's ability to provide quick energy without the need for insulin makes it a subject of interest for those studying diabetes and obesity.
With its versatile applications and beneficial properties, decanoic acid stands out as a compound of significant relevance to both industry professionals and researchers alike.
Decanoic acid Chemical Properties
Melting point: 27-32 °C(lit.)
Boiling point: 268-270 °C(lit.)
Density: 0.893 g/mL at 25 °C(lit.)
Bulk density: 690kg/m3
Vapor pressure: 15 mm Hg ( 160 °C)
Refractive index: 1.4169
FEMA: 2364 | DECANOIC ACID
Fp: >230 °F
Storage temp.: room temp
Solubility: Chloroform (Slightly), Methanol (Slightly)
Pka: 4.79±0.10(Predicted)
Form: Crystalline Solid
Color: White
PH: 4 (0.2g/l, H2O, 20℃)
Odor: Odorless
Odor Type: fatty
Biological source: plant
Water Solubility: 0.15 g/L (20 º C)
Merck: 14,1758
JECFA Number: 105
BRN: 1754556
Stability: Stable. Incompatible with bases, reducing agents, oxidizing agents.
LogP: 4.1 at 20℃
CAS DataBase Reference: 334-48-5(CAS DataBase Reference)
NIST Chemistry Reference: Decanoic acid(334-48-5)
EPA Substance Registry System: Decanoic acid (334-48-5)
Uses
Manufacturing of esters for artificial fruit flavors and perfumes.
Also as an intermediate in chemical syntheses.
Decanoic acid is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.
Pharmaceuticals
Decanoate salts and esters of various drugs are available.
Since decanoic acid is a fatty acid, forming a salt or ester with a drug will increase its lipophilicity and its affinity for fatty tissue.
Since distribution of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a Depot injection) by using its decanoate form.
Some examples of drugs available as a decanoate ester or salt include nandrolone, fluphenazine, bromperidol, haloperidol and vanoxerine.
Decanoic acid is used in manufacturing of esters for artificial fruit flavors and perfumes.
manufacture of esters for artificial fruit flavors and perfumes; as an intermediate in other chemical syntheses.
Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. Decanoic acid is also used as an intermediate in chemical syntheses.
Decanoic acid 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 Decanoic acid is a fatty acid, forming a salt or ester with a drug will increase its lipophilicity and its affinity for adipose tissue.
Since distribution of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a depot injection) by using its caprate form.
Some examples of drugs available as a caprate ester include nandrolone (as nandrolone decanoate), fluphenazine (as fluphenazine decanoate), bromperidol (as bromperidol decanoate), and haloperidol (as haloperidol decanoate).
Production Methods
Decanoic acid can be prepared from oxidation of primary alcohol decanol, by using chromium trioxide (CrO3) oxidant under acidic conditions.
Neutralization of decanoic acid or saponification of its esters, typically triglycerides, with sodium hydroxide will give sodium decanoate.
This salt (CH3(CH2)8COO-Na+) is a component of some types of soap.
Production
Decanoic acid can be prepared from oxidation of the primary alcohol decanol by using chromium trioxide (CrO3) oxidant under acidic conditions.
Neutralization of capric acid or saponification of its triglyceride esters with sodium hydroxide yields sodium caprate, CH3(CH2)8CO−2Na+.
This salt is a component of some types of soap.
Effects
Decanoic 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 Decanoic acid in the brain contributes to the anticonvulsant effect of the MCT ketogenic diet.
Decanoic acid and the AMPA receptor antagonist drug perampanel act at separate sites on the AMPA receptor, and so Decanoic acid is possible that they have a cooperative effect at the AMPA receptor, suggesting that perampanel and the ketogenic diet could be synergistic.
Decanoic acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, and that this may occur via PPARγ receptor agonism and its target genes involved in mitochondrial biogenesis.
Complex I activity of the electron transport chain is substantially elevated by decanoic acid treatment.
Decanoic acid 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 to produce carbon dioxide, acetate and ketone bodies.
Whether the ketones, β-hydroxybutyrate and acetone have direct antiseizure activity is unclear.
Reactivity Profile
Decanoic acid reacts exothermically to neutralize bases.
Can react with active metals to form gaseous hydrogen and a metal salt.
May absorb enough water from the air and dissolve sufficiently in Capric acid to corrode or dissolve iron, steel, and aluminum parts and containers.
Reacts with cyanide salts or solutions of cyanide salts to generate gaseous hydrogen cyanide.
Reacts exothermically with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides to generate flammable and/or toxic gases.
Can react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide).
Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents; a wide variety of products is possible.
May initiate polymerization reactions or catalyze (increase the rate of) reactions among other materials.
Biochem/physiol Actions
Decanoic acid is helpful in the attenuation of oxidative stress.
Decanoic acid in ketogenic diet is involved in mitochondrial biogenesis thereby enhancing the citrate synthase and complex I activity of electron transport chain.
