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Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid.
Capric acid's formula is CH3(CH2)8COOH.
Salts and esters of Capric acid are called caprates or decanoates.
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;CAPRIC ACID;334-48-5;n-Decanoic acid;n-Capric acid;Decylic acid;Caprinic acid;Decoic acid;n-Decylic acid;1-Nonanecarboxylic acid;n-Decoic acid;Caprynic acid;Hexacid 1095;Econosan Acid Sanitizer;NSC 5025;Decanoic acid (natural);FEMA No. 2364;C10:0;Dekansaeure;Emery 659;Kaprinsaeure;CCRIS 4610;HSDB 2751;EINECS 206-376-4;UNII-4G9EDB6V73;MFCD00004441;EPA Pesticide Chemical Code 128955;BRN 1754556;4G9EDB6V73;DTXSID9021554;Prifac 296;CHEBI:30813;AI3-04453;Prifac 2906;NSC-5025;Lunac 10-95;Lunac 10-98;PRIFAC-2906;DTXCID201554;PALMAC-99-10;NSC5025;caprynate;decoate;decylate
;4-02-00-01041 (Beilstein Handbook Reference);n-caprate;n-decoate;n-decylate;Lead caprate;NCGC00091320-02;1-nonanecarboxylate;Decanoic acid anion;DKA;CH3-(CH2)8-COOH;CH3-[CH2]8-COOH;Versatic 10;CAS-334-48-5;caprinsaure;decansaure;Decansaeure;Docansaure;Decatoic acid;1-decanoic acid;nonanecarboxylic acid;fatty acid 10:0;Prifrac 296;Prifrac 2906;Acid C10;Decanoic acid, 96%;Decansaeure (Altstoff);Nonane-1-carboxylic acid;Decanoic acid (Standard);DECANsaure (ALTSTOFF);bmse000370;SCHEMBL2682;WLN: QV9;DECANOIC ACID [FCC];Decanoic acid (Capric acid);N-CAPRIC ACID [MI];DECANOIC ACID [FHFI];DECANOIC ACID [HSDB];Decanoic acid, >=98.0%;MLS002415724;IS_D19-DECANOIC ACID;(1(1)(3)C)Decanoic acid;CHEMBL107498;GTPL5532;1-NONANE CARBOXYLIC ACID;N-CAPRIC ACID [WHO-DD];Decanoic acid, lead (2+) salt;NAA 102;Decanoic acid, analytical standard;HMS2267B15;HY-W015309R;Decanoic acid, >=98.0% (GC);Tox21_113533;Tox21_202209;Tox21_300366;LMFA01010010;s6906;STL445666;Decanoic acid, >=98%, FCC, FG;AKOS000119623;CS-W016025;DB03600;FA 10:0;HY-W015309;USEPA/OPP Pesticide Code: 128955;NCGC00091320-01;NCGC00091320-03;NCGC00091320-04;NCGC00091320-05;NCGC00254437-01;NCGC00259758-01;AS-14704;BP-27911;FA(10:0);SMR001252255;SY061635;D0017;Decanoic acid, natural, >=98%, FCC, FG;NS00005224;EN300-19724;C-1095;C01571;D70225;CAPRIC ACID (CONSTITUENT OF SAW PALMETTO);Q422613;W-202368;CAPRIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC];Z104474944;98230577-0D20-4F70-B532-00AC60132CFE;InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12
The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
Capric acid is a saturated fatty acid with a 10-carbon backbone.
Capric acid occurs naturally in coconut oils, palm kernel oil, and the milk of cow/goat.
Capric acid is most commonly used in the cosmetic and personal care, food/beverage, and pharmaceutical industries.
Capric acid is also used as an intermediate in chemical syntheses.
Furthermore, Capric 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.
Capric acid's formula is CH3(CH2)8COOH.
Salts and esters of Capric acid are called decanoates or "caprates".
The term capric acid arises from the Latin "capric" which pertains to goats due to their olfactory similarities.
Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4 %), otherwise it is uncommon in typical seed oils.
Capric 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.
Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils.
Capric 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 acid (a C6:0 fatty acid) and caprylic acid (a C8:0 fatty acid).
Along with capric acid, these total 15% in goat milk fat.
Capric acid is a C10, straight-chain saturated fatty acid.
Capric 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.
Capric acid is a straight-chain saturated fatty acid and a medium-chain fatty acid.
Capric acid is a conjugate acid of a decanoate.
Capric acid derives from a hydride of a decane.
Capric acid is a saturated fatty acid that has been used as a pharmaceutical agent for the treatment of congestive heart failure.
Capric 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).
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.
Capric Acid is a renewable, vegetable based fatty acid that acts as an emollient in personal care products.
Capric acid is typically used in soaps, creams, and lotion applications.
Capric acid Chemical Properties
Melting point: 27-32 °C(lit.)
Boiling point: 268-270 °C(lit.)
Density: 0.893 g/mL at 25 °C(lit.)
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
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: Capric acid(334-48-5)
EPA Substance Registry System: Capric acid (334-48-5)
Uses
Manufacturing of esters for artificial fruit flavors and perfumes.
Also as an intermediate in chemical syntheses.
Capric acid is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.
Capric 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.
Pharmaceuticals
Capric acid salts and esters of various drugs are available.
Since Capric acidis 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.
Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. Capric acid is also used as an intermediate in chemical syntheses.
Capric 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 capric 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).
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.
Decanoic acid and the AMPA receptor antagonist drug perampanel 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, 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.
Capric 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.
Production
Capric 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.
Production Methods
Capric acid can be prepared from oxidation of primary alcohol decanol, by using chromium trioxide (CrO3) oxidant under acidic conditions.
Neutralization of Capric 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.
Reactivity Profile
Capric 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.
