# Capric acid

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Saturated fatty acid

Not to be confused with [Caproic acid](/source/Caproic_acid) or [Caprylic acid](/source/Caprylic_acid).

Decanoic acid Skeletal formula of decanoic acid Ball-and-stick model of decanoic acid Names Preferred IUPAC name Decanoic acid Other names Caprinic acid; Caprynic acid; Decoic acid; Decylic acid; 1-Nonanecarboxylic acid; C10:0 (Lipid numbers) Identifiers CAS Number 334-48-5 Y 1002-62-6 (sodium salt) Y 3D model (JSmol) Interactive image ChEBI CHEBI:30813 Y ChEMBL ChEMBL107498 Y ChemSpider 2863 Y DrugBank DB03600 N ECHA InfoCard 100.005.798 EC Number 206-376-4 IUPHAR/BPS 5532 KEGG C01571 Y PubChem CID 2969 RTECS number HD9100000 UNII 4G9EDB6V73 Y 4I820XKV2A (sodium salt) Y CompTox Dashboard (EPA) DTXSID9021554 InChI InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) Y Key: GHVNFZFCNZKVNT-UHFFFAOYSA-N Y InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) Key: GHVNFZFCNZKVNT-UHFFFAOYAC SMILES O=C(O)CCCCCCCCC Properties Chemical formula C10H20O2 Molar mass 172.268 g·mol−1 Appearance White crystals Odor Strong rancid and unpleasant[1] Density 0.893 g/cm3 (25 °C)[2] 0.8884 g/cm3 (35.05 °C) 0.8773 g/cm3 (50.17 °C)[3] Melting point 31.6 °C (88.9 °F; 304.8 K)[6] Boiling point 268.7 °C (515.7 °F; 541.8 K)[4] Solubility in water 0.015 g/100 mL (20 °C)[4] Solubility Soluble in alcohol, ether, CHCl3, C6H6, CS2, acetone[1] log P 4.09[4] Vapor pressure 4.88·10−5 kPa (25 °C)[1] 0.1 kPa (108 °C)[4] 2.03 kPa (160 °C)[5][2] Acidity (pKa) 4.9[1] Thermal conductivity 0.372 W/m·K (solid) 0.141 W/m·K (liquid)[3] Refractive index (nD) 1.4288 (40 °C)[1] Viscosity 4.327 cP (50 °C)[4] 2.88 cP (70 °C)[3] Structure Crystal structure Monoclinic (−3.15 °C)[7] Space group P21/c[7] Lattice constant a = 23.1 Å, b = 4.973 Å, c = 9.716 Å[7] α = 90°, β = 91.28°, γ = 90° Thermochemistry Heat capacity (C) 475.59 J/mol·K[5] Std enthalpy of formation (ΔfH⦵298) −713.7 kJ/mol[4] Std enthalpy of combustion (ΔcH⦵298) 6079.3 kJ/mol[5] Hazards Occupational safety and health (OHS/OSH): Main hazards Medium toxicity Ingestion hazards May be toxic Inhalation hazards May cause irritation Skin hazards May be toxic on contact GHS labelling: Pictograms [2] Signal word Warning Hazard statements H315, H319, H335[2] Precautionary statements P261, P305+P351+P338[2] NFPA 704 (fire diamond) [8] 2 1 0 Flash point 110 °C (230 °F; 383 K)[2] Lethal dose or concentration (LD, LC): LD50 (median dose) 10 g/kg (rats, oral)[8] Safety data sheet (SDS) External MSDS Related compounds Related fatty acids Nonanoic acid, Undecanoic acid Related compounds Decanol Decanal Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

**Capric acid**, also known as **decanoic acid** or **decylic acid**, is a [saturated fatty acid](/source/Saturated_fatty_acid), [medium-chain fatty acid](/source/Medium-chain_fatty_acid) (MCFA), and [carboxylic acid](/source/Carboxylic_acid). Its formula is CH3(CH2)8COOH. [Salts](/source/Carboxylate_salt) and [esters](/source/Ester) 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.[9]

## Occurrence

Capric acid occurs naturally in [coconut oil](/source/Coconut_oil) (about 10%) and [palm kernel oil](/source/Palm_kernel_oil) (about 4%), otherwise it is uncommon in typical seed oils.[10] It is found in the [milk](/source/Milk) of various mammals and to a lesser extent in other animal fats.[6]

Two other acids are named after goats: [caproic acid](/source/Caproic_acid) (a C6:0 fatty acid) and [caprylic acid](/source/Caprylic_acid) (a C8:0 fatty acid). Along with capric acid, these total 15% in goat milk fat.[11]

## Production

Capric acid can be prepared from [oxidation](/source/Redox) of the primary alcohol [decanol](/source/1-Decanol) by using [chromium trioxide](/source/Chromium_trioxide) (CrO3) [oxidant](/source/Oxidizing_agent) under acidic conditions.[12]

Neutralization of capric acid or [saponification](/source/Saponification) of its [triglyceride](/source/Triglyceride) esters with [sodium hydroxide](/source/Sodium_hydroxide) yields sodium caprate, CH3(CH2)8CO−2Na+. This [salt](/source/Salt_(chemistry)) is a component of some types of [soap](/source/Soap).

## Uses

Capric acid is used in the manufacture of [esters](/source/Ester) 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.[8]

### Pharmaceuticals

Caprate ester [prodrugs](/source/Prodrug) of various pharmaceuticals are available. Since capric acid is a fatty acid, forming a salt or ester with a drug will increase its [lipophilicity](/source/Lipophilicity) and its affinity for [adipose tissue](/source/Adipose_tissue). Since [distribution](/source/Distribution_(pharmacology)) of a drug from [fatty tissue](/source/Adipose_tissue) is usually slow, one may develop a long-acting injectable form of a drug (called a [depot injection](/source/Depot_injection)) by using its caprate form. Some examples of drugs available as a caprate ester include [nandrolone](/source/Nandrolone) (as [nandrolone decanoate](/source/Nandrolone_decanoate)),[13] [fluphenazine](/source/Fluphenazine) (as fluphenazine decanoate),[14] [bromperidol](/source/Bromperidol) (as [bromperidol decanoate](/source/Bromperidol_decanoate)),[15] and [haloperidol](/source/Haloperidol) (as [haloperidol decanoate](/source/Haloperidol_decanoate)).[15]

## Effects

Capric acid acts as a non-competitive [AMPA receptor](/source/AMPA_receptor) antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner, and this is sufficient to explain its [antiseizure](/source/Seizure) effects.[16] This direct inhibition of excitatory neurotransmission by capric acid in the brain contributes to the [anticonvulsant](/source/Anticonvulsant) effect of the [MCT](/source/Medium-chain_triglyceride) [ketogenic diet](/source/Ketogenic_diet).[16] Decanoic acid and the AMPA receptor antagonist drug [perampanel](/source/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.[16]

Capric acid may be responsible for the mitochondrial proliferation associated with the [ketogenic diet](/source/Ketogenic_diet), and that this may occur via [PPARγ receptor](/source/Peroxisome_proliferator-activated_receptor_gamma) agonism and its target genes involved in [mitochondrial biogenesis](/source/Mitochondrial_biogenesis).[17][18] [Complex I](/source/Electron_transport_chain#Complex_I) activity of the [electron transport chain](/source/Electron_transport_chain) is substantially elevated by decanoic acid treatment.[17]

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](/source/Portal_vein), and are quickly metabolized via [coenzyme A](/source/Coenzyme_A) intermediates through [β-oxidation](/source/%CE%92-oxidation) and the [citric acid cycle](/source/Citric_acid_cycle) to produce [carbon dioxide](/source/Carbon_dioxide), [acetate](/source/Acetate) and [ketone bodies](/source/Ketone_bodies).[19] Whether the ketones, [β-hydroxybutyrate](/source/%CE%92-hydroxybutyrate), and [acetone](/source/Acetone) have direct antiseizure activity is unclear.[16][20][21][22]

## See also

- [List of saturated fatty acids](/source/List_of_saturated_fatty_acids)

- [List of carboxylic acids](/source/List_of_carboxylic_acids)

- [Undecylic acid](/source/Undecylic_acid)

- [Pelargonic acid](/source/Pelargonic_acid), a medium-chain fatty acid, also with antiseizure activity

## References

1. ^ [***a***](#cite_ref-pubchem_1-0) [***b***](#cite_ref-pubchem_1-1) [***c***](#cite_ref-pubchem_1-2) [***d***](#cite_ref-pubchem_1-3) [***e***](#cite_ref-pubchem_1-4) [CID 2969](https://pubchem.ncbi.nlm.nih.gov/compound/2969) from [PubChem](/source/PubChem)

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v t e Lipids: fatty acids Saturated Acetic (C2) Propionic (C3) Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecylic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Carboceric (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38) Nonatriacontanoic (C39) Tetracontanoic (C40) ω−3 Unsaturated Octenoic (8:1) Decenoic (10:1) Decadienoic (10:2) Lauroleic (12:1) Laurolinoleic (12:2) Myristovaccenic (14:1) Myristolinoleic (14:2) Myristolinolenic (14:3) Palmitolinolenic (16:3) Palmitidonic (16:4) α-Linolenic (18:3) Stearidonic (18:4) α-Parinaric (18:4) Dihomo-α-linolenic (20:3) Eicosatetraenoic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) 9,12,15,18,21-Tetracosapentaenoic (24:5) 6,9,12,15,18,21-Tetracosahexaenoic (24:6) ω−5 Unsaturated Myristoleic (14:1) Palmitovaccenic (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) 7,10,13-Octadecatrienoic (18:3) 9,12,15-Eicosatrienoic (20:3) β-Eicosatetraenoic (20:4) ω−6 Unsaturated Obtusilic acid (10:1) 8-Tetradecenoic (14:1) 12-Octadecenoic (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) Dihomo-linoleic (20:2) Dihomo-γ-linolenic (20:3) Sciadonic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5) ω−7 Unsaturated Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) 7,10,13-Eicosatrienoic (20:3) ω−9 Unsaturated Hypogeic (16:1) Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) 8,11-Eicosadienoic (20:2) Mead (20:3) Ximenic (26:1) ω−10 Unsaturated Sapienic (16:1) ω−11 Unsaturated Gadoleic (20:1) Cetoleic (22:1) Lumequeic (30:1) ω−12 Unsaturated 4-Hexadecenoic (16:1) Petroselinic (18:1) 8-Eicosenoic (20:1)

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Adapted from the Wikipedia article [Capric acid](https://en.wikipedia.org/wiki/Capric_acid) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Capric_acid?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.