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Decanoic acid

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Decanoic acid Basic information
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.)
  • vapor pressure 15 mm Hg ( 160 °C)
  • refractive index 1.4169
  • Flash point:>230 °F
  • storage temp. room temp
  • pka4.79±0.10(Predicted)
  • form Crystalline Solid
  • color White
  • PH4 (0.2g/l, H2O, 20℃)
  • OdorOdorless
  • Water Solubility 0.15 g/L (20 º C)
  • JECFA Number105
  • Merck 14,1758
  • BRN 1754556
  • Stability:Stable. Incompatible with bases, reducing agents, oxidizing agents.
  • CAS DataBase Reference334-48-5(CAS DataBase Reference)
  • NIST Chemistry ReferenceDecanoic acid(334-48-5)
  • EPA Substance Registry SystemDecanoic acid (334-48-5)
Safety Information
Decanoic acid Usage And Synthesis
  • DescriptionDecanoic acid (capric acid) is a saturated fatty acid with a 10-carbon backbone. It 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. It is also used as an intermediate in chemical syntheses. Furthermore, it is used in organic synthesis and in the manufacture of lubricants, greases, rubber, plastics, and dyes.
  • References[1]
  • DescriptionDecanoic acid, or capric acid, is a saturated fatty acid. Its 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.
    Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4 %), otherwise it is uncommon in typical seed oils. It 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.
  • Chemical PropertiesWhite crystalline solid or needles. Unpleasant, rancid odor.
  • Chemical Propertieswhite crystals with an unpleasant odour
  • Chemical PropertiesFatty, unpleasant, rancid odor.
  • OccurrenceReported found in apple, beer, preferments of bread, butter, oil, cheese, blue cheese, Romano cheese, cheddar cheese, Roquefort cheese, roasted cocoa bean, cognac, muscat grape, grape musts and wine, and other natural sources. Also reported in citrus peel oils, orange juice, apricots, guava, papaya, strawberry, butter, yogurt, milk, mutton, hop oil, Bourbon and Scotch whiskey, rum, coffee, mango and tea.
  • UsesManufacturing of esters for artificial fruit flavors and perfumes. Also 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.
    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.
  • UsesDecanoic acid is used in manufacturing of esters for artificial fruit flavors and perfumes.
  • Usesmanufacture of esters for artificial fruit flavors and perfumes; as an intermediate in other chemical syntheses.
  • UsesIntermediates of Liquid Crystals
  • Production MethodsDecanoic 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.
  • DefinitionChEBI: A C10, straight-chain saturated fatty acid.
  • PreparationPrepared by oxidation of decanol.
  • Aroma threshold valuesDetection: 2.2 to 102 ppm
  • Synthesis Reference(s)Synthetic Communications, 20, p. 1617, 1990 DOI: 10.1080/00397919008053081
    Synthesis, p. 99, 1970
  • General DescriptionWhite crystalline solid with a rancid odor. Melting point 31.5°C. Soluble in most organic solvents and in dilute nitric acid; non-toxic. Used to make esters for perfumes and fruit flavors and as an intermediate for food-grade additives.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileCapric 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.
  • Health HazardHarmful if swallowed or inhaled. Material is irritating to tissues of mucous membranes, and upper respiratory tract, eyes and skin.
  • Fire HazardCapric acid is combustible.
  • Safety ProfilePoison by intravenous route. Mutation data reported. A moderate skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Potential ExposureDeconoic acid (fatty acids, saturated, linear, number of C-atoms ≥8 and ≤12, with termi- nating carboxyl group) is a carboxylic acid microbiocide used in cleaning, sanitizing and disinfecting applications for food processors and dairy farmers.
  • ShippingUN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
  • Purification MethodsThe acid is best purified by conversion into its methyl ester, b 114.0o/15mm (using excess MeOH, in the presence of H2SO4). The H2SO4 and MeOH are removed, the ester is distilled in vacuo through a 3ft column packed with glass helices. The acid is then obtained from the ester by saponification and vacuum distillation. [Trachtman & Miller J Am Chem Soc 84 4828 1962, Beilstein 2 IV 1041.]
  • IncompatibilitiesAn organic carboxylic acid. Keep away from oxidizers, sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, isocyanates, alkylene oxides, and epichlorohydrin. Corrosive solution; attacks most common metals. React violently with strong oxidizers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders or dust. Mixture with some silver compounds forms explosive salts of silver oxalate. Incompatible with silver compounds.
  • Waste DisposalRecycle any unused portion of the material for its approved use or return it to the manu- facturer or supplier. Ultimate disposal of the chemical must consider: the material’s impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations .
Decanoic acid Preparation Products And Raw materials
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