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Description
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Decanoic 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. |
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Chemical Properties
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White crystalline solid or needles. Unpleasant,
rancid odor. |
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Occurrence
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Reported 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. |
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Uses
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Manufacturing 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. 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. |
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Production Methods
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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. |
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Definition
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ChEBI: A C10, straight-chain saturated fatty acid. |
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Preparation
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Prepared by oxidation of decanol. |
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Aroma threshold values
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Detection: 2.2 to 102 ppm |
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Synthesis Reference(s)
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Synthetic Communications, 20, p. 1617, 1990 DOI: 10.1080/00397919008053081Synthesis, p. 99, 1970 |
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General Description
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White 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. |
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Air & Water Reactions
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Insoluble in water. |
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Reactivity Profile
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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. |
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Health Hazard
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Harmful if swallowed or inhaled. Material is irritating to tissues of mucous membranes, and upper respiratory tract, eyes and skin. |
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Fire Hazard
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Capric acid is combustible. |
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Flammability and Explosibility
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Notclassified |
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Biochem/physiol Actions
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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. |
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Safety Profile
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Poison by intravenous
route. Mutation data reported. A moderate
skin irritant. When heated to decomposition
it emits acrid smoke and irritating fumes. |
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Potential Exposure
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Deconoic 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. |
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Shipping
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UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous
hazardous material, Technical Name Required. |
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Purification Methods
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The 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.] |
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Incompatibilities
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An 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. |
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Waste Disposal
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Recycle 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
. |
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Who Evaluation
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Evaluation year: 1984 |
