Description
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.
References
[1] https://www.efsa.europa.eu
[2] https://circabc.europa.eu
[3] http://www.chemicalland21.com
[4] http://www.prnewswire.com/news-releases/global-capric-acid-market-2017-2021-300423638.html
Description
Decanoic acid, or capric acid, is a saturated fatty acid. Its formula is CH
3(CH
2)
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 Properties
White crystalline solid or needles. Fatty, unpleasant, rancid odor.
Occurrence
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.
Uses
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.
Uses
manufacture of esters for artificial fruit flavors and perfumes; as an intermediate in other chemical syntheses.
Uses
Intermediates of Liquid Crystals
Uses
Decanoic acid is used in manufacturing of esters for artificial fruit flavors and perfumes.
Preparation
Decanoic acid is prepared from Coconut oil by saponification.
Definition
ChEBI: Decanoic acid is a C10, straight-chain saturated fatty acid. It 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. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of a decanoate. It derives from a hydride of a decane.
Production Methods
Decanoic acid can be prepared from oxidation of primary alcohol decanol, by using chromium trioxide (CrO
3) oxidant under acidic conditions.
Neutralization of decanoic acid or saponification of its esters, typically triglycerides, with sodium hydroxide will give sodium decanoate. This salt (CH
3(CH
2)
8COO-Na
+) is a component of some types of soap.
Aroma threshold values
Detection: 2.2 to 102 ppm
General Description
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.
Air & Water Reactions
Insoluble in water.
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.
Health Hazard
Harmful if swallowed or inhaled. Material is irritating to tissues of mucous membranes, and upper respiratory tract, eyes and skin.
Fire Hazard
Capric acid is combustible.
Flammability and Explosibility
Not classified
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.
Safety Profile
Poison by intravenous
route. Mutation data reported. A moderate
skin irritant. When heated to decomposition
it emits acrid smoke and irritating fumes.
Potential Exposure
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.
Shipping
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous
hazardous material, Technical Name Required.
Purification Methods
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.]
Incompatibilities
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.
Waste Disposal
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
.
