334-48-5 Usage
Description
Capric acid, also known as decanoic acid, is a saturated fatty acid with a 10-carbon backbone. It is a white crystalline solid with a rancid odor and occurs naturally in coconut oils, palm kernel oil, and the milk of cow/goat. Capric acid is found in various natural sources such as apple, beer, cheese, and wine, among others. It is used in the cosmetic and personal care, food/beverage, and pharmaceutical industries, as well as an intermediate in chemical syntheses.
Uses
Used in Cosmetic and Personal Care Industry:
Capric acid is used as an ingredient in the cosmetic and personal care industry for its emollient and moisturizing properties, providing a smooth and soft texture to the skin.
Used in Food and Beverage Industry:
Capric acid is used as an intermediate in the manufacturing of esters for artificial fruit flavors and perfumes, enhancing the aroma and taste of various food and beverage products.
Used in Pharmaceutical Industry:
Capric acid is used in the production of decanoate salts and esters of various drugs, increasing their lipophilicity and affinity for fatty tissue. This allows for the development of long-acting injectable forms of drugs (Depot injections) with slower distribution from fatty tissue.
Used in Chemical Synthesis:
Capric acid serves as an intermediate in chemical syntheses, contributing to the production of various compounds and products.
Used in Manufacturing of Lubricants, Greases, Rubber, Plastics, and Dyes:
Capric acid is utilized in the production of lubricants, greases, rubber, plastics, and dyes due to its chemical properties and versatility in industrial applications.
Used in Organic Synthesis:
Capric acid is employed in organic synthesis for the creation of various organic compounds and materials.
Occurrence:
Capric acid is reported to be found 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.
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
Production Methods
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.
Preparation
Prepared by oxidation of decanol.
Synthesis Reference(s)
Synthetic Communications, 20, p. 1617, 1990 DOI: 10.1080/00397919008053081Synthesis, p. 99, 1970
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
Notclassified
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
.
Check Digit Verification of cas no
The CAS Registry Mumber 334-48-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,3 and 4 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 334-48:
(5*3)+(4*3)+(3*4)+(2*4)+(1*8)=55
55 % 10 = 5
So 334-48-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)
334-48-5Relevant articles and documents
Hydrogenation of Unsaturated Carboxylic Acid Catalyzed by Platinum-Silica Coupled with Alkylsilyl Chloride
Kuno, Hideyuki,Takahashi, Kyoko,Shibagaki, Makoto,Matsushita, Hajime
, p. 3320 - 3322 (1990)
Platinum-silica catalysts coupled with alkylsilyl chloride were prepared for the regioselective hydrogenation of unsaturated compounds.These catalysts were stable in polar solvents.It was found that the carbon-carbon double bond far from a hydrophilic site was more rapidly hydrogenated in this catalyst system.
A new method for the protection of carboxylic acids with a triisopropylsiloxymethyl group
Yoshimura, Hikaru,Eto, Kohei,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
, p. 1334 - 1339 (2012)
An effective method for the protection of carboxylic acids with a triisopropylsiloxymethyl (TIPSOCH2) group is described. The reactions of various carboxylic acids with C12H25SCH 2OTIPS in the presence of CuBrs
One-step solvent-free aerobic oxidation of aliphatic alcohols to esters using a tandem Sc-Ru?MOF catalyst
Feng, Tingkai,Li, Conger,Li, Tao,Zhang, Songwei
supporting information, p. 1474 - 1480 (2022/03/08)
Esters are an important class of chemicals in industry. Traditionally, ester production is a multi-step process involving the use of corrosive acids or acid derivatives (e.g. acid chloride, anhydride, etc.). Therefore, the development of a green synthetic protocol is highly desirable. This work reports the development of a metal-organic framework (MOF) supported tandem catalyst that can achieve direct alcohol to ester conversion (DAEC) using oxygen as the sole oxidizing agent under strictly solvent-free conditions. By incorporating Ru nanoparticles (NPs) along with a homogeneous Lewis acid catalyst, scandium triflate, into the nanocavities of a Zr MOF, MOF-808, the compound catalyst, Sc-Ru?MOF-808, can achieve aliphatic alcohol conversion up to 92% with ester selectivity up to 91%. A mechanistic study reveals a unique “via acetal” pathway in which the alcohol is first oxidized on Ru NPs and rapidly converted to an acetal on Sc(iii) sites. Then, the acetal slowly decomposes to release an aldehyde in a controlled manner for subsequent oxidation and esterification to the ester product. To the best of our knowledge, this is the first example of DAEC of aliphatic alcohols under solvent-free conditions with high conversion and ester selectivity.
Atomically Dispersed Co Clusters Anchored on N-doped Carbon Nanotubes for Efficient Dehydrogenation of Alcohols and Subsequent Conversion to Carboxylic Acids
Dong, Zhengping,Fang, Jian,Li, Boyang,Xu, Dan,Zhang, Fengwei,Zhao, Hong,Zhu, Hanghang
, p. 4536 - 4545 (2021/09/22)
The catalytic dehydrogenation of readily available alcohols to high value-added carbonyl compounds is a research hotspot with scientific significance. Most of the current research about this reaction is performed with noble metal-based homogeneous catalysts of high price and poor reusability. Herein, highly dispersed Co-cluster-decorated N-doped carbon nanotubes (Co/N-CNTs) were fabricated via a facile strategy and used for the dehydrogenation of alcohols with high efficiency. Various characterization techniques confirmed the presence of metallic Co clusters with almost atomic dispersion, and the N-doped carbon supports also enhanced the catalytic activity of Co clusters in the dehydrogenation reaction. Aldehydes as dehydrogenation products were further transformed in situ to carboxylic acids through a Cannizzaro-type pathway under alkaline conditions. The reaction pathway of the dehydrogenation of alcohols was clearly confirmed by theoretical calculations. This work should provide an effective and simple approach for the accurate design and synthesis of small Co-clusters catalysts for the efficient dehydrogenation-based transformation of alcohols to carboxylic acids under mild reaction conditions.
Oxidation of aromatic and aliphatic aldehydes to carboxylic acids by Geotrichum candidum aldehyde dehydrogenase
Hoshino, Tomoyasu,Yamabe, Emi,Hawari, Muhammad Arisyi,Tamura, Mayumi,Kanamaru, Shuji,Yoshida, Keisuke,Koesoema, Afifa Ayu,Matsuda, Tomoko
, (2020/07/20)
Oxidation reaction is one of the most important and indispensable organic reactions, so that green and sustainable catalysts for oxidation are necessary to be developed. Herein, biocatalytic oxidation of aldehydes was investigated, resulted in the synthesis of both aromatic and aliphatic carboxylic acids using a Geotrichum candidum aldehyde dehydrogenase (GcALDH). Moreover, selective oxidation of dialdehydes to aldehydic acids by GcALDH was also successful.
