334-48-5 Usage
Description
Different sources of media describe the Description of 334-48-5 differently. You can refer to the following data:
1. 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.
2. Decanoic 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.
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
Chemical Properties
Different sources of media describe the Chemical Properties of 334-48-5 differently. You can refer to the following data:
1. White crystalline solid or needles. Unpleasant,
rancid odor.
2. 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
Different sources of media describe the Uses of 334-48-5 differently. You can refer to the following data:
1. 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.
2. Decanoic acid is used in manufacturing of esters for artificial fruit flavors and perfumes.
3. manufacture of esters for artificial fruit flavors and perfumes; as an intermediate in other chemical syntheses.
4. Intermediates of Liquid Crystals
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.
Definition
ChEBI: A C10, straight-chain saturated fatty acid.
Preparation
Prepared by oxidation of decanol.
Aroma threshold values
Detection: 2.2 to 102 ppm
Synthesis Reference(s)
Synthetic Communications, 20, p. 1617, 1990 DOI: 10.1080/00397919008053081Synthesis, p. 99, 1970
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
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.
Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds
Fu, Hua,Liu, Can,Liu, Yong,Yang, Haijun,Zhu, Xianjin
supporting information, p. 4357 - 4363 (2020/07/14)
Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is
