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CAS NUMBER: 79-31-2
EC NUMBER: 201-195-7
MOLECULAR FORMULA: C4H8O2
MOLECULAR WEIGHT: 88.11
Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH.
Isobutyric acid is an isomer of n-butyric acid.
Isobutyric acid is classified as a short-chain fatty acid.
Deprotonation or esterification gives derivatives called isobutyrates.
Isobutyric acid is a colorless liquid with a somewhat unpleasant odor.
Isobutyric acid is soluble in water and organic solvents.
Isobutyric acid is found naturally in carobs (Ceratonia siliqua), in vanilla, and in the root of Arnica dulcis, and as an ethyl ester in croton oil.
Isobutyric acid is manufactured by the oxidation of isobutyraldehyde, which is a byproduct of the hydroformylation of propylene.
Many routes are known including the hydrolysis of isobutyronitrile with alkalis and the oxidation of isobutanol with potassium dichromate in the presence of sulfuric acid.
In the presence of proton donors, the action of sodium amalgam on methacrylic acid also gives isobutyric acid.
Isobutyric acid reacts as a typical carboxylic acid: Isobutyric acid can form amide, ester, anhydride, and chloride derivatives.
Isobutyric acids acid chloride is commonly used as the intermediate to obtain the others.
When heated with a chromic acid solution Isobutyric acid is oxidized to acetone.
Alkaline potassium permanganate oxidizes Isobutyric acid to α-hydroxyisobutyric acid, (CH3)2C(OH)-CO2H.
Isobutyric acid and its volatile esters are present naturally in a wide variety of foods and, at varying concentrations, can impart a range of flavors.
The compound's safety as a food additive was reviewed by an FAO and WHO panel, who concluded that there were no concerns at the likely levels of intake.
Isobutyric acid, along with several other short-chain fatty acids collectively known as "copulins," is found abundantly in human vaginal secretions.
Levels of isobutyric acid fluctuate throughout the menstrual cycle, and it is hypothesized to act as an indicator of ovulatory status.
Isobutyric acid appears as a colorless liquid with a light odor of rancid butter.
Corrosive to metals and tissue.
Isobutyric acid is a branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.
Isobutyric acid has a role as a volatile oil component, a plant metabolite and a Daphnia magna metabolite.
Isobutyric acid is a branched-chain saturated fatty acid, a methyl-branched fatty acid and a fatty acid 4:0.
Isobutyric acid is a conjugate acid of an isobutyrate.
Isobutyric Acid ((CH3)2CHCOOH) is a colorless, medium boiling liquid.
Esters of isobutyric acid are used as solvents for various applications where desirable odors and flavor characteristics are important.
Isobutyric acid of isobutyric acid is effective as a solubility promoter in the caustic extraction of mercaptans from sour petroleum stocks.
Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell.
Small amount of isobutyrate is generated via microbial (gut) metabolism.
Small amounts may also be found in certain foods or fermented beverages.
Isobutyric acid for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000 ).
Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents.
Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes.
Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.
Isobutyric acid is an essential amino acid important for growth and production of thyroid hormone, neurotransmitters, and melanin.
Isobutyric acid is caused by deficiency of tetrahydrobiopterin (BH4)–dependent phenylalanine hydroxylase that catalyzes the conversion of phenylalanine to tyrosine.
Isobutyric acid may also be caused by deficiency of enzymes that are required for BH4 synthesis.
Isobutyric Acid ((CH3)2CHCOOH) is a colorless, medium boiling liquid.
Esters of isobutyric acid are used as solvents for various applications where desirable odors and flavor characteristics are important.
The potassium salt of isobutyric acid is effective as a solubility promoter in the caustic extraction of mercaptans from sour petroleum stocks.
Isobutyric acid, also known as isobutyrate or iso-C3H7COOH, belongs to the class of organic compounds known as carboxylic acids.
Isobutyric acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
Isobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Isobutyric acid exists in all living species, ranging from bacteria to humans.
Isobutyric Acid is a high-purity (minimum of 99%) intermediate used as a solvent in applications where desirable odors and flavor characteristics are important.
Isobutyric acid is used to prepare esters for flavors and perfumes.
Isobutyric acid is also used as a disinfecting agent, preservative and tanning agent.
Isobutyric acid finds applications in textile, varnish and the leather industry.
Further, Isobutyric acid is used as a lactation stimulant in dairy cattle.
In addition to this, Isobutyric acid is used in the preparation of tetramethylsuccinic acid and diisopropyl ketone.
Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula (CH3)2-CH-COOH.
Isobutyric acid is found in the free state in carobs (Ceratonia siliqua), in vanilla and in the root of Arnica dulcis, and as an ethyl ester in croton oil.
Isobutyric acid is an isomer of n-butyric acid; they have the same chemical formula C4H8O2 but a different structure.
Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acidwith structural formula (CH3)2-CH-COOH.
Isobutyric acid is used to eliminate calcium in leather industry.
Isobutyric acid family products, such as their esters, are used for the production of plastics, plasticizers, surfactants and textile auxiliaries.
They are used in food additives, flavorings, varnishes, perfumes, pharmaceuticals and disinfectants.
Isobutyric acid (from Ancient Greek: βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H.
Isobutyric acid is an oily, colorless liquid with an unpleasant odor.
Isobutyric acid (2-methylpropanoic acid) is an isomer.
Isobutyric acids and esters of butyric acid are known as butyrates or butanoates.
Isobutyric acid does not occur widely in nature, but its esters are widespread.
Isobutyric acid is a common industrial chemical and an important component in the mammalian gut.
Butyric acid was first observed in impure form in 1814 by the French chemist Michel Eugène Chevreul.
Isobutyric acid had purified it sufficiently to characterize Isobutyric acid.
Isobutyric acid deposited his findings in manuscript form with the secretary of the Academy of Sciences in Paris, France.
Isobutyric acid was also researching the composition of butter and was publishing his findings, and this led to disputes about priority.
Isobutyric acid is used in the preparation of various butyrate esters.
Isobutyric acid is used to produce cellulose acetate butyrate (CAB), which is used in a wide variety of tools, paints, and coatings, and is more resistant to degradation than cellulose acetate.
Isobutyric acid can degrade with exposure to heat and moisture, releasing butyric acid.
Low-molecular-weight esters of butyric acid, such as Isobutyric acid, have mostly pleasant aromas or tastes.
As a consequence, they are used as food and perfume additives.
Isobutyric acid is an approved food flavoring in the EU FLAVIS database (number 08.005).
Due to its powerful odor, Isobutyric acid has also been used as a fishing bait additive.
Many of the commercially available flavors used in carp (Cyprinus carpio) baits use butyric acid as their ester base.
Isobutyric acid is not clear whether fish are attracted by the butyric acid itself or the substances added to it.
Isobutyric acid was one of the few organic acids shown to be palatable for both tench and bitterling.
Isobutyric acid has been used as a stink bomb by Sea Shepherd Conservation Society to disrupt Japanese whaling crews.
Isobutyric acid (pKa 4.82) is fully ionized at physiological pH, so its anion is the material that is mainly relevant in biological systems.
Isobutyric acid is one of two primary endogenous agonists of human hydroxycarboxylic acid receptor 2 (HCA2, aka GPR109A), a Gi/o-coupled G protein-coupled receptor.
Like other short-chain fatty acids (SCFAs), butyrate is an agonist at the free fatty acid receptors FFAR2 and FFAR3, which function as nutrient sensors that facilitate the homeostatic control of energy balance; however, among the group of SCFAs, only butyrate is an agonist of HCA2.
Isobutyric acid is also an HDAC inhibitor (specifically, HDAC1, HDAC2, HDAC3, and HDAC8), a drug that inhibits the function of histone deacetylase enzymes, thereby favoring an acetylated state of histones in cells.
Histone acetylation loosens the structure of chromatin by reducing the electrostatic attraction between histones and DNA.
In general, Isobutyric acid is thought that transcription factors will be unable to access regions where histones are tightly associated with DNA (i.e., non-acetylated, e.g., heterochromatin).
Therefore, Isobutyric acid is thought to enhance the transcriptional activity at promoters, which are typically silenced or downregulated due to histone deacetylase activity.
Isobutyric acid that is produced in the colon through microbial fermentation of dietary fiber is primarily absorbed and metabolized by colonocytes and the liver for the generation of ATP during energy metabolism; however, some butyrate is absorbed in the distal colon, which is not connected to the portal vein, thereby allowing for the systemic distribution of butyrate to multiple organ systems through the circulatory system.
Isobutyric acid that has reached systemic circulation can readily cross the blood-brain barrier via monocarboxylate transporters (i.e., certain members of the SLC16A group of transporters).
Other transporters that mediate the passage of butyrate across lipid membranes include SLC5A8 (SMCT1), SLC27A1 (FATP1), and SLC27A4 (FATP4).
Isobutyric acid is metabolized by various human XM-ligases (ACSM1, ACSM2B, ASCM3, ACSM4, ACSM5, and ACSM6), also known as butyrate–CoA ligase.
Isobutyric acid has numerous effects on energy homeostasis and related diseases (diabetes and obesity), inflammation, and immune function (e.g., Isobutyric acid has pronounced antimicrobial and anticarcinogenic effects) in humans.
These effects occur through Isobutyric acids metabolism by mitochondria to generate ATP during fatty acid metabolism or through one or more of Isobutyric acids histone-modifying enzyme targets (i.e., the class I histone deacetylases) and G-protein coupled receptor targets (i.e., FFAR2, FFAR3, and HCA2).
Isobutyric acid, also known as butyl ethanoate, is an ester that is a colorless, flammable liquid at room temperature.
Isobutyric acid is found in many types of fruit, where along with other chemicals, Isobutyric acid imparts characteristic flavors and has a sweet smell of banana or apple.
Isobutyric acid is used as a synthetic fruit flavoring in foods such as candy, ice cream, cheeses, and baked goods.
Isobutyric acid is often used as a high-boiling solvent of moderate polarity.
Isobutyric acid is also used as a solvent in nail polish along with ethyl acetate.
The other three isomers of Isobutyric acid are isobutyl acetate, tert-butyl acetate, and sec-butyl acetate.
Isobutyric acid appears as a colorless liquid with a penetrating and unpleasant odor. Flash point 170°F.
Corrosive to metals and tissue.
Density 8.0 lb /gal.
Isobutyric acid is a saturated short-chain fatty acid with a 4-carbon backbone.
Isobutyric acid is commonly found in esterified form in animal fats and plant oils.
Isobutyric acid is a straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy
Isobutyric acid has a role as a Mycoplasma genitalium metabolite and a human urinary metabolite.
Isobutyric acid is a straight-chain saturated fatty acid and a fatty acid 4:0.
Isobutyric acid is a conjugate acid of a butyrate.
Isobutyric acid is a fatty acid that’s created when the good bacteria in your gut break down dietary fiber.
Isobutyric acid’s also found in animal fats and vegetable oils.
However, the amount of Isobutyric acid found in foods like butter and ghee is small compared to the amount that’s made in your gut.
Isobutyric acid has many important applications in chemical, food, and pharmaceutical industries.
The consumption of Isobutyric acid to produce thermoplastics cellulose acetate butyrate is a major use in the chemical industry.
Isobutyric acid tributyrate and other esters also play an important role in plastic materials.
Isobutyric acid is used to supply butter-like notes in food flavors, and its esters are widely used as additives to increase fruit fragrance in the food industry.
As one of the short-chain fatty acids generated by bacterial fermentation of dietary fibers in the colon, butyric acid is a main energy source for human body and also marked as a suppressor.
Isobutyric acids biological effects have been widely studied, which includes therapeutic effect for hemoglobinopathies, and gastrointestinal diseases.
A family of Isobutyric acid prodrugs is presently in clinical development.
Isobutyric acid derivatives have also been developed to produce antithyroid and vasoconstrictor drugs and used in anesthetis.
Isobutyric acid (CH3CH2CH2CO2H), also called butanoic acid, a fatty acid occurring in the form of esters.
Isobutyric acid (an ester containing an acid and glycerol), it makes up 3–4 percent of butter; the disagreeable odour of rancid butter is that of hydrolysis of the butyric acid glyceride.
Isobutyric acid is of considerable commercial importance as a raw material in the manufacture of esters of lower alcohols for use as flavouring agents; its anhydride is used to make cellulose butyrate, a useful plastic.
Isobutyric acid is manufactured by catalyzed air oxidation of butanal (butyraldehyde).
Isobutyric acid is a colourless liquid, soluble in water and miscible with common organic solvents; Isobutyric acid freezes at −7.9 °C (17.8 °F) and boils at 163.5 °C (326.3 °F).
Isobutyric acid is found both in the free state and as its ethyl ester in a few plant oils.
Although Isobutyric acid is commercially less important than butyric acid, Isobutyric acid is generally similar to butyric acid; Isobutyric acid freezes at −46.1 °C (−51 °F) and boils at 153.2 °C (307.8 °F).
Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula (CH3)2CHCO2H.
Isobutyric acid is a colorless liquid with a somewhat unpleasant odor.
Isobutyric acid is soluble in water and organic solvents.
Isobutyric acid is an isomer of n-butyric acid.
Deprotonation or esterification of isobutyric acid gives derivatives called isobutyrates.
The preparation of isobutyric acid is similar with butyric acid, which is performed by the direct oxidation of isobutyl alcohol and isobutyraldehyde.
Isobutyric acid can be directly generated from the oxidation of isobutyraldehyde in air or oxygen.
Other manufacturing methods have isobutyronitrile hydrolysis and methacrylic acid hydrogenation.
The oxidation of Isobutyric acid to prepare isobutyric acid can also obtain a higher yield.
The purification of Isobutyric acid can be realized by azeotropic distillation with water, and anhydrous isobutyric acid can be obtained by the extractive distillation from carbon tetrachloride.
Propylene and formic acid ester can react at 50 °C with the catalysis of hydrofluoric acid to generate methyl isobutyrate and propyl isobutyrate.
Application: Isobutyric acid is not more important than butyric acid, but has the similar uses with n-butyric acid.
Isobutyric acid is mainly used to produce the corresponding esters, such as methyl isobutyrate with apricot incense, propyl isobutyrate with pineapple flavor, isobutyl isobutyrate with banana flavor, octyl isobutyrate with grapes taste, benzyl isobutyrate with jasmine smell, etc.
Isobutyric acid can be used for preparing flavors and solvents and also used in the manufacture of varnishes and plasticizers.
Isobutyric acid has some important derivatives that, in the industry, is actually used for the production of isobutyronitrile intermediates, and then converted to isobutylamidine hydrochloride that is the raw materials of pesticide diazinon.
Isobutyric acid is used to prepare esters for flavors and perfumes.
Isobutyric acid is also used as a disinfecting agent, preservative and tanning agent.
Isobutyric acid finds applications in textile, varnish and the leather industry.
Further, Isobutyric acid is used as a lactation stimulant in dairy cattle.
In addition to this, it is used in the preparation of tetramethylsuccinic acid and diisopropyl ketone.
Isobutyric Acid is a high-purity (minimum of 99%) intermediate used as a solvent in applications where desirable odors and flavor characteristics are important.
Isobutyric Acid is a flavoring agent that is a colorless liquid with a strong, penetrating odor, resembling butter.
Isobutyric acid is miscible in alcohol, propylene glycol, glycerin, mineral oil, and most fixed oils and sol- uble in water.
Isobutyric acid is obtained by chemical synthesis.
Isobutyric acid is also termed isopropylformic acid.
USES:
-Used to manufacture esters for flavors and perfumes
-as a disinfecting agent
-in varnish
-for deliming hides
-as a tanning agent
-as starting material for diisopropyl ketone; as an herbicide
-in the manufacture of salts used as textile chemicals, tanning compounds, stabilizers, catalysts, and preservatives
-Occurs naturally in food (cheese, milk protein, vinegar, and beer) and in the body as a metabolic product
-Has been used as a lactation stimulant in dairy cattle
USAGES:
-Isobutyric acid is mainly used in the synthesis of isobutyric acid esters, such as methyl isobutyrate, propyl ester, isoamyl ester and benzyl ester.
-Isobutyric acid can also be used as edible flavor and used in pharmaceutical.
-GB 2760-1996 provides for isobutyric acid as the food flavors allowed to use.
-Isobutyric acid is mainly used for the preparation of butter, apple, caramel, cheese, bread, yeast and other flavors.
-Isobutyric acid is not more important than butyric acid, but has the similar uses with n-butyric acid.
-Isobutyric acid is mainly used to produce the corresponding esters, such as methyl isobutyrate with apricot incense, propyl isobutyrate with pineapple flavor, isobutyl isobutyrate with banana flavor, octyl isobutyrate with grapes taste, benzyl isobutyrate with jasmine smell, etc.
-Isobutyric acid can be used for preparing flavors and solvents and also used in the manufacture of varnishes and plasticizers.
-Isobutyric acid has some important derivatives that, in the industry, is actually used for the production of isobutyronitrile intermediates, and then converted to isobutylamidine hydrochloride that is the raw materials of pesticide diazinon.
-Used for the raw materials of perfume and perfume ester, and also used as the solvents of textile auxiliaries (in the form of salt) and a variety of chemical reactions.
APPLICATIONS:
-Agriculture intermediates
-Dyes / pigments / paints
-Food flavors & food fragrances
-Fragrance ingredients
-Herbicides - intermediate for other
-Intermediates
-Other-food chemicals
-Pharmaceutical chemicals
-Protective coatings
PROPERTIES:
-Quality Level: 100
-vapor density: 3.04 (vs air)
-vapor pressure: 1.5 mmHg ( 20 °C)
-assay: 99%
-autoignition temp.: 824 °F
-expl. lim.: 10 %
-refractive index: n20/D 1.393 (lit.)
-bp: 153-154 °C (lit.)
-mp: −47 °C (lit.)
-density: 0.95 g/mL at 25 °C (lit.)
PHYSICAL AND CHEMICAL PROPERTIES:
-Boiling point: 152-155°C
-Melting point: -47°C
-Relative density (water = 1): 0.95
-Solubility in water, g/100ml at 20°C: 20
-Vapour pressure, kPa at 14.7°C: 0.13
-Relative vapour density (air = 1): 3.0
-Flash point: 56°C c.c.
-Auto-ignition temperature: 481°C
-Explosive limits, vol% in air: 2-9
-Octanol/water partition coefficient as log Pow: 0.88
TECHNICAL INFORMATIONS:
-Physical State :Liquid
-Solubility :Soluble in water
-Storage :Store at 4° C
-Melting Point :-47° C (lit.)
-Boiling Point :153-154° C (lit.)
-Density :0.95 g/cm3 at 25° C (lit.)
STORAGE:
Fireproof.
Separated from strong bases and food and feedstuffs.
SYNONYM:
n-Butyric acid
n-Butanoic acid
propylformic acid
ethylacetic acid
Butanic acid
1-propanecarboxylic acid
1-Butyric acid
Buttersaeure
butanoate
Butyric acid (natural)
Kyselina maselna
Propanecarboxylic acid
Buttersaeure [German]
1-butanoic acid
FEMA Number 2221
Kyselina maselna [Czech]
FEMA No. 2221
CCRIS 6552
HSDB 940
butoic acid
2-butanoate
NSC 8415
UNII-40UIR9Q29H
MFCD00002814
UN2820
AI3-15306
C4:0
CH3-[CH2]2-COOH
40UIR9Q29H
CHEBI:30772
NSC8415
butanate
propylformate
