Names | |||
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Preferred IUPAC name 2-Methylpropanoic acid [2] | |||
Other names Isobutyric acid 2-Methylpropionic acid Isobutanoic acid | |||
Identifiers | |||
3D model (JSmol) | |||
3DMet | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.001.087 | ||
EC Number |
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KEGG | |||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 2529 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
C4H8O2 | |||
Molar mass | 88.11 g/mol | ||
Density | 0.9697 g/cm3 (0 °C) | ||
Melting point | −47 °C (−53 °F; 226 K) | ||
Boiling point | 155 °C (311 °F; 428 K) | ||
Acidity (pKa) | 4.86 [3] | ||
-56.06x10−6 cm3/mol | |||
Hazards [4] [5] | |||
GHS labelling: | |||
Danger | |||
H226, H302, H311, H314 | |||
P210, P280, P301+P312+P330, P303+P361+P353, P305+P351+P338+P310 | |||
NFPA 704 (fire diamond) | |||
Flash point | 55 °C (131 °F; 328 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of butyric acid. It 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. It is soluble in water and organic solvents. It is found naturally in carobs ( Ceratonia siliqua ), in vanilla, and in the root of Arnica dulcis, and as an ethyl ester in croton oil. [6]
Isobutyric acid is manufactured by the oxidation of isobutyraldehyde, which is a byproduct of the hydroformylation of propylene. [7]
It can also be prepared by the high pressure hydrocarboxylation (Koch reaction) from propylene: [7]
Isobutyric acid can also be manufactured commercially using engineered bacteria with a sugar feedstock. [8]
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. [9] In the presence of proton donors, the action of sodium amalgam on methacrylic acid also gives isobutyric acid. [6]
The acid reacts as a typical carboxylic acid: it can form amide, ester, anhydride, and chloride derivatives. [10] Its acid chloride is commonly used as the intermediate to obtain the others. When heated with a chromic acid solution it is oxidized to acetone. Alkaline potassium permanganate oxidizes it to α-hydroxyisobutyric acid, (CH3)2C(OH)-CO2H. [6]
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. [11] 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. [12]
In humans, isobutyric acid is a minor product of the gut microbiome and can also be produced by metabolism of its esters found in food. [13] It has a characteristic odor like rancid butter [14] (4-carbon organic compounds take the root, butyl, which is in turn from butyric which is in turn from the Latin word for butter and the Greek, βούτυρον) but anosmia for it has been reported in about 2.5% of people. [15]
The metabolism of isobutyric acid in plants has been studied. [16]
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. [17] Similar cycles are observed in chimpanzees. [18]
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to carbon. Alcohols range from the simple, like methanol and ethanol, to complex, like sugars and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.
Butyric acid, also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.
Propionic acid is a naturally occurring carboxylic acid with chemical formula CH
3CH
2CO
2H. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH
3CH
2CO−
2 as well as the salts and esters of propionic acid are known as propionates or propanoates.
Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C (156.9 °F) °C and a pKa of 4.50.
In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.
Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.
Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.
Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
3-Methylbutanoic acid, also known as β-methylbutyric acid or more commonly isovaleric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.
Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).
Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.
Hydroxybutyric acid is a group of four-carbon organic compounds that have both hydroxyl and carboxylic acid functional groups. They can be viewed as derivatives of butyric acid. The carboxylate anion and the esters of hydroxybutyric acids are known as hydroxybutyrates. β-hydroxybutyric acid is relevant to human health as it is a member of a class of products of fatty acid oxidation referred to as ketone bodies.
Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.
Decenoic acid is any mono-carboxylic acid with an unbranched chain of ten carbons connected by eight single bonds and one double bond; that is, a chemical compound with formula HO(O=)C–(CH
2)
k–CH=CH–(CH
2)
7-k–H, where k is between 0 and 7 inclusive.
Methyl isobutyrate is an organic compound with the formula CH3O2CCH(CH3)2. This colorless liquid, the methyl ester of isobutyric acid, is used as a solvent.
2-Methylbutanoic acid, also known as 2-methylbutyric acid is a branched-chain alkyl carboxylic acid with the chemical formula CH3CH2CH(CH3)CO2H, classified as a short-chain fatty acid. It exists in two enantiomeric forms, (R)- and (S)-2-methylbutanoic acid. (R)-2-methylbutanoic acid occurs naturally in cocoa beans and (S)-2-methylbutanoic occurs in many fruits such as apples and apricots, as well as in the scent of the orchid Luisia curtisii.
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