Butyric acid naming

It IS hard to find a class of compounds in which the common names of its members have influenced organic nomenclature more than carboxylic acids Not only are the common names of carboxylic acids themselves abundant and widely used but the names of many other compounds are derived from them Benzene took its name from benzoic acid and propane from propionic acid not the other way around The name butane comes from butyric acid present m rancid butter The common names of most aldehydes are derived from the common names of carboxylic acids—valeraldehyde from valeric acid for exam pie Many carboxylic acids are better known by common names than by their systematic ones and the framers of the lUPAC rules have taken a liberal view toward accepting these common names as permissible alternatives to the systematic ones Table 19 1 lists both common and systematic names for a number of important carboxylic acids... 

The common method of naming aldehydes corresponds very closely to that of the related acids (see Carboxylic acids), in that the term aldehyde is added to the base name of the acid. For example, formaldehyde (qv) comes from formic acid, acetaldehyde (qv) from acetic acid, and butyraldehyde (qv) from butyric acid. If the compound contains more than two aldehyde groups, or is cycHc, the name is formed using carbaldehyde to indicate the functionaUty. The lUPAC system of aldehyde nomenclature drops the final e from the name of the parent acycHc hydrocarbon and adds al If two aldehyde functional groups are present, the suffix -dialis used. The prefix formjlis used with polyfunctional compounds. Examples of nomenclature types are shown in Table 1. 

Many carboxylic acids were first isolated from natural sources and were given names based on their origin. Fonnic acid (Latin formica, meaning ant ) was obtained by distilling ants. Since ancient times acetic acid (Latin acetum, for vinegar ) has been known to be present in wine that has turned sour. Butyric acid (Latin butyrum, meaning butter ) contributes to the odor of both rancid butter and ginkgo benies, and lactic acid (Latin lac, for milk ) has been isolated from sour milk. 

Chemical Name 7-Amino-/3-(p[Pg.127]

The word butter comes from the Greek butyros. Butanoic acid (common name butyric acid) gives rancid butter its distinctive odour. Calculate the pH of a 1.0 x 10 mol/L solution of butanoic acid... 

O), and that, too, in like proportions—namely, C HgO. If now we equate butyric acid to propyl formate, then, in the first place, propyl formate would be, in this relation, merely a form of existence of C HgO and in the second place, we should be stating that butyric acid also consists of There-... 

More than seventy years ago the impressive discovery was made that bioreduction of mannitol, glycerol and starch yields butanol. Fermentations in which butyric acid, butanol and acetone are formed from carbohydrates by different bacilli (butyl bacteria) belong in this group. The term butyl bacteria as a generic name for microbes producing the genetically related substances of the four-carbon series was proposed in 1921" and has been applied since then. The approximate course of these reactions is shown by the following formulations which, however, do not explain the mechanism ... 

The most accurately determined example of the third class has already been cited, namely the effect of butyric acid on the interfacial tension benzene-water. Harkins has found the concentration of acid in both layers for each pair of phases in equilibrium, but did not measure that of the second solvent. The mutual solubility must however almost certainly increase with the addition of a body soluble in either, but the interfacial tension is still diminished, adsorption of the solute counterbalancing the greater resemblance of the two phases. Bubanovic has also determined the interfacial tensions of the same solutions against olive oil, obtaining very similar results. He has also examined solutions of chloral hydrate. 

Butyric acid is a carboxylic acid also classified as a fatty acid. It exists in two isomeric forms as shown previously, but this entry focuses on n-butyric acid or butanoic acid. It is a colorless, viscous, rancid-smelling liquid that is present as esters in animal fats and plant oils. Butyric acid exists as a glyceride in butter, with a concentration of about 4% dairy and egg products are a primary source of butyric acid. When butter or other food products go rancid, free butyric acid is liberated by hydrolysis, producing the rancid smell. It also occurs in animal fat and plant oils. Butyric acid gets its name from the Latin butyrum, or butter. It was discovered by Adolf Lieben (1836—1914) and Antonio Rossi in 1869. 

Butyric acid is one of the simplest fatty acids. Fatty acids, which are the building units of fats and oils, are natural compounds of carbon chains with a carboxyl group (-COOH) at one end. Most natural fatty acids have an unbranched carbon chain and contain an even number of carbon atoms because during biosynthesis they are built in two carbon units from acetyl coenzyme A (CoA). Butyric acid is an unsaturated fatty acid, which means all carbon-carbon bonds are single bonds. Common names for fatty acids stem from their natural sources. In addition to butyric acid, some other common saturated fatty acids include lauric acid, palmitic acid, and stearic acid. Lauric acid was first discovered in Lauraceae (Laurus nobilis) seeds, palmitic oil was prepared from palm oil, and stearic acid was discovered in animal fat and gets its name from the Greek word stear for tallow. 

Ethyl alcohol has been made by the hydration of ethylene (9) since 1930. Like isopropyl alcohol, part of the output is used as a solvent, but most is converted to other oxygenated chemicals. Its most important raw material use is conversion to acetaldehyde by catalytic air oxidation. Acetaldehyde, in turn, is the raw material source of acetic acid, acetic anhydride, pentaerythritol, synthetic n-butyl alcohol (via aldol condensation), butyraldehyde, and other products. Butyraldehyde is the source of butyric acid, polyvinyl butyral resin, and 2-ethylhexanol (octyl alcohol). The last-named eight-carbon alcohol is based on the aldol condensation of butyraldehyde and is used to make the important plasticizer di-2-ethylhexyl phthalate. A few examples of the important reactions of acetaldehyde are as follows ... 

Chemical Name y-Amino-p-(p-chlorophenyl)butyric acid... 

Therapeutic Function Antiinflammatory, Analgesic Chemical Name 2-(p-Isobutylphenyl)butyric acid Common Name Butilopan Structural Formula ... 

Chemical Name 4-(2,4-dichlorophenoxy)butanoic acid 4-(2,4-dichlorophenoxy)butyric acid... 

Chemical Name 4-(4-chloro-2-methylphenoxy)butanoic acid 4-(4-chloro-2-methylphenoxy)-butyric acid Uses herbicide for post-emergence control of annual and perennial broadleaf weeds in cereals, clovers, sainfoin, groundnuts, peas, etc. and also used to control broadleaf and woody weeds in forestry. 

The high-value HMG-CoA reductase inhibitor Simvastatin (8) is marketed by Merck under the name Zocor. The active ingredient is obtained from a fermentation approach. It is very similar in structure to lovastatin, which has fallen from the top-sellers list. Lovastatin (9) is also a cholesterol-reducing drug that is isolated from Aspergillus terreus.51-60 It is still obtained by fermentation,61 and with the current advances in molecular biology,62 64 chemical approaches are not able to compete in a cost-effective manner.65-67 The usage of lipases allows for the manipulation of the butyric acid sidechain to access other HMG-CoA reductase inhibitors such as simvastatin.68 A number of routes to various portions of lovastatin have been reported.69... 

C The COOH group means that the molecule is a carboxylic acid and its name will use the suffix -oic acid. The presence of 4 carbon atoms means the prefix butan- will be used. An alternate name for the molecule is butyric acid. Choices A and B would be used for aldehydes (CHO group). Choices B and D would be used for 3 carbon atoms ... 

This is quite undesirable in a perfume because many carboxylic acids have objectionable odors. For example, the sharp, penetrating odor of vinegar is due to acetic acid, butanoic acid (butyric acid) smells like rancid butter, and 2-methylpropanoic acid (isobutyric acid) is a component of sweat. A common name for hexanoic acid is caproic acid, derived from the Latin word caper, which means goat. If you have ever been around goats, perhaps you can imagine the odor of hexanoic acid. 

Systematic names for carboxylic acids use the -oic acid suffix, but historical names are commonly used. Formic acid was first isolated from ants, genus Formica. Acetic acid, found in vinegar, gets its name from the Latin word for sour (acetum). Propionic acid gives the tangy flavor to sharp cheeses, and butyric acid provides the pungent aroma of rancid butter. 

Several aliphatic carboxylic acids have been known for centuries, and their common names reflect their historical sources. Formic acid was extracted from ants formica in Latin. Acetic acid was isolated from vinegar, called acetum ( sour ) in Latin. Propionic acid was considered to be the first fatty acid, and the name is derived from the Greek protos pion ( first fat ). Butyric acid results from the oxidation of butyraldehyde, the principal flavor of butter butyrum in Latin. Caproic, caprylic, and capric acids are found in the skin secrehons of goats caper in Lahn. The names and physical properties of some carboxylic acids are listed in Table 20-1. 

The names of common fatty acids under several conventions, carbon numbers, and selected properties are shown in Table 34.1. The common (trivial) names of some fatty acids are of long standing, and often indicate the initial source studied. As examples butyric acid is a major component of butter flavor the 6, 8, and 10 saturated fatty acids have been called the goaty acids because they impart the characteristic flavors of goat and... 

Cheese/hutter flavor. Pregastric lipases, have, been used for years to intensify flavor in Menzyme-modified cheese , and for an intensified butter flavor in lipolyzed butter. Generally the fatty acid residues that need to be split off (to generate the right flavor) are the short chain fatty acids, especially the C to C-jq acids typical of Italian cheeses. The butyric acids are produced from butterfat more specifically by newly developed lipases (really esterases) from Mucor meihei and a very new one, from Aspergillus oryzae, especially for cheddar cheese flavor development. The latter enzyme is marketed under the name Flavor Age (4). Flavors produced in this manner are used widely in cheese-flavored snack foods the value of the intensified cheese flavors is on the order of 50 million, but the. value of the enzymes employed is only about 2-3 million. 

Synonym. Aminomethyl Chlorohydrocinnamic Acid Proprietary Name. Lioresal 4-Amino-3-(4-chlorophenyl)butyric acid CioHi2C1N02 = 213.7 CAS—1134-47-0... 

Chemical Name i-butyric acid, isobutyric acid CAS Registry No 79-31-2 Molecular Formula C4H8O2, (CH3)2CHCOOH Molecular Weight 88.106 Melting Point (°C) ... 

The trivial names that indicate the initial source of fatty acids are used more often than the lUPAC names in the industry. For example, butyric acid is a major component of butter flavor, palmitic acid comes from palm kernel, and oleic acid from olives. 

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