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Butyric acid
IUPAC name Butyric acid
Other names Butanoic acid
Identifiers
CAS number [107-92-6]
PubChem 264
MeSH Butyric+acid
SMILES CCCC(=O)O
Properties
Molecular formula C4H8O2
Molar mass 88. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component Medical Subject Headings ( MeSH) is a huge Controlled vocabulary (or metadata system for the purpose of indexing journal articles and books A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 1051 g/mol
Density 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 96 g/mL
Melting point

-7. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 9 °C (265. 1 K)
Boiling point

163. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 5 °C (436. 5 K)
Solubility in water miscible
Hazards
Main hazards Corrosive; Harmful to aquatic organisms
R-phrases 34
S-phrases 26 36 45
Flash point 72 °C
Autoignition
temperature		 452 °C
RTECS number ES5425000
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Butyric acid (from Greek βούτυρος = butter), also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air The autoignition temperature or kindling point of a substance is the lowest temperature at which it will spontaneously ignite in a normal atmosphere without an external Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Greek (el ελληνική γλώσσα or simply el ελληνικά — "Hellenic" is an Indo-European language, spoken today by 15-22 million people mainly Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Carboxyl group or CO2H is a Functional group present in Amino acids and Carboxylic acids Its structure is composed of one carbon atom attached It is found in rancid butter, parmesan cheese, vomit, and body odor and has an unpleasant smell and acrid taste, with a sweetish aftertaste (similar to ether). Butter is a Dairy product made by churning fresh or fermented Cream or Milk. Parmigiano-Reggiano is a hard fat Granular cheese, cooked but not pressed named after the producing areas of Parma, Reggio Emilia, Modena, Vomiting (also called throwing up, emesis) is the forceful expulsion of the contents of one's Stomach through the Mouth and sometimes the Body odor (spelled body odour outside the United States often abbreviated as B Taste (or more formally gustation) is a form of direct Chemoreception and is one of the traditional five Senses Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a Butyric acid can be detected by mammals with good scent detection abilities such as dogs at 10 ppb, whereas humans can detect it in concentrations above 10 ppm. Mammals ( class Mammalia) are a class of Vertebrate Animals characterized by the presence of Sweat glands, including sweat glands The dog ( Canis lupus familiaris) is a domesticated Subspecies of the gray wolf, a Mammal of the Canidae family of the order "Parts-per" notation is used especially in Science and Engineering, to denote Ratios (relative proportions in measured quantities particularly Human beings, humans or man (Origin 1590–1600 L homō man OL hemō the earthly one (see Humus "Parts-per" notation is used especially in Science and Engineering, to denote Ratios (relative proportions in measured quantities particularly

Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. In Chemistry, especially Biochemistry, a fatty acid is a Carboxylic acid often with a long unbranched Aliphatic tail ( chain) which Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least The glyceride of butyric acid makes up 3% to 4% of butter. Glycerides, more correctly known as acylglycerols, are Esters formed from Glycerol and Fatty acids Glycerol has three Hydroxyl When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis leading to the unpleasant odor. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions It is an important member of the fatty acid sub-group called short chain fatty acids. Short chain fatty acids are a sub-group of Fatty acids with Aliphatic tails of less than eight carbons Butyric acid is a weak acid with a pKa of 4. A weak acid is an Acid that does not completely donate all of its hydrogens when dissolved in water 82, similar to acetic acid which has pKa 4. Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste 76. [1] The similar strength of these acids results from their common -CH2COOH terminal structure. [2] Butyric acid has density 0. 96 g/cm3 and molecular mass 88. 1051; thus pure butyric acid is 10. 9 molar. In Chemistry, concentration is the measure of how much of a given substance there is mixed with another substance

Butyric acid or fermentation butyric acid is also found as a hexyl ester (hexyl butanoate) in the oil of Heracleum giganteum (a type of cow parsnip) and as an octyl ester (octyl butanoate) in parsnip (Pastinaca sativa); it has also been noticed in the fluids of the flesh and in perspiration. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least The Cow Parsnip ( Heracleum maximum; also known as Indian Celery or Pushki) is the only member of the Hogweed genus native to The parsnip ( Pastinaca sativa) is a Root vegetable related to the Carrot.

It is industrially prepared by the fermentation of sugar or starch, brought about by the addition of putrefying cheese, with calcium carbonate added to neutralize the acids formed in the process. Sugar is a class of edible Crystalline substances mainly Sucrose, Lactose, and Fructose. Starch, CAS # 9005-25-8 Chemical formula (C6H10O5n is a Polysaccharide Cheese is a Food made from Milk, usually the milk of cows, Buffalo, Goats or sheep, by coagulation. Calcium carbonate is a Chemical compound with the Chemical formula Ca[[Carbon C]] O 3 The butyric fermentation of starch is aided by the direct addition of Bacillus subtilis. Bacillus subtilis Sporejpg|thumb|right|Sporulating Bacillus subtilis ]] Bacillus subtilis is a Gram-positive, Catalase -positive Salts and esters of the acid are called butanoates. Butyric acid (from Greek βούτυρος = butter) also known under the systematic name butanoic acid, is a Carboxylic acid with the structural

Butyric acid is used in the preparation of various butanoate esters. Low-molecular-weight esters of butyric acid, such as methyl butanoate, have mostly pleasant aromas or tastes. Methyl butyrate, also known under the systematic name methyl butanoate, is the Methyl Ester of Butyric acid. As a consequence, they find use as food and perfume additives. They are also used in organic laboratory courses, to teach the Fischer esterification reaction. Hermann Emil Fischer (9 October 1852 - 15 July 1919 was a German Chemist and recipient of the Nobel Prize for Chemistry in 1902

The acid is an oily colorless liquid that freezes at -8 °C; it boils at 164 °C. The Celsius Temperature scale was previously known as the centigrade scale. It is easily soluble in water, ethanol, and ether, and is precipitated out of its aqueous solution by the addition of calcium chloride. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl Calcium chloride (CaCl2 is an ionic compound of Calcium and Chlorine. Potassium dichromate and sulfuric acid oxidize it to carbon dioxide and acetic acid, while alkaline potassium permanganate oxidizes it to carbon dioxide. Potassium dichromate, K2Cr2O7 is a common inorganic chemical reagent most commonly used as an Oxidizing agent in various laboratory Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste Potassium permanganate is the Chemical compound K[[manganese Mn]] O 4 The calcium salt, Ca(C4H7O2)2·H2O, is less soluble in hot water than in cold.

Butyric acid has a structural isomer called isobutyric acid (2-methylpropanoic acid). Structural isomerism, or constitutional isomerism, is a form of isomerism in which Molecules with the same Molecular formula have Atoms Isobutyric acid, also known as 2-methylpropanoic acid, is a Carboxylic acid with structural formula ( C[[hydrogen H]]32-CH-

Contents

Butanoate fermentation

Butanoate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria. An anaerobic organism is any Organism that does not require Oxygen for growth and may even die in its presence The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have Fermented Kombucha "tea" includes butyric acid as a result of the fermentation. Kombucha is the Western name for sweetened tea or Tisane that has been fermented using a macroscopic solid mass of microorganisms called a "kombucha colony" This fermentation pathway was discovered by Louis Pasteur in 1861. Louis Pasteur (27 December 1822 – 28 September 1895 a French Chemist and Microbiologist, is best known for remarkable breakthroughs in the causes and Year 1861 ( MDCCCLXI) was a Common year starting on Tuesday (link will display the full calendar of the Gregorian calendar (or a Common Examples of butanoate-producing species of bacteria:

The pathway starts with the glycolytic cleavage of glucose to two molecules of pyruvate, as happens in most organisms. In Biology, a species is one of the basic units of Biological classification and a Taxonomic rank. Clostridium acetobutylicum, included in the genus Clostridium, is a commercially valuable Bacterium. Fusobacterium is a genus of filamentous anaerobic, Gram-negative bacteria similar to Bacteroides. See also Gluconeogenesis, which carries out a process wherein glucose is synthesized rather than catabolized Glucose (Glc a Monosaccharide (or simple Sugar) also known as grape sugar, is an important Carbohydrate in Biology. In Chemistry, a molecule is defined as a sufficiently stable electrically neutral group of at least two Atoms in a definite arrangement held together by Pyruvic acid (CH3COCO2H is an alpha-keto acid. The Carboxylate Anion of pyruvic acid is known as pyruvate. Pyruvate is then oxidized into acetyl coenzyme A using a unique mechanism that involves an enzyme system called pyruvate-ferredoxin oxidoreductase. Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state Acetyl-CoA is an important molecule in metabolism used in many biochemical reactions Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins Two molecules of carbon dioxide (CO2) and two molecules of elemental hydrogen (H2) are formed as wastes products from the cell. Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Then:

Action Responsible enzyme
Acetyl coenzyme A converts into acetoacetyl coenzyme A acetyl-CoA-acetyl transferase
Acetoacetyl coenzyme A converts into β-hydroxybutyryl CoA β-hydroxybutyryl-CoA dehydrogenase
β-hydroxybutyryl CoA converts into crotonyl CoA crotonase
Crotonyl CoA converts into butyryl CoA (CH3CH2CH2C=O-CoA) butyryl CoA dehydrogenase
A phosphate group replaces CoA to form butyryl phosphate phosphobutyrylase
The phosphate group joins ADP to form ATP and butyrate butyrate kinase

ATP is produced, as can be seen, in the last step of the fermentation. Acetoacetyl CoA is the precursor of HMG-CoA in the the Mevalonate pathway which is essential for cholesterol synthesis Acetyl-Coenzyme A acetyltransferase (or thiolase) is an enzyme which converts two units of Acetyl-CoA to Acetoacetyl CoA in the Mevalonate pathway Beta-hydroxybutyryl-CoA (or 3-hydroxybutyryl-coenzyme A) is an intermediate in the fermentation of Butyric acid, and in the metabolism of Lysine Beta-hydroxybutyryl-CoA dehydrogenase is an enzyme which converts Beta-hydroxybutyryl-CoA and Acetoacetyl CoA. Crotonyl-coenzyme A is an intermediate in the fermentation of Butyric acid, and in the metabolism of Lysine and Tryptophan. Biological Significance Metabolism Enoyl-CoA hydratase Catalyzes the second step in the break down of Fatty acids or the second step of β-oxidation Butyryl-coenzyme A (or butyryl-CoA) is the Coenzyme A -activated form of Butyric acid. Butyryl CoA dehydrogenase is a Flavoprotein. It acts upon Butyryl-coenzyme A. A phosphate, an Inorganic chemical, is a salt of Phosphoric acid. Butyryl phosphate is an intermediate in the fermentation of Butyric acid. Adenosine diphosphate, abbreviated ADP, is a Nucleotide. It is an Ester of Pyrophosphoric acid with the Nucleoside Adenosine Adenosine-5'-triphosphate ( ATP) is a multifunctional Nucleotide that is most important as a " molecular currency" of intracellular Energy In Enzymology, a butyrate kinase ( is an Enzyme that catalyzes the Chemical reaction ATP + butanoate \rightleftharpoons Three molecules of ATP are produced for each glucose molecule, a relatively high yield. The balanced equation for this fermentation is:

C6H12O6 → C4H8O2 + 2CO2 + 2H2

Acetone and butanol fermentation

Several species form acetone and butanol in an alternative pathway, which starts as butyrate fermentation. Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Butanol or butyl alcohol (sometimes also called biobutanol when produced biologically is a Primary alcohol with a 4 Carbon structure and the Molecular Some of these species are:

These bacteria begin with butanoate fermentation as described above, but, when the pH drops below 5, they switch into butanol and acetone production in order to prevent further lowering of the pH. Clostridium acetobutylicum, included in the genus Clostridium, is a commercially valuable Bacterium. Clostridium beijerinckii is a Gram positive, rod shaped, Motile Bacterium of the genus Clostridium. pH is the measure of the acidity or alkalinity of a Solution. Two molecules of butanol are formed for each molecule of acetone.

The change in the pathway occurs after acetoacetyl CoA formation. This intermediate then takes two possible pathways:

Butyric acid function/activity

Highly-fermentable fibers like oat bran, pectin, and guar are transformed by colonic bacteria into short chain fatty acids including butyrate. Bran is the hard outer layer of Grain and consists of combined Aleurone and Pericarp. Pectin (from Greek πηκτικός - pektikos, "congealed curdled" a white to light brown powder is a Heteropolysaccharide The guar bean or cluster bean (Cyamopsis tetragonolobus an annual Legume, is the source of Guar gum. The gut flora are the Microorganisms that normally live in the Digestive tract and can perform a number of useful functions for their hosts Short chain fatty acids are a sub-group of Fatty acids with Aliphatic tails of less than eight carbons

Butanoate has diverse and, it seems, paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate, and the intracellular milieu. The term cell growth is used in two different ways in Biology. In Developmental biology, cellular differentiation is the process by which a less specialized cell becomes a more specialized Cell type. Butanoate is thought by some to be protective against colon cancer. Colorectal cancer, also called colon cancer or large bowel cancer, includes Cancerous growths in the colon, Rectum and However, not all studies support a chemopreventive effect, and the lack of agreement (particularly between in vivo and in vitro studies) on butyrate and colon cancer has been termed the "butyrate paradox. In vivo ( Latin: within the living means that which takes place inside an organism. In vitro ( Latin: within the glass refers to the technique of performing a given experiment in a controlled environment outside of a living Organism " There are many reasons for this discrepant effect, including differences between the in vitro and in vivo environments, the timing of butanoate administration, the amount administered, the source (usually dietary fiber) as a potential confounder, and an interaction with dietary fat. Together, the studies suggest that the chemopreventive benefits of butanoate depend in part on amount, time of exposure with respect to the tumorigenic process, and the type of fat in the diet. [3] Low carbohydrate diets like the Atkins diet are known to reduce the amount of butanoate produced in the colon. Atkins Nutritional Approach, popularly known as the Atkins Diet or just 'Atkins' is a well-known Low-carbohydrate diet created by Dr

Butyric acid has been associated with the ability to inhibit the function of histone deacetylase enzymes, thereby favouring an acetylated state of histones in the cell. Histone deacetylases (HDAC ( EC number 351 are a class of Enzymes that remove Acetyl groups from an ε-N-acetyl Lysine Amino acid In Biology, histones are the chief Protein components of Chromatin. Acetylated histones have a lower affinity for DNA than non-acetylated histones, due to the neutralisation of electrostatic charge interactions. Deoxyribonucleic acid ( DNA) is a Nucleic acid that contains the genetic instructions used in the development and functioning of all known Electrostatics is the branch of Science that deals with the Phenomena arising from what seems to be stationary Electric charges Since Classical In general, it is thought that transcription factors will be unable to access regions where histones are tightly associated with DNA (ie non-acetylated, e. In the field of Molecular biology, a transcription factor (sometimes called a sequence-specific DNA binding factor is a Protein that binds to specific sequences g. , heterochromatin). Therefore, it is thought that butyric acid enhances the transcriptional activity at promoters, which are typically silenced/downregulated due to histone deacetylase activity.

This article incorporates information from the 1911 encyclopedia.

References

  1. ^ Adimix Sodium Butanoate information.
  2. ^ Using the pKa table.
  3. ^ Microbial Degradation Products Influence Colon Cancer Risk: the Butyrate Controversy - Lupton 134 (2): 479 - Journal of Nutrition

See also

External links

Indole-3-butyric acid (1H-Indole-3-butanoic acid IBA is a white to light-yellow crystalline solid with the molecular formula C12H13NO2

Dictionary

butyric acid

-noun

  1. (organic chemistry) Either of the two isomeric carboxylic acids, normal butyric acid and isobutyric acid, with the chemical formula C3H7COOH, occurring in animal milk fat.
  2. (organic chemistry) Normal butyric acid, n-butyric acid, or n-butanoic acid CH3(CH2)2COOH, a short chain fatty acid; its glyceride is one of the principle components of the flavour of butter.
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