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Encyclopedia > Butyric acid
Butyric acid
Butyric acid
General
Systematic name butanoic acid
Other names butyric acid
n-butyric acid
ethylacetic acid
propane-1-carboxylic acid
Molecular formula C4H8O2
SMILES CCCC(O)=O
Molar mass 88.10 g/mol
Appearance colorless oily liquid
CAS number [107-92-6]
Properties
Density and phase 0.959 g/cm3, liquid
Solubility in water miscible
Melting point -7.9 °C (265.1 K)
Boiling point 163.5 °C (436.5 K)
Acidity (pKa) 4.81
Viscosity  ? cP at ? °C
Hazards
MSDS External MSDS
Main hazards  ?
NFPA 704
Flash point 72 °C
R/S statement R: 34
S: 26 36 45
RTECS number ES5425000
Related compounds
Related compounds butyraldehyde
methyl butyrate
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 βουτυρος = butter) IUPAC name n-Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2-COOH. It is notably found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid can be detected by mammals with good scent detection abilities (e.g., dogs) at 10 ppb, while humans can detect it in concentrations above 10 ppm. Image File history File links Butanoic_acid. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... The pitch drop experiment at the University of Queensland. ... The poise (P) is the cgs unit of viscosity, 1 P = 1 g·cm-1·s-1 The SI analog is 1 pascal second (Pa·s) = 1 kg·m-1·s-1 = 10 P. It is named after Jean Louis Marie Poiseuille. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... Butanal (C4H8O; alternate names include butyraldehyde, butyl aldehyde, butal, and butanaldehyde) is the aldehyde analog of butane. ... Methyl butyrate is an ester with a fruity fragrance resembling apples or pineapples. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... The International Union of Pure and Applied Chemistry (IUPAC) is an international non-governmental organization devoted to the advancement of chemistry. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -(C=O)-OH, usually written as -COOH. In general, the salts and anions... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... In chemistry, a carboxyl group is a functional group consisting of a carbon atom doubly bonded to an oxygen atom and single-bonded to a hydroxyl (-OH) group, typically written as -COOH: where R is a hydrogen or an organic group. ... Butter is commonly sold in sticks (pictured) or small blocks, and frequently served with the use of a butter knife. ... It has been suggested that this article or section be merged into Parmigiano_Reggiano. ... Vomiting (or emesis) is the forceful expulsion of the contents of ones stomach through the mouth. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... Orders Multituberculata (extinct) Palaeoryctoides (extinct) Triconodonta (extinct) Subclass Australosphenida Ausktribosphenida Monotremata Subclass Eutheria (excludes extinct ancestors) Afrosoricida Anagaloidea (extinct) Arctostylopida (extinct) Artiodactyla Carnivora Cetacea Chiroptera Cimolesta (extinct) Cingulata Creodonta (extinct) Condylarthra (extinct) Dermoptera Desmostylia (extinct) Dinocerata (extinct) Embrithopoda (extinct) Hyracoidea Insectivora Lagomorpha Leptictida (extinct) Litopterna (extinct) Macroscelidea Mesonychia (extinct) Notoungulata... Trinomial name Canis lupus familiaris The dog is a mammal in the order Carnivora. ... Parts per billion (ppb) is a measure of concentration that is used where low levels of concentration are significant. ... Trinomial name Homo sapiens sapiens Linnaeus, 1758 Humans, or human beings, are bipedal apes belonging to the mammalian species Homo sapiens (Latin for wise man or knowing man) under the family Hominidae (known as the great apes). ... Parts per million (ppm) is a measure of concentration that is used where low levels of concentration are significant. ...


Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. The glyceride of butyric acid makes up 3% to 4% of butter. When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis leading to the unpleasant odor. In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Glycerides are esters of glycerol and fatty acids. ... Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ...


Normal butyric acid or fermentation butyric acid is also found as a hexyl ester in the oil of Heracleum giganteum (cow parsnip) and as an octyl ester in parsnip (Pastinaca sativa); it has also been noticed in the fluids of the flesh and in perspiration. General formula of a carboxylate ester. ... Binomial name Pastinaca sativa L. The parsnip (Pastinaca sativa) is a root vegetable related to the carrot. ...


It is ordinarily 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. The butyric fermentation of starch is aided by the direct addition of Bacillus subtilis. Magnification of typical sugar showing monoclinic hemihedral crystal stucture. ... Starch(CAS# 9005-25-8) is a complex carbohydrate which is insoluble in water; it is used by plants as a way to store excess glucose. ... Cheese is a solid food made from the milk of cows, goats, sheep, and other mammals. ... Calcium carbonate is a chemical compound, with chemical formula CaCO3. ... Binomial name Bacillus subtilis (Ehrenberg 1835) Cohn 1872 Bacillus subtilis is a Gram-positive, catalase-positive bacterium commonly found in soil. ...


Butryic acid is used in the preparation of various butyrate esters. Low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. The butyrate (also butanoate) ion is C3H7COO- (butyric acid minus one hydrogen ion). ... Methyl butyrate is an ester with a fruity fragrance resembling apples or pineapples. ...


The acid is an oily colorless liquid that solidifies at -8 °C; it boils at 164 °C. It is easily soluble in water, ethanol and ether, and is thrown out of its aqueous solution by the addition of calcium chloride. Potassium dichromate and sulfuric acid (also known as sulphuric acid) oxidize it to carbon dioxide and acetic acid, while alkaline potassium permanganate oxidizes it to carbon dioxide. The calcium salt, Ca(C4H7O2)2·H2O, is less soluble in hot water than in cold. Celsius is, or relates to, the Celsius temperature scale. ... Water is an odourless substance that is essential to all known forms of life and is known as the universal solvent. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless, mildly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... Calcium chloride is a chemical compound of calcium and chlorine. ... Potassium dichromate, K2Cr2O7 is used in oxidation reactions. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... Carbon dioxide is a chemical compound composed of one carbon and two oxygen atoms. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... Potassium permanganate is the chemical compound KMnO4. ... Carbon dioxide is a chemical compound composed of one carbon and two oxygen atoms. ...


There is an isomer, isobutyric acid, which has the same chemical formula C4H8 O2 but a different structure. It has similar chemical properties but different physical properties. In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ... Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula (CH3)2-CH-COOH. It is found in the free state in carobs (Ceratonia siliqua) and in the root of Arnica dulcis, and as an ethyl ester in croton oil. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ...


Butyrate fermentation

Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria. This fermentation pathway was discovered by Louis Pasteur in 1861. Examples of butyrate producing species: An anaerobic organism or anaerobe is any organism that does not require oxygen for growth. ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ... Louis Pasteur (December 27, 1822 – September 28, 1895) was a French microbiologist and chemist. ... 1861 is a common year starting on Tuesday. ... In biology, a species is one of the basic units of biodiversity. ...

  • Clostridium butyricum
  • Clostridium kluyveri
  • Clostridium pasteurianum
  • Fusobacterium nucleatum
  • Butyrivibrio fibrisolvens
  • Eubacterium limosum

The pathway starts with the glycolytic cleavage of glucose to two molecules of pyruvate, as happens in most organisms. Pyruvate is then oxidized into acetyl coenzyme A using a unique mechanism that involves an enzyme system called pyruvate-ferredoxin oxidoreductase. Two molecules of carbon dioxide (CO2) and two molecules of elemental hydrogen (H2) are formed in the process and exit the cell. Then: Glycolysis is a metabolic pathway by which a 6-carbon glucose (Glc) molecule is oxidized to two molecules of pyruvic acid (Pyr). ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... In chemistry, a molecule is an aggregate of two or more atoms in a definite arrangement held together by chemical bonds [1] [2] [3] [4] [5]. Chemical substances are not infinitely divisible into smaller fractions of the same substance: a molecule is generally considered the smallest particle of a pure... Pyruvate (CH3COCOO−) is the ionized form of pyruvic acid. ... The most fundamental reactions in chemistry are the redox processes. ... Categories: Biochemistry stubs | Thiols ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Carbon dioxide is a chemical compound composed of one carbon and two oxygen atoms. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ...

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

ATP is produced, as can be seen, in the last step of the fermentation. 3 ATPs are produced for each glucose molecule, a relatively high yield. The balanced equation for this fermentation is: Above is a ball-and-stick model of the inorganic hydrogenphosphate anion (HPO42−). Colour coding: P (orange); O (red); H (white). ... Adenosine diphosphate, abbreviated ADP, is a nucleotide. ... Adenosine 5-triphosphate (ATP), discovered in 1929 by Karl Lohmann,[1] is a multifunctional nucleotide primarily known in biochemistry as the molecular currency of intracellular energy transfer. ... In biochemistry, a kinase is a type of enzyme that transfers phosphate groups from high-energy donor molecules, such as ATP, to specific target molecules (substrates); the process is termed phosphorylation. ...


C6H12O6 → C4H8O2 + 2CO2 + 2H2


Acetone and butanol fermentation

Several species form acetone and butanol in an alternative pathway which starts as butyrate fermentation. Some of these species are: In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Butanol or butyl alcohol (sometimes also called biobutanol when produced biologically), is an alcohol with a 4 carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. ...

  • Clostridium acetobutylicum: the most prominent acetone and butanol producer, used also industrially
  • Clostridium beijerinckii
  • Clostridium tetanomorphum
  • Clostridium aurantibutyricum

These bacteria begin with butyrate 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. Two molecules of butanol are formed for each molecule of acetone. Clostridium acetobutylicum () is a commercially valuable bacterium, included in the genus Clostridium. ... . The initial letter is shown capitalized due to technical restrictions. ...


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

  • Acetoacetyl CoA → acetoacetate → acetone, or
  • Acetoacetyl CoA → butyryl CoA → butanal → butanol.

Butanal (C4H8O) is the aldehyde analog of butane. ...

Butyric acid function/activity

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. Acetylated histones have a lower affinity for DNA than non-acetylated histones, due to the neutralisation of electrostatic charge interections. It is generally thought that transcription factors will be unable to access regions where histones are tightly associated with DNA (ie non-acetylated, eg heterochromatin). Therefore, it is thought that butyric acid enhances the transcriptional activity at promoters which are typically silenced/downregulated due to histone deacetylase activity. In the context of genetics, a transcription factor is a regulatory protein that initiates the transcription of certain genes upon binding with DNA. The binding of a transcription factor to a specific DNA sequence can result in either an increased rate of transcription of the gene, known as activated transcription...


This article incorporates information from the 1911 encyclopedia.


  Results from FactBites:
 
Butyric acid at AllExperts (312 words)
Normal butyric acid or fermentation butyric acid is found in butter, as a hexyl ester in the oil of Heracleum giganteum (cow parsnip) and as an octyl ester in parsnip (Pastinaca sativa); it has also been noticed in the fluids of the flesh and in perspiration.
The acid is an oily colorless liquid that solidifies at -5 °C; it boils at 164 °C. It is easily soluble in water, ethanol and ether, and is thrown out of its aqueous solution by the addition of calcium chloride.
Potassium dichromate and sulfuric acid (also known as sulphuric acid) oxidize it to carbon dioxide and acetic acid, while alkaline potassium permanganate oxidizes it to carbon dioxide.
  More results at FactBites »

 
 

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