Propionic acid (systematically named propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH₃CH₂COOH. In the pure state, it is a colorless, corrosive liquid with a pungent odor. The anion CH₃CH₂COO⁻ as well as the salts and esters of propionic acid are known as propionates (or propanoates). Image File history File links File links The following pages link to this file: Propionic acid ... Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... 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. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... 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. ... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... Viscosity is a measure of the resistance of a fluid to deform under shear stress. ... The pascal second (symbol Pa·s) is the SI unit of dynamic viscosity. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... ... 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. ... Image File history File links NFPA_704. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... 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. ... ... ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... ... ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... It has been suggested that NMR Data Processing be merged into this article or section. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or informally, mass-spec and MS) is an analytical technique used to measure the mass-to-charge ratio of ions. ... An electrostatic potential map of the nitrate ion (NO3−). Areas coloured red are lower in energy than areas colored yellow An ion is an atom or group of atoms which have lost or gained one or more electrons, making them negatively or positively charged. ... Sodium propionate or Sodium propanoate has formula Na(C2H5COO). ... 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 -COOH or -CO2H. [1] Carboxylic acids are Bronsted... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... 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). ... Propan-1-ol is is a primary alcohol with the formula CH3CH2CH2OH. It is also known as 1-propanol, 1-propyl alcohol n-propyl alcohol, or simply propanol. ... R-phrases , S-phrases , , Flash point −26°C Autoignition temperature 175°C RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... Propanoic anhydride, also called propionic anhydride, is a simple carboxylic anhydride. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... 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 -COOH or -CO2H. [1] Carboxylic acids are Bronsted... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 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) Standard atomic weight 15. ... An anion is an ion with negative charge. ... For other uses, see Salt (disambiguation). ... A carboxylic acid ester. ... The propionate (also propanoate) ion is C2H5COO− (propionic acid minus one hydrogen ion). ...

History

Propionic acid was first described in 1844 by Johann Gottlieb, who found it among the degradation products of sugar. Over the next few years, other chemists produced propionic acid in various other ways, none of them realizing they were producing the same substance. In 1847, the French chemist Jean-Baptiste Dumas established that all the acids were the same compound, which he called propionic acid, from the Greek words protos = "first" and pion = "fat", because it was the smallest H(CH₂)_nCOOH acid that exhibited the properties of the other fatty acids, such as producing an oily layer when salted out of water and having a soapy potassium salt. Jan. ... Magnification of grains of sugar, showing their monoclinic hemihedral crystalline structure. ... 1847 was a common year starting on Friday (see link for calendar). ... Jean Baptiste Andr Dumas Jean Baptiste Andr Dumas (July 14, 1800 - April 10, 1884), French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights (relative atomic masses) by measuring vapor densities. ... 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. ... This article is about the computer protocol. ... General Name, Symbol, Number potassium, K, 19 Chemical series alkali metals Group, Period, Block 1, 4, s Appearance silvery white Standard atomic weight 39. ...

Properties

Propionic acid has physical properties intermediate between those of the smaller carboxylic acids, formic and acetic acid, and the larger fatty acids. It is miscible with water, but it can be removed from water by adding salt. Like acetic and formic acids, its vapor grossly violates the ideal gas law because it does not consist of individual propionic acid molecules, but instead of hydrogen bonded pairs of molecules. It also undergoes this pairing in the liquid state. Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... 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. ... Isotherms of an ideal gas The ideal gas law is the equation of state of a hypothetical ideal gas, first stated by Benoît Paul Émile Clapeyron in 1834. ... An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ...

Chemically, propionic acid displays the general properties of carboxylic acids, and like most other carboxylic acids, it can form amide, ester, anhydride, and chloride derivatives. It can undergo alpha-halogenation with bromine in the presence of PBr₃ as catalyst (the HVZ reaction) to form CH₃CHBrCOOH. Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... A carboxylic acid ester. ... Acid anhydrides are chemical compounds that look like, and sometimes are, the product resulting from dehydration of an acid. ... General Chemical Structure of an Acyl Chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound which is a reactive derivative of a carboxylic acid. ... Halogenation is a chemical reaction that replaces a hydrogen atom with a halogen atom. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... Phosphorus tribromide is a colourless liquid with the formula PBr3. ... It has been suggested that this article or section be merged into Catalysis. ... The Hell-Volhard-Zelinsky halogenation reaction halogenates carboxylic acids at the α carbon. ...

Production

Industrially, propionic acid is usually made from the air oxidation of propionaldehyde. In the presence of cobalt or manganese ions, this reaction proceeds rapidly even at mild temperatures. Usually, the industrial process is carried out at 40-50°C, and is represented by the chemical equation The most fundamental reactions in chemistry are the redox processes. ... R-phrases , S-phrases , , Flash point −26°C Autoignition temperature 175°C RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... wikipedia sucks big balls For other uses, see Cobalt (disambiguation). ... General Name, Symbol, Number manganese, Mn, 25 Chemical series transition metals Group, Period, Block 7, 4, d Appearance silvery metallic Standard atomic weight 54. ... An electrostatic potential map of the nitrate ion (NO3−). Areas coloured red are lower in energy than areas colored yellow An ion is an atom or group of atoms which have lost or gained one or more electrons, making them negatively or positively charged. ... A chemical equation is a symbolic representation of a chemical reaction where the reactant entities are given on the left hand side and the product entities on the right hand side. ...

CH₃CH₂CHO + ½ O₂ → CH₃CH₂COOH

Large amounts of propionic acid were once produced as a byproduct of acetic acid manufacture, but changes in the way acetic acid is made have made this a very minor source of propionic acid today. Current world's largest producer is BASF, with approximately 80 ktpa production capacity. R-phrases , S-phrases , , Flash point −26°C Autoignition temperature 175°C RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... This article is about the German chemical company. ...

Propionic acid is produced biologically as its Coenzyme A ester, propionyl-CoA, from the metabolic breakdown of fatty acids containing odd numbers of carbon atoms, and also it the breakdown of some amino acids. Bacteria of the genus Propionibacterium produce propionic acid as the end product of their anaerobic metabolism. This class of bacteria is commonly found in the stomachs of ruminants, and the sweat glands of humans, and their activity is partially responsible for the odor of both Swiss cheese and sweat. Propionyl-CoA is a coenzyme A derivative of propionic acid. ... A few of the metabolic pathways in a cell. ... In mathematics, any integer (whole number) is either even or odd. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... Phenylalanine is one of the standard amino acids. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... Binomial name Propionibacterium acnes Propionibacterium acnes is a bacterium that is linked to the skin condition acne. ... Anaerobic respiration refers to the oxidation of molecules in the absence of oxygen to produce energy, in opposition to Aerobic respiration which does use oxygen. ... This article does not adequately cite its references or sources. ... Binomial name Propionibacterium acnes (Gilchrist 1900) Douglas & Gunter 1946 Propionibacterium acnes is a relatively slow growing, (typically) aerotolerant anaerobe gram positive bacterium that is linked to the skin condition acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. ... Cubes of Swiss cheese For related uses of the word swiss cheese please see Swiss cheese (disambiguation) This article is about a variety of cheese known as Swiss cheese in some areas. ... SWEAT is an OLN/TSN show hosted by Julie Zwillich that aired in 2003-2004. ...

Uses

Propionic acid inhibits the growth of mold and some bacteria. Accordingly, most propionic acid produced is used as a preservative for both animal feed and food for human consumption. Can be used as a preservative for Ballistics Gel. For animal feed, it is used either directly or as its ammonium salt. In human foods, especially bread and other baked goods, it is used as its sodium or calcium salt. Similar usage occurs in some of the older anti-fungal foot powders. It has been suggested that Toxic mold be merged into this article or section. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... A preservative is a natural or synthetic chemical that is added to products such as foods, pharmaceuticals, paints, biological samples, etc. ... A ball-and-stick model of the ammonium cation Fumes from hydrochloric acid and ammonia forming a white cloud of ammonium chloride Ammonium is also an old name for the Siwa Oasis in western Egypt. ... Percentages are relative to US recommendations for adults. ... General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Standard atomic weight 22. ... General Name, Symbol, Number calcium, Ca, 20 Chemical series alkaline earth metals Group, Period, Block 2, 4, s Appearance silvery white Standard atomic weight 40. ...

Propionic acid is also useful as a chemical intermediate. It can be used to modify synthetic cellulose fibers. It is also used to make pesticides and pharmaceuticals. The esters of propionic acid are sometimes used as solvents or artificial flavorings. Cellulose as polymer of β-D-glucose Cellulose in 3D Cellulose (C6H10O5)n is a polysaccharide of beta-glucose. ... A cropduster spreading pesticide. ... Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... A carboxylic acid ester. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ...

Safety

The chief danger from propionic acid is chemical burns that can result from contact with the concentrated liquid. In studies on laboratory animals, the only adverse health effect associated with long-term exposure to small amounts of propionic acid has been ulceration of the esophagus and stomach from consuming a corrosive substance. No toxic, mutagenic, carcinogenic, or reproductive effects have ever been observed. In the body propionic acid is readily metabolized so it does not bioaccumulate. Endoscopic images of a duodenal ulcer. ... The esophagus (also spelled oesophagus/Å“sophagus, Greek ), or gullet is an organ in vertebrates which consists of a muscular tube through which food passes from the pharynx to the stomach. ... In anatomy, the stomach is a bean-shaped hollow muscular organ of the gastrointestinal tract involved in the second phase of digestion, following mastication. ... In biology, a mutagen (Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ...

A recent publication by MacFabe and colleagues found that intraventricular infusions of propionic acid produced reversible behavior that was very similar to that seen in autism. Behaviors included: hyperactivity, dystonia, turning, retropulsion. In addition, the treated rats demonstrated caudate spiking and the progressive development of limbic kindled seizures. The paper concludes that this is an excellent animal model of autism and warrants further study (MacFabe, 2007). Autism is classified by the World Health Organization and American Psychological Association as a developmental disability that results from a disorder of the human central nervous system. ...

Metabolism

The metabolism of propionic acid begins with its conversion to propionyl coenzyme A (propionyl-CoA), the usual first step in the metabolism of carboxylic acids. Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... 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 -COOH or -CO2H. [1] Carboxylic acids are Bronsted...

Since propionic acid has three carbons, propionyl-CoA can enter neither beta oxidation nor the citric acid cycle Schematic demonstrating mitochondrial fatty acid beta-oxidation and effects of LCHAD deficiency Beta oxidation is the process by which fatty acids, in the form of Acetyl-CoA molecules, are broken down in the mitochondria to generate Acetyl-CoA, the entry molecule for the Krebs Cycle. ... Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle, after Hans Adolf Krebs who identified the cycle) is a series of chemical reactions of central importance in all living cells that use oxygen as part...

In most vertebrates propionyl-CoA is carboxylated to D-methylmalonyl-CoA, isomerised to L-methylmalonyl-CoA, and rearranged to yield succinyl-CoA via a vitamin B12-dependent enzyme. Succinyl-CoA is an intermediate of the citric acid cycle and can be readily incorporated there. Classes and Clades See below Male and female Superb Fairy-wren Vertebrates are members of the subphylum Vertebrata (within the phylum Chordata), specifically, those chordates with backbones or spinal columns. ... A carboxyl or carboxylic group is a functional group consisting of a carbon atom doubly bonded to an oxygen atom and single-bonded to a hydroxyl (-OH) group. ... In chemistry, isomerization is the transformation of a molecule into a different isomer. ... Categories: Biochemistry stubs ... Cobalamin or vitamin B12 is a chemical compound that is also known as cyanocobalamine. ...

Human occurrence

The human skin is host to a species of bacteria known as Propionibacterium acnes, which is named after its ability to produce propionic acid. This bacteria lives mainly in the sebaceous glands of the skin and is one of the principle causes of acne. In zootomy and dermatology, skin is the largest organ of the integumentary system made up of multiple layers of epithelial tissues that guard underlying muscles and organs. ... Binomial name Propionibacterium acnes (Gilchrist 1900) Douglas & Gunter 1946 Propionibacterium acnes is a relatively slow growing, (typically) aerotolerant anaerobe gram positive bacterium that is linked to the skin condition acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. ... The sebaceous glands are glands found in the skin of mammals. ...

Reference

MacFabe, DF, et al, "Neurobiological effects of intraventricular propionic acid in rats: Possible role of short chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders," Behavioral Brain Research, 2007, 176:149-169.

See also

• Propionic acid (data page)

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External links

• NIST Standard Reference Database
• European Chemicals Bureau
• International Chemical Safety Card 0806
• NIOSH Pocket Guide to Chemical Hazards
• Technical data of propionic acid of BASF
• Links to external chemical sources