| Fumaric acid | |
|---|---|
 | |
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| IUPAC name | (E)-Butenedioic acid |
| Other names | trans-1,2-Ethylenedicarboxylic acid 2-Butenedioic acid Allomaleic acid Boletic acid Lichenic acid |
| Identifiers | |
| CAS number | [110-17-8] |
| EINECS number | |
| SMILES | OC(=O)C=CC(=O)O |
| Properties | |
| Molecular formula | C4H4O4 |
| Molar mass | 116. 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 The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each Chemical substance commercially available in the 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) 07 g/mol |
| Appearance | White solid |
| Density | 1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 635 g/cm³, solid |
| Melting point | 287 °C |
| Solubility in water | 0. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 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. 63 g/100 mL |
| Acidity (pKa) | pka1 = 3. 03, pka2 = 4. 44 |
| Hazards | |
| EU classification | Irritant (Xi) |
| R-phrases | R36 |
| S-phrases | (S2) S26 |
| Related compounds | |
| Related carboxylic acids | Maleic acid Succinic acid |
| Related compounds | Fumaryl chloride Fumaronitrile Dimethyl fumarate Iron(II) fumarate |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Fumaric acid is the chemical compound with the formula HO2CCH=CHCO2H. Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws regulations and administrative provisions relating to the classification packaging and labelling 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 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Maleic acid or ( Z)-butenedioic acid or cis -butenedioic acid or malenic acid or maleinic acid or toxilic Succinic acid ( IUPAC Systematic name: butanedioic acid; historically known as spirit of amber) is a Dicarboxylic acid. Dimethyl fumarate is the methyl Ester of Fumaric acid. Reactions Dimethyl fumarate is an Ester and an αβ-unsaturated electrophilic Iron(II fumarate, also known as ferrous fumarate is the iron (II salt of Fumaric acid, occurring as a Reddish orange powder used to supplement In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. This colorless crystalline compound is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid wherein the carboxylic acid groups are cis. In Materials science, a crystal is a Solid in which the constituent Atoms Molecules or Ions are packed in a regularly ordered repeating Dicarboxylic acids are Organic compounds that are substituted with two Carboxylic acid Functional groups In molecular formulae for dicarboxylic acids these Maleic acid or ( Z)-butenedioic acid or cis -butenedioic acid or malenic acid or maleinic acid or toxilic It has a fruit-like taste. The term fruit has different meanings dependent on context and the term is not synonymous in Food preparation and Biology. Taste (or more formally gustation) is a form of direct Chemoreception and is one of the traditional five Senses The salts and esters of fumaric acid are known as fumarates. A salt, in Chemistry, is defined as the product formed from the neutralisation reaction of Acids and bases. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least
Fumaric acid, when added to food products, is denoted by E number E297. E numbers are number codes for Food additives and are usually found on Food labels throughout the European Union.
Contents |
Biology
Fumaric acid is found in fumitory (Fumaria officinalis), bolete mushrooms (specifically Boletus fomentarius var. Fumaria is a genus of about fifty annual Herbaceous Flowering plants in the family Fumariaceae, native to temperate Europe and A bolete is a type of fungal Fruiting body characterized by the presence of a pileus that is clearly differentiated from the stipe, with A mushroom is the fleshy Spore -bearing Fruiting body of a Fungus, typically produced above ground on soil or on its food source pseudo-igniarius), lichen, and Iceland moss. Lichens (ˈlaɪkən or /lɪtʃən/ are symbiotic associations of a Fungus (the mycobiont with a photosynthetic partner (the photobiont also known as Iceland moss ( Cetraria islandica) is a Lichen whose erect or ascending foliaceous habit gives it something of the appearance of a Moss, whence probably
Fumarate is an intermediate in the citric acid cycle used by cells to produce energy in the form of adenosine triphosphate (ATP) from food. The citric acid cycle, also known as the tricarboxylic acid cycle ( TCA cycle) or the Krebs cycle, (or rarely the Szent-Györgyi–Krebs cycle The cell is the structural and functional unit of all known living Organisms It is the smallest unit of an organism that is classified as living and is often called Adenosine-5'-triphosphate ( ATP) is a multifunctional Nucleotide that is most important as a " molecular currency" of intracellular Energy Food is any substance usually composed primarily of Carbohydrates Fats water and/or Proteins that can be eaten or drunk by an It is formed by the oxidation of succinate by the enzyme succinate dehydrogenase. Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state Succinic acid ( IUPAC Systematic name: butanedioic acid; historically known as spirit of amber) is a Dicarboxylic acid. Succinate-coenzyme Q reductase ( EC 1351; succinate dehydrogenase) is an Enzyme complex bound to the inner Mitochondrial membrane Fumarate is then converted by the enzyme fumarase to malate. Fumarase (or fumarate hydratase) is an Enzyme involved in the Krebs Cycle (aka the Tricarboxylic Acid Cycle aka the Citric Acid Cycle that Catalyzes Malic acid is an Organic compound with the formula HO2CCH2CHOHCO2H Human skin naturally produces fumaric acid when exposed to sunlight. Sunlight, in the broad sense is the total spectrum of the Electromagnetic radiation given off by the Sun.
Fumarate is also a byproduct of the urea cycle. The urea cycle (also known as the ornithine cycle) is a cycle of biochemical reactions occurring in many animals that produces Urea ( N[[hydrogen
Medicine
Fumaric acid esters are sometimes used to treat psoriasis, as it has been suggested that the condition is caused by an impairment of fumaric acid production in the skin. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least Psoriasis (səˈraɪəsɪs ( suh-RI-uh-sus) is a non-contagious disorder which affects the Skin and Joints It commonly causes red scaly A starting dose is 60-105 mg daily, which may be gradually increased to as much as 1,290 mg per day. Medication, also referred to as medicine, can be loosely defined as any substance intended for use in the diagnosis cure mitigation treatment or prevention of disease Side-effects include kidney or gastrointestinal disorders, as well as skin flushing; these are mainly caused by excess intake. An adverse drug reaction (abbreviated ADR) or adverse drug event (abbreviated ADE) is an expression that describes the unwanted negative consequences The kidneys are complicated organs that have numerous biological roles For a person to flush is to become markedly Red in the Face and often other areas of the skin from various physiological conditions Decreased white blood cell counts have been reported with prolonged use.
Food
Fumaric acid is a food acidulent used since 1946 because it is non-toxic. It is generally used in beverages and baking powders for which requirements are placed on purity. Baking powder is a dry chemical Leavening agent used in cooking mainly baking It is generally used as a substitute for tartaric acid and occasionally in place of citric acid, at a rate of 1. Tartaric acid is a white crystalline Organic acid. It occurs naturally in many plants particularly Grapes Bananas and Tamarinds and is Citric acid is a weak organic Acid. It is a natural Preservative and is also used to add an acidic or sour taste to foods and Soft drinks 36 g of citric acid to every 0. 91 grams of fumaric acid for the same taste. It is also used in candy to add sourness, similar to the way malic acid is used. Malic acid is an Organic compound with the formula HO2CCH2CHOHCO2H
Chemistry
Fumaric acid is inexpensive, so it is typically purchased rather than prepared. It was first prepared from succinic acid. Succinic acid ( IUPAC Systematic name: butanedioic acid; historically known as spirit of amber) is a Dicarboxylic acid. [1] A traditional synthesis involves oxidation of furfural (from the processing of maize) using sodium chlorate in the presence of a vanadium-based catalyst. The Chemical compound furfural is an industrial chemical derived from a variety of agricultural byproducts including corncobs, Oat and Sodium chlorate ( Na[[Chlorine Cl]] O 3 is an Oxidizing agent. Vanadium (vəˈneɪdiəm is a Chemical element that has the symbol V and Atomic number 23 Catalysis is the process in which the rate of a Chemical reaction is increased by means of a Chemical substance known as a catalyst [2]
The chemical properties of fumaric acid can be anticipated from its component functional groups. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions This weak acid forms a diester, it undergoes additions across the double bond, and it is an excellent dienophile. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least In Organic chemistry, an alkene, olefin, or olefine is an unsaturated Chemical compound containing at least one Carbon The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene,
Other uses
Fumaric acid is used in the manufacture of polyester resins and polyhydric alcohols and as a mordant for dyes. Polyester is a category of Polymers which contain the Ester Functional group in their main chain Resin, not to be confused with Rosin, is a Hydrocarbon Secretion of many Plants particularly coniferous trees. A sugar alcohol (also known as a Polyol, polyhydric alcohol, or polyalcohol) is a hydrogenated form of Carbohydrate, whose A mordant is a substance used to set Dyes on fabrics by forming an insoluble compound with the dye
Safety
Fumaric acid converts to the irritant maleic anhydride, upon partial combustion. Maleic anhydride ( cis -butenedioic anhydride toxilic anhydride dihydro-25-dioxofuran is an Organic compound with the formula C4H2O3
See also
- Dermatology
- Photosynthesis
- Maleic acid, the cis-isomer of fumaric acid
References
- ^ Volhard, J. Dermatology (from Greek grc δέρμα derma, "skin" and grc -λογία -logia) is a branch of Medicine dealing with Photosynthesis is a Metabolic pathway that converts Light Energy into Chemical energy. Maleic acid or ( Z)-butenedioic acid or cis -butenedioic acid or malenic acid or maleinic acid or toxilic "Darstellung von Maleïnsäureanhydrid" Justus Liebig's Annalen der Chemie 1892, volume 268, page 255-6. DOI: 10. 1002/jlac. 18922680108
- ^ Milas, N. A. "Fumaric Acid" Organic Synthesis 1943, Collective Volume 2, page 302. Online version
External links
Dictionary
fumaric acid
-noun
- (chemistry) an unsaturated organic dicarboxylic acid, HOOCCH=CHCOOH, the geometric isomer of maleic acid from which it may be prepared by heating; it is found in many plants, including fungi and mosses, and is essential in the chemistry of respiration; it has a number of industrial applications, and its esters, the fumarates are used in the treatment of psoriasis
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