Fumaric acid
General
Common name	fumaric acid
Systematic name	(E)-butenedioic acid
Other names	trans-1,2-ethylenedicarboxylic acid
Molecular formula	C4H4O4
SMILES	OC(=O)C=CC(=O)O
Molar mass	116.07 g/mol
Appearance	white solid
CAS number	[110-17-8]
Properties
Density and phase	1.635 g/cm3, solid
Solubility in water	0.63g/100ml
Solubility in ethanol	Soluble
Melting point	287 °C
Acidity (pKa)	?
Thermodynamic data
Standard enthalpy of formation ΔfH°solid	? kJ/mol
Standard enthalpy of combustion ΔcH°solid	? kJ/mol
Standard molar entropy S°solid	? J.K−1.mol−1
Hazards
EU classification	Irritant (Xi)
R-phrases	R36
S-phrases	S2, S26
NFPA 704
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Regulatory data	Flash point, RTECS number, etc.
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 (IUPAC systematic name: 2-butenedioic acid), also called allomaleic acid, boletic acid or lichenic acid, is a colorless crystalline flammable carboxylic acid based on butene and molecular formula C₄H₄O₄. Irritating maleic anhydride fumes are produced by its combustion. Having a fruitlike taste, it is found in fumitory (Fumaria officinalis), bolete mushrooms (specifically Boletus fomentarius var. pseudo-igniarius), lichen, and Iceland moss. Image File history File links Fumaric_acid. ... In science, a common name is any name by which a species or other concept is known that is not the official scientific name. ... 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. ... It has been suggested that this article or section be merged with Solution. ... 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. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... 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 standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atmosphere... Standard enthalpy of Combustion is the Enthalpy change when one mole of a substance is totally combusted in oxygen, and is measured at 298K and 1 atmospheric pressure. ... In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. ... 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 of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... 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. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Basic schematic of a mass spectrometer Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... 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. ... 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... Maleic acid or (Z)-Butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). ... Succinic acid, originally called spirit of amber, is a carboxylic acid with the formula: HOOC-CH2-CH2-COOH At room temperature, pure succinic acid is a solid that forms colorless, odorless prisms. ... Iron(II) fumarate, also known as ferrous fumarate is an iron-containing compound, occurring as a reddish-orange powder, used to supplement iron intake. ... 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. ... There are millions of possible objects that can be described in science, too many to create common names for every one. ... Color is an important part of the visual arts. ... Quartz crystal In chemistry and mineralogy, a crystal is a solid in which the constituent atoms, molecules, or ions are packed in a regularly ordered, repeating pattern extending in all three spatial dimensions. ... Flammable or Flammability refers to the ease at which a substance will ignite, causing fire or combustion. ... 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... Butylene, also known as butene, is the name of the three isomeric hydrocarbon gases with chemical formula C4H8. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... 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. ... R-phrases , , S-phrases , , , , Flash point 102 °C RTECS number UE5950000 Supplementary data page Structure and properties n, εr, etc. ... Fruit stall in Barcelona, Spain. ... Taste is one of the most common and fundamental of the senses of animals. ... Species See text Fumaria is a genus of annual herbaceous flowering plants in the family Fumariaceae, native to temperate Europe and Asia. ... 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 spongy surface of pores (rather than gills) on the underside of the pileus. ... The relative sizes of the Cap (pileus) and Stalk (stipe) vary widely. ... Lichenes from Ernst Haeckels Artforms of Nature, 1904 Crustose and foliose lichens on a wall A foliose lichen on basalt. ... [[{{{diversity_link}}}|Diversity]] {{{diversity}}} Binomial name Cetraria islandica Trinomial name {{{trinomial}}} Type Species {{{type_species}}} {{{subdivision_ranks}}} [[Image:{{{range_map}}}|{{{range_map_width}}}|]] Synonyms {{{synonyms}}} Iceland Moss (Cetraria islandica) is a lichen whose erect or ascending foliaceous habit gives it something of the appearance of a moss, whence probably the name. ...

Fumaric acid is an acid used in the manufacture of polyester resins and polyhydric alcohols, as a mordant for dyes, or as a flavoring. It is a common component of food additives and dietary supplements, and is sometimes used as a substitute for tartaric acid in beverages or baking powder. SEM picture of a bend in a high surface area polyester fiber with a seven-lobed cross section Polyester is a category of polymers, or, more specifically condensation polymers, which contain the ester functional group in their main chain. ... Resin of a pine Insect trapped in resin. ... A sugar alcohol (also known as a polyol, polyhydric alcohol, or polyalcohol) is a hydrogenated form of carbohydrate, whose carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. ... Look up Mordant on Wiktionary, the free dictionary A mordant is a substance used to set dyes. ... Flavouring (or flavoring) is a product which is added to food in order to change or augment its taste. ... Food additives are substances added to food to preserve flavour or improve its taste and appearance. ... A prescribed dietary supplement is intended to supply nutrients (vitamins, minerals, fatty acids or amino acids) that are missing or not consumed in sufficient quantity in a persons diet. ... Tartaric acid or H2C4H4O6 is a white crystalline organic acid. ... The word drink is primarily a verb, meaning to ingest liquids, see Drinking. ... Baking powder is a dry chemical leavening agent used in baking. ...

Biology

Related to malic acid, fumaric acid is used by cells to produce energy from food. Human skin naturally produces fumaric acid when exposed to sunlight. Malic acid is a tart-tasting organic acid that plays a role in many sour or tart foods. ... Drawing of the structure of cork as it appeared under the microscope to Robert Hook from Micrographia which is the origin of the word cell. Cells in culture, stained for keratin (red) and DNA (green). ... 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). ... In zootomy and dermatology, skin is an organ of the integumentary system made up of multiple layers of epithelial tissues that guard underlying muscles and organs. ... It has been suggested that solar radiation be merged into this article or section. ...

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. A starting dose is 60-105mg daily, which may be gradually increased to as much as 1,290mg per day. Side effects include kidney or gastrointestinal disorders, as well as skin flushing; these are mainly caused by excess intake. Decreased white blood cell counts have been reported with prolonged use. General formula of a carboxylate ester. ... Oral medication A medication is a licenced drug taken to cure or reduce symptoms of an illness or medical condition. ... An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Human kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... For the Physics term GUT, please refer to Grand unification theory The gastrointestinal or digestive tract, also referred to as the GI tract or the alimentary canal or the gut, is the system of organs within multicellular animals which takes in food, digests it to extract energy and nutrients, and... For a person to flush is to become markedly red in the face and often other areas of the skin, from various physiological conditions. ... To meet Wikipedias quality standards, this article may require cleanup. ...

Food

Fumaric acid is a food acidulant used since 1946 because it is non-toxic. It is generally used in beverages and baking powders for which requirements are placed on purity, such as Welch's Grape Drink. It is generally used as a substitute for tartaric acid and occasionally in place of citric acid, at a rate of 1.36 g of citric acid to every 0.91 grams of fumaric acid for the same taste. Tartaric acid or H2C4H4O6 is a white crystalline organic acid. ... Citric acid is a weak organic acid found in citrus fruits. ...

See also

• Dermatology
• Photosynthesis
• Maleic acid, the cis-isomer of fumaric acid

Dermatology (from Greek derma, skin) is a branch of medicine dealing with the skin and its appendages (hair, nails, sweat glands etc). ... The leaf is the primary site of photosynthesis in plants. ... Maleic acid or (Z)-Butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). ...

References

• http://www.shreeadditives.com/htmlsite/3d.htm

External links

• International Chemical Safety Card 1173
• Link page to external chemical sources.