Fumaric acid

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Fumaric acid

Fumaric acid is the chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
with the formula HO₂CCH=CHCO₂H. This white crystal

Crystal

A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions....
line compound is one of two isomeric unsaturated dicarboxylic acid

Dicarboxylic acid

Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkane, alkene, or alkyne group....
s, the other being maleic acid

Maleic acid

Maleic acid or -butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound that is a dicarboxylic acid ....
wherein the carboxylic acid groups are cis. It has a fruit

Fruit

The term fruit has different meanings dependent on context, and the term is not synonymous in food preparation and biology. In botany, which is the scientific study of plants, fruits are the ripened Ovary of flowering plants....
-like taste

Taste

Sorry, no overview for this topic
. The salts and ester

Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s of fumaric acid are known as fumarates.

Fumaric acid, when added to food products, is denoted by E number

E number

E numbers are number codes for food additives and are usually found on food labels throughout the European Union. The numbering scheme follows that of the International Numbering System as determined by the Codex Alimentarius committee....
E297.

ric acid is found in fumitory (Fumaria officinalis), bolete

Bolete

A bolete is a type of fungus fruiting body characterized by the presence of a pileus that is clearly differentiated from the stipe , with a spongy surface of pores on the underside of the pileus....
mushroom

Mushroom

A mushroom is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground on soil or on its food source. The standard for the name "mushroom" is the cultivated white button mushroom, Agaricus bisporus, hence the word mushroom is most often applied to those fungi that have a stem , a cap , and gills on the unde...
s (specifically Boletus fomentarius var.

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Encyclopedia

Fumaric acid is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
with the formula HO₂CCH=CHCO₂H. This white crystal
Crystal

A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions....
line compound is one of two isomeric unsaturated dicarboxylic acid
Dicarboxylic acid

Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkane, alkene, or alkyne group....
s, the other being maleic acid
Maleic acid

Maleic acid or -butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound that is a dicarboxylic acid ....
wherein the carboxylic acid groups are cis. It has a fruit
Fruit

The term fruit has different meanings dependent on context, and the term is not synonymous in food preparation and biology. In botany, which is the scientific study of plants, fruits are the ripened Ovary of flowering plants....
-like taste
Taste

Sorry, no overview for this topic
. The salts and ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s of fumaric acid are known as fumarates.

Fumaric acid, when added to food products, is denoted by E number
E number

E numbers are number codes for food additives and are usually found on food labels throughout the European Union. The numbering scheme follows that of the International Numbering System as determined by the Codex Alimentarius committee....
E297.

Biology
Fumaric acid is found in fumitory (Fumaria officinalis), bolete
Bolete

A bolete is a type of fungus fruiting body characterized by the presence of a pileus that is clearly differentiated from the stipe , with a spongy surface of pores on the underside of the pileus....
mushroom
Mushroom

A mushroom is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground on soil or on its food source. The standard for the name "mushroom" is the cultivated white button mushroom, Agaricus bisporus, hence the word mushroom is most often applied to those fungi that have a stem , a cap , and gills on the unde...
s (specifically Boletus fomentarius var. pseudo-igniarius), lichen
Lichen

Lichens are composite organisms consisting of a symbiosis association of a fungus with a Photosynthesis partner , usually either a green algae or Cyanobacteria ....
, and Iceland moss
Iceland moss

Iceland moss is a lichen whose erect or ascending foliaceous habit gives it something of the appearance of a moss, whence probably the name. It is often of a pale chestnut color, but varies considerably, being sometimes almost entirely greyish white; and grows to a height of from 3 to 4 in., the branches being channelled or rolled into tubes...
.

Fumarate is an intermediate in the citric acid cycle
Citric acid cycle

The citric acid cycle ? also known as the tricarboxylic acid cycle ; the Krebs cycle; or, more rarely, the Szent-Gy?rgyi-Krebs cycle) ? is a series of enzyme-catalysed chemical reactions of central importance in all living cell s that use oxygen as part of cellular respiration....
used by cells
Cell (biology)

The cell is the structural and functional unit of all known Life organisms. It is the smallest unit of an organism that is classified as living, and is often called the building bricks of life....
to produce energy in the form of adenosine triphosphate
Adenosine triphosphate

This article is about the chemical used by cells as an energy carrier. For other uses, see ATP .Adenosine-5'-triphosphate is a multifunctional nucleotide, and plays an important role in cell biology as a coenzyme that is the "molecule unit of currency" of intracellular energy transfer....
(ATP) from food
Food

Food is any substance, usually composed of carbohydrates, fats, proteins and water, that can be Eating or Drinking by an animal or human for nutrition or pleasure....
. It is formed by the oxidation of succinate by the enzyme succinate dehydrogenase. Fumarate is then converted by the enzyme fumarase
Fumarase

Fumarase is an enzyme that catalyzes the reversible hydration/dehydration of Fumarate to S-malate. Fumarase comes in two forms: mitochondrial and cytosolic....
to malate
Malic acid

Malic acid is an organic compound with the formula HO2CCH2CHOHCO2H. This dicarboxylic acid is the active ingredient in many sour or tart foods....
. Human skin naturally produces fumaric acid when exposed to sunlight
Sunlight

Sunlight, in the broad sense, is the total spectroscopy of the electromagnetic radiation given off by the Sun. On Earth, sunlight is Filter ed through the Earth's atmosphere, and the solar radiation is obvious as daylight when the Sun is above the horizon....
.

Fumarate is also a byproduct of the urea cycle
Urea cycle

The urea cycle is a cycle of biochemistry reactions occurring in many animals that produces urea 2carbonoxygen from ammonia . This cycle was the first metabolic cycle discovered ....
.

Medicine
Fumaric acid ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s are sometimes used to treat psoriasis
Psoriasis

Psoriasis is a chronic, non-contagious autoimmune disease which affects the skin and joints. It commonly causes red scaly patches to appear on the skin....
, as it has been suggested that the condition is caused by an impairment of fumaric acid production in the skin. (Citation - Br J Dermatol 05; 152(4):597-615), BR J Dermatol 98;138(3): 456-460) A starting dose
Medication

A pharmaceutical drug, also referred to as medicine or medicament, can be loosely defined as any substance intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease....
is 60-105 mg daily, which may be gradually increased to as much as 1,290 mg per day. Side-effects
Adverse drug reaction

An adverse drug reaction or adverse drug event is an expression that describes the unwanted, negative consequences associated with the use of given medications....
include kidney
Kidney

The kidneys are Organ that have numerous biological roles. Their primary role is to maintain the homeostasis balance of bodily fluids by filtering and secreting Metabolomics#Metabolitess and minerals from the blood and excreting them, along with water , as urine....
or gastrointestinal disorders, as well as skin flushing
Flushing (physiology)

For a person to flush is to become markedly red in the face and often other areas of the skin, from various physiology conditions. Flushing is generally distinguished, despite a close physiological relation between them, from blushing, which is milder, generally restricted to the face or cheeks, and generally assumed to reflect embarrassment....
; these are mainly caused by excess intake. Decreased white blood cell
White blood cell

White blood cells , or leukocytes , are cell of the immune system defending the body against both infectious disease and foreign materials....
(WBC) counts have been reported with prolonged use.

Food
Fumaric acid is a food acidulent
Acidulated

Acidulated describes something that has been rendered acid or sour.* Acidulated drops are an old-fashioned candy similar to modern lemon and lime drops....
used since 1946. It is non-toxic. It is generally used in beverages and baking powder
Baking powder

Baking powder is a dry chemical leavening agent used to increase the volume and lighten the texture of baked goods such as muffins, cakes, and cookies ....
s for which requirements are placed on purity. It is generally used as a substitute for tartaric acid
Tartaric acid

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds, and is one of the main acids found in wine....
and occasionally in place of citric acid
Citric acid

Citric acid is a weak organic chemistry acid, and it is a natural preservative and is also used to add an acidic, or sour, taste to foods and soft drinks....
, at a rate of 1.36 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
Taste

Sorry, no overview for this topic
, similar to the way malic acid
Malic acid

Malic acid is an organic compound with the formula HO2CCH2CHOHCO2H. This dicarboxylic acid is the active ingredient in many sour or tart foods....
is used.

Chemistry
Fumaric acid was first prepared from Succinic acid
Succinic acid

Succinic acid is a dicarboxylic acid. Succinate plays a biochemical role in the citric acid cycle....
. A traditional synthesis involves oxidation of furfural
Furfural

The chemical compound furfural is an industrial chemical derived from a variety of agriculture byproducts, including maize, oat and wheat bran, and sawdust....
(from the processing of maize) using sodium chlorate
Sodium chlorate

Sodium chlorate is a chemical compound with the chemical formula . When pure, it is a white crystalline powder that is readily soluble in water....
in the presence of a vanadium
Vanadium

Vanadium is the chemical element with the symbol V and atomic number 23. It is a soft, silvery grey, ductile transition metal. The formation of an oxide layer stabilizes the metal against oxidation....
-based catalyst. Nowadays industrial synthesis of fumaric acid is mostly based on catalytic isomerisation
Isomerisation

In chemistry isomerisation is the process by which one molecule is transformed into another molecule which has exactly the same atoms, but the atoms are rearranged e.g....
of maleic acid
Maleic acid

Maleic acid or -butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound that is a dicarboxylic acid ....
(which in turn is accessible in large volumes as a hydrolysis product of maleic anhydride, produced by catalytic oxidation of benzene or butane) in aqueous solutions.

The chemical properties of fumaric acid can be anticipated from its component functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
s. This weak acid forms a diester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
, it undergoes additions across the double bond
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
, and it is an excellent dienophile.

Other uses
Fumaric acid is used in the manufacture of polyester
Polyester

Polyester is a category of polymers which contain the ester functional group in their main chain. Although there are many polyesters, the term "polyester" as a specific material most commonly refers to polyethylene terephthalate ....
resin
Resin

Resin is a hydrocarbon secretion of many plants, particularly Pinophyta. It is valued for its chemical constituents and uses, such as varnishes and adhesives, as an important source of raw materials for organic synthesis, or for incense and perfume....
s and polyhydric alcohols and as a mordant
Mordant

A mordant is a substance used to set dyes on fabrics by forming an insoluble compound with the dye. It may be used for dyeing fabrics, or for intensifying stains in cell or tissue preparations....
for dyes.

Safety
Fumaric acid converts to the irritant maleic anhydride
Maleic anhydride

Maleic anhydride is an organic compound with the formula C4H2O3. In its pure state it is a colourless or white solid with an acrid odour....
, upon partial combustion.

See also

Dermatology
Dermatology

Dermatology is the branch of medicine dealing with the skin and Skin disease, a unique specialty with both medical and surgical aspects. The name of this specialty originated in the form of the words dermologie and, a little later, dermatologia ....
Photosynthesis
Photosynthesis

File:Seawifs global biosphere.jpgPhotosynthesis is a metabolic pathway that converts carbon dioxide into organic compounds, especially sugars, using the energy from sunlight....
Maleic acid
Maleic acid

Maleic acid or -butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound that is a dicarboxylic acid ....
, the cis-isomer of fumaric acid

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