FUMARIC ACID (FUMARİK ASİT)
Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H.
A white solid, fumaric acid occurs widely in nature.
Fumaric acid has a fruit-like taste and has been used as a food additive. Its E number is E297.
Fumaric acid is used as a food acidulant in beverages and baking powders.
Fumaric acid is used to manufacture medicines, drinks, food, animal feed, cleansing agents, unsaturated polyester, alkyd resins, and printing inks.
Fumaric Acid results in long-lasting sourness and flavor impact when used as a food additive.
Fumaric Acid is generally used in beverages and baking pre-mixes for Tortilla breads and bakery products.
Furthermore, fumaric acid is a pharmaceutically active substance used to treat psoriasis or multiple sclerosis.
Originally, fumaric acid was isolated from plants belonging to the genus Fumaria, from which its name is derived.
Fumaric acid is an intermediate of the tricarboxylic acid cycle.
Fumaric acid is a valuable intermediate in several chemical syntheses, including esterification and polymerization, and in manufacturing sizing resins for the paper industry.
Fumaric acid is a vital specialty chemical with wide industrial applications ranging from its use as feedstock for synthesizing polymeric resins to acidulants in foods and pharmaceuticals.
Fumaric acid, or trans-butenedioic acid, is a white crystalline chemical compound widely found in nature.
Fumaric acid is a critical intermediate in the tricarboxylic acid cycle for organic acid biosynthesis in humans and other mammals.
Fumaric acid is also an essential ingredient in plant life.
When used as a food additive, the hydrophobic nature of fumaric acid results in persistent, long-lasting sourness and flavor impact.
The versatile compound also decreases the pH with minimal added sourness in products with pHs more significant than 4.5.
Its low molecular weight gives fumaric acid more buffering capacity than other food acids at pHs near 3.
Because of its strength, less fumaric acid is required than other organic food acids, reducing costs per unit weight.
Fumaric acid esters treat various skin disorders, including psoriasis, cutaneous sarcoidosis, necrobiosis lipoidica diabeticorum, and disseminated granuloma annulare.
Preferred IUPAC name: (2E)-But-2-enedioic acid
Other names:Fumaric acid
trans-1,2-Ethylenedicarboxylic acid
2-Butenedioic acid
trans-Butenedioic acid
Allomaleic acid
Boletic acid
Donitic acid
Lichenic acid
Identifiers
CAS Number: 110-17-8
EC / List no.: 203-743-0
CAS no.: 110-17-8
Mol. formula: C4H4O4
Chemical formula: C4H4O4
Molar mass: 116.072 g·mol−1
Appearance: White solid
Density: 1.635 g/cm3
Melting point: 287 °C (549 °F; 560 K) (decomposes)[2]
Solubility in water: 4.9 g/L at 20 °C[1]
Acidity (pKa)
pka1 = 3.03, pka2 = 4.44 (15 °C, cis isomer)
Magnetic susceptibility (χ): −49.11·10−6 cm3/mol
Dipole moment: non zero
Fumaric Acid is added to foods as an acidity regulator and flavoring agent and may be used as a substitute for cream of tartar. Typical products include bread, fruit drinks, pie fillings, poultry, wine, jams, and jelly.
Fumaric Acid is used as a mordant in dyeing and in the manufacture of synthetic resins and polyhydric alcohols.
Fumaric acid (E297 ) is a four-carbon dicarboxylic acid used as a food acidity regulator.
Fumaric acid is often a beverage ingredient but applies to bakery products, powdery dessert mixes, and confectionary.
Next to food applications, fumaric acid is used in feed as an antibacterial agent.
It is a well-known chemical used in the production of polymers and as an intermediate in the production of L-malic and L-aspartic acids.
Fumaric acid is predominantly produced by petroleum-based chemical synthesis.
However, research focusing on microbial fumaric acid production from starchy materials is optimizing and commercializing this ‘green’ technique.
The salts and esters are known as fumarates. Fumarate can also refer to the C4H2O2−4 ion (in solution).
Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.
Uses
Food
Fumaric acid has been used as a food acidulant since 1946.
Fumaric acid is approved as a food additive in the EU, USA, Australia, and New Zealand.
As a food additive, it is used as an acidity regulator and can be denoted by the E number E297.
Fumaric acid is generally used in beverages and baking powders for which requirements are placed on purity.
Fumaric acid is used in making wheat tortillas as a food preservative and leavening acid.
Fumaric acid is generally used as a substitute for tartaric acid and occasionally in place of citric acid, at a rate of 1 g of fumaric acid to every ~1.5 g of citric acid, to add sourness, similarly to the way malic acid is used.
As well as being a component of some artificial vinegar flavors, such as "Salt and Vinegar" flavored potato chips, it is also used as a coagulant in stove-top pudding mixes.
The European Commission Scientific Committee on Animal Nutrition, part of DG Health, found 2014 that fumaric acid is "practically non-toxic," but high doses are probably nephrotoxic after long-term use.
Medicine
Fumaric acid was developed as a medicine to treat psoriasis autoimmune condition in the 1950s in Germany as a tablet containing three esters, primarily dimethyl fumarate, and marketed as Fumaderm by Biogen Idec in Europe.
Biogen would later develop the primary ester, dimethyl fumarate, as a treatment for multiple sclerosis.
In patients with relapsing-remitting multiple sclerosis, the ester dimethyl fumarate (BG-12, Biogen) significantly reduced relapse and disability progression in a phase 3 trial.
It activates the Nrf2 antioxidant response pathway, the primary cellular defense against the cytotoxic effects of oxidative stress.
Other uses
INDUSTRIES
Fumaric acid has various applications in different industries.
Here are some common uses of fumaric acid:
Food and Beverage Industry: Fumaric acid is used as a food additive, primarily as an acidulant and flavor enhancer.
Fumaric acid is often found in beverages, fruit-flavored drinks, candies, gelatin desserts, baking powders, and other food products.
Fumaric acid provides a sour taste similar to citric acid and helps preserve and enhance the flavor of food and beverages.
Cosmetics and Personal Care Products: Fumaric acid has applications in cosmetic formulations and personal care products.
Fumaric acid is applied as an ingredient in creams, lotions, and ointments, where it functions as a pH adjuster, buffering agent, and skin-conditioning agent.
Resins and Polymers: Fumaric acid produces unsaturated polyester resins (UPR) and alkyd resins.
Fumaric acid acts as a crosslinking agent and helps enhance the properties of these resins, including their strength, durability, and heat resistance.
Cleaning Products: Fumaric acid is utilized in certain cleaning products, such as detergents and dishwashing liquids.
Fumaric acid aids in removing dirt, stains, and scale deposits due to its acidic properties.
Fumaric acid is used to manufacture polyester resins, polyhydric alcohols, and as a mordant for dyes.
When fumaric acid is added to their feed, lambs produce up to 70% less methane during digestion.
Function
In foods and baked goods, it serves many functions:
Acidity control (measured by pH or, more accurately, by TTA)
Highly effective acidulant
Substitute for other acids such as citric, lactic, and tartaric1,2
Strong buffering capacity around pH 3.04
Antimicrobial/preservative activity
Chemical leavening - highly effective, with a Neutralization Value of 145
Dough machinability improver
Flavor/ taste sourness enhancer
Foam promoter in egg-white foams and a stabilizer of over-beaten egg whites
Translated names
acide fumarique (fr)
acido fumarico (it)
Fumaarhape (et)
Fumaarihappo (fi)
fumaarzuur (nl)
fumarna kiselina (hr)
fumarna kislina (sl)
fumaro rūgštis (lt)
fumarová kyselina (cs)
fumarsyra (sv)
fumarsyre (da)
fumarsyre (no)
Fumarsäure (de)
fumársav (hu)
fumārskābe (lv)
kyselina fumarová (sk)
ácido fumárico (es)
ácido fumárico (pt)
φουμαρικό οξύ (el)
фумарова киселина (bg)
IUPAC names
(2E)-but-2-enedioic acid
(E) but-2-enedioic acid
(E)-but-2-enedioic acid
(E)-Butenedioic acid
1,2-ethylene dicarboxylic acid
2-BUTENEDIOIC ACID
2-Butenedioic acid (2E)-Fumaric acid
2-Butenedioic acid, E-
acide fumarique
But-2-enedioic acid
but-2-enedioic acid
E-butenedioic Acid
FA Flakes
FUMARIC ACID
Fumaric Acid
Fumaric acid
fumaric acid
Fumaric Acid
Fumaric acid
fumaric acid
fumaric acid , Butenedioic acid , Allomaleic acid, Boletic acid, Donitic acid, Lichenic acid
Fumarsäure
trans-1,2-Ethylenedicarboxylic
trans-2-Butenedioïc acid
trans-Butendisäure
Trans-Butenedioic Acid
Trade names
(E)-2-Butenedioic acid
1,2-ethylene dicarboxylic acid
Allomaleic acid
Boletic acid
Butenedioic acid, (E)-
Fumaric Acid
trans-1,2-Ethylenedicarboxylic acid
TRANS-BUTENEDICARBOXYLIC ACID
SYNONYMS:
fumaric acid
110-17-8
trans-Butenedioic acid
Allomaleic acid
fumarate
Lichenic acid
Boletic acid
2-Butenedioic acid
(2E)-but-2-enedioic acid
Tumaric acid
trans-1,2-Ethylenedicarboxylic acid
Allomalenic acid
But-2-enedioic acid
trans-2-Butenedioic acid
Butenedioic acid
(E)-2-Butenedioic acid
Fumaricum acidum
2-Butenedioic acid, (E)-
Kyselina fumarova
2-Butenedioic acid (E)-
USAF EK-P-583
Butenedioic acid, (E)-
FEMA No. 2488
(2E)-2-butenedioic acid
Caswell No. 465E
FEMA Number 2488
NSC-2752
Fumarsaeure
(E)-but-2-enedioic acid
Allomaleic-acid
Boletic-acid
2-Butenedioic acid (2E)-
1,2-Ethylenedicarboxylic acid, (E)
CCRIS 1039
HSDB 710
2-(E)-Butenedioic acid
trans-but-2-enedioic acid
U-1149
(E)-Butenedioic acid
1,2-Ethenedicarboxylic acid, trans-
EPA Pesticide Chemical Code 051201
6915-18-0
AI3-24236
EINECS 203-743-0
BRN 0605763
Fumaric acid (NF)
Fumaric acid [NF]
INS NO.297
DTXSID3021518
UNII-88XHZ13131
CHEBI:18012
INS-297
NSC2752
ethylenedicarboxylic acid
Maleic-2,3-d2 acid
88XHZ13131
E297
DTXCID601518
Maleic acid-2,3-13C2
E-297
2(TRANS)-BUTENEDIOIC ACID
EC 203-743-0
FC 33
4-02-00-02202 (Beilstein Handbook Reference)
MFCD00002700
fum
Lichenic acid (VAN)
FUMARIC ACID (II)
FUMARIC ACID [II]
(E)-2-Butenedioate
Fumaric acid 1000 microg/mL in Acetonitrile:Water
Kyselina fumarova [Czech]
FUMARIC ACID (MART.)
FUMARIC ACID [MART.]
FUMARIC ACID (USP-RS)
FUMARIC ACID [USP-RS]
(2E)-but-2-enedioate
FUMARIC ACID (USP IMPURITY)
FUMARIC ACID [USP IMPURITY]
Donitic acid
but-2-enedioicacid
CAS-110-17-8
fumarate, 10
trans-1,2-Ethenedicarboxylic acid
MALIC ACID IMPURITY A (EP IMPURITY)
MALIC ACID IMPURITY A [EP IMPURITY]
(E)-1,2-Ethylenedicarboxylic acid
trans-1,2-Ethylenediccarboxylic acid
E-2-Butenedioic acid
Fumaric acid (8CI)
26099-09-2
FC 33 (acid)
SODIUM AUROTHIOMALATE IMPURITY B (EP IMPURITY)
SODIUM AUROTHIOMALATE IMPURITY B [EP IMPURITY]
Futrans-2-Butenedioic Acid
fumarsaure
Allomaleate
Boletate
Lichenate
Acido lichenico
fumeric acid
Acido boletico
Acido fumarico
Acido allomaleico
trans-Butenedioate
NCGC00091192-02
Fumaric Acid,(S)
trans-2-Butendisaure
trans-2-Butenedioate
2-(E)-Butenedioate
Fumaric acid, 99%
Acido trans butendioico
trans-Ethylendicarbonsaure
(Trans)-butenedioic acid
F0067
Fumaric acid, >=99%
FEMA Number: 2488
bmse000083
FUMARIC ACID [MI]
WLN: QV1U1VQ-T
FUMARIC ACID [FCC]
SCHEMBL1177
FUMARIC ACID [FHFI]
FUMARIC ACID [HSDB]
FUMARIC ACID [INCI]
FUMARIC ACID [VANDF]
MLS002454406
1,2-ethylenedicarboxylic acid
2-butenedioic acid, (2E)-
(2E)-2-Butenedioic acid #
FUMARIC ACID [WHO-DD]
CHEMBL503160
FUMARICUM ACIDUM [HPUS]
trans-1,2-Ethylenedicarboxylate
BDBM26122
CHEBI:22958
HMS2270C12
Pharmakon1600-01301022
Fumaric acid, >=99.0% (T)
AMY30339
STR02646
Acido trans 1,2-etenedicarbossilico
Tox21_201769
Tox21_302826
2-Butenedioic acid (2E)- (9CI)
Acido trans 1,2-etilendicarbossilico
Fumaric acid, >=99%, FCC, FG
NSC760395
s4952
AKOS000118896
Fumaric acid, qNMR Standard for DMSO
CCG-266065
CS-W016599
DB01677
HY-W015883
NSC-760395
USEPA/OPP Pesticide Code: 051201
NCGC00091192-01
NCGC00091192-03
NCGC00256360-01
NCGC00259318-01
BP-13087
Fumaric acid, tested according to USP/NF
LS-12976
SMR000112117
Fumaric acid, puriss., >=99.5% (T)
NS00074156
EN300-17996
Fumaric acid, Vetec(TM) reagent grade, 99%
1, (E)
C00122
D02308
D85166
Q139857
Fumaric acid, BioReagent, suitable for cell culture
J-002389
Fumarate; 2-Butenedioic acid; Trans-Butenedioic acid
Z57127460
F8886-8257
Fumaric acid, certified reference material, TraceCERT(R)
26B3632D-E93F-4655-90B0-3C17855294BA
Fumaric acid, anhydrous, free-flowing, Redi-Dri(TM), >=99%
Fumaric acid, European Pharmacopoeia (EP) Reference Standard
Fumaric acid, United States Pharmacopeia (USP) Reference Standard
Fumaric Acid, Pharmaceutical Secondary Standard; Certified Reference Material
Fumaric Acid
It is often used as a beverage ingredient but also finds application in bakery products, powdery dessert mixes, and confectionary (Santini et al., 2012).
Next to food applications, fumaric acid is used in feed as an antibacterial agent and is a well-known chemical used in the production of polymers and as an intermediate in the production of L-malic and L-aspartic acid.
Fumaric acid is predominantly produced by petroleum-based chemical synthesis, but research focusing on microbial fumaric acid production (e.g., using Rhizopus oryzae) from starchy materials is in the process of optimizing and commercializing this ‘green' technique (Xu et al., 2012; Yang et al., 2011; Alonso et al., 2014).
Fumaric acid is used as a food ingredient in beverages and baking powders.
Furthermore, fumaric acid is a pharmaceutically active substance used to treat psoriasis or multiple sclerosis (Gold et al., 2011).
The current world market is about 90,000 t y-1. However, particular interest in fumaric acid - as in all dicarboxylic acids described in this chapter - is derived from its suitability as a building block chemical.
Use as a bulk chemical in the polymer industry is conceivable.
Also, its chemical relatedness to aspartic acid, a precursor for aspartame, a widely used sweetener, makes it an interesting product, provided that the production costs are low enough.
Originally, fumaric acid was isolated from plants belonging to the genus Fumaria, from which its name is derived.
Applications
Fumaric acid has been used in food and beverage products since 1946.
Fumaric Acid is currently used in wheat and corn tortillas, sourdough and rye bread, refrigerated biscuit doughs, fruit juice and nutraceutical drinks, gelatin desserts, gelling aids, pie fillings, and wine.
Food research shows that Fumaric acid improves quality and reduces the costs of many food and beverage products.
It is also used in animal feed.
Like malic acid, fumaric acid is a dicarboxylic acid with pK values of 3.03 and 4.44.
It has a strong acid taste, but a positive flavor effect is that it blends with certain flavors to intensify its aftertaste.
Fumaric acid is used in fruit drinks, gelatine desserts, pie fillings, biscuit doughs, and wines.
It is naturally present in rice, sugar cane, wine, plant leaves, mushrooms, and gelatine (Barbosa-Canovas et al., 1997).
Like citric acid, it also has antimicrobial properties, working as a chelator, binding micronutrients essential for bacterial growth.
As for malic acid, the antimicrobial mechanism for fumaric acid has only been investigated to a limited extent. One of the main effects is probably due to its pH lowering.
Fumaric acid, also known as fumarate or E297, belongs to the class of organic compounds known as dicarboxylic acids and derivatives.
These are organic compounds containing exactly two carboxylic acid groups.
Fumaric acid is a weakly acidic compound (based on its pKa). Fumaric acid exists in all living species, ranging from bacteria to humans.
Within yeast, fumaric acid participates in some enzymatic reactions.
It is formed by the oxidation of succinic acid by succinate dehydrogenase.
DETAILED APPLICATIONS
Animal Feed
Fumaric Acid has proven to be a particularly effective additive to piglet feed during the post-weaning period.
Including Fumaric Acid and the resultant adjustment of the pH value demonstrate improved weight gain, food consumption, and feed conversion ratio. Fumaric Acid remains longer in the gut and helps to maintain pH throughout, killing harmful microorganisms.
Industrial Uses
Industrial uses of fumaric acid include unsaturated polyester, alkyd resins, printing inks, paper sizing, and starch, and it helps lower reaction temperatures and modify properties.
Cleaning Agents for Dentures/Bath Salts
Fumaric Acid can be used with other ingredients to make cleaning agents for dentures and bath salts.
Low moisture absorption and solubility help to keep the integrity of formulations.
Tacos
The shelf life of dry tortilla mixes is extended because Fumaric Acid does not absorb moisture during storage and distribution.
In wheat flour tortillas, adding Fumaric Acid results in easily machined dough and faster production rates.
Bread
Fumaric Acid acts as an instant flavoring agent for rye and sourdough breads.
Fumaric Acid is added to dough ingredients during the dry blending step.
In English muffins, Fumaric Acid significantly increases porosity.
Dough machinability is improved, and more sourness is provided per unit weight.
Fruit Juice Drinks
Fumaric Acid provides more sourness per unit weight than other acidulants used in fruit juice drinks.
This substantially reduces the acidulant cost.
Using Fumaric Acid helps stabilize the pH of a fruit juice drink, stabilizing color and flavor.
Wine
Fumaric Acid can economically acidify wine with no detectable difference in flavor.
Fumaric Acid also prevents secondary fermentation after bottling and can act as a clarifier when low concentrations of copper and iron are present.
Confectioneries
Fumaric Acid extends the shelf life of acid-coated candies because it does not absorb moisture during storage and distribution. Maintaining a low moisture level retards sucrose inversion.
Gelatin Desserts
Fumaric Acid significantly reduces acidulant costs in gelatin desserts.
Fumaric Acid maintains non-caking and free-flowing qualities.
By keeping the moisture content low, fumaric acid helps maintain the stability of flavor components.
Fumaric Acid also increases gel strength so that food processors may reduce standard gelatin content by about 2%.
Pie Fillings
Fumaric Acid can be mixed directly with the starch and sugar ingredients in pie fillings.
Fumaric Acid lowers costs by reducing the quantity of food acid needed in product formulations.
Fumaric Acid also improves smoothness and extends the critical cook times for optimum gelation.
Egg White Foams
Fumaric Acid can promote maximum volume in egg-white foams and end products based on egg-white foams.
Confectioneries
Fumaric acid extends the shelf life of acid-coated candies because it does not absorb moisture during storage and distribution.
Maintaining a low moisture level retards sucrose inversion.
Acidulant cost is also reduced as fumaric acid provides more sourness per unit weight than other acidulants used in dry form.
Jellies and Jams
Fumaric acid can cut food acid costs when used as an acidulant for jams, jellies, and preserves.
As little as two pounds of fumaric acid can be used to replace every three pounds of Citric, Malic, or Tartaric acid. At the 2:3 replacement ratio, fumaric acid does not produce significant gel strength or pH differences.
Fumarik asit, HO2CCH=CHCO2H formülüne sahip organik bir bileşiktir.
Beyaz bir katı olan fumarik asit doğada yaygın olarak bulunur.
Fumarik asit meyveye benzer bir tada sahiptir ve gıda katkı maddesi olarak kullanılmıştır. E numarası E297'dir.
Fumarik asit, içeceklerde ve kabartma tozlarında gıda asitliği düzenleyici olarak kullanılır.
Ayrıca fumarik asit, sedef hastalığını veya multipl sklerozu tedavi etmek için kullanılan farmasötik olarak aktif bir maddedir.
Başlangıçta fumarik asit, adının türetildiği Fumaria cinsine ait bitkilerden izole edildi.
Fumarik asit, trikarboksilik asit döngüsünün bir ara ürünüdür.
Fumarik asit, esterifikasyon ve polimerizasyon dahil çeşitli kimyasal sentezlerde ve kağıt endüstrisi için haşıl reçinelerinin üretiminde değerli bir ara maddedir.
Fumarik asit, polimerik reçinelerin sentezlenmesi için hammadde olarak kullanımından gıda ve farmasötik ürünlerdeki asitleştiricilere kadar geniş endüstriyel uygulamaları olan hayati bir özel kimyasaldır.
Fumarik asit veya trans-bütendioik asit, doğada yaygın olarak bulunan beyaz kristalli bir kimyasal bileşiktir.
Fumarik asit, insanlarda ve diğer memelilerde organik asit biyosentezi için trikarboksilik asit döngüsünde kritik bir ara maddedir.
Fumarik asit aynı zamanda bitki yaşamında da önemli bir bileşendir.
Gıda katkı maddesi olarak kullanıldığında, fumarik asidin hidrofobik yapısı kalıcı, uzun süreli ekşilik ve lezzet etkisi sağlar.
Çok yönlü bileşik aynı zamanda pH'ı 4,5'tan yüksek olan ürünlerde minimum düzeyde ekşilik ekleyerek pH'ı azaltır.
Düşük moleküler ağırlığı, fumarik asitin 3'e yakın pH'larda diğer gıda asitlerine göre daha fazla tamponlama kapasitesi sağlar.
Gücünden dolayı diğer organik gıda asitlerine kıyasla daha az fumarik asit gerekir, bu da birim ağırlık başına maliyetleri azaltır.
Fumarik asit esterleri, sedef hastalığı, kutanöz sarkoidoz, nekrobiyoz lipoidika diyabetikorum ve yayılmış granüloma annulare dahil olmak üzere çeşitli cilt bozukluklarını tedavi eder.
Tercih edilen IUPAC adı: (2E)-But-2-enedioik asit
Diğer isimler:Fumarik asit
trans-1,2-etilendikarboksilik asit
2-Butendioik asit
trans-Butendioik asit
Allomaleik asit
Boletik asit
Donitik asit
Likenik asit
Tanımlayıcılar
CAS Numarası: 110-17-8
EC / Liste no.: 203-743-0
CAS numarası: 110-17-8
Mol. formül: C4H4O4
Kimyasal formül: C4H4O4
Molar kütle: 116,072 g·mol−1
Görünüm: Beyaz katı
Yoğunluk: 1,635 g/cm3
Erime noktası: 287 °C (549 °F; 560 K) (ayrışır)[2]
Suda çözünürlük: 20 °C'de 4,9 g/L[1]
Asitlik (pKa)
pka1 = 3,03, pka2 = 4,44 (15 °C, cis izomer)
Manyetik duyarlılık (χ): −49,11·10−6 cm3/mol
Dipol momenti: sıfır değil
Fumarik Asit gıdalara asitlik düzenleyici ve tat verici madde olarak eklenir ve tartar kremasının yerine kullanılabilir. Tipik ürünler arasında ekmek, meyveli içecekler, pasta dolguları, kümes hayvanları, şarap, reçeller ve jöle bulunur.
Fumarik Asit, boyamada ve sentetik reçinelerin ve polihidrik alkollerin üretiminde mordan olarak kullanılır.
Fumarik asit (E297 veya INS297), gıda asitliği düzenleyicisi olarak kullanılan dört karbonlu bir dikarboksilik asittir (Birleşmiş Milletler Gıda ve Tarım Örgütü ve Dünya Sağlık Örgütü, 2017).
Düşük maliyeti ve toksik olmaması, 1946'dan bu yana gıda katkı maddesi olarak popülerliğinin temelidir.
Fumarik asitin sitrik asitten 1,5 kat daha fazla asit olduğu iddia edilmektedir.
Mikrobiyal inaktivasyon çalışmaları, fumarik asidin gıda kaynaklı patojenleri etkisiz hale getirebildiğini ve taze sığır eti gibi ürünlerin raf ömrünü uzatabildiğini göstermiştir (Tango ve diğerleri, 2014).
Fumarik asit genellikle bir içecek bileşenidir ancak unlu mamuller, toz tatlı karışımları ve şekerlemeler için de geçerlidir (Santini ve diğerleri, 2012).
Gıda uygulamalarının yanı sıra, yemlerde antibakteriyel madde olarak fumarik asit kullanılmaktadır.
Polimerlerin üretiminde ve L-malik ve L-aspartik asitlerin üretiminde ara madde olarak kullanılan iyi bilinen bir kimyasaldır.
Fumarik asit ağırlıklı olarak petrol bazlı kimyasal sentezle üretilir.
Ancak nişastalı malzemelerden mikrobiyal fumarik asit üretimine odaklanan araştırmalar bu 'yeşil' tekniği optimize ediyor ve ticarileştiriyor.
Tuzlar ve esterler fumaratlar olarak bilinir. Fumarat aynı zamanda C4H2O2−4 iyonuna da (çözelti halinde) atıfta bulunabilir.
Fumarik asit, bütendioik asidin trans izomeridir, maleik asit ise cis izomeridir.
Kullanım Alanları
Yiyecek
Fumarik asit 1946'dan beri gıda asitliği düzenleyici olarak kullanılmaktadır.
Fumarik asit AB, ABD, Avustralya ve Yeni Zelanda'da gıda katkı maddesi olarak onaylanmıştır.
Gıda katkı maddesi olarak asitlik düzenleyici olarak kullanılır ve E numarası E297 ile gösterilebilir.
Fumarik asit genellikle saflık gereksinimlerinin olduğu içeceklerde ve kabartma tozlarında kullanılır.
Fumarik asit, buğday ekmeği yapımında gıda koruyucu ve mayalayıcı asit olarak kullanılır.
Fumarik asit genellikle tartarik asitin yerine ve bazen de sitrik asitin yerine, malik asidin kullanıldığına benzer şekilde ekşilik eklemek için her ~1.5 g sitrik asit için 1 g fumarik asit oranında kullanılır.
DG Health'in bir parçası olan Avrupa Komisyonu Hayvan Besleme Bilimsel Komitesi, 2014 yılında fumarik asidin "pratik olarak toksik olmadığını" ancak yüksek dozların uzun süreli kullanımdan sonra muhtemelen nefrotoksik olduğunu tespit etti.
İlaç
Fumarik asit, 1950'li yıllarda Almanya'da sedef hastalığı otoimmün durumunu tedavi etmek için bir ilaç olarak, başta dimetil fumarat olmak üzere üç ester içeren bir tablet olarak geliştirildi ve Avrupa'da Biogen Idec tarafından Fumaderm olarak pazarlandı.
Biogen daha sonra multipl skleroz tedavisi için birincil ester olan dimetil fumarat'ı geliştirecekti.
Tekrarlayan-düzelen multipl skleroz hastalarında, ester dimetil fumarat (BG-12, Biogen), bir faz 3 denemesinde nüksetmeyi ve sakatlık ilerlemesini önemli ölçüde azalttı.
Oksidatif stresin sitotoksik etkilerine karşı birincil hücresel savunma olan Nrf2 antioksidan yanıt yolunu aktive eder.
Diğer kullanımlar
ENDÜSTRİLER
Fumarik asitin farklı endüstrilerde çeşitli uygulamaları vardır.
Fumarik asidin bazı yaygın kullanımları şunlardır:
Yiyecek ve İçecek Endüstrisi: Fumarik asit, öncelikle asitliği düzenleyici ve lezzet arttırıcı olarak gıda katkı maddesi olarak kullanılır.
Fumarik asit genellikle içeceklerde, meyve aromalı içeceklerde, şekerlerde, jelatinli tatlılarda, kabartma tozlarında ve diğer gıda ürünlerinde bulunur.
Fumarik asit, sitrik asite benzer ekşi bir tat sağlar ve yiyecek ve içeceklerin lezzetinin korunmasına ve arttırılmasına yardımcı olur.
Kozmetik ve Kişisel Bakım Ürünleri: Fumarik asitin kozmetik formülasyonlarda ve kişisel bakım ürünlerinde uygulamaları vardır.
Fumarik asit kremler, losyonlar ve merhemlerde bir bileşen olarak uygulanır ve burada pH ayarlayıcı, tamponlayıcı madde ve cilt bakım maddesi olarak işlev görür.
Reçineler ve Polimerler: Fumarik asit, doymamış polyester reçineler (UPR) ve alkid reçineler üretir.
Fumarik asit, çapraz bağlama maddesi olarak görev yapar ve bu reçinelerin mukavemet, dayanıklılık ve ısı direnci dahil olmak üzere özelliklerinin geliştirilmesine yardımcı olur.
Temizlik Ürünleri: Fumarik asit, deterjanlar ve bulaşık deterjanları gibi bazı temizlik ürünlerinde kullanılmaktadır.
Fumarik asit, asidik özellikleri nedeniyle kir, leke ve kireç birikintilerinin giderilmesine yardımcı olur.
Fumarik asit, polyester reçinelerin, polihidrik alkollerin üretiminde ve boyalar için mordan olarak kullanılır.
Yemlerine fumarik asit eklendiğinde kuzular sindirim sırasında %70'e kadar daha az metan üretir.
İşlev
Gıdalarda ve unlu mamullerde birçok fonksiyona hizmet eder:
Asitlik kontrolü (pH ile veya daha doğrusu TTA ile ölçülür)
Son derece etkili asitleştirici
Sitrik, laktik ve tartarik gibi diğer asitlerin yerine kullanılır1,2
pH 3,04 civarında güçlü tamponlama kapasitesi
Antimikrobiyal/koruyucu aktivite
Kimyasal mayalama - 145 Nötralizasyon Değeri ile son derece etkili
Hamurun işlenebilirliğini iyileştirici
Lezzet/tat ekşiliği arttırıcı
Yumurta akı köpüklerinde köpük arttırıcı ve aşırı dövülmüş yumurta aklarının stabilizatörü
Çevrilmiş isimler
asit fumarik (fr)
asito fumarico (o)
Fumaarhape (ve)
Fumaarihappo (fi)
fumaarzuur (nl)
fumarna kiselina (saat)
fumarna kislina (sl)
fumaro rūgštis (lt)
fumarová kyselina (cs)
fumarsyra (sv)
fumarsyre (da)
fumarsyre (hayır)
Fumarsäure (de)
fumarsav (hu)
fumarskābe (lv)
Kyselina Fumarová (sk)
ácido fumárico (es)
ácido fumárico (pt)
φουμαρικό οξύ (el)
фумарова киселина (bg)
IUPAC adları
(2E)-but-2-enodioik asit
(E) but-2-enodioik asit
(E)-but-2-enodioik asit
(E)-Butendioik asit
1,2-etilen dikarboksilik asit
2-BÜTENİYOİK ASİT
2-Butendioik asit (2E)-Fumarik asit
2-Butendioik asit, E-
asit fumarik
But-2-endioik asit
but-2-endioik asit
E-bütendioik Asit
FA Gevreği
FUMARİK ASİT
Fumarik asit
Fumarik asit
Fumarik asit
Fumarik asit
Fumarik asit
Fumarik asit
fumarik asit, Butendioik asit, Allomaleik asit, Boletik asit, Donitik asit, Likenik asit
Fumarsäure
trans-1,2-etilendikarboksilik
trans-2-Butendioik asit
trans-Butendisäure
Trans-Butendioik Asit
Ticari isimler
(E)-2-Butendioik asit
1,2-etilen dikarboksilik asit
Allomaleik asit
Boletik asit
Butendioik asit, (E)-
Fumarik asit
trans-1,2-etilendikarboksilik asit
TRANS-BÜTENİKARBOKSİLİK ASİT
EŞ ANLAMLI:
Fumarik asit
110-17-8
trans-Butendioik asit
Allomaleik asit
fumarat
Likenik asit
Boletik asit
2-Butendioik asit
(2E)-but-2-enodioik asit
Tumarik asit
trans-1,2-etilendikarboksilik asit
Allomalenik asit
But-2-endioik asit
trans-2-Butendioik asit
Butendioik asit
(E)-2-Butendioik asit
Fumaricum asit
2-Butendioik asit, (E)-
Kyselina fumarova
2-Butendioik asit (E)-
USAF EK-P-583
Butendioik asit, (E)-
FEMA No.2488
(2E)-2-butendioik asit
Caswell No.465E
FEMA Numarası 2488
NSC-2752
Fumarsaeure
(E)-but-2-enodioik asit
Allomaleik asit
Boletik asit
2-Butendioik asit (2E)-
1,2-etilendikarboksilik asit, (E)
CCRIS 1039
HSDB710
2-(E)-Butendioik asit
trans-but-2-endioik asit
U-1149
(E)-Butendioik asit
1,2-Etendikarboksilik asit, trans-
EPA Pestisit Kimyasal Kodu 051201
6915-18-0
AI3-24236
EINECS 203-743-0
BRN 0605763
Fumarik asit [NF]
INS NO.297
DTXSID3021518
UNII-88XHZ13131
ÇEBİ:18012
INS-297
NSC2752
etilendikarboksilik asit
Maleik-2,3-d2 asit
88XHZ13131
E297
DTXCID601518
Maleik asit-2,3-13C2
E-297
2(TRANS)-BÜTENİYOİK ASİT
EC 203-743-0
FC 33
4-02-00-02202 (Beilstein El Kitabı Referansı)
MFCD00002700
duman
Likenik asit (VAN)
FUMARİK ASİT (II)
FUMARİK ASİT [II]
(E)-2-Butendioat
Asetonitril:Suda fumarik asit 1000 mikrog/mL
Kyselina fumarova [Çek]
FUMARİK ASİT (MART.)
FUMARİK ASİT [MART.]
FUMARİK ASİT (USP-RS)
FUMARİK ASİT [USP-RS]
(2E)-but-2-edioat
FUMARIC ASİT (USP KATLIŞLIĞI)
FUMARIC ASİT [USP KATLIŞLIĞI]
Donitik asit
but-2-endioik asit
CAS-110-17-8
fumarat, 10
trans-1,2-Etendikarboksilik asit
MALİK ASİT KATLIŞLIĞI A (EP KATLIŞLIĞI)
MALİK ASİT KATLIŞLIĞI A [EP KATLIŞLIĞI]
(E)-1,2-etilendikarboksilik asit
trans-1,2-etilendikkarboksilik asit
E-2-Butendioik asit
Fumarik asit (8CI)
26099-09-2
FC 33 (asit)
SODYUM AUROTİOMALAT KATLIŞLIĞI B (EP KATLIŞLIĞI)
SODYUM AUROTİYOMALAT KATLIŞLIĞI B [EP KATLIŞLIĞI]
Futrans-2-Butendioik Asit
fumarsaure
Allomaleat
Boletat
Likenat
Asido likeniko
fumerik asit
Asido boletico
Asido fumarico
Asido allomaleiko
trans-Butendioat
NCGC00091192-02
Fumarik Asit,(S)
trans-2-Butendisaure
trans-2-Butendioat
2-(E)-Butendioat
Fumarik asit, %99
Asido trans butendioico
trans-Etilendikarbonsaure
(Trans)-butendioik asit
F0067
Fumarik asit, >=%99
FEMA Numarası: 2488
bmse000083
FUMARİK ASİT [MI]
WLN: QV1U1VQ-T
FUMARİK ASİT [FCC]
SCHEMBL1177
FUMARİK ASİT [FHFI]
FUMARİK ASİT [HSDB]
FUMARİK ASİT [INCI]
FUMARİK ASİT [VANDF]
MLS002454406
1,2-etilendikarboksilik asit
2-butendioik asit, (2E)-
(2E)-2-Butendioik asit #
FUMARIC ASİT [WHO-DD]
CHEMBL503160
FUMARICUM ASİT [HPUS]
trans-1,2-etilendikarboksilat
BDBM26122
CHEBI:22958
HMS2270C12
Pharmakon1600-01301022
Fumarik asit, >=%99,0 (T)
AMY30339
STR02646
Asido trans 1,2-etenedicarbossilico
Tox21_201769
Tox21_302826
2-Butendioik asit (2E)- (9CI)
Asido trans 1,2-etilendicarbossilico
Fumarik asit, >=%99, FCC, FG
NSC760395
s4952
AKOS000118896
Fumarik asit, DMSO için qNMR Standardı
CCG-266065
CS-W016599
DB01677
HY-W015883
NSC-760395
USEPA/OPP Pestisit Kodu: 051201
NCGC00091192-01
NCGC00091192-03
NCGC00256360-01
NCGC00259318-01
BP-13087
Fumarik asit, USP/NF'ye göre test edilmiştir
LS-12976
SMR000112117
Fumarik asit, saf., >=%99,5 (T)
NS00074156
EN300-17996
Fumarik asit, Vetec™ reaktif sınıfı, %99
1, (E)
C00122
D02308
D85166
Q139857
Fumarik asit, BioReaktif, hücre kültürüne uygun
J-002389
Fumarat; 2-Butendioik asit; Trans-Butendioik asit
Z57127460
F8886-8257
Fumarik asit, sertifikalı referans malzemesi, TraceCERT®
26B3632D-E93F-4655-90B0-3C17855294BA
Fumarik asit, susuz, serbest akışlı, Redi-Dri(TM), >=%99
Fumarik asit, Avrupa Farmakopesi (EP) Referans Standardı
Fumarik asit, Amerika Birleşik Devletleri Farmakopesi (USP) Referans Standardı
Fumarik Asit, Farmasötik İkincil Standart; Sertifikalı Referans Materyali
