Fumaric Acid

Base Information

• Chemical Name: Fumaric Acid
• CAS No.: 110-17-8
• Deprecated CAS: 623158-97-4,909873-99-0
• Molecular Formula: C4H4O4
• Molecular Weight: 116.073
• Hs Code.: 2942000000
• European Community (EC) Number: 203-743-0,607-861-7,634-144-6,866-556-9
• ICSC Number: 1173
• NSC Number: 760395,2752
• UN Number: 9126
• UNII: 88XHZ13131
• DSSTox Substance ID: DTXSID3021518
• Nikkaji Number: J292.521D,J2.880K
• Wikipedia: Fumaric_acid,Ammonium_fumarate
• Wikidata: Q139857
• NCI Thesaurus Code: C63655
• RXCUI: 25389
• Metabolomics Workbench ID: 37095
• ChEMBL ID: CHEMBL503160
• Mol file: 110-17-8.mol

Synonyms:(E)-2-butenedioic acid;2-butenedioic acid;ammonium fumarate;fumarate dianion;fumarate(2-);fumaric acid;Furamag;mafusol;magnesium fumarate;sodium fumarate

Chemical Property of Fumaric Acid

Chemical Property:

• Appearance/Colour: white powder or colourless crystals
• Melting Point: 295-300 ºC
• Boiling Point: 355.5°Cat760mmHg
• Flash Point: 230 ºC
• PSA: 74.60000
• Density: 1.499 g/cm³
• LogP: -0.28820
• Water Solubility.: 0.63 g/100 mL (25℃)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 116.01095860
• Heavy Atom Count: 8
• Complexity: 119

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36:
• Safety Statements: S26:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(=CC(=O)O)C(=O)O
• Isomeric SMILES: C(=C/C(=O)O)\C(=O)O
• Recent ClinicalTrials: Study of Secukinumab Compared to Fumaderm? in Adults With Moderate to Severe Psoriasis.
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Use Description: Fumaric acid, a specific chemical compound, serves diverse roles in various fields. In the food industry, it acts as a food additive and acidulant, enhancing the flavor and preserving the quality of various products. In the pharmaceutical sector, it plays a crucial role as an ingredient in the formulation of medications, particularly in controlled-release drug delivery systems. Moreover, in the field of polymer science, fumaric acid is used in the production of biodegradable plastics and resins, contributing to the development of more sustainable materials. Its applications in food, pharmaceuticals, and polymers underscore its significance in improving taste, enabling drug delivery, and promoting environmental sustainability within these distinct fields.
• Industrial Applications and Production: Fumaric acid, also known as trans-1,2-ethylenedicarboxylic acid, is extensively used in various industries including food, chemicals, agriculture, and pharmaceuticals. Its multifunctional structure, featuring a carbon-carbon double bond and two carboxylic acid groups, allows for easy esterification and polymerization, making it a key chemical feedstock for producing paper resins, unsaturated polyester resins, alkyd resins, plasticizers, and other industrial products. Additionally, its non-toxic nature and unique flavor have led to its widespread use as a food acidulant and beverage ingredient.
• Synthesis Methods: Fumaric acid is primarily synthesized through the isomerization of maleic acid, typically catalyzed by mineral acids, peroxy compounds, or thiourea. This petrochemical method, while yielding high production rates, often involves high temperatures, leading to the formation of by-products and significant energy consumption. Alternatively, microbial fermentation processes have gained attention due to their sustainability and environmentally friendly characteristics, offering a potential alternative to petrochemical synthesis.
• Uses in Various Industries: Fumaric acid finds applications in diverse industries, including food, medicine, and construction. It is used for native chitosan modification and as an active material in antioxidant, antibacterial, and antiviral reagents. It is also recognized as one of the "top 12" chemical building blocks due to its wide-ranging applications and importance in industrial processes.
• Biological Functions: Fumaric acid is a component of the tricarboxylic acid (TCA) cycle and plays a role in metabolic pathways in various organisms. Some lactobacilli utilize the TCA cycle in the direction of reductive reactions, metabolizing fumarate to malic acid or succinic acid. Additionally, fumaric acid and its salts are commonly used in terrestrial animal feeds.
• Use in Wine Production: Fumaric acid is permitted as an additive for wine acidification and inhibition of malolactic fermentation (MLF). It can effectively inhibit MLF in red wines at specific concentrations, improving microbiological stability and freshness while allowing for the reduction of SO2 levels. Tastings have shown that fumaric acid enhances acidity and body in wines, making it a valuable technological additive in winemaking.

Technology Process of Fumaric Acid

There total 485 articles about Fumaric Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(R)-4,4,4-trichloro-3-hydroxybutanoic acid (80513-23-1) → D-Malic acid (636-61-3,78644-42-5) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 24h;

DOI:10.1021/ja00365a030

Reference yield: 66.0%

furfural (98-01-1) → 2-furanoic acid (88-14-2) + succinic acid (110-15-6) + maleic acid (110-16-7,26099-09-2) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2)

Guidance literature:

With dihydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate; methyltrioxorhenium(VII); In water; at 20 ℃;

Reference yield: 34.4%

furfural (98-01-1) → 5-hydroxy-2-(5H)-furanone (14032-66-7) + 2-furanoic acid (88-14-2) + formic acid (64-18-6) + malic acid (617-48-1,78644-42-5) + succinic acid (110-15-6) + 2-buten-4-olide (497-23-4) + maleic acid (110-16-7,26099-09-2) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; In water; at 49.84 ℃; for 3h; Reagent/catalyst;

DOI:10.1016/j.cattod.2014.01.041

upstream raw materials:

piperidine

pyridine

malonic acid

Glyoxilic acid

Downstream raw materials:

4-methoxycarbonyl-pyrazoline-3-carboxylic acid methyl ester

succinylbenzene

3,4-dimethyl-6-(2-methyl-propenyl)-cyclohex-4-ene-1,2-dicarboxylic acid

norbornene-5,6-dicarboxylic acid

Refernces

• 1、 Rozelle,Alberty. "-". . p. 1637. Retrieved 1957.
• 2、 Reid,Sack. "". . p. 1985,1987. Retrieved 1951.
• 3、 Ishii,Hida,Iinuma,Muroi,Nozaki. "TAN-1323 C and D, new concanamycin-group antibiotics; Detection of the angiostatic activity with a wide range of macrolide antibiotics". . p. 12 - 20. Retrieved 1995.
• 4、 Macegoniuk, Katarzyna,Kowalczyk, Rafa?,Rudzińska, Anna,Psurski, Mateusz,Wietrzyk, Joanna,Berlicki, ?ukasz. "Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling". . p. 1346 - 1350. Retrieved 2017.
• 5、 Banerjee, Sanchari,Agrawal, Monika J.,Mishra, Diptimayee,Sharan, Siddharth,Balaram, Hemalatha,Savithri, Handanhal S.,Murthy, Mathur R. N.. "Structural and kinetic studies on adenylosuccinate lyase from Mycobacterium smegmatis and Mycobacterium tuberculosis provide new insights on the catalytic residues of the enzyme". . p. 1642 - 1658. Retrieved 2014.
• 6、 Botting, Nigel P.,Akhtar, Mahmoud,Cohen, Mark A.,Gani, David. "Mechanism of the Enzymic Elimination of Ammonia from 3-Substituted Aspartic Acids by 3-Methylaspartase". . p. 1371 - 1373. Retrieved 1987.
• 7、 Hudlicky, M.,Glass, T. E.. "ELIMINATION OF HYDROGEN FLUORIDE FROM FLUORINATED SUCCINIC ACIDS.(II) KINETICS OF DEHYDROFLUORINATION OF FLUORO-, 2,2-DIFLUORO-, MESO- AND DL-2,3-DIFLUORO-, AND TRIFLUOROSUCCINIC ACIDS". . p. 15 - 28. Retrieved 1983.
• 8、 Molloy,Lively,Gale,Gorman,Boeck. "A new dipeptide antibiotic from Streptomyces collinus, Lindenbein.". . p. 137 - 140. Retrieved 1972.
• 9、 Wynberg, Hans,Staring, Emiel G. J.. "Asymmetric Synthesis of (S)- and (R)-Malic Acid from Ketene and Chloral". . p. 166 - 168. Retrieved 1982.
• 10、 Pollard, John R.,Richardson, Susan,Akhtar, Mahmoud,Lasry, Philippe,Neal, Tracy,Botting, Nigel P.,Gani, David. "Mechanism of 3-methylaspartase probed using deuterium and solvent isotope effects and active-site directed reagents: Identification of an essential cysteine residue". . p. 949 - 975. Retrieved 1999.