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Fumaric acid structure

Fumaric acid
Fumaric acid is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products. Meanwhile, it is also an important kind of derivatives of maleic anhydride, being widely used in food, coatings, resins and plasticizers. In the food industry, fumaric acid, used as souring agent, can be applied to soft drinks, western-class wine, cold drinks, fruit juice concentrate, canned fruit, pickles and ice cream. As an acidic substance used as solid beverage gas production agent, it has excellent bubble durability with delicate product organization.Fumaric acid has been used as a food acidulant since 1946. As a food additive, it is used as an acidity regulator and can be denoted by the E number E297. Chemically it is an unsaturated dicarbonic acid and is part of the citric acid cycle. Fumaric acid is a common food additive included in many processed foods to keep them stable and to add tartness. The substance has a more sour flavor than citric acid, another common food additive. Fumaric acid occurs naturally in fumitory, bolete mushrooms, lichen and Iceland moss. As an additive, fumaric acid is produced synthetically, mainly from malic acid from apples. Fumaric acid as an additive is regulated under the Codex Alimentarius General Standard for Food Additives (GSFA), a collection of internationally recognized standards.The U.S. Food and Drug Administration considers it safe. View more+
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1. Names and Identifiers
1.1 Name
Fumaric acid
1.2 Synonyms
(2E)-2-Butenoic acid - formic acid (1:1); 2-Butenoic acid, (2E)-, compd. with formic acid (1:1); ACIDUM FUMARICUM; Boletic acid; but-2-en-1,4-dioic acid; EINECS 203-743-0; FEMA 2488; fumaric; FUMARSAEURE; Fumarsure; MFCD00002700; RARECHEM AL BO 0142; TMEDA; TRANS-1,2-ETHYLENEDICARBOXYLIC ACID; TRANS-1,2-ETHYLENTRICARBOXYLIC ACID; TRANS-2-BUTEN-1,4-DIOIC ACID; TRANS-2-BUTENEDIOIC ACID; TRANS-BUTENEDICARBOXYLIC ACID; TRANS-BUTENEDIOIC ACID; U-1149;
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1.3 CAS No.
110-17-8
1.4 CID
444972
1.5 EINECS
203-743-0
1.6 Molecular Formula
C4H4O4
1.7 Inchi
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
1.8 InChkey
VZCYOOQTPOCHFL-OWOJBTEDSA-N
1.9 Canonical Smiles
C(=CC(=O)O)C(=O)O
1.10 Isomers Smiles
C(=C/C(=O)O)\C(=O)O
2. Properties
2.1 Solubility
95% ethanol: soluble0.46g/10 mL, clear, colorless
2.2 Λmax
220nm
2.3 AnalyticLaboratory Methods
... DETECTED IN AIR BY GAS CHROMATOGRAPHY AFTER METHYLATION WITH BORON TRIFLUORIDE;.
2.4 Appearance
Fumaric acid appears as a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses.
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2.5 AutoIgnition
1364° F (USCG, 1999)
2.6 Storage
Ambient temperatures.
2.7 Carcinogenicity
No evidence of carcinogenicitywas found in several chronic studies with rats inwhich fumaric acid was added to the diet at concentrationsup to 1.5%. As for dermal application, Swissmice were treated topically twice weekly with a 1% solution in acetone (volume not specified). Moderate focalhyperplasia was found in the treated group, but no tumorsdeveloped.The inhibitory effect of fumaric acid on hepatocarcinogenesiswas examined in male IBR mice fed 0.035% thioacetamidein the diet for 40 weeks and then fed a basal diet for48 weeks. The inhibitory effect of 1% fumaric acid in thebasal diet on thioacetamide carcinogenesis was so markedthat no hepatic carcinomas were found in any of the 15 animalsfed fumaric acid in combination with thioacetamide. Similar inhibitory effects of fumaric acid onforestomach and lung carcinogenesis in mice (that resultedfrom exposure to potassium naphthyridine-3-carboxylate)have been identified.
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2.8 Chemical Properties
Fumaric acid is naturally presented in Corydalis, mushrooms and fresh beef. Product precipitated from the water is monoclinic needle-like, prismatic or leaf-like white crystalline or crystalline powder. It is odorless with a special and strong sour, which is about 1.5 times that of the citric acid. It has a melting point 287 ° C, the boiling point of 290 ° C with subjecting to sublimation at temperature above 200 ° C. When being heated to 230 ° C, it will lose water and become maleic anhydride. Its co-boiling with water can produce DL-malic acid. It is soluble in ethanol, slightly soluble in water and ether, but insoluble in chloroform. The pH value of the 3% aqueous solution is 2.0 to 2.5 with a strong buffering performance, in order to maintain the pH of the aqueous solution at around 3.0. This product is non-toxic; rat-oral LD50: 8000mg/kg.
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2.9 Color/Form
Needles, monoclinic prisms or leaflets from water
Colorless crystals
WHITE CRYSTALLINE POWDER
2.10 Heat of Combustion
-4,970 Btu/lb = 2,760 cal/g = -116X10+5 J/kg
2.11 Odor
Odorless
2.12 PH
3,0-3,2 (0,05 % solution at 25 °C)
2.13 Physical
FUMARIC ACID; is a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses.
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2.14 pKa
3.02, 4.38(at 25℃)
2.15 Water Solubility
Solubility in water, g/100ml at 25°C: 0.63 (poor)
2.16 Spectral Properties
MAX ABSORPTION (WATER): 208 NM (LOG E= 4.20); SADTLER REFERENCE NUMBER: 472 (IR, PRISM); 127 (IR, GRATING)
IR: 1278 (Coblentz Society Spectral Collection)
UV: 165 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 4407 (Sadtler Research Laboratories Spectral Collection)
Raman: 12 (Sadtler Research Laboratories Spectral Collection)
MASS: 1989 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
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2.17 Stability
Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.
2.18 StorageTemp
Store below +30°C.
3. Use and Manufacturing
3.1 Definition
ChEBI: A butenedioic acid in which the C2C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.
3.2 Description

Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.


Fumaric acid or trans-butenedioic acid is the chemical compound with the formula HO2CCH=CHCO2H. This white crystalline compound is one of two isomeric unsaturated dicarboxylic acids, the other being maleic acid. In fumaric acid the carboxylic acid groups are trans (E) and in maleic acid they are cis (Z). Fumaric acid has a fruit-like taste. The salts and esters are known as fumarates.

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3.3 General Description
A colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses.
3.4 GHS Classification
Signal: Warning
GHS Hazard Statements
H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statement Codes
P264, P280, P305+P351+P338, P33, and P313
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3.5 Methods of Manufacturing
Commercially, fumaric acid; may be prepared from glucose; by the action of fungi such as Rhizopus nigricans, as a by-product in the manufacture of maleic and phthalic anhydrides, and by the isomerization of maleic acid; using heat or a catalyst. On the laboratory scale, fumaric acid; can be prepared by the oxidation of furfural; with sodium chlorate; in the presence of vanadium pentoxide;.
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3.6 Potential Exposure
Fumaric acid is used in production ofresins, polyesters, plasticizers, and alkyl surface coatings; asa food additive; as an antioxidant in resins; to make dyes.
3.7 Produe Method
Commercially, fumaric acid may be prepared from glucose by theaction of fungi such as Rhizopus nigricans, as a by-product in themanufacture of maleic and phthalic anhydrides, and by theisomerization of maleic acid using heat or a catalyst.On the laboratory scale, fumaric acid can be prepared by theoxidation of furfural with sodium chlorate in the presence ofvanadium pentoxide.
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3.8 Purification Methods
Crystallise it from hot M HCl or water and dry it at 100o. [Beilstein 2 IV 2202.]
3.9 Usage
fumaric acid is used to add fragrance to products and to decrease product pH. It can also help keep the pH stable. It is generally used in cleansers. Fumaric acid is naturally occurring in plants, such as lichen and Iceland moss, and in animals. For example, the skin produces fumaric acid when exposed to light. It can also F be synthetically manufactured.
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3.10 Waste Disposal
Use a licensed professionalwaste disposal service to dispose of this material. Dissolveor mix the material with a combustible solvent and burn ina chemical incinerator equipped with an afterburner andscrubber. All federal, state, and local environmental regula tions must be observed.
4. Safety and Handling
4.1 Exposure Standards and Regulations
Fumaric acid and its calcium, ferrous, magnesium, potassium, and sodium salts may be safely used in food in accordance with the following prescribed conditions: (a) The additives meet the following specifications: (1) Fumaric acid contains a minimum of 99.5 percent by weight of fumaric acid, calculated on the anhydrous basis. (2) The calcium, magnesium, potassium, and sodium salts contain a minimum of 99 percent by weight of the respective salt, calculated on the anhydrous basis. Ferrous fumarate contains a minimum of 31.3 percent total iron and not more than 2 percent ferric iron. (b) With the exception of ferrous fumarate, fumaric acid and the named salts are used singly or in combination in food at a level not in excess of the amount reasonably required to accomplish the intended effect. (c) Ferrous fumarate is used as a source of iron in foods for special dietary use, when the use is consistent with good nutrition practice.
Fumaric acid is an indirect food additive for use only as a component of adhesives.
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4.2 Octanol/Water Partition Coefficient
log Kow = 0.46
4.3 Other Preventative Measures
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
If material not on fire and not involved in fire: keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: avoid breathing vapors or dusts ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
Handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.
In case of skin contact: Wash off with soap and plenty of water. Consult a physician.
In case of eye contact: Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Hygiene measures: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
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4.4 Cleanup Methods
Environmental considerations - land spill: Dig a pit, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fiefighting water. Neutralize with agricultural lime (CaO), crushed limestone (CaCO3), or sodium bicarbonate (NaHCO3).
Environmental considerations - water spill: Neutralize with agricultural lime (CaO), crushed limestone (CaCO3), or sodium bicarbonate (NaHCO3). If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Adjust pH to neutral (pH = 7). Use mechanical dredges or lifts to remove immobililzed masses of pollutants and precipitates.
Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation.
Environmental precautions: Do not let product enter drains.
Methods for cleaning up: Pick up and arrange disposal withour creating dust. Keep in suitable, closed containers for disposal.
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4.5 DisposalMethods
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
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4.6 Fire Fighting Procedures
If material on fire or involved in fire: use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemicals, or carbon dioxide.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
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4.7 FirePotential
SLIGHT
4.8 Safety Profile
Poison by intraperitoneal route. Mildly toxic by ingestion and skin contact. A skin and eye irritant. Mutation data reported. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.
4.9 Formulations/Preparations
Grades: Technical; crystal; FCC /Food Chemicals Codex/.
ASTM D3504-76 > 99.5%
Resin grade: 99.6%
FCC /Food Chemicals Codex/; fine granular, fine powders, powder (80 mesh) and technical grades.
4.10 Protective Equipment and Clothing
Wear appropriate chemical protective gloves, boots, and goggles.
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Hand protection: The selected protective gloves have to satisfy the specifications of EU Directive 89/689/EEC and the standard EN 374 derived from it. Handle with gloves.
Eye protection: Safety glasses.
Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.
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4.11 Reactivities and Incompatibilities
Fumaric acid undergoes reactions typical of an organic acid.
Materials to avoid: Oxidizing agents, amines, strong bases.
4.12 Skin, Eye, and Respiratory Irritations
It is a mild irritant of skin and mucous membranes ...
Dust: Irritating to eyes, nose and throat. If inhaled will cause coughing or difficult breathing. Solid: Irritating to skin and eyes.
May cause respiratory tract irritation. May cause skin irritation. Causes eye irritation.
4.13 Safety

Hazard Codes:?IrritantXi
Risk Statements: 36?
R36:Irritating to eyes.
Safety Statements: 26?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 9126
WGK Germany: 1
RTECS: LS9625000
Fumaric acid converts to the irritant maleic anhydride, upon partial combustion.

?

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4.14 Specification

?Fumaric acid ,?its cas register number is?110-17-8. It also can be called?1,2-Ethenedicarboxylic acid, trans- ; 1,2-Ethylenedicarboxylic acid, (E) ; 2-Butenedioic acid, (E)- ; Allomaleic acid ; Allomalenic acid ; Butenedioic acid, (E)- ; Kyselina fumarova ; Lichenic acid ; Tumaric acid ; trans-1,2-Ethylenedicarboxylic acid ;
?trans-Butenedioic acid .

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4.15 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg) ? National Technical Information Service. Vol. AD277-689,
mouse LD50 unreported 5gm/kg (5000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Toksikologicheskii Vestnik. Vol. (2), Pg. 25, 1994.
rabbit LDLo oral 5gm/kg (5000mg/kg) ? Industrial and Engineering Chemistry. Vol. 15, Pg. 628, 1923.
rat LD50 oral 9300mg/kg (9300mg/kg) ? Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.
rat LD50 unreported 6800mg/kg (6800mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: EXCITEMENT		 Toksikologicheskii Vestnik. Vol. (2), Pg. 25, 1994.
rat LDLo intraperitoneal 587mg/kg (587mg/kg) GASTROINTESTINAL: OTHER CHANGES

LIVER: OTHER CHANGES

BLOOD: HEMORRHAGE		 Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 35, Pg. 298, 1946.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H319 Causes serious eye irritation
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : Predict  
1H NMR : parameter in DMSO-d6  
1H NMR : Predict  
Predict 1H proton NMR  
IR : KBr disc  
IR : nujol mull  
Raman : 4880 A,200 M,powder  
Mass  
Mass spectrum (electron ionization)  
7. Synthesis Route
110-17-8Total: 156 Synthesis Route
 
98-67-9
98-67-9 90 Suppliers
 
110-17-8
110-17-8 815 Suppliers
 
98-11-3
98-11-3 162 Suppliers
 
110-17-8
110-17-8 815 Suppliers
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8. Precursor and Product
precursor:
92-52-4
92-52-4
98-01-1
98-01-1
87-69-4
87-69-4
92-55-7
92-55-7
56-84-8
56-84-8
98-11-3
98-11-3
97-67-6
97-67-6
98-67-9
98-67-9
product:
70-49-5
70-49-5
627-63-4
627-63-4
526-78-3
526-78-3
617-48-1
617-48-1
77-92-9
77-92-9
56-84-8
56-84-8
608-36-6
608-36-6
79-10-7
79-10-7
97-67-6
97-67-6
110-15-6
110-15-6
9. Computed Properties
10.Other Information
Usage
Fumaric acid is used as a food additive and acid regulator. It is used in the production of polyester resins and polyhydric alcohols. It is also used as a mordant for dyes, paint additives, coating additives, plasticizers, processing aids and specific to petroleum production. Further, it is used in dentifrices as a stain remover and to make other chemicals. In addition to this, it is used in rosin esters, drying oils, printing inks and flavoring agent.
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Merck
14,4287
BRN
605763
Description
Fumaric acid is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products. Meanwhile, it is also an important kind of derivatives of maleic anhydride, being widely used in food, coatings, resins and plasticizers. In the food industry, fumaric acid, used as souring agent, can be applied to soft drinks, western-style wine, cold drinks, fruit juice concentrate, canned fruit, pickles and ice cream. As an acidic substance used as solid beverage gas production agent, it has excellent bubble durability with delicate product organization.
Fumaric acid has been used as a food acidulant since 1946. As a food additive, it is used as an acidity regulator and can be denoted by the E number E297. Chemically it is an unsaturated dicarbonic acid and is part of the citric acid cycle.
Fumaric acid is a common food additive included in many processed foods to keep them stable and to add tartness. The substance has a more sour flavor than citric acid, another common food additive. Fumaric acid occurs naturally in fumitory, bolete mushrooms, lichen and Iceland moss. As an additive, fumaric acid is produced synthetically, mainly from malic acid from apples. Fumaric acid as an additive is regulated under the Codex Alimentarius General Standard for Food Additives (GSFA), a collection of internationally recognized standards.The U.S. Food and Drug Administration considers it safe.
View all
Chemical Properties
Fumaric acid is naturally presented in Corydalis, mushrooms and fresh beef. Product precipitated from the water is monoclinic needle-like, prismatic or leaf-like white crystalline or crystalline powder. It is odorless with a special and strong sour, which is about 1.5 times that of the citric acid. It has a melting point 287 ° C, the boiling point of 290 ° C with subjecting to sublimation at temperature above 200 ° C. When being heated to 230 ° C, it will lose water and become maleic anhydride. Its co-boiling with water can produce DL-malic acid. It is soluble in ethanol, slightly soluble in water and ether, but insoluble in chloroform. The pH value of the 3% aqueous solution is 2.0 to 2.5 with a strong buffering performance, in order to maintain the pH of the aqueous solution at around 3.0. This product is non-toxic; rat-oral LD50: 8000mg/kg.
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Chemical Properties
Fumaric acid is a colorless to white, odorless crystalline powder. Fruity-acidic taste.
Chemical Properties
Fumaric acid occurs as white, odorless or nearly odorless, granules or as a crystalline powder that is virtually nonhygroscopic.
Chemical Properties
White, odorless granules or crystalline powder. It is soluble in alcohol, slightly soluble in water and in ether, and very slightly soluble in chloroform.
Fumaric acid is used as a replacement for tartaric acid. It has an odorless, tart, acidic-sour flavor. It may be synthesized by the action of certain fungi (Rhizopus nigricans) on glucose; by oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide.
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Chemical Properties
Fumaric acid is odorless with a tart, acidic-sour favor Fumaric acid is used as a replacement of tartaric acid.
Occurrence
Reported found in several plants, Fumaria offcinalis L , Boletus scaber Boll and lean raw fsh
Uses
fumaric acid is used to add fragrance to products and to decrease product pH. It can also help keep the pH stable. It is generally used in cleansers. Fumaric acid is naturally occurring in plants, such as lichen and Iceland moss, and in animals. For example, the skin produces fumaric acid when exposed to light. It can also F be synthetically manufactured.
View all
Uses
Fumaric Acid is an acidulant that is a nonhygroscopic, strong acid of poor solubility. it has a solubility of 0.63 g in 100 ml of distilled water at 25°c. it dissolves slowly in cold water, but if mixed with dioctyl sodium sulfosuccinate its solubility improves. the solubility rate also increases with smaller particle size. a quantity of 0.317 kg of can replace 0.453 kg of citric acid. it is used in dry mixes such as desserts, pie fillings, and candy. it is used in dry bever- age mixes because it is storage stable, free flowing, and nonhygro- scopic. it functions as a synergistic antioxidant with bha and bht in oiland lard-base products. in gelatin desserts, it improves the flavor stability and increases shelf life and gel strength.
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Uses
1. Fumaric acid is used for the production of unsaturated polyester resin. This kind of resin is characterized by excellent resistance to chemical corrosion as well as heat resistance; the copolymer of fumaric acid and vinyl acetate is a kind of excellent adhesive. Its copolymer with styrene copolymer is the raw material for the manufacture of glass fiber. The plasticizer of the fumaric acid is non-toxic and can be applied to the vinyl acetate latex contact with food. This product is the intermediate of pharmaceutical and optical bleaching agents and other fine chemicals. Neutralization of fumaric acid with sodium carbonate can generate sodium fumarate ([17013-01-3]), and then replaced with ferrous sulfate to get iron fumarate, being the drug Fersamal used for the treatment of small red blood cell anemic. The product, as a food additive-sourness agent, used in soft drinks, fruit sugar, jelly, ice cream with most of them used in combination with sourness agent, citric acid. The monosidum salt made from the reaction between fumaric acid and sodium hydroxide can also used as sour seasoning, also used as the intermediate of synthetic resin and mordant.
2. Fumaric acid is included in many dairy-based products. These include dairy drinks such as chocolate milk, cocoa, eggnog, condensed milk and whey protein beverages. It also may be added to clotted cream, milk and cream powders and milk and cream analogues (substitutes). Fumaric acid is added to cheese products, including processed cheese and cheese substitutes. Dairy-based desserts, such as pudding, flavored yogurt, sherbet and sorbet may include fumaric acid as well. Dairy fat spreads and blended spreads can include fumaric acid, and so can preserved eggs and egg-based desserts such as custard.
3. Some processed and packaged foods have fumaric acid added to them to help stabilize them and enhance their flavor. For example, many processed meats, such as bacon and canned meats, have added fumaric acid. Frozen seafood, smoked meats and the edible casings around sausages might also have fumaric acid added to them. Fermented, canned, dried and processed fruits and vegetables can contain the food additive as well. Rice cakes and other precooked rice foods, dried or preserved eggs, mustard, vinegar, cider, wine and other alcoholic beverages are additional examples of foods that might contain fumaric acid.
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Uses
Occurs in many plants. Essential to vegetable and tissue respiration. Used as an antioxidant.
Definition
ChEBI: A butenedioic acid in which the C2C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.
Preparation
By the action of certain fungi (Rhizopus nigricans) on glucose; by oxidation of furfural with sodium chlorate in the pres- ence of vanadium pentoxide.
Definition
Either of two isomers. Transbutenedioic acid (fumaric acid) is a crystalline compound found in certain plants. Cisbutenedioic acid (maleic acid) is used in the manufacture of synthetic resins. It can be converted into the trans isomer by heating at 120°C.
Definition
butenedioic acid: Either oftwo isomers with the formulaHCOOHC:CHCOOH. Both compoundscan be regarded as derivativesof ethene in which a hydrogenatom on each carbon has been replacedby a –COOH group. The compoundsshow cis–trans isomerism.The trans form is fumaric acid (r.d.1.64; sublimes at 165°C) and the cisform is maleic acid (r.d. 1.59; m.p.139–140°C). Both are colourless crystallinecompounds used in makingsynthetic resins. The cis form israther less stable than the trans formand converts to the trans form at120°C. Unlike the trans form it caneliminate water on heating to form acyclic anhydride containing a–CO.O.CO– group (maleic anhydride).Fumaric acid is an intermediate inthe Krebs cycle.
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Production Methods
Commercially, fumaric acid may be prepared from glucose by the action of fungi such as Rhizopus nigricans, as a by-product in the manufacture of maleic and phthalic anhydrides, and by the isomerization of maleic acid using heat or a catalyst.
On the laboratory scale, fumaric acid can be prepared by the oxidation of furfural with sodium chlorate in the presence of vanadium pentoxide.
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Biotechnological Production
Currently, fumaric acid is mainly manufactured by chemical synthesis via the precursor maleic acid, which is produced using either benzene or n-butane via catalytic oxidation. However, there are enzymatic and fermentative production routes for fumaric acid. Prior to the advent of inexpensive petroleumbased chemistry, fumaric acid was produced commercially by fermentation using organisms of the genus Rhizopus with an annual production of 4,000 metric tons . Product concentrations from 30 to 130 g.L-1 with yields from 0.3 to 1.0 g of fumaric acid per gram of glucose and productivities of 0.46–2.0 g.L-1.h-1 have been reported growing on glucose .
In recent years, new approaches using metabolic engineering have been studied. For example, fumaric acid concentrations of 28.2 g.L-1 with a productivity of 0.448 g.L-1.h-1 have been reached in fed-batch cultivation of a genetic modified E. coli . To achieve this result, eight modifications have been implemented.
Fumaric acid could be alternatively synthesized by an enzymatic process starting from maleic acid as in the chemical synthesis. By whole-cell biocatalysis of the Pseudomonas alcaligenes strain XD-1, a yield of 0.698 g of fumaric acid per gram of maleic acid and a production rate of 6.98 g.L-1.h-1 have been reached . The process has been optimized. The formation of the byproduct malic acid was avoided due to an inactivation of fumarase by a heat treatment of the cells beforehand. Finally, a yield of 0.95 g fumaric acid per gram maleic acid and a production rate of 14.25 g.L-1.h-1 have been observed.
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General Description
A colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Fumaric acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Fumaric acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. Partial carbonization and formation of maleic anhydride occur at 446° F (open vessel).
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Health Hazard
Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation.
Pharmaceutical Applications
Fumaric acid is used primarily in liquid pharmaceutical preparations as an acidulant and flavoring agent. Fumaric acid may be included as the acid part of effervescent tablet formulations, although this use is limited as the compound has an extremely low solubility in water. It is also used as a chelating agent which exhibits synergism when used in combination with other true antioxidants.
In the design of novel pelletized formulations manufactured by extrusion–spheronization, fumaric acid was used to aid spheronization, favoring the production of fine pellets. It has also been investigated as an alternative filler to lactose in pellets.
Fumaric acid has been investigated as a lubricant for effervescent tablets, and copolymers of fumaric acid and sebacic acid have been investigated as bioadhesive microspheres.It has been used in film-coated pellet formulations as an acidifying agent and also to increase drug solubility.
Fumaric acid is also used as a food additive at concentrations up to 3600 ppm, and as a therapeutic agent in the treatment of psoriasis and other skin disorders.
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Safety Profile
Poison by intraperitoneal route. Mildly toxic by ingestion and skin contact. A skin and eye irritant. Mutation data reported. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety
Fumaric acid is used in oral pharmaceutical formulations and food products, and is generally regarded as a relatively nontoxic and nonirritant material. However, acute renal failure and other adverse reactions have occurred following the topical and systemic therapeutic use of fumaric acid and fumaric acid derivatives in the treatment of psoriasis or other skin disorders. Other adverse effects of oral therapy have included disturbances of liver function, gastrointestinal effects, and flushing.
The WHO has stated that the establishment of an estimated acceptable daily intake of fumaric acid or its salts was unnecessary since it is a normal constituent of body tissues.
LD50 (mouse, IP): 0.1 g/kg
LD50 (rat, oral): 9.3 g/kg
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Potential Exposure
Fumaric acid is used in production of resins, polyesters, plasticizers, and alkyl surface coatings; as a food additive; as an antioxidant in resins; to make dyes.
Carcinogenicity
No evidence of carcinogenicity was found in several chronic studies with rats in which fumaric acid was added to the diet at concentrations up to 1.5%. As for dermal application, Swiss mice were treated topically twice weekly with a 1% solution in acetone (volume not specified). Moderate focal hyperplasia was found in the treated group, but no tumors developed.
The inhibitory effect of fumaric acid on hepatocarcinogenesis was examined in male IBR mice fed 0.035% thioacetamide in the diet for 40 weeks and then fed a basal diet for 48 weeks. The inhibitory effect of 1% fumaric acid in the basal diet on thioacetamide carcinogenesis was so marked that no hepatic carcinomas were found in any of the 15 animals fed fumaric acid in combination with thioacetamide . Similar inhibitory effects of fumaric acid on forestomach and lung carcinogenesis in mice (that resulted from exposure to potassium naphthyridine-3-carboxylate) have been identified.
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storage
Fumaric acid is stable although it is subject to degradation by both aerobic and anaerobic microorganisms. When heated in sealed vessels with water at 150–170°C it forms DL-malic acid.
The bulk material should be stored in a well-closed container in a cool, dry place.
Purification Methods
Crystallise it from hot M HCl or water and dry it at 100o. [Beilstein 2 IV 2202.]
Incompatibilities
Dust cloud from powder or granular form mixed with air can explode. Incompatible with oxidi zers (chlorates, nitrates, peroxides, permanganates, perchlo rates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, sulfuric acid, caustics, ammonia, amines, isocyanates, alkylene oxi des; epichlorohydrin. Decomposes above 350℃ forming toxic fumes of maleic anhydride.
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Incompatibilities
Fumaric acid undergoes reactions typical of an organic acid.
Waste Disposal
Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regula tions must be observed.
Regulatory Status
GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (oral capsules, suspensions, syrups, extended release and sustained action chewable tablets). Included in the Canadian List of Acceptable Nonmedicinal Ingredients.
Storage features
Separated from oxidizing materials.
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12. Related Questions
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