Fumaric acid
- CAS No.
- 110-17-8
- Chemical Name:
- Fumaric acid
- Synonyms
- FA;fumaric;2-BUTENEDIOIC ACID;Butenedioic acid;ACIDUM FUMARICUM;(E)-2-Butenedioic acid;TRANS-2-BUTEN-1,4-DIOIC ACID;Fumaric Acid (Food and Technical);bjss;U-1149
- CBNumber:
- CB5852804
- Molecular Formula:
- C4H4O4
- Molecular Weight:
- 116.07
- MOL File:
- 110-17-8.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/9/5 22:20:32
| Melting point | 298-300 °C (subl.) (lit.) |
|---|---|
| Boiling point | 137.07°C (rough estimate) |
| Density | 1.62 |
| vapor pressure | 1.7 mm Hg ( 165 °C) |
| refractive index | 1.5260 (estimate) |
| FEMA | 2488 | FUMARIC ACID |
| Flash point | 230 °C |
| storage temp. | Store below +30°C. |
| solubility | 95% ethanol: soluble0.46g/10 mL, clear, colorless |
| form | Fine Crystalline Powder |
| pka | 3.02, 4.38(at 25℃) |
| color | White |
| PH | 3.19(1 mM solution);2.57(10 mM solution);2.03(100 mM solution); |
| Odor | odorless |
| Odor Type | odorless |
| explosive limit | 40% |
| Water Solubility | 0.63 g/100 mL (25 ºC) |
| Merck | 14,4287 |
| JECFA Number | 618 |
| BRN | 605763 |
| Stability | Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible. |
| InChIKey | VZCYOOQTPOCHFL-OWOJBTEDSA-N |
| LogP | -4.02 at 20℃ |
| CAS DataBase Reference | 110-17-8(CAS DataBase Reference) |
| NIST Chemistry Reference | Fumaric acid(110-17-8) |
| EPA Substance Registry System | Fumaric acid (110-17-8) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H319 | |||||||||
| Precautionary statements | P264-P280-P305+P351+P338-P337+P313 | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36 | |||||||||
| Safety Statements | 26 | |||||||||
| RIDADR | UN 9126 | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | LS9625000 | |||||||||
| Autoignition Temperature | 375 °C | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29171900 | |||||||||
| Toxicity | LD50 orally in Rabbit: 9300 mg/kg LD50 dermal Rabbit 20000 mg/kg | |||||||||
| NFPA 704 |
|
Fumaric acid price More Price(33)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | W248835 | Fumaric acid natural (US), ≥98%, FG | 110-17-8 | 1SAMPLE-K | ₹5196 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W248835 | Fumaric acid natural (US), ≥98%, FG | 110-17-8 | 1KG | ₹14364.78 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W248835 | Fumaric acid natural (US), ≥98%, FG | 110-17-8 | 5KG | ₹50303.78 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W248800 | Fumaric acid FCC, FG | 110-17-8 | 1SAMPLE-K | ₹5141.88 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | W248800 | Fumaric acid FCC, FG | 110-17-8 | 1KG | ₹6971.3 | 2022-06-14 | Buy |
Fumaric acid Chemical Properties,Uses,Production
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.
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.
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.
Uses
Occurs in many plants. Essential to vegetable and tissue respiration. Used as an antioxidant.
Fumaric acid is used in food products as an
acidifier with an acid type of taste that blends
particularly well with caramellic or sugarsweetened products, baked products, etc.
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.
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.
Definition
Butenedioic Acid: Either of two isomers with the formula HCOOHC:CHCOOH. Both compounds can be regarded as derivatives of ethene in which a hydrogenatom on each carbon has been replaced by a –COOH group. The compounds show 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 crystalline compounds used in making synthetic resins. The cis form is rather less stable than the trans form and converts to the trans form at120°C. Unlike the trans form it can eliminate water on heating to form acyclic anhydride containing a–CO.O.CO– group (maleic anhydride).Fumaric acid is an intermediate in the Krebs cycle.
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.
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.
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
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.
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
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.
Fumaric acid Preparation Products And Raw materials
Raw materials
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