Фумаровая кислота

Описание

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.

Химические свойства

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.

Вхождение

Reported found in several plants, Fumaria offcinalis L , Boletus scaber Boll and lean raw fsh

Использование

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.

Методы производства

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.

Подготовка

By the action of certain fungi (Rhizopus nigricans) on glucose; by oxidation of furfural with sodium chlorate in the pres- ence of vanadium pentoxide.

Определение

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.

Общее описание

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.

Реакции воздуха и воды

Slightly soluble in water.

Угроза здоровью

Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation.

Фармацевтические приложения

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.

Профиль безопасности

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.

Безопасность

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

Возможный контакт

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.

Канцерогенность

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.

хранилище

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.

Методы очистки

Crystallise it from hot M HCl or water and dry it at 100o. [Beilstein 2 IV 2202.]

Несовместимости

Fumaric acid undergoes reactions typical of an organic acid.

Утилизация отходов

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.

Регуляторный статус

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.