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푸말산

푸말산
푸말산 구조식 이미지
카스 번호:
110-17-8
한글명:
푸말산
동의어(한글):
말레산;파라말레인산;아로말레인산;푸마릭산;푸말산;퓨마릭산;후말산;후마릭산;트랜스-부텐노산;트랜스-에틸렌디카르복시릭산;알로말레산;볼레틱산;푸마릭애씨드;푸마릭산;푸마르산;푸마릭 산
상품명:
Fumaric acid
동의어(영문):
FA;bjss;U-1149;fumaric;NSC-2752;Fumarsure;FEMA 2488;boleticacid;FUMARSAEURE;Boletic acid
CBNumber:
CB5852804
분자식:
C4H4O4
포뮬러 무게:
116.07
MOL 파일:
110-17-8.mol

푸말산 속성

녹는점
298-300 °C (subl.) (lit.)
끓는 점
137.07°C (rough estimate)
밀도
1.62
증기압
1.7 mm Hg ( 165 °C)
굴절률
1.5260 (estimate)
FEMA
2488 | FUMARIC ACID
인화점
230 °C
저장 조건
Store below +30°C.
용해도
95% ethanol: soluble0.46g/10 mL, clear, colorless
물리적 상태
Fine Crystalline Powder
산도 계수 (pKa)
3.02, 4.38(at 25℃)
색상
White
수소이온지수(pH)
2.1 (4.9g/l, H2O, 20℃)
폭발한계
40%
수용성
0.63 g/100 mL (25 ºC)
Merck
14,4287
JECFA Number
618
BRN
605763
안정성
Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.
InChIKey
VZCYOOQTPOCHFL-OWOJBTEDSA-N
CAS 데이터베이스
110-17-8(CAS DataBase Reference)
NIST
Fumaric acid(110-17-8)
EPA
Fumaric acid (110-17-8)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 36
안전지침서 26
유엔번호(UN No.) UN 9126
WGK 독일 1
RTECS 번호 LS9625000
자연 발화 온도 375 °C
TSCA Yes
HS 번호 29171900
유해 물질 데이터 110-17-8(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 9300 mg/kg LD50 dermal Rabbit 20000 mg/kg
기존화학 물질 KE-13658
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
예방조치문구:
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P337+P313 눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.
NFPA 704
1
2 0

푸말산 C화학적 특성, 용도, 생산

개요

푸마르산은 고체 유기산 중 가격이 저렴하고 그 효과가 커서 가장 경제적인 산으로 알려져 있다. 푸마르산은 강하고 독특한 수렴성 신맛을 가지고 있는데, 시트르산의 신맛보다 1.8배 강하다. 포화수용액의 pH는 2.2~2.7이며, 녹는점은 287℃이다. 인체 대사과정인 크렙스 회로(Krebs Cycle)의 중간체로 생성되며 인체에 중요한 유기산이다.

용도

푸마르산은 물에 잘 녹지 않아 청량음료, 과일 통조림 등에 시트르산 혹은 타타르산과 함께 사용하며 이때 시트르산의 20~30% 정도 첨가한다. 비흡습성이므로 분말식품에 사용하면 효과적이고 물에 용해도가 낮아 분말주스의 발포제로 사용하면 기포의 지속성에 좋다. 이외에 합성 청주나 절임류에 푸마르산일나트륨과 석신산이나트륨 등과 함께 사용한다. 팽창제의 지효성 산성물질로 사용되며, 유지식품의 산화방지제와 함께 사용하면 산화방지 효과가 증대된다. 밀폐용기에 보관한다.

개요

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.

화학적 성질

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.

화학적 성질

Fumaric acid is a colorless to white, odorless crystalline powder. Fruity-acidic taste.

화학적 성질

Fumaric acid occurs as white, odorless or nearly odorless, granules or as a crystalline powder that is virtually nonhygroscopic.

화학적 성질

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.

화학적 성질

Fumaric acid is odorless with a tart, acidic-sour favor Fumaric acid is used as a replacement of tartaric acid.

출처

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

용도

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.

용도

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.

용도

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.

용도

Occurs in many plants. Essential to vegetable and tissue respiration. Used as an antioxidant.

정의

ChEBI: A butenedioic acid in which the C2C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.

제조 방법

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

정의

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.

정의

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.

생산 방법

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.

생명 공학 생산

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.

일반 설명

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.

공기와 물의 반응

Slightly soluble in water.

반응 프로필

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).

건강위험

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

잠재적 노출

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.

저장

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.]

비 호환성

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.

비 호환성

Fumaric acid undergoes reactions typical of an organic acid.

폐기물 처리

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.

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