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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.
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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.
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순도시험
(1) 용상 : 이 품목 0.5g을 수산화나트륨시액 10mL에 녹일 때, 그 액은 무색 징명하여야 한다.
(2) 황산염 : 이 품목 1g에 물 30mL를 가하여 흔들어 섞고 페놀프탈레인시액 1방울을 가하여 액이 엷은 홍색을 나타낼 때까지 암모니아시액을 적가하여 녹이고 묽은염산 1mL를 가하여 이를 시험용액으로 하여 황산염시험법에 따라 시험할 때, 그 양은 0.01N 황산 0.2mL에 대응하는 양 이하이어야 한다.
(3) 비소 : 이 품목을 비소시험법에 따라 시험할 때, 그 양은 4.0ppm 이하이어야 한다.
(4) 납 : 이 품목 5.0g을 취하여 원자흡광광도법 또는 유도결합플라즈마발광광도법에 따라 시험할 때, 그 양은 2.0ppm 이하이어야 한다.
(5) 수은 : 이 품목을 수은시험법에 따라 시험할 때, 그 양은 1.0ppm 이하이어야 한다.
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확인시험
(1) 이 품목을 가열하면 승화한다.
(2) 이 품목 50mg을 시험관에 취하고, 레소르신 2～3mg 및 황산 1mL를 가하여 흔들어 섞어 120～130℃에서 5분간 가열하고, 식힌 다음 물을 가하여 5mL로 한다. 이를 식히면서 수산화나트륨용액(2→5)을 적가하여 알칼리성으로 하고 다시 물을 가하여 10mL로 한 액은 자외선 아래에서 청록색의 형광을 나타낸다.
(3) 이 품목 0.5g에 물 10mL를 가하여 끓여서 녹이고 뜨거울 때 브롬시액 2～3방울을 가하면 시액의 색은 없어진다.
(4) 이 품목을 105℃에서 3시간 건조할 때, 그 융점은 287～302℃이다.
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정량법
이 품목 약 1g을 정밀히 달아 물에 녹여 250mL로 하고 그 중 25mL를 취하여 0.1N 수산화나트륨용액으로 적정한다(지시약 : 페놀프탈레인시액 2방울).
0.1N 수산화나트륨용액 1mL ＝ 5.804mg C4H4O4
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강열잔류물
이 품목의 강열잔류물은 0.05% 이하이어야 한다.
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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.
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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.
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출처
Reported found in several plants, Fumaria offcinalis L , Boletus scaber Boll and lean raw fsh
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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.
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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.
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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.
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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.
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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.
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공기와 물의 반응
Slightly soluble in water.
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건강위험
Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation.
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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.
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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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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.
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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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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.
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Purification Methods
Crystallise it from hot M HCl or water and dry it at 100o. [Beilstein 2 IV 2202.]
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비 호환성
Fumaric acid undergoes reactions typical of an organic acid.
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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.
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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.
