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아스파탐

아스파탐
아스파탐 구조식 이미지
카스 번호:
22839-47-0
한글명:
아스파탐
동의어(한글):
아스파르탐;아스파탐;아스파르탐(ASPARTAME)
상품명:
Aspartame
동의어(영문):
APM;mer;RP38;E962;Equal;E 951;c-mer;sc18862;ASPARTAM;canderel
CBNumber:
CB4345527
분자식:
C14H18N2O5
포뮬러 무게:
294.3
MOL 파일:
22839-47-0.mol

아스파탐 속성

녹는점
242-248 °C
알파
15.5 º (c=4, 15N formic acid)
끓는 점
436.08°C (rough estimate)
밀도
1.2051 (rough estimate)
굴절률
14.5 ° (C=4, 15mol/L Formic Acid)
저장 조건
2-8°C
용해도
Sparingly soluble or slightly soluble in water and in ethanol (96 per cent), practically insoluble in hexane and in methylene chloride.
산도 계수 (pKa)
pKa 3.19±0.01 (H2O t=25.0 I=0.100(NaCl))(Approximate);7.87±0.02(H2O t=25.0 I=0.100(NaCl))(Approximate)
물리적 상태
Powder
색상
White
수소이온지수(pH)
pH(8g/l, 25℃) : 4.5~6.0
수용성
Soluble in formic acid, dimethyl sulfoxide. Sparingly soluble in water and ethanol.
Merck
14,839
BRN
2223850
안정성
Stable. Incompatible with strong oxidizing agents.
InChIKey
IAOZJIPTCAWIRG-QWRGUYRKSA-N
CAS 데이터베이스
22839-47-0(CAS DataBase Reference)
EPA
L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester(22839-47-0)

안전

안전지침서 22-24/25
WGK 독일 2
RTECS 번호 WM3407000
TSCA Yes
HS 번호 29242990
유해 물질 데이터 22839-47-0(Hazardous Substances Data)

아스파탐 MSDS


Aspartame

아스파탐 C화학적 특성, 용도, 생산

개요

아스파탐은 합성 감미료의 일종인 아스파틸-페닐알라닌-1-메틸 에스터의 이름으로, 일반 설탕인 자당의 약 200배의 단맛을 낸다. 대표적인 아미노산계 합성 감미료로 그 사용 폭이 매우 넓다.

용도

고감미 감미료 중 설탕과 가장 비슷한 맛이 날뿐 아니라 설탕의 200분의 1 정도만 사용하면 되기 때문에, 많은 식품에 설탕 대용의 저칼로리 감미료로 쓰이고 있다. 특히, 다이어트 콜라와 같은 저가당 식품에 많이 쓰인다.

개요

Aspartame is the most popular artificial sweetener in the United States. It is sold as sweeteners such as NutraSweet and Equal, but it is also incorporated into thousands of food products.

화학적 성질

Aspartame occurs as an off white, almost odorless crystalline powder with an intensely sweet taste.

화학적 성질

white powder or tablets

화학적 성질

Aspartame (N-L-aspartyl-L-phenylalanine-1-methyl ester, 3-amino-N-(a-carbomethoxy- phenethyl)-succinamic acid-N-methyl ester) is an intense sweetener widely used in foods and beverages. Its solubility in water is approximately 10 g/L at room temperature. Aspartame is not fully stable under common processing and storage conditions of foods and beverages with the highest stability around pH 4.3. Aspartame is about 200 times sweeter than sucrose with a clean, but slightly lingering sweetness. It is used as the single sweetener, but often also in blends with other intense sweeteners owing to synergistic taste enhancement and taste quality improvement often seen in such blends.
In the European Union, aspartame is approved as E 951 for a large number of food applications. In the United States, it is approved as a multipurpose sweetener for food and beverage uses and it is also approved in many other countries.

화학적 성질

Aspartame has no odor, but has an intense sweet taste. It is a high intensity sweetener, about 160 to 200 times sweeter than sucrose. Normal digestive processes convert aspartame to phenylalanine, aspartic acid and methanol. Metabolism of aspartame in the body provides approximately 17 kJ (4 kcal)/g. The stability of aspartame is affected by moisture, pH and temperature. For a detailed description of this compound, refer to Burdock (1997).

역사

Aspartame was discovered accidentally in 1965 during a search for drugs to treat gastric ulcers. James M. Schlatter, an organic chemist working for G. D. Searle & Company, was using aspartyl-phenylalanine methyl ester (aspartame) in a synthesis procedure and inadvertently got some of the compound on his hands.

용도

Aspartame in powder form for limited uses such as cereals, powdered drinks, and chewing gum. When aspartame is used in baked goods and baking mixes, it should not exceed 0.5% by weight. Packages of the dry, free-fl owing aspartame are required to prominently display the sweetening equivalence in teaspoons of sugar.

용도

Non-nutritive sweetener.

용도

Aspartame is a high-intensity sweetener that is a dipeptide, provid- ing 4 cal/g. it is synthesized by combining the methyl ester of phenylalanine with aspartic acid, forming the compound n-l-alpha- aspartyl-l-phenylalanine-1-methyl ester. it is approximately 200 times as sweet as sucrose and tastes similar to sugar. it is compara- tively sweeter at low usage levels and at room temperature. its mini- mum solubility is at ph 5.2, its isoelectric point. its maximum solubility is at ph 2.2. it has a solubility of 1% in water at 25°c. the solubility increases with temperature. aspartame has a certain insta- bility in liquid systems which results in a decrease in sweetness. it decomposes to aspartylphenylalanine or to diketropiperazine (dkp) and neither of these forms is sweet. the stability of aspartame is a function of time, temperature, ph, and water activity. maximum stability is at approximately ph 4.3. it is not usually used in baked goods because it breaks down at the high baking temperatures. it contains phenylalanine, which restricts its use for those afflicted with phenylketonuria, the inability to metabolize phenylalanine. uses include cold breakfast cereals, desserts, topping mixes, chew- ing gum, beverages, and frozen desserts. the usage level ranges from 0.01 to 0.02%.

용도

A dipeptide ester about 160 times sweeter than sucrose in aqueous solution. A non-nutritive sweetener.

정의

ChEBI: A dipeptide composed of methyl L-phenylalaninate and L-aspartic acid joined by a peptide linkage.

생산 방법

Aspartame is synthesized using the L enantiomer of phenylalanine. The L enantiomer is separated from the D enantiomer, the racemic mixture, by reacting it with acetic anhydride (CH32

생산 방법

Aspartame is produced by coupling together L-phenylalanine (or Lphenylalanine methyl ester) and L-aspartic acid, either chemically or enzymatically. The former procedure yields both the sweet aaspartame and nonsweet β-aspartame from which the α-aspartame has to be separated and purified. The enzymatic process yields only α-aspartame.

제조 방법

By coupling the amino acids L-phenylalanine and L-aspartic acid, and the esterification of the carboxyl group of the phenylalanine moiety to produce the methyl ester. This esterification can occur before or after coupling. The crystallized slurry is centrifuged and the resulting “wet-cake” is washed to remove impurities.

생명 공학 생산

Aspartame is produced from L-aspartic acid and L-phenylalanine and methanol or alternatively L-phenylalanine methyl ester. The standard process uses common chemical methods of peptide synthesis. Enzymatic coupling of the two amino acids is also possible. N-formyl-L-aspartic acid and L- or D.L-phenylalanine methyl ester can be condensed to aspartame by thermolysin-like proteases. The formylated aspartame can be deformylated chemically or with a formylmethionyl peptide deformylase to yield the sweetener.The enzymatic coupling does not require L-phenylalanine but can start from the racemic product obtained in chemical synthesis, and the remaining D-phenylalanine can be racemized again.
Production processes based on fermentation are available for the two main components, aspartic acid and phenylalanine.

Pharmaceutical Applications

Aspartame is used as an intense sweetening agent in beverage products, food products, and table-top sweeteners, and in pharmaceutical preparations including tablets, powder mixes, and vitamin preparations. It enhances flavor systems and can be used to mask some unpleasant taste characteristics; the approximate sweetening power is 180–200 times that of sucrose.
Unlike some other intense sweeteners, aspartame is metabolized in the body and consequently has some nutritive value: 1 g provides approximately 17 kJ (4 kcal). However, in practice, the small quantity of aspartame consumed provides a minimal nutritive effect.

Safety

Aspartame is widely used in oral pharmaceutical formulations, beverages, and food products as an intense sweetener, and is generally regarded as a nontoxic material. However, the use of aspartame has been of some concern owing to the formation of the potentially toxic metabolites methanol, aspartic acid, and phenylalanine. Of these materials, only phenylalanine is produced in sufficient quantities, at normal aspartame intake levels, to cause concern. In the normal healthy individual any phenylalanine produced is harmless; however, it is recommended that aspartame be avoided or its intake restricted by those persons with phenylketonuria.
The WHO has set an acceptable daily intake for aspartame at up to 40 mg/kg body-weight. Additionally, the acceptable daily intake of diketopiperazine (an impurity found in aspartame) has been set by the WHO at up to 7.5 mg/kg body-weight.
A number of adverse effects have been reported following the consumption of aspartame, particularly in individuals who drink large quantities (up to 8 liters per day in one case) of aspartame-sweetened beverages. Reported adverse effects include: headaches; grand mal seizure;memory loss;gastrointestinal symptoms; and dermatological symptoms. However, scientifically controlled peer-reviewed studies have consistently failed to produce evidence of a causal effect between aspartame consumption and adverse health events. Controlled and thorough studies have confirmed aspartame’s safety and found no credible link between consumption of aspartame at levels found in the human diet and conditions related to the nervous system and behavior, nor any other symptom or illness. Aspartame is well documented to be nongenotoxic and there is no credible evidence that aspartame is carcinogenic.
Although aspartame has been reported to cause hyperactivity and behavioral problems in children, a double-blind controlled trial of 48 preschool-age children fed diets containing a daily intake of 38 ± 13 mg/kg body-weight of aspartame for 3 weeks showed no adverse effects attributable to aspartame, or dietary sucrose, on children’s behavior or cognitive function.

효소 저해제

This popular artificial sweetener (FW = 294.31 g/mol), also known as N- (L-a-aspartyl)-L-phenylalanine methyl ester and EQUAL?, is a dipeptide ester that is ~160x sweeter than in aqueous sucrose. Aspartame exhibits dose-dependent inhibition of L-glutamate binding to the N-methyl-D- aspartame (NMDA) receptor in rat brain synaptosomes. Target(s): peptidyl-dipeptidase A, or angiotensin-converting enzyme; weakly inhibited; thrombin, weakly inhibited; acetylcholinesterase, weakly inhibited. Note: L-Aspartyl-L-phenylalanine, formed by the action of esterases, inhibits Angiotensin Converting Enzyme from rabbit lung (Ki = 11 μM, comparable to the IC50 of 12 μM for 2-D-methyl-succinyl-L- proline, an orally active antihypertensive agent in rats.

신진 대사 경로

The rate of aspartame degradation is faster in a phosphate buffer solution than in a citrate buffer solution at the same pH and buffer concentration. The primary mechanism by which aspartame degrades, the formation of diketo piperazine, involves the nucleophilic attack of carbonyl by the free amine, which requires proton transfer.

저장

Aspartame is stable in dry conditions. In the presence of moisture, hydrolysis occurs to form the degradation products L -aspartyl-Lphenylalanine and 3-benzyl-6-carboxymethyl-2,5-diketopiperazine with a resulting loss of sweetness. A third-degradation product is also known, β-L-aspartyl-L-phenylalanine methyl ester. For the stability profile at 258℃ in aqueous buffers.
Stability in aqueous solutions has been enhanced by the addition of cyclodextrins, and by the addition of polyethylene glycol 400 at pH 2. However, at pH 3.5–4.5 stability is not enhanced by the replacement of water with organic solvents.
Aspartame degradation also occurs during prolonged heat treatment; losses of aspartame may be minimized by using processes that employ high temperatures for a short time followed by rapid cooling.
The bulk material should be stored in a well-closed container, in a cool, dry place.

비 호환성

Differential scanning calorimetry experiments with some directly compressible tablet excipients suggests that aspartame is incompatible with dibasic calcium phosphate and also with the lubricant magnesium stearate. Reactions between aspartame and sugar alcohols are also known.

Regulatory Status

Accepted for use as a food additive in Europe and in the USA. Included in the FDA Inactive Ingredients Database (oral powder for reconstitution, buccal patch, granules, syrups, and tablets). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

아스파탐 준비 용품 및 원자재

원자재

준비 용품


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