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アルパルテーム

アルパルテーム 化学構造式
22839-47-0
CAS番号.
22839-47-0
化学名:
アルパルテーム
别名:
アルパルテーム;N-L-α-アスパルチル-L-フェニルアラニン1-メチル;カンデレル;N-(α-アスパルチル)-L-フェニルアラニン1-メチル;スイートジペプチド;アスパルテーム;アスパルタム;N-(α-アスパルチル)-L-Phe-OMe;ジペプチド甘味料;L-アスパルチル-L-フェニルアラニンメチルエステル;アスパルテーム標準品;α-L-アスパルチル-L-フェニルアラニンメチルエステル;L‐アスパルチル‐L‐フェニルアラニンメチルエステル;N-L-Α-アスパルチル-L-フェニルアラニン-1-メチルエステル;ASP-PHEメチルエステル
英語化学名:
Aspartame
英語别名:
APM;mer;RP38;E962;Equal;E 951;c-mer;sc18862;ASPARTAM;canderel
CBNumber:
CB4345527
化学式:
C14H18N2O5
分子量:
294.3
MOL File:
22839-47-0.mol

アルパルテーム 物理性質

融点 :
242-248 °C
比旋光度 :
15.5 º (c=4, 15N formic acid)
沸点 :
436.08°C (rough estimate)
比重(密度) :
1.2051 (rough estimate)
屈折率 :
14.5 ° (C=4, 15mol/L Formic Acid)
貯蔵温度 :
2-8°C
溶解性:
Sparingly soluble or slightly soluble in water and in ethanol (96 per cent), practically insoluble in hexane and in methylene chloride.
酸解離定数(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)
外見 :
Powder
色:
White
PH:
pH(8g/l, 25℃) : 4.5~6.0
水溶解度 :
Soluble in formic acid, dimethyl sulfoxide. Sparingly soluble in water and ethanol.
Merck :
14,839
BRN :
2223850
安定性::
Stable. Incompatible with strong oxidizing agents.
InChIKey:
IAOZJIPTCAWIRG-QWRGUYRKSA-N
CAS データベース:
22839-47-0(CAS DataBase Reference)
EPAの化学物質情報:
L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester(22839-47-0)

安全性情報

Sフレーズ  22-24/25
WGK Germany  2
RTECS 番号 WM3407000
TSCA  Yes
HSコード  29242990
有毒物質データの 22839-47-0(Hazardous Substances Data)
化審法 (9)-1616

アルパルテーム 価格 もっと(32)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01BCS4000411
H-Asp-Phe-OMe
22839-47-0 5g ¥36000 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01BCS4000411
H-Asp-Phe-OMe
22839-47-0 25g ¥147000 2018-12-26 購入
東京化成工業 A0997 アスパルテーム >98.0%(HPLC)(T)
Aspartame >98.0%(HPLC)(T)
22839-47-0 1g ¥3300 2018-12-04 購入
東京化成工業 A0997 アスパルテーム >98.0%(HPLC)(T)
Aspartame >98.0%(HPLC)(T)
22839-47-0 25g ¥11500 2018-12-04 購入
関東化学株式会社(KANTO) 01693-96 アスパルテーム標準品 >99.0%(HLC)
Aspartame standard >99.0%(HLC)
22839-47-0 500mg ¥5500 2018-12-13 購入

アルパルテーム MSDS


Aspartame

アルパルテーム 化学特性,用途語,生産方法

外観

白色, 結晶性粉末~粉末

定義

本品は、アスパラギン酸(*)とフェニルアラニン(*)からなるジペプチドであり、次の化学式で表される。
参照表示名称:アスパラギン酸, フェニルアラニン

溶解性

水にやや溶けやすい。

用途

食品中のアスパルテームの定量用。

化粧品の成分用途

香味剤

効能

甘味料

説明

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.

化学的特性

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).

化学的特性

white powder or tablets

化学的特性

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.

化学的特性

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

来歴

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.

使用

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.

使用

Non-nutritive sweetener.

使用

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%.

使用

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

定義

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

調製方法

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.

調製方法

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

製造方法

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.

Biotechnological Production

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.

応用例(製薬)

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.

安全性

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.

酵素阻害剤

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.

代謝経路

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.

貯蔵

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.

不和合性

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.

規制状況(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.

アルパルテーム 上流と下流の製品情報

原材料

準備製品


アルパルテーム 生産企業

Global( 386)Suppliers
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22839-47-0(アルパルテーム)キーワード:


  • 22839-47-0
  • H-ASP-PHE-OME
  • Equal
  • APM
  • ASPARTAM
  • ASPARTAME
  • ASP-PHE METHYL ESTER
  • (S)-3-AMINO-N-((S)-1-METHOXYCARBONYL-2-PHENYL-ETHYL)-SUCCINAMIC ACID
  • nutrasweet
  • N-L-ALPHA-ASPARTYL-L-PHENYLALANINE 1-METHYL ESTER
  • N-L-ALPHA-ASPARTYL-L-PHENYLALANINE METHYL ESTER
  • 1-methyln-l-alpha-aspartyl-l-phenylalanine
  • 3-amino-n-(alpha-carboxyphenethyl)succinamicacidn-methylester
  • 3-amino-n-(alpha-carboxyphenethyl)succinamicacidn-methylester,stereoisome
  • 3-amino-n-(alpha-methoxycarbonylphenethyl)succinamicacid
  • sc18862
  • succinamicacid,3-amino-n-(alpha-carboxyphenethyl)-,n-methylester,stereoiso
  • succinamicacid,3-amino-n-(alpha-carboxyphenethyl)-,n-methylester,stereoisomer
  • sweetdipeptide
  • tri-sweet
  • ASPARTAME, 500MG, NEAT
  • Aspartame, Granular
  • L-fenilalnine
  • N-(L-a-Aspartyl)-L-fenilalanine1-metilester
  • ASPARTAME, PHARMA
  • L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester
  • ASPARTAME,FCC
  • ASPARTAME,POWDER,NF
  • 3-amino-3-[(1-methoxycarbonyl-2-phenyl-ethyl)carbamoyl]propanoic acid
  • ASPARTAME(RG)
  • ASPARTAME-ACESULFAMESALT
  • アルパルテーム
  • N-L-α-アスパルチル-L-フェニルアラニン1-メチル
  • カンデレル
  • N-(α-アスパルチル)-L-フェニルアラニン1-メチル
  • スイートジペプチド
  • アスパルテーム
  • アスパルタム
  • N-(α-アスパルチル)-L-Phe-OMe
  • ジペプチド甘味料
  • L-アスパルチル-L-フェニルアラニンメチルエステル
  • アスパルテーム標準品
  • α-L-アスパルチル-L-フェニルアラニンメチルエステル
  • L‐アスパルチル‐L‐フェニルアラニンメチルエステル
  • N-L-Α-アスパルチル-L-フェニルアラニン-1-メチルエステル
  • ASP-PHEメチルエステル
  • オリゴペプチド
  • ペプチド合成
  • 生化学
  • 人工甘味料
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