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アリターム

アリターム 化学構造式
80863-62-3
CAS番号.
80863-62-3
化学名:
アリターム
别名:
アリターム
英語化学名:
Alitame
英語别名:
Alitame;CP 54802;l-α-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide;l-alpha-aspartyl-n-(2,2,4,4-tetramethyl-3-thietanyl)-d-alaninamide;(S)-3-((R)-1-(2,2,4,4-TETRAMETHYLTHIETAN-3-YLCARBAMOYL)ETHYLCARBAMOYL)-3-AMINOPROPANOIC ACID;(S)-3-Amino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetramethylthietan-3-yl)amino)propan-2-yl)amino)bu;(S)-3-Amino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetramethylthietan-3-yl)amino)propan-2-yl)amino)butan;(S)-3-amino-4-(((R)-1-amino-1-oxopropan-2-yl)(2,2,4,4-tetramethylthietan-3-yl)amino)-4-oxobutanoic acid;(S)-3-AMino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetraMethylthietan-3-yl)aMino)propan-2-yl)aMino)butanoic acid;(3S)-3-amino-4-oxo-4-[[(2R)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid
CBNumber:
CB0855163
化学式:
C14H25N3O4S
分子量:
331.43
MOL File:
80863-62-3.mol

アリターム 物理性質

融点 :
136-147°
比旋光度 :
D25 +40 to +50° (c = 1 in water)
沸点 :
608.5±55.0 °C(Predicted)
比重(密度) :
1.25±0.1 g/cm3(Predicted)
酸解離定数(Pka):
3.71±0.10(Predicted)
CAS データベース:
80863-62-3

安全性情報

HSコード  29400090

アリターム 価格 もっと(8)

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) W01COBQA-0539 アリターム
Alitame
80863-62-3 1g ¥60100 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-0539 アリターム
Alitame
80863-62-3 250mg ¥30200 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01TRCA536500 アリターム
Alitame
80863-62-3 500mg ¥56300 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01FLC079520
(S)-3-Amino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetramethylthietan-3-yl)amino)propan-2-yl)amino)butanoic acid
80863-62-3 1g ¥116200 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01TRCA536500 アリターム
Alitame
80863-62-3 1g ¥131300 2018-12-26 購入

アリターム 化学特性,用途語,生産方法

用途

甘味料

化学的特性

White Solid

化学的特性

Alitame is a white nonhygroscopic crystalline powder; odorless or having a slight characteristic odor.

物理的性質

Alitame [L-a-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide] is a sweetener based on an amino acid. It is a very intense sweetener, possessing a sweetening power of about 2000 times that of sucrose. It also exhibits a clean sweet taste similar to sucrose. Although it is metabolized, so little is needed that its caloric contribution is insignificant. Alitame is prepared from the amino acids, L-aspartic acid, D-alamine, and a novel amine.

特性

Alitame is an amino acidbased sweetener developed by Pfizer Central Research from l-aspartic acid, d-alanine, and 2,2,4,4-tetraethylthioethanyl amine. A terminal amide group instead of the methyl ester constituent of ASP was used to improve the hydrolytic stability. The incorporation of d-alanine as a second amino acid in place of l-phenylalanine has resulted in optimum sweetness. The increased steric and lipophilic bulk on a small ring with a sulfur derivative has provided a very sweet product and good taste qualities.
Alitame offers several benefits such as stability at high temperatures and a broader pH range. For instance, it is stable for over a year at pH 6–8 and room temperature and withstands pasteurization. However, prolonged storage of acidic solutions at high temperatures or in combination with certain ingredients (hydrogen peroxide or sodium bisulfite) may produce off-flavors. In the presence of high levels of reducing sugars, alitame can undergo Maillard reactions.

使用

Alitame [L-a-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide] is a sweetener based on an amino acid. It is a very intense sweetener, possessing a sweetening power of about 2000 times that of sucrose. It also exhibits a clean sweet taste similar to sucrose. Although it is metabolized, so little is needed that its caloric contribution is insignificant. Alitame is prepared from the amino acids, L-aspartic acid, D-alamine, and a novel amine.

使用

Non-nutritive sweetener.

使用

Alitame is a dipeptide amide derivative of aspartic acid used as an artificial sweetener. Alitame is about ten times sweeter than Aspartame (A790015) with a half life about twice as long.

調製方法

Alitame may be synthesized by a number of routes.For example, 3-(D-alaninamido)-2,2,4,4-tetramethylthietane is dissolved in water and L-aspartic acid N-thiocarboxyanhydride is then added in portions with vigorous stirring, maintaining the pH of 8.5–9.5. The pH is then adjusted to 5.5 and p-toluenesulfonic acid monohydrate is added over a period of one hour. The precipitated crystalline p-toluenesulfonate salt is collected by filtration. To obtain alitame from its salt, a mixture of Amberlite LA-1 (liquid anion exchange resin), dichloromethane, deionized water, and the salt is stirred for one hour, resulting in two clear layers. The aqueous layer is treated with carbon, clarified by filtration, and cooled to crystallize alitame.
Alternatively, tetramethylthietane amine is condensed with anNprotected form of D-alanine to give alanyl amide. This is then coupled to a protected analogue of L-aspartic acid to give a crude form of alitame. The crude product is then purified.

応用例(製薬)

Alitame is an intense sweetening agent developed in the early 1980s and is approximately 2000 times sweeter than sucrose. It has an insignificant energy contribution of 6 kJ (1.4 kcal) per gram of alitame.
Alitame is currently primarily used in a wide range of foods and beverages at a maximum level of 40–300 mg/kg.

安全性プロファイル

The Joint Expert Committee on Food Additives (JECFA) concluded that alitame was not carcinogenic and did not show reproductive toxicity. In 1996, an ADI of 0–1 mg/kg of body weight was allocated. It is approved for use in Australia, New Zealand, Mexico, and China. A food additive petition was submitted to the FDA in 1986, and approval is awaited. In the petition, the estimated daily intake is 0.34 mg/kg of body weight, which represents the amount if alitame is the only sweetener in the diet. The level at which no observed adverse effects occur in animals is 100 mg/ kg. Potential uses include baked goods, baking mixes, hot and cold beverages, dry beverage mixes, tabletop sweeteners, chewing gum, candies, frozen desserts, and pharmaceuticals. Alitame has been approved for use in some countries such as Australia, Mexico, New Zealand, and China, but not in the United States or the EU.

安全性

Alitame is a relatively new intense sweetening agent used primarily in foods and confectionary. It is generally regarded as a relatively nontoxic and nonirritant material.
Chronic animal studies in mice, rats, and dogs carried out for a minimum of 18 months at concentrations >100 mg/kg per day exhibited no toxic or carcinogenic effects. In people, no evidence of untoward effects were observed following ingestion of 15 mg/kg per day for two weeks.
Following oral administration 7–22% of alitame is unabsorbed and excreted in the feces. The remaining amount is hydrolyzed to aspartic acid and alanine amide. The aspartic acid is metabolized normally and the alanine amide excreted in the urine as a sulfoxide isomer, as the sulfone, or conjugated with glucuronic acid.
The WHO has set an acceptable daily intake of alitame at up to 0.1 mg/kg body-weight.
LD50 (mouse, oral): >5 g/kg
LD50 (rabbit, skin): >2 g/kg
LD50 (rat, oral): >5 g/kg

代謝

Alitame is noncariogenic. From an oral intake, 7%–22% is unabsorbed and excreted in the feces. The remainder is hydrolyzed to aspartic acid and alanine amide. The aspartic acid is normally metabolized, and the alanine amide is excreted in the urine as a sulfoxide isomer, sulfone, or conjugated with glucuronic acid. The incomplete absorption and metabolism result in a core value of 1.4 kcal g?1.

貯蔵

Alitame is stable in dry, room temperature conditions but undergoes degradation at elevated temperatures or when in solution at low pH. Alitame can degrade in a one-stage process to aspartic acid and alanine amide (under harsh conditions) or in a slow two-stage process by first degrading to its β-aspartic isomer and then to aspartic acid and alanine amide. At pH 5–8, alitame solutions at 238℃ have a half-life of approximately 4 years. At pH 2 and 238℃ the half-life is 1 year.
Alitame should be stored in a well-closed container in a cool, dry place.

不和合性

Alitame may be incompatible with oxidizing and reducing substances or strong acids and bases.

規制状況(Regulatory Status)

Alitame is approved for use in food applications in a number of countries worldwide including Australia, Chile, China, Mexico, and New Zealand.

アリターム 上流と下流の製品情報

原材料

準備製品


アリターム 生産企業

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80863-62-3(アリターム)キーワード:


  • 80863-62-3
  • (3s)-3-amino-4-oxo-4-[[(2r)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid
  • Alitame
  • l-alpha-aspartyl-n-(2,2,4,4-tetramethyl-3-thietanyl)-d-alaninamide
  • l-α-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)-D-alaninamide
  • CP 54802
  • (S)-3-AMino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetraMethylthietan-3-yl)aMino)propan-2-yl)aMino)butanoic acid
  • (3S)-3-amino-4-oxo-4-[[(2R)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid
  • (S)-3-Amino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetramethylthietan-3-yl)amino)propan-2-yl)amino)butan
  • (S)-3-amino-4-(((R)-1-amino-1-oxopropan-2-yl)(2,2,4,4-tetramethylthietan-3-yl)amino)-4-oxobutanoic acid
  • (S)-3-Amino-4-oxo-4-(((R)-1-oxo-1-((2,2,4,4-tetramethylthietan-3-yl)amino)propan-2-yl)amino)bu
  • (S)-3-((R)-1-(2,2,4,4-TETRAMETHYLTHIETAN-3-YLCARBAMOYL)ETHYLCARBAMOYL)-3-AMINOPROPANOIC ACID
  • アリターム
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