Alitame
Catalog Number: BT-258128
CAS Number: 80863-62-3
Molecular Formula: C14H25N3O4S
Molecular Weight: 331.43 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Alitame is a non-nutritive sweetener that is commonly used as a sugar substitute in various food and beverage products. It is a dipeptide derivative of aspartame and is approximately 2000 times sweeter than sugar. Alitame was first discovered in 1984 and was approved for use in food and beverages by the US Food and Drug Administration (FDA) in 1996. Since then, it has been used in a wide range of products, including soft drinks, chewing gum, and baked goods.
Properties
CAS Number
80863-62-3
Product Name
Alitame
IUPAC Name
(3S)-3-amino-4-oxo-4-[[(2R)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid
Molecular Formula
C14H25N3O4S
Molecular Weight
331.43 g/mol
InChI
InChI=1S/C14H25N3O4S/c1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5/h7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19)/t7-,8+/m1/s1
InChI Key
IAQFTAYMCCMTSN-SFYZADRCSA-N
SMILES
CC(C(=O)NC1C(SC1(C)C)(C)C)NC(=O)C(CC(=O)O)N
Solubility
In water, approximately 130 g/L at pH 5.0 and room temperature; solubility increases at higher and lower pH, and higher temperature
Synonyms
alitame
alpha-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)alaninamide
alpha-aspartyl-N-(2,2,4,4-tetramethyl-3-thietanyl)alaninamide
Canonical SMILES
CC(C(=O)NC1C(SC1(C)C)(C)C)NC(=O)C(CC(=O)O)N
Isomeric SMILES
C[C@H](C(=O)NC1C(SC1(C)C)(C)C)NC(=O)[C@H](CC(=O)O)N
Method of Synthesis or Extraction
Alitame is synthesized using a multi-step process that involves the reaction of aspartic acid with a variety of other chemicals. The most commonly used method involves the reaction of aspartic acid with 2,2,4-trimethyl-1,3-pentanediol (TMPD) to form the intermediate compound N-(2,2,4-trimethylpentyl)-L-aspartyl-L-phenylalanine 1-methyl ester. This intermediate is then reacted with acetic anhydride to form alitame.
The efficiency and yield of the synthesis process depend on several factors, including the purity of the starting materials, the reaction conditions, and the quality of the final product. The yield of alitame synthesis is typically around 50%, which is relatively low compared to other sweeteners. However, the high sweetness potency of alitame means that only small amounts are needed to achieve the desired level of sweetness.
Environmental and safety considerations are important factors in the synthesis of alitame. The chemicals used in the synthesis process can be hazardous if not handled properly, and the waste products generated during the process can be harmful to the environment. Therefore, it is important to follow strict safety protocols and dispose of waste products in an environmentally responsible manner.
The efficiency and yield of the synthesis process depend on several factors, including the purity of the starting materials, the reaction conditions, and the quality of the final product. The yield of alitame synthesis is typically around 50%, which is relatively low compared to other sweeteners. However, the high sweetness potency of alitame means that only small amounts are needed to achieve the desired level of sweetness.
Environmental and safety considerations are important factors in the synthesis of alitame. The chemicals used in the synthesis process can be hazardous if not handled properly, and the waste products generated during the process can be harmful to the environment. Therefore, it is important to follow strict safety protocols and dispose of waste products in an environmentally responsible manner.
Chemical Structure and Biological Activity
The chemical structure of alitame is similar to that of aspartame, with the addition of a 2,2,4-trimethylpentyl group on the aspartic acid side chain. This modification increases the stability of the molecule and enhances its sweetness potency.
The mechanism of action of alitame is similar to that of other sweeteners, such as aspartame and sucralose. It binds to sweet taste receptors on the tongue, triggering a response that signals the brain to perceive sweetness. Alitame has been shown to have a high binding affinity for sweet taste receptors, which contributes to its high sweetness potency.
Alitame has been found to have a range of biological activities, including antioxidant and anti-inflammatory effects. It has also been shown to have potential therapeutic effects in the treatment of diabetes and obesity, although further research is needed to confirm these findings.
The mechanism of action of alitame is similar to that of other sweeteners, such as aspartame and sucralose. It binds to sweet taste receptors on the tongue, triggering a response that signals the brain to perceive sweetness. Alitame has been shown to have a high binding affinity for sweet taste receptors, which contributes to its high sweetness potency.
Alitame has been found to have a range of biological activities, including antioxidant and anti-inflammatory effects. It has also been shown to have potential therapeutic effects in the treatment of diabetes and obesity, although further research is needed to confirm these findings.
Biological Effects
Alitame has been shown to have a range of effects on cell function and signal transduction. It has been found to modulate the activity of several enzymes and receptors involved in glucose metabolism, which may contribute to its potential therapeutic effects in diabetes and obesity.
Potential therapeutic and toxic effects of alitame are still being studied. Some studies have suggested that alitame may have beneficial effects on glucose metabolism and insulin sensitivity, while others have raised concerns about its potential toxicity and carcinogenicity. Further research is needed to fully understand the biological effects of alitame and its potential therapeutic and toxic effects.
Potential therapeutic and toxic effects of alitame are still being studied. Some studies have suggested that alitame may have beneficial effects on glucose metabolism and insulin sensitivity, while others have raised concerns about its potential toxicity and carcinogenicity. Further research is needed to fully understand the biological effects of alitame and its potential therapeutic and toxic effects.
Applications
Alitame has a wide range of applications in medical, environmental, and industrial research. In medical research, it has been used as a sugar substitute in clinical trials investigating the effects of diet on various health outcomes, such as diabetes and obesity. It has also been studied for its potential therapeutic effects in these conditions.
In environmental research, alitame has been studied for its effects on ecosystems and its role in pollution management. It has been found to have low toxicity and environmental impact, making it a potentially useful tool in pollution management and sustainability efforts.
In industrial research, alitame has been used in manufacturing processes to improve product quality and efficiency. It has also been studied for its health and safety considerations in industrial settings, such as its potential toxicity and carcinogenicity.
In environmental research, alitame has been studied for its effects on ecosystems and its role in pollution management. It has been found to have low toxicity and environmental impact, making it a potentially useful tool in pollution management and sustainability efforts.
In industrial research, alitame has been used in manufacturing processes to improve product quality and efficiency. It has also been studied for its health and safety considerations in industrial settings, such as its potential toxicity and carcinogenicity.
Future Perspectives and Challenges
Despite its potential benefits, there are still several limitations to the use and study of alitame. One of the main challenges is the lack of long-term safety data, particularly with regard to its potential toxic and carcinogenic effects. Further research is needed to fully understand the biological effects of alitame and its potential therapeutic and toxic effects.
Possible solutions and improvements include the development of new synthesis methods that are more efficient and environmentally friendly, as well as the use of advanced analytical techniques to better understand the biological effects of alitame. Future trends and prospects in the application of alitame in scientific research will depend on the results of ongoing studies and the development of new technologies and methods.
Possible solutions and improvements include the development of new synthesis methods that are more efficient and environmentally friendly, as well as the use of advanced analytical techniques to better understand the biological effects of alitame. Future trends and prospects in the application of alitame in scientific research will depend on the results of ongoing studies and the development of new technologies and methods.
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