| Identification | Back Directory | [Name]
Neotame | [CAS]
165450-17-9 | [Synonyms]
NEOTAME
NEOTAME (200 MG)
L-Phenylalanine,N-(3,3-diMethylbutyl)-L-a-aspartyl-,2-Methyl ester
N-[N-(3,3-dimethylbutyl)-L--aspartyl]-L-phenylalanine 1-methyl ester
N-(N-(3,3-Dimethylbutyl)-L-alpha-aspartyl)-L-phenylalanine 1-methyl ester
L-PHENYLALANINE, N-[N-(3,3-DIMETHYLBUTYL)-L-.ALPHA.-ASPARTYL]-, 1-METHYL ESTER
(S)-3-((3,3-DiMethylbutyl)aMino)-4-(((S)-1-Methoxy-1-oxo-3-phenylpropan-2-yl)aMino)-4-oxobutanoic acid | [EINECS(EC#)]
253-404-6 | [Molecular Formula]
C20H30N2O5 | [MDL Number]
MFCD09039056 | [MOL File]
165450-17-9.mol | [Molecular Weight]
378.46 |
| Chemical Properties | Back Directory | [Melting point ]
83-85°C | [alpha ]
D -54.84° (c = 1 in methanol); D20 -39.8° (c = 0.5 in water) | [Boiling point ]
565.3±50.0 °C(Predicted) | [density ]
1.133±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Sparingly), Ethanol (Sparingly), Ethyl Acetate (Sparingly), Methanol | [form ]
neat | [pka]
pKa1 3.01; pKa2 8.02(at 25℃) | [color ]
White to Off-White | [optical activity]
[α]/D -41.0±3.0°, c = 0.5 in H2O | [BRN ]
8352678 | [Stability:]
Hygroscopic | [InChI]
InChI=1/C20H30N2O5/c1-20(2,3)10-11-21-15(13-17(23)24)18(25)22-16(19(26)27-4)12-14-8-6-5-7-9-14/h5-9,15-16,21H,10-13H2,1-4H3,(H,22,25)(H,23,24)/t15-,16-/s3 | [InChIKey]
HLIAVLHNDJUHFG-HOTGVXAUSA-N | [SMILES]
C(=O)([C@@H](NCCC(C)(C)C)CC(O)=O)N[C@@H](CC1=CC=CC=C1)C(OC)=O |&1:2,15,r| | [LogP]
3.834 (est) | [Uses]
Neotame is a high intensity sweetener and flavor enhancer for use in
foods, except in meat and poultry. it is 7,000–13,000 times sweeter
than sugar and has a clean, sweet taste. it is a derivative of the dipep-
tide composed of amino acids, aspartic acid, and phenylalanine. it
can be blended with nutritive sweeteners such as sucrose and high
fructose corn syrup as well as with high intensity sweeteners such
as aspartame and sucralose. uses include beverages, baked goods,
desserts, cereals. it functions as a flavor enhancer in certain applica-
tions and flavor systems, such as mint-flavored chewing gum. |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Usage]
A labelled alkylated dipeptide reported to be 6000 to 10000 times sweeter than sucrose; structurally related to Aspartame. A non-nutritive sweetener. | [Usage]
An alkylated dipeptide reported to be 6000 to 10000 times sweeter than sucrose; structurally related to Aspartame. A non-nutritive sweetener. | [Definition]
ChEBI: A dipeptide composed of N-(3,3-dimethylbutyl)-L-aspartic acid and methyl L-phenylalanate units joined by a peptide linkage. | [Preparation]
Neotame is manufactured by the reaction of aspartame and 3,3-dimethylbutyraldehyde, followed by purification, drying
and milling | [Production Methods]
Neotame is manufactured by the reaction of aspartame and 3,3-
dimethylbutyraldehyde, followed by purification, drying, and
milling. | [benefits]
Neotame is sweet. 7,000 to 13,000 times sweeter than sugar.
It has no unwanted off-taste or aftertaste that many other sweeteners is burden with.
Neotame does not contribute energy (0 kcal), does not affect blood sugar levels (glycaemic index GI is 0) and does not cause caries.
Compared to aspartame, it is cheaper and has several food technology advantages. | [Pharmaceutical Applications]
Neotame is a water-soluble, nonnutritive, intense sweetening agent
used in beverages and foods. It is structurally related to aspartame
and is about 7000–13 000 times sweeter than sucrose, and about
30–60 times sweeter than aspartame, making it the sweetest
artificial sweetener available. Neotame is said to have a ‘clean’
sweet taste in contrast to the bitter, metallic aftertaste associated
with saccharin. Although neotame has approximately the same
caloric value as sucrose (1.2 kJ/g) the small quantities used to
achieve a desired level of sweetness in a formulation mean that it is
essentially nonnutritive.
Neotame may be used in sub-sweetening quantities as a flavor
enhancer, e.g. with mint or strawberry flavor. | [Safety]
Neotame is a nonnutritive intense sweetening agent used in
beverages and foods. Studies in animals and humans have shown
that neotame is a relatively nontoxic, nonteratogenic, and
noncarcinogenic substance. It is reported as safe for use during
pregnancy and lactation, and by children and persons with diabetes.
At least 30% of ingested neotame is rapidly absorbed. Neotame
is metabolized to de-esterified neotame and methanol, with
practically all neotame being eliminated from the body in the urine
and feces. Peak plasma concentrations of neotame are observed at approximately 30–60 minutes after ingestion. Human studies in
healthy and diabetic patients suggest that neotame is well-tolerated
at doses up to 1.5 mg/kg body-weight daily (the highest dose
studied). Following reviews of over 100 animal and human toxicity
studies the European Food Safety Authority and WHO have
established an acceptable daily intake for neotame at up to 2 mg/kg
body-weight. | [Metabolism]
In the body, neotame is broken down rapidly and completely.
The residual products are de-esterified neotame (92 per cent) and methanol (8 per cent).
80 per cent have left the body the natural way within two days. The rest will follow. 64 per cent via faeces. The rest via urine. Nothing accumulates in the body. | [storage]
Neotame is stable in bakery products and pasteurized dairy
products.
The bulk material should be stored in a well-closed container, in
a cool, dry place; it is stable for up to 5 years at room temperature. | [Regulatory Status]
Accepted for use as a food additive in several countries including the
USA, Mexico, Australia, and New Zealand. Approved for use in
India in pharmaceutical preparations. |
| Questions And Answer | Back Directory | [Intensity sweetener]
Sweetener (intense Sweetener). Its sweetness is very high, usually it is 50 times higher than that of sucrose. According to different sources, there is a natural extract, natural product chemistry modified semisynthetic products and pure chemical synthesis products. A large supply of natural extracts is the main Stevia extract and long winded Sweet and natural product chemistry modified products such as aspartame, neotame and sucralose, pure synthetic chemical products such as saccharin, cyclamate and acesulfame.
Sweetener can be used for low calorie baked food sweetener, but must have a good thermal stability. Aspartame has been approved for use in food, but due to its poor thermal stability and is not suitable for baking food. American newt company newest development of neotame is aspartame derivative, its thermal stability and sweetness have greatly improved and sweet pure than aspartame, sweet good distribution is used for baking food, which has great potential for development of the sweetener.
Neotame is aspartate dipeptide derivatives, is a new product developed at a cost of $80 million by American newt company after aspartame, representing the latest achievements of sweetener research field. It is according to the human sweet receptor double hydrophobic binding hypothesis. In aspartame molecule with a hydrophobic groups and the formation of aspartame derivatives. It can also act on the human sweet receptor of two hydrophobic binding sites and therefore sweetness increased greatly, 6000 to 10000 times sweeter than sucrose, 30 to 60 times than Biasiba sweet.
It retains many excellent characteristics such as aspartame, pure sweet taste and good flavor enhancing properties distribution, no energy, no caries, stable in acidic medium. Moreover, it is still a lot better than aspartame in dry conditions, it has a longer shelf life; in neutral medium or instantaneous high temperature sterilization conditions, its stability greatly exceed aspartame, which can be used as a sweetener in baking. Neotame can also be used together with reducing sugar and aldehyde flavor without adverse reaction, its safety is better than aspartame and has been greatly improved. Due to its high sweetness, etc. Sweeter is lower than the cost of aspartame. Therefore, neotame has huge market potential. In December of 1998, neotame as food sweeteners status of application have been proposed in the United States, and some other countries for the certification work is in July 9, 2002 . The U. S. Food and Drug Administration (FDA) confirmed the neotame safety and functional type, currently is in March 10, worldwide more regulatory agency and national review in 2003, China's Ministry of Health approval for neotame as a sweetener used in all kinds of food. | [Solubility]
The solubility of neotame in water, is 12.6g/L at 25℃, aspartame is 10g/L. Achieve multiple solubility with 10% of sucrose solution equal sweetness, namely MRS10% numerical, is about 740. That is, neotame solubility ratio to reach 10% sucrose solution equal sweetness of solubility about 740 times. In contrast, the multiples of the aspartame is only about 19. It is worth that neotame is as salt (such as phosphate) or complex (such as beta-the link dextrin compound), its dissolution rate in water will increase significantly. Neotame in anhydrous ethanol solubility is very high, at 25℃ about 950g/L, over aspartame (25℃for 3.7g/l) 250 times.
The above information is edited by the Chemicalbook Han Ya.
| [Aspartame]
Aspartame is a kind of artificial sweeteners, which belongs to the two amino acid peptide derivatives, found by the chemist in 1965. With the development of ulcer drugs in low dosage, high sweetness (sugar sweetness 150~200 times), good taste, can improve citrus and other fruit flavor, reduce the heat, do not produce dental caries, toxicity is artificial sweeteners saccharin and other advantages, is widely used in food and beverage, diabetes, some health food, cola drink in our daily life. This product contains formula,which was the main degradation of aspartame in metabolic processes in vivo for phenylalanine, aspartic acid and methanol, does not enter blood circulation, accumulation not in the human body, harmless in healthy people. But because of phenylketonuria (PKU) patients with metabolic defects, excessive body phenylalanine can affect their development, so the patients are banned to add aspartame Food. | [Sweetness characteristics]
It is the world's most sweet sweetener by far, is also the world's most safe sweetener tastes closest to sucrose.
Neotame pure sweet, is very close to aspartame, no other strong sweet agent, often with the bitterness and metallic taste. Under a variety of conditions, its flavor distribution are no significant difference from aspartame , while the neotame sweet stimulate the formation and sucrose is similar, but compared with aspartame, can feel the sweetness of the initial lag slightly, and the sweet taste of duration, slightly long. Similar with aspartame, in complex food system, it is according to need to be other ingredients, such as polyol, sucrose or containing oxygen acid to change these temporary effect.
In October 2003, China's Ministry of Health approved neotame as a sweetener common in a variety of foods and beverages, add the amount according to the requirement of production, neotame is China's Ministry of health only approved in food, is not limited to use of a safe sweetener. A large number of the results show that , neotame is practical to include children, pregnant women, lactating women and patients with diabetes mellitus, all populations. The usage of neotame without of phenylketonuric patients indicates especially, neotame is the sweetener market only without taboo groups of artificial sweet taste agent.
Neotame in the human body can be quickly metabolism. The main metabolic pathway is through the body to produce the enzyme in the hydrolysis of methyl ester, the last generation of the defatted neotame and methanol. Neotame in human generated by decomposition of methanol is far not enough to pose a health hazard to the human body. Compared with ordinary food such as fruit, vegetables and vegetable juice, decomposed from neotame methanol volume is minimal. For example, tomato juice in methanol content exceeded containing neotame beverages 200 times. Neotame can with urine and feces completely eliminated from the body, not in the human body accumulation.
It can also enhance the flavor of certain foods and beverages, especially acid type fruit flavor (such as orange, lemon and grapes) and cherry flavor. And aspartame is different, neotame and acesulfame, saccharin has no synergistic effect between sweetness, providing more convenience for the new product development of food and beverage manufacturers, because neotame can be used alone, or with other nutritional or non nutritive sweeteners mixed use. Its appearance provides a more flexible solution for sweet food manufacturers. Adding can inhibit the aging of starch in starch food, prolong the shelf life of food products; in the egg, adding inhibited protein denaturation , keep good taste in fish protein rich food such as food.
| [Safety and Toxicology]
Neotame enters the human body, about half of the two 3,3-methyl butyl aspartyl phenylalanine (DMB-Asp-Phe) form by the fecal excretion. The other half is wholly intact absorption, then further hydrolyzed into methanol and DMB-Asp-Phe. Most of the DMB-Asp-Phe (half2life 2H) through the urine, and there is no more in any organization other residues; only a small portion of the metabolism of the body, the formation of two 3,3-methyl butyric acid is by oxidation of 3,3-two methyl butyl part, as a kind of human carnitine esters (Carnitine ester, less than the new sweet intake of 5%) in the urine. It is worth noting that aspartame metabolism is very different from the neotame. Aspartame in the lumen of the gut or mucosal cell is decomposed into 3 components: aspartic acid (Asp), phenylalanine (Phe) and methanol. These components are absorbed into the body. Venous circulation is in amino acid metabolism. So it can be concluded that, aspartame is metabolized completely absorbed, while more than 90% of neotame are excreted through the feces.
In the process of metabolism, aspartame can release 55% of phenylalanine. Phenylalanine is one kind of 8 kinds of essential amino acids in the metabolic pathways of metabolism usually enter, but suffering from phenylketonuria (PKU) of the patients lack the ability to metabolize phenylalanine. Although compared with the meat, milk and other protein foods, phenylalanine content aspartame is very low. But many countries stipulate that foods containing aspartame must be indicated on the packaging of the product, which contains phenylalanine, PKU to remind the patient's attention. Because of the concentration to increase its sweet food in neotame than aspartame low (low to 2.5%), so that the content of phenylalanine products is very low. Hydrate containing 17mg/L neotame single equivalent 7.08mg/L containing phenylalanine, phenylalanine was significantly lower than fruit juice. Moreover, 17mg in phenylalanine metabolic pathway by neotame Into the body of the effective number is lower, insufficient 0.7mg, release than aspartame low to about 0.25%. Therefore, neotame increase sweet food. There is no need to specify which contains phenylalanine.
From the extensive safety testing, it can be seen, neotame and its main metabolic products DMB-Asp-Phe for normal body are safe and non mutagenic, teratogenic or carcinogenic, not on reproductive or target organ toxicity. Very low usage, and the molecular and major metabolic product of very favorable pharmacokinetic properties make it very high security.
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