Neotame

• CAS: 165450-17-9
• Catalog Number: ACM165450179-2
• Category: Main Products
• Molecular Weight: 378.46
• Molecular Formula: C20H30N2O5
• Synonyms: L-Phenylalanine, N-(3,3-dimethylbutyl)-L-α-aspartyl-, 2-methyl ester
• IUPAC Name: (3S)-3-(3,3-Dimethylbutylamino)-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
• Canonical SMILES: CC(C)(C)CCNC(CC(=O)O)C(=O)NC(CC1=CC=CC=C1)C(=O)OC
• InChI: InChI=1S/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-/m0/s1
• InChI Key: HLIAVLHNDJUHFG-HOTGVXAUSA-N
• Boiling Point: 565.3±50.0 °C
• Melting Point: 83-85 °C
• Flash Point: 295.7 °C
• Density: 1.133±0.06 g/cm³
• Appearance: White to off-white powder
• Storage: Keep in dark place, sealed in dry, 2-8 °C
• Active Content: 95%
• Assay: 0.98
• Complexity: 495
• Exact Mass: 378.21547206
• Isomeric SMILES: CC(C)(C)CCN[C@@H](CC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)OC
• Monoisotopic Mass: 378.21547206
• Packaging: 1 kg
• Physical State: Solid
• pKa: pK1: 3.01, pK2: 8.02
• Refractive Index: 1.521
• Topological Polar Surface Area: 105 Ų

Case Study

Effects of the Sweetener Neotame on Weaned Pig Feeding

Zhu, L., et al. Animal Feed Science and Technology, 2016, 214, 86-94.

The study investigated how the sweetener neotame (N-[N-(3,3-dimethylbutyl)-l-α-aspartyl]-l-phenylalanine-1-methyl ester) affects dietary preference and production performance as well as hematological and biochemical parameters in weaned piglets.
· Evaluation methods
Three experiments were conducted using weaned piglets. Experiment 1, a 15-day preference study with 48 piglets (9.05 ± 0.04 kg initial BW), compared a maize-soybean meal diet against the same diet supplemented with 30 mg/kg neotame. Experiment 2, a 35-day growth trial with 216 piglets (7.35 ± 0.06 kg initial BW), evaluated six neotame supplementation levels (0, 10, 20, 30, 40, or 50 mg/kg). Experiment 3, also a 35-day trial with 108 piglets (7.34 ± 0.08 kg initial BW), assessed the impact of 0, 50, and 500 mg/kg neotame on hematological and biochemical parameters.
· Evaluation results
In Experiment 1, piglets preferred the 30 mg/kg neotame diet (P < 0.05) on days 7 and 10, and throughout the 10-day experimental period.
Increasing neotame doses led to linear average daily feed intake (ADFI) improvements throughout both phase I (days 1-22) and the full 35-day study period (P < 0.05). The quadratic impact of neotame (P < 0.05) affected both average daily gain (ADG) and ADFI throughout all phases with optimal concentrations determined at 21.7 mg/kg for ADG and 20.7 mg/kg for ADFI.
Experiment 3 found no significant differences (P > 0.05) in blood parameters, organ indices, or morphology across the three neotame levels. Optimal neotame concentrations for maximizing ADG and ADFI ranged from 18.0 to 20.4 mg/kg during phase I, 22.0 to 22.9 mg/kg during phase II, and 20.7 to 21.7 mg/kg overall, with no observed adverse health effects up to 500 mg/kg.

Effects of the Artificial Sweetener Neotame on Intestinal Bacteria

Chi, Liang, et al. Molecules, 2018, 23(2), 367.

Neotame represents a relatively new compound in artificial sweeteners offering low calories and high sweetness that finds extensive use in food production. The research team used high-throughput sequencing alongside gas chromatography-mass spectrometry (GC-MS) metabolomics to evaluate how neotame impacted the intestinal microflora and fecal metabolite patterns in CD-1 mice.
· A four-week consumption of neotame was found to decrease alpha-diversity and alter beta-diversity in the gut microbiome. Specifically, there was a significant reduction in Firmicutes and an increase in Bacteroidetes.
· Analysis using the Phylogenetic Investigation of Communities by Reconstruction of Unobserved States (PICRUSt) revealed distinct metabolic patterns between control and neotame-treated mice, with a reduction in key genes related to butyrate synthesis.
· Additionally, the fecal metabolite profiles were also modified, showing markedly higher concentrations of various fatty acids, lipids, and cholesterol in the feces of neotame-treated mice compared to controls, while levels of metabolites like malic acid and glyceric acid were significantly lower.

Custom Q&A

What is the molecular formula of neotame?

The molecular formula of neotame is C20H30N2O5.

What is the molecular weight of neotame?

The molecular weight of neotame is 378.5 g/mol.

What is the IUPAC name of neotame?

The IUPAC name of neotame is (3S)-3-(3,3-dimethylbutylamino)-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid.

What is the InChIKey of neotame?

The InChIKey of neotame is HLIAVLHNDJUHFG-HOTGVXAUSA-N.

What are the synonyms of neotame?

Some synonyms of neotame include 165450-17-9, (S)-3-((3,3-Dimethylbutyl)amino)-4-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoic acid, VJ597D52EX, and NC 00723.

What is the CAS number of neotame?

The CAS number of neotame is 165450-17-9.

What is the density of neotame?

The density of neotame is not provided in the reference.

What is the boiling point of neotame?

The boiling point of neotame is not provided in the reference.

Is neotame a sweetening agent?

Yes, neotame is described as a sweetening agent in the reference.

Can neotame be an environmental contaminant?

Yes, neotame can act as an environmental contaminant according to the reference.