Neotame | CAS#165450-17-9 | dipeptide methyl ester

MedKoo Cat#: 597781 | Name: Neotame

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Neotame is a white colored, dipeptide methyl ester, which is found to be a highly potent and non-nutritive sweetener or flavour enhancer and hence finds applications in variety of foods. It is manufactured from aspartame and 3,3-dimethylbutyraldehyde in a one-step chemical synthesis process.

Chemical Structure

Neotame

CAS#165450-17-9

Theoretical Analysis

MedKoo Cat#: 597781

Name: Neotame

CAS#: 165450-17-9

Chemical Formula: C20H30N2O5

Exact Mass: 378.2155

Molecular Weight: 378.47

Elemental Analysis: C, 63.47; H, 7.99; N, 7.40; O, 21.14

Price and Availability

Size	Price	Availability	Quantity
1g	USD 190.00
2g	USD 350.00
5g	USD 650.00
10g	USD 950.00
25g	USD 1,650.00

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Related CAS #

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Synonym

Neotame; NC 00723; NC-00723; NC00723; HSDB 7965;

IUPAC/Chemical Name

(S)-3-((3,3-dimethylbutyl)amino)-4-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoic acid

InChi Key

HLIAVLHNDJUHFG-HOTGVXAUSA-N

InChi Code

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

SMILES Code

O=C([C@H](Cc1ccccc1)NC([C@@H](NCCC(C)(C)C)CC(O)=O)=O)OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Neotame is a derivative of Aspartame and is a low-caloric and high-intensity artificial sweetener.

In vitro activity:

TBD

In vivo activity:

The Phylogenetic Investigation of Communities by Reconstruction of Unobserved States (PICRUSt) analysis also indicated that the control mice and neotame-treated mice have different metabolic patterns and some key genes such as butyrate synthetic genes were decreased. Moreover, neotame consumption also changed the fecal metabolite profiles. Dramatically, the concentrations of multiple fatty acids, lipids as well as cholesterol in the feces of neotame-treated mice were consistently higher than controls. Reference: Molecules. 2018 Feb 9;23(2):367. https://pubmed.ncbi.nlm.nih.gov/29425148/

	Solvent	mg/mL	mM
Solubility
	DMSO	88.0	232.52
	Ethanol	76.0	200.81
	Water	76.0	200.81

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 378.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

Chi L, Bian X, Gao B, Tu P, Lai Y, Ru H, Lu K. Effects of the Artificial Sweetener Neotame on the Gut Microbiome and Fecal Metabolites in Mice. Molecules. 2018 Feb 9;23(2):367. doi: 10.3390/molecules23020367. PMID: 29425148; PMCID: PMC6017827.

In vitro protocol:

TBD

In vivo protocol:

1: Kumari A, Choudhary S, Arora S, Sharma V. Stability of aspartame and neotame in pasteurized and in-bottle sterilized flavoured milk. Food Chem. 2016 Apr 1;196:533-8. doi: 10.1016/j.foodchem.2015.09.082. Epub 2015 Sep 26. PubMed PMID: 26593524. 2: Bathinapatla A, Kanchi S, Singh P, Sabela MI, Bisetty K. Fabrication of copper nanoparticles decorated multiwalled carbon nanotubes as a high performance electrochemical sensor for the detection of neotame. Biosens Bioelectron. 2015 May 15;67:200-7. doi: 10.1016/j.bios.2014.08.017. Epub 2014 Aug 19. PubMed PMID: 25216979. 3: Hu F, Xu L, Luan F, Liu H, Gao Y. Determination of neotame in non-alcoholic beverage by capillary zone electrophoresis. J Sci Food Agric. 2013 Oct;93(13):3334-8. doi: 10.1002/jsfa.6181. Epub 2013 May 29. PubMed PMID: 23595253. 4: Yang D, Chen B. Determination of neotame in beverages, cakes and preserved fruits by column-switching high-performance liquid chromatography. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Sep;27(9):1221-5. doi: 10.1080/19440049.2010.487875. PubMed PMID: 20526922. 5: Doug Z, Padden BE, Salsbury JS, Munson EJ, Schroeder SA, Prakash I, Grant DJ. Neotame anhydrate polymorphs I: preparation and characterization. Pharm Res. 2002 Mar;19(3):330-6. PubMed PMID: 11934241. 6: Dong Z, Munson EJ, Schroeder SA, Prakash I, Grant DJ. Conformational flexibility and hydrogen-bonding patterns of the neotame molecule in its various solid forms. J Pharm Sci. 2002 Sep;91(9):2047-56. PubMed PMID: 12210051. 7: Mayhew DA, Comer CP, Stargel WW. Food consumption and body weight changes with neotame, a new sweetener with intense taste: differentiating effects of palatability from toxicity in dietary safety studies. Regul Toxicol Pharmacol. 2003 Oct;38(2):124-43. PubMed PMID: 14550755. 8: Dong Z, Salsbury JS, Zhou D, Munson EJ, Schroeder SA, Prakash I, Vyazovkin S, Wight CA, Grant DJ. Dehydration kinetics of neotame monohydrate. J Pharm Sci. 2002 Jun;91(6):1423-31. PubMed PMID: 12115842. 9: Prakash I, Bishay IE, Desai N, Walters DE. Modifying the temporal profile of the high-potency sweetener neotame. J Agric Food Chem. 2001 Feb;49(2):786-9. PubMed PMID: 11262029. 10: Chattopadhyay S, Raychaudhuri U, Chakraborty R. Artificial sweeteners - a review. J Food Sci Technol. 2014 Apr;51(4):611-21. doi: 10.1007/s13197-011-0571-1. Epub 2011 Oct 21. Review. PubMed PMID: 24741154; PubMed Central PMCID: PMC3982014. 11: Flamm WG, Blackburn GL, Comer CP, Mayhew DA, Stargel WW. Long-term food consumption and body weight changes in neotame safety studies are consistent with the allometric relationship observed for other sweeteners and during dietary restrictions. Regul Toxicol Pharmacol. 2003 Oct;38(2):144-56. PubMed PMID: 14550756. 12: Dong Z, Young VG Jr, Sheth A, Munson EJ, Schroeder SA, Prakash I, Grant DJ. Crystal structure of neotame anhydrate polymorph G. Pharm Res. 2002 Oct;19(10):1549-53. PubMed PMID: 12425475. 13: Qurrat-ul-Ain, Khan SA. Artificial sweeteners: safe or unsafe? J Pak Med Assoc. 2015 Feb;65(2):225-7. Review. PubMed PMID: 25842566. 14: Witt J. Discovery and development of neotame. World Rev Nutr Diet. 1999;85:52-7. Review. PubMed PMID: 10647335. 15: Rodrigues JB, Paixão JA, Cruz AG, Bolini HM. Chocolate Milk with Chia Oil: Ideal Sweetness, Sweeteners Equivalence, and Dynamic Sensory Evaluation Using a Time-Intensity Methodology. J Food Sci. 2015 Dec;80(12):S2944-9. doi: 10.1111/1750-3841.13120. Epub 2015 Nov 2. PubMed PMID: 26523944. 16: Garbow JR, Likos JJ, Schroeder SA. Structure, dynamics, and stability of beta-cyclodextrin inclusion complexes of aspartame and neotame. J Agric Food Chem. 2001 Apr;49(4):2053-60. PubMed PMID: 11308366. 17: Neotame - a new artificial sweetener. Med Lett Drugs Ther. 2002 Aug 19;44(1137):73-4. PubMed PMID: 12205430. 18: Baturina VA, Sharafetdinov KhKh, Meshcheriakova VA, Plotnikova OA, Sokolov AI, Gapparov MM. [Effect of food additive Neotame (N-[N-(3,3-dimethylbutyl)-L-alpha-aspartyl]-L-phenylalanine-1-methyl) on glucose level in blood of patients with diabetes mellitus type 2]. Vopr Pitan. 2004;73(6):18-20. Russian. PubMed PMID: 15685854. 19: Matsumoto H, Hirata K, Sakamaki N, Hagino K, Ushiyama H. [Simultaneous determination of neotame, alitame and aspartame in foods by HPLC]. Shokuhin Eiseigaku Zasshi. 2008 Feb;49(1):31-6. Japanese. PubMed PMID: 18344656. 20: Walters DE, Prakash I, Desai N. Active conformations of neotame and other high-potency sweeteners. J Med Chem. 2000 Mar 23;43(6):1242-5. PubMed PMID: 10737757.