Neotame

The new sweet kid on the block

Group 3 - Helen Susan and Venky

Objective and Outline
 Objective: introduce and evaluate neotame in a
scientific manner
 Presentation outline
 Background and Introduction
 Discovery of neotame
 Sensory characteristics
 Chemical and physical properties
 Safety and regulations
 Manufacture and applications
 Advantages and disadvantages
Sweeteners
 Classification of sweeteners
Non-caloric Low-caloric
Aspartame 4 cal/g
Sorbitol 2.6 Cal/g
Acesulfame-K 0
Sucralose 0
Neotame 0

 Benefits of sweeteners
 Reduce caloric intake and prevent tooth decay
 Sweetness for people who have diabetes
Neotame
 Non caloric sweetener
 A derivative of aspartame

 Much higher in sweetness intensity than

sucrose and aspartame

 Sugar like sweet taste

 Result of a long term research

Example products
 Products using neotame as a sweetener
Sweetness Receptor
 G protein coupled receptors (GPCR)

Pure & Appl.

Chem., Vol. 69 (4):
p 702. 1997
Discovery
 Hydrophobic binding pockets (HBP)
2nd HBP Sweetness
Potency
1 (Me)3CCH2CH2 11,000
2 (Et)2CHCH2 2,200
3 c-C5H9CH2 1,650
4 (Me)2CHCH2CH2 1,400
5 c-C8H15 1,200
6 c-C7H13 1,000
7 c-C6H11CH12 900
…

Nofre & Tinti, Food Chemistry. Volume 69: p246. 2000

Discovery
 2nd Hydrophobic Binding Pocket

Nofre & Tinti, Food Chemistry. Volume 69: p246. 2000

Sensory Characteristics
 What are criteria when we
evaluate a sweetener in terms of
sensory?
 Sweetness intensity
 No off flavors
 Interaction with other tastants
Sensory Characteristics
 Sweetness potency
 6000 – 13000 times of sucrose
 30 – 60 times of aspartame
 15.1% sucrose equivalence in water

Food Technology. Volume 56(7): p37

Sensory Characteristics
 Clean, sugar like taste without undesirable off-
flavors

Food Technology. Volume 56(7): p38

 Sensory Characteristics
 Comparison of temporal profile for neotame,
sucrose and aspartame
Sweetness Intensity

ACS Symposium Series 979: Sweetness & Sweeteners, p 517, 2006

Sensory Characteristics
 Sugar Substitution

Food Technology. Volume 56(7): p38

Sensory Characteristics
 Flavor enhancement or modification
 Bitterness
 Astringency
 Bean flavor
 Chemical burning or cooling
 Essential oils
 Vitamins
 Plant extracts
Objective and Outline
 Objective: introduce and evaluate neotame in a
scientific manner
 Presentation outline
 Background and Introduction
 Discovery of neotame
 Sensory characteristics
 Chemical and physical properties
 Safety and regulations
 Manufacture and applications
 Advantages and disadvantages
Chemical and physical characteristics

Aspartame (APM) Neotame (NTM)

Physical state White crystaline powder White crystaline powder

Bulk chemical Stable under dry storage Stable under dry storage
stability condition condition (several years);
Sweetness potency ± 200 ± 8,000
(sucrose=1)

Melting point 246—247 ℃ 80.9—83.4℃

Solubility(25℃) H2O: 10g/l H2O: 12.6g/l
abs. EtOH: 3.7g/l abs. EtOH: 950g/l
Stability (pH, Hydrolyze into its constituent More stable under high
temperature) amino acids under conditions temperature (80 ℃) and
of elevated temperature or high neutral pH
pH.
Chemical and physical characteristics

 High-
temperature short
time (HTST)
processing

4.5

Stability of NTM as a function of pH (in 0.1M

phosphate buffers) at 25℃ Food Chemistry Vol 69: 245-257, 2000
Chemical and physical characteristics

Aspartame (APM) Neotame (NTM)

Compatibility Reducing sugars No reaction with

(Maillard reactions) reduding sugars

Caloric value 4kcal/g 4kcal/g

Typical use Tabletop: 37mg/unit; Tabletop: 0.9mg/unit;

levels carbonated soft drinks: carbonated soft drinks:
525mg/l 17mg/l
Chemical and physical characteristics

 Insignificant viscosity
 no mixing problems
 Negligible lowering of the surface tension and
pH
 no excessive foaming
Matabolism

 De-esterification

De-esterified Neotame

Food Chemistry Vol 69: 245-257, 2000

Safety

Total (potential + actual) methanol content of various vegetable or fruit

juices compared to that of beverages formulated with APM (525mg/l)
or NTM (17mg/l). Food Chemistry Vol 69: 245-257, 2000
Safety

"Level of exposure is of no toxicological concern

because humans are exposed to much greater levels
of methanol intake from their daily diets." U.S.
FDA, 2002; E.U. EFSA, 2007 (EFSA: European
Food Safety Agency).
Safety

 Not mutagenic, teratogenic or carcinogenic

 Safe for use by the general populaiton
 Children
 Pregnant women
 Diabetics
 Phenylketonurics
Safety

Comparision between the phenylalanine (Phe) content (i) of a

beverage formulated with 525mg/l of APM, (ii) of two typical fruit juices,
(iii) of a beverage formulated with 17mg/l of NTM Food Chemistry Vol 69: 245-257, 2000
Safety

 Not mutagenic, teratogenic or carcinogenic

 Safe for use by the general populaiton
 Children
 Pregnant women
 Diabetics
 Phenylketonurics

 "Contains phenylalanine"
Regulation Status
 Approval: FDA (2002); EU(2009).
 More than 35 countries
Regulation Status

 Acceptable Daily Intake (ADI):

 0-2 mg/kg body weight (JECFA in 2003; EFSA
in 2007).
Objective and Outline
 Objective: introduce and evaluate neotame in a
scientific manner
 Presentation outline
 Background and Introduction
 Discovery of neotame
 Sensory characteristics
 Chemical and physical properties
 Safety and regulations
 Manufacture and applications
 Advantages and disadvantages
 Synthesis of Neotame

 N-[N-(3,3-diimethylbutyl)-l α-aspartyl]-l-
phenylalanine1-methyl ester
 First patent
 issued in 1996 to Nofre and Tinti (NutraSweet®)
(Patent # 5480668)

 6 patents issued for synthesis and purification

 4 to Monsanto®
 Synthesis of Neotame
 One step synthesis using Aspartame

H
N
H

Aspartame H2

Palladium/C
CH3

CH3--- C ---CH2 -- CH2 -- CHO Neotame

CH3 3,3-dimethyl
butyraldehyde Nofre and Trinti (1996) patent # 5480668
Utility
 Non-nutritive, non-caloric sweetener
 Caloric value
 Neotame as a dipeptide- 4kcal /g
 Effective caloric value- 0.3kcal/g

 Non-cariogenic
 Application in chewing gums
 compatible with reducing sugars (such as
glucose, fructose, high-fructose corn syrup,
lactose, maltose) and aldehyde-based
flavouring agents (such as vanilla, cinnamon,
cherry,bitter almond, lemon)
 Suitable for wider applications
Utility
 Application in carbonated beverages
 Stable at pH 3-5
 17mg/l  0.004kcal
 Table-top sweetner
 More stable at pH 7 compared to other
sweeteners
 Baking applications
 Flavor enhancer and modifiers
 Potassium chloride in salt substitutes, soy milk,
essential oil, and plant extracts
Suggested Neotame use levels

Application Use level

Tabletop sweetener 0.9 mg/unit *

Lemon tea (hot packed) 8 mg/l

Yogurt 15 mg/l

Powdered soft drink 16 mg/l#

Carbonated soft drink 17 mg/l

Cake (yellow cake) 35 mg/kg

Chewing gum 250 mg/kg

* Equivalent to the sweetness of 2 teaspoons of sugar.
# Final concentration in the reconstituted beverage.

Nofre and Trinti. Food Chemistry 69 (2000) 245-57

Advantages

 Cost effective
 Safe
 Clean sweet taste(close to sucrose)
 No off-flavour or metallic taste
 Non-caloric and non-cariogenic
 Stability and shelf life
 Chemical inertness towards reducing sugars and flavoring
agents
 No foaming and less effect on viscosity and suface tension
 One step synthesis
Disadvantages
 No Maillard reaction in bakery products
 misconception
Thanks
Questions

Thank you