neotame final1

NeotameThe 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

Benefits of sweeteners Reduce caloric intake and prevent tooth decay Sweetness for people who have diabetes

Non-caloric Low-caloric

Aspartame 4 cal/g

Sorbitol 2.6 Cal/g

Acesulfame-K 0

Sucralose 0

Neotame 0

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

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

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Sensory Characteristics

Sugar Substitution

Food Technology. Volume 56(7): p38

Sensory Characteristics

Flavor enhancement or modificationBitternessAstringencyBean flavorChemical burning or coolingEssential oilsVitamins 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 stability

Stable under dry storage condition

Stable under dry storage condition (several years);

Sweetness potency (sucrose=1)

± 200 ± 8,000

Melting point 246—247 ℃ 80.9—83.4℃

Solubility(25℃) H2O: 10g/l

abs. EtOH: 3.7g/l

H2O: 12.6g/labs. EtOH: 950g/l

Stability (pH, temperature)

Hydrolyze into its constituent amino acids under conditions of elevated temperature or high pH.

More stable under high temperature (80 ℃) and neutral pH

Stability of NTM as a function of pH (in 0.1M phosphate buffers) at 25℃

Chemical and physical characteristics

Food Chemistry Vol 69: 245-257, 2000

4.5

High- temperature short time (HTST) processing

Chemical and physical characteristics

Aspartame (APM) Neotame (NTM)

Compatibility Reducing sugars (Maillard reactions)

No reaction with reduding sugars

Caloric value 4kcal/g 4kcal/g

Typical use levels

Tabletop: 37mg/unit; carbonated soft drinks: 525mg/l

Tabletop: 0.9mg/unit; carbonated soft drinks: 17mg/l

Insignificant viscosity no mixing problems

Negligible lowering of the surface tension and pH no excessive foaming

Chemical and physical characteristics

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).

Not mutagenic, teratogenic or carcinogenic

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

Safety

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

Not mutagenic, teratogenic or carcinogenic

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

"Contains phenylalanine"

Safety

Regulation Status

Approval: FDA (2002); EU(2009). More than 35 countries

Acceptable Daily Intake (ADI): 0-2 mg/kg body weight (JECFA in 2003;

EFSA in 2007).

Regulation Status

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®

CH3

CH3

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

Synthesis of Neotame

One step synthesis using Aspartame

Nofre and Trinti (1996) patent # 5480668

Aspartame

Palladium/C

H2

Neotame

3,3-dimethyl butyraldehyd

e

N

H

H

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

Thank you

Questions