CLEAN-LABEL & COST-EFFECTIVE MODULATORS OF SWEET AND UMAMI TASTES - GRANT E DUBOIS OCTOBER 20, 2020
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Clean-Label & Cost-Effective
Modulators of Sweet and Umami
Tastes
Grant E DuBois
October 20, 2020
Almendra Americas, LLC 1
Outline
I. Metrics for Commercial Viability
II. History of Sweetness Technology Innovation
A. Synthetic Non-Caloric Sweeteners
B. Sweetener Receptor PAMs
C. Natural Non-Caloric Sweeteners
III. Sweetener Taste Modulation
IV. Umami Taste Modulation
Almendra Americas, LLC 2
I. Metrics for Commercial Viability
1. Safety
2. Taste Quality
3. Taste Quality
4. Taste Quality
5. Taste Quality
6. Stability
7. Solubility
8. Cost
9. Patentability
10.Consumer Acceptability
G E DuBois, “Sweeteners and Sweetness Modulators: Requirements for Commercial Viability”, Chapter 29 in Sweetness
and Sweeteners, G E DuBois and D Weerasinghe, Eds., ACS Symposium Series 979, ACS Books, Washington, DC, 2008.
Almendra Americas, LLC 3Metric 2: Taste Quality - Maximal Response
I Cyclamate-Na C/R Function in Citrate Buffer
Saccharin-Na C/R Function in Citrate Buffer
14.00
I 10.00
12.00
8.00 10.00
6.00 8.00
4.00 R = 9.1C/(105+C) 6.00
2.00 4.00
R = 18.4C/(2840+C)
2.00
0.00
0.00
0 500 1000 1500
0 2000 4000 6000
Concentration (mg/L) Concentration (mg/L)
Rebaudioside A C/R Function in Citrate Buffer
Aspartame C/R Function in Citrate Buffer I 10.00
I 20.00
8.00
15.00
6.00
10.00 R = 9.7C/(245 + C)
4.00
5.00 R = 24.7C/(782 + C)
0.00 2.00
0 500 1000 1500 2000 0.00
0 200 400 600 800 1000 1200
Concentration (mg/L) Concentration (mg/L)
G E DuBois, “Advances in the Science of Sweet Taste and Sweetness Enhancement”, Invited Lecture, Institute of Food Technologists
Annual Meeting, New Orleans, LA, June 14, 2011.
Almendra Americas, LLC 4Metric 3: Taste Quality - Flavor Profile
Sweetener Flavor Profiles
7.0 7.0 7.0 7.0 7.0 7.0
Taste Intensity
2.7 2.5 2.6
0.9 0.0 1.0 1.0 0.9
0.0 0.0 0.0 0.0
SUCROSE SACCHARIN-NA CYCLAMATE-NA ASPARTAME REBAUDIOSIDE A THAUMATIN
Sweetness Bitterness Licorice-Like Taste
G E DuBois, “Advances in the Science of Sweet Taste and Sweetness Enhancement”, Invited Lecture, Institute of Food Technologists Annual
Meeting, New Orleans, LA, June 14, 2011.
Almendra Americas, LLC 5Metric 4: Taste Quality – Temporal Profile
Sweetener Temporal Profiles in Water
I 8
Sucrose
7
Saccharin-Na
Cyclamate-Na
6
Aspartame
5 Rebaudioside A
Thaumatin
4
3
2
1
0
0 50 100 150 200
Time (Sec)
G E DuBois, “Advances in the Science of Sweet Taste and Sweetness Enhancement”, Invited Lecture, Institute of Food Technologists
Annual Meeting, New Orleans, LA, June 14, 2011.
Almendra Americas, LLC 6Metric 5: Taste Quality –
Sweetness Desensitization
B T Carr, S D Pecore, K M Gibes and G E DuBois, “Sensory Methods for Sweetener Evaluation”, Chapter 11 In Flavor Measurement,
CT Ho and CH Manley, Eds., Marcel Dekker, New York, NY, 1993.
Almendra Americas, LLC 7Metric 8: Cost
The Cost Challenge…….for 0-Cal Beverages
[HFSS-55] [SAC-Na] [APM] in [APM] in [APM] in [REBA] in [ERY] in COST
in mg/L @ in mg/L @ mg/L @ mg/L @ mg/L @ mg/L @ mg/L @ (Cents /
1 2 3 3 4 5 6 7
No. $0.90/ Kg $7.58/ Kg $220/ Kg $110/ Kg $10/ Kg $120/ Kg $3.50/ Kg UC) Comments
1 105,240 0 0 0 0 0 0 54.0 US Coca-Cola Classic
2 0 210 90 0 0 0 0 12.2 US Diet Coke / 1983-1985
3 0 0 0 500 0 0 0 32.6 US Diet Coke / 1985-1992
4 0 0 0 0 500 0 0 3.0 US Diet Coke Today
5 0 0 0 0 0 500 0 34.2 Hypothetical Today
6 0 0 0 0 0 300 35000 90.3 Hypothetical Today
1 2 3
August 2016 US Price (www.cornnaturally.com). Early 2000s US Price. Searle Pharmaceutical Company Price to Beverage Industry from
1983-1985 was ca. $220/Kg; in 1985, Price to TCCC and Pepsi was dropped to ca. $110/Kg when both companies agreed to formulate CSDs
4
w/ 100% Aspartame (No Saccharin); Both Prices were enabled by a Searle Patent Estimate of Current Price to CSD Industry (Niutang Internet
5 TM 6 7
Price = $12.97/Kg). Steviose 100 (>/= 99.5% REBA). Cargill Erythritol 2016 Price Quote. Unit Case = 24 8oz Bottles = 5.7L.
Key Point: There is a great need for a Cost-Effective Taste Modulator for REBA!
Almendra Americas, LLC 8II. History of Sweetness Technology Innovation
Sy 1850 - 2000
nth
et
Sw ic N
eet onc
en alo
ers ri
c Sugar w/ 1995 - Present
PAMs
/FMPs
Sugar
Taste
2000 - Present
c
alori
Nonc s w/ rs 2000 - Present
l
ra ener ulato
tu N
Na weet Mod No atura
S ess
n Sw ncalo l
w eet eet ric
ene
S rs
Almendra Americas, LLC 9Rebaudioside A (REBA)
Almendra Americas, LLC 10Metrics for Commercial Viability
1. Safety
2. Taste Quality: Maximal Sweetness Response
3. Taste Quality: Flavor Profile
The Challenge!
4. Taste Quality: Temporal Profile
5. Taste Quality: Sweetness Desensitization
6. Stability
7. Solubility
8. Cost
9. Patentability
10. Consumer Acceptability
Almendra Americas, LLC 11III. Sweetener Taste Modulation
Empirical Observations:
1987: NaCl increases the potencies of stevia sweeteners (Maruzen Pharmaceutical Co.).
1992: NaCl eliminates the Sweetness Linger of aspartame (LaVaugn Hill / The NutraSweet
Company).
1993: NaCl and KCl add Mouthfeel and reduce the Sweetness Linger of aspartame.
1993: Aspartame in tea exhibits negligible Sweetness Linger.
2005: Erythritol, NaCl, KCl and many osmolytes found to reduce or eliminate REBA Sweetness
Linger.
2016: Astringent pre-rinses increase Sweetness Intensity, accelerate Sweetness Onset Rate and
attenuate Sweetness Linger of REBA.
2016: REBA solutions, if tasted first thing in the morning w/o any oral rinse, have low Sweetness
Intensity, very markedly delayed Sweetness Onset Rate and very pronounced Sweetness
Linger.
Almendra Americas, LLC 12Mechanistic Rationale for Delayed Sweetness
Onset/Sweetness Linger & Mouthfeel Perception
• Low Sweetness Intensity / Delayed Sweetness Onset / Sweetness Linger: The lingual epithelium
is covered by a mucous hydrogel film, where the major structural component is the glycoprotein
mucin, and amphipathic molecules like high-potency sweeteners bind to hydrophobic sites on
mucin resulting in delayed diffusion to and from the receptor. Slowed diffusion to the receptor
results in low sweetness Intensity and delayed sweetness Appearance Time and slowed diffusion
away from the receptor results in iterative activation of the receptor, thereby leading to Sweetness
Linger.
References:
1. R. Matsuo and G. H. Carpenter, “The Role of Saliva in Taste Transduction”, Handbook of Gustation and Olfaction,
3rd Edition, R. L. Doty, Ed., 2015, J. Wiley & Sons, Inc., Chapter 28.
2. K. Ribbeck et al., “An Absorption Chromatography Assay to Probe Bulk Particle Transport through Hydrogels”, J.
Pharm. Sci. 2012, 101, 436-442; also multiple other publications from the Ribbeck laboratory.
• Mouthfeel: The Calcium Sensing Receptor (CSR) is expressed by a subset of taste bud cells and its
activation leads to perception of a sugar-like Mouthfeel which has been referred to as Kokumi
Taste.
References:
1. Y. Maruyama et al., “Kokumi Substances, Enhancers of Basic Tastes, Induce Responses in Calcium-Sensing Receptor
Expressing Taste Cells”, PLoS ONE, 2012, 7 (4).
2. M. Kuroda and N. Miyamura, “Mechanism of the Perception of Kokumi Substances and the Sensory Characteristics
of the Kokumi Peptide g-Glu-Val-Gly”, Flavour, 2015, 4, 11.
Almendra Americas, LLC 13KCl, MgCl2 and CaCl2 Blends as
REBA Taste Modulators in CAB
12.0
10.0
8.0
6.0
4.0
2.0
0.0
S So Sa B MF A AT SL SD
10.0% Sucrose 500mg/L REBA
500mg/L REBA / KCl 500mg/L REBA / MgCl2
500mg/L REBA / CaCl2 500mg/L REBA / KCl / MgCl2 / CaCl2
Key Point: K, Mg and Ca mineral salts are synergistic in enhancement of sweetness,
acceleration of Sweetness Onset, reduction of Sweetness Linger and addition of Mouthfeel!
Almendra Americas, LLC 14KCl/MgSO4/Ca(Lactate)2 Blends
as REBA Taste Modulators in LAB
12.0
10.0
8.0
6.0
4.0
2.0
0.0
S So Sa B MF A AT SL SD
10.0% Sucrose
500mg/L REBA
500mg/L REBA w/ KCl / MgSO4 / Ca(Lactate)2 Level 1
500mg/L REBA w/ KCl / MgSO4 / Ca(Lactate)2 Level 2
Key Point: The taste modulator activity of K/Mg/Ca mineral salt blends is independent of
anion composition.
Almendra Americas, LLC 15KCl/MgCl2/CaCl2 Blends w/ REBA in Comparison to
REBA, REBD and REBM in Zero-Calorie Lemon-Lime
Still Beverage Prototypes
12.0
10.0
8.0
6.0
4.0
2.0
0.0
S So Sa B MF A AT SL SD
10.0% Sucrose 500mg/L REBA
500mg/L REBD 500mg/L REBM
500mg/L REBA / KCl / MgCl2 / CaCl2 Level 1 500mg/L REBA / KCl / MgCl2 / CaCl2 Level 2
Key Point: The taste quality of REBA formulated with K/Mg/Ca taste modulators is
superior to that of REBD or REBM!
Almendra Americas, LLC 16KCl/MgSO4/Ca3(Citrate)2
Spiked into a Commercial Aspartame-Sweetened
Zero-Calorie Cola Beverage
12
10
8
6
4
2
0
S So Sa B MF A AT SL SD
Zero Calorie Cola Zero Calorie Cola / KCl / MgSO4 / Ca3(Citrate)2
Key Point: K/Mg/Ca mineral salt taste modulators can dramatically improve the taste
quality of beverages sweetened with aspartame and other synthetic sweeteners.
Almendra Americas, LLC 17KCl/MgCl2/CaCl2 Taste Modulator
Spiked into a Commercial REBA/Sucrose Sweetened
Mid-Calorie Sparkling Lemonade
12.0
10.0
8.0
6.0
4.0
2.0
0.0
S So Sa B MF A AT SL SD
Control Beverage
Control Bevrage w/ KCl / MgCl2 / CaCl2 Level 1
Control Beverage w/ KCl / MgCl2 / CaCl2 Level 2
Key Point: The K/Mg/Ca taste modulator can dramatically improve the sugar-like
Mouthfeel of mid-calorie beverages!
Almendra Americas, LLC 18A KCl/MgSO4/Ca(Lactate)2 Taste Modulator
in a Sucrose Beverage Prototype
12.0
10.0
8.0
6.0
4.0
2.0
0.0
S So Sa B MF A AT SL SD
10% Sucrose 10% Sucrose w/ KCl / MgSO4 / Ca(Lactate)2
Key Point: The K/Mg/Ca mineral salts dramatically improve the sugar-like Mouthfeel of
full-calorie beverages.
Almendra Americas, LLC 19Beverage Sweetener System Costs
[HFSS-55] [SAC-Na] [APM] in [APM] in [APM] in [REBA] in [REBA] in [ERY] in [GMS] in COST
in mg/L @ in mg/L @ mg/L @ mg/L @ mg/L @ mg/L @ mg/L @ mg/L @ mg/L @ (Cents /
1 2 3 3 4 5 6 7 8 9
No. $0.90/ Kg $7.58/ Kg $220/ Kg $110/ Kg $10/ Kg $120/ Kg $50/ Kg $3.50/ Kg $15.00/ Kg UC) Comments
1 105,240 0 0 0 0 0 0 0 0 54.0 US Coca-Cola Classic
2 0 210 90 0 0 0 0 0 0 12.2 US Diet Coke / 1983-1985
3 0 0 0 500 0 0 0 0 0 32.6 US Diet Coke / 1985-1992
4 0 0 0 0 500 0 0 0 0 3.0 US Diet Coke Today
5 0 0 0 0 0 500 0 0 0 34.2 Hypothetical Today
6 0 0 0 0 0 300 0 35000 0 90.3 Hypothetical Today
7 0 0 0 0 0 500 0 0 1000 42.8 Hypothetical Today
8 0 0 0 0 0 500 0 0 2000 51.3 Hypothetical Today
9 0 0 0 0 0 0 500 0 0 14.3 Hypothetical Tomorrow
10 0 0 0 0 0 0 500 0 1000 23.8 Hypothetical Tomorrow
11 0 0 0 0 0 0 500 0 2000 31.4 Hypothetical Tomorrow
1 2 3
August 2016 US Price (www.cornnaturally.com). Early 2000s US Price. Searle Pharmaceutical Company Price to Beverage Industry from 1983-1985 was ca.
$220/Kg; in 1985, Price to TCCC and Pepsi was dropped to ca. $110/Kg when both companies agreed to formulate CSDs w/ 100% Aspartame (No Saccharin); Both
Prices were enabled by a Searle Patent 4Estimate of Current Price to CSD Industry (Niutang Internet Price = $12.97/Kg). 5StevioseTM100 (>/= 99.5% REBA).
6 7 8
Projected StevioseTM100 Price after Full Commercial Development of Almendra Agricultural Technology. Cargill Erythritol 2016 Price Quote. Almendra Pre-
commercialization Price Quote. 9Unit Case = 24 8oz Bottles = 5.7L.
Key Point: The K/Mg/Ca mineral salt taste modulators enable formulation of all-natural
sweetener system zero-calorie beverages with taste qualities comparable to synthetic sweetener
system beverages and with acceptable costs!
Almendra Americas, LLC 20IV. Umami Taste Modulation:
KCl/MgCl2/CaCl2 Taste Modulator with MSG
7
6
5
4
3
2
1
0
U So Sa B MF A
MSG Control MSG + KCl/MgCl2/CaCl2
Key Point: The K/Mg/Ca mineral salt composition dramatically improves the Mouthfeel
of MSG umami formulations.
Almendra Americas, LLC 21Umami Taste Modulation Demonstration
Samples:
1. MSG in Distilled Water Control
2. MSG in Distilled Water with Taste Modulator
Instructions: Taste the MSG Control first, followed by the MSG with Taste Modulator
1. Rinse with ½ oz water while swishing gently followed by swallowing;
2. Take ½ oz of the sample into the mouth and swish around gently for 15 sec scaling
• Umami Intensity (U),
• Saltiness Intensity (Sa), and
• Mouthfeel Intensity (MF) on 0-15 scales;
3. Rinse with ½ oz water w/ gentle agitation and swallow; and
4. Wait a minimum of 2 min and repeat with the MSG with Taste Modulator Sample.
Almendra Americas, LLC 22KCl/MgCl2/CaCl2 Taste Modulator with a Commercial
Mushroom/Onion/Mustard/Pepper Umami Seasoning
7
6
5
4
3
2
1
0
U So Sa B MF A
TJU Control TJU + KCl/MgCl2/CaCl2
Key Point: The K/Mg/Ca mineral salt composition significantly enhances the Mouthfeel
of Umami Seasonings.
Almendra Americas, LLC 23KCl/MgCl2/CaCl2 Taste Modulator with a
Commercial Hydrolyzed Pea Protein
3.5
3
2.5
2
1.5
1
0.5
0
U So Sa B MF A
ZHP Control ZHP + KCl/MgCl2/CaCl2
Key Point: The K/Mg/Ca mineral salt composition significantly enhances the Mouthfeel
of hydrolyzed vegetable proteins.
Almendra Americas, LLC 24Summary
1.Non-Caloric Sweetener Formulations: Sweetness Enhancement,
Accelerated Sweetness Onset, attenuated the Sweetness Linger
and Increased Sugar-Like Mouthfeel.
2.Mid- and Full-Calorie Sweetener Formulations: Increased
Sugar-Like Mouthfeel.
3.Umami Formulations: Increased Savory Mouthfeel.
DuBois, Grant, E. and San Miguel, Rafael, I., “Methods and Compositions for Improved Taste Quality”, US Patent
10,602,758 (March 31, 2020).
People Interested in Samples, please contact: Rajesh Cherian: rajesh.c@almendra.com or Eric Zabin:
eric.z@almendra.com
People having technical questions, please contact Grant DuBois: grant.d@almendra.com
Almendra Americas, LLC 25You can also read
