Download Development of Consumer Products Based on

Commercialization
Development of Consumer Products Guerbet
Glycosides
Rauzah Hashim
April 2015
Project Background
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MOSTI Strategic Research Top-Down
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Glycolipids as Functional Material
2002-2006
High Impact Research- MOHE
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April 2015
Fundamental Science in Self-Assembly
Understanding Guerbet glycosides self-assembly
structures and dynamics for functional nanobiotechnology
2011-2016
Mimicking Natural Products
Phospholipids
Phosphotidyl- Sphingomyline
choline
Glycolipids
MGDG
Glucosylcerebroside
Branched
Chain
Glycosides
Synthetic Glycolipids
Alkylpolyglucoside
OH
OH
HO
OH
OH
HO
O
O
O
HO
nO
n
Ease of Preparation
Guerbet Glycosides at
Geneva ITEX 2005
Nature-Like Synthetic Alkyl Branched-Chain Glycolipids: A Review on Chemical
Structure and Self-Assembly Properties. Liq. Cryst. 2012, 39, 1–17.
Success in Geneva
Gold Medal, I.TEX Geneva, 2005
Special Award,
The Mayor of Taipei and
Taiwan ProvincialGovernment, 2005
Gold
Medal
One of best manuscripts Liquid Crystals 2012
4/29/2017
2005
4
Glycolipids Self-Assembly
Structural Determination
Gurbert Glycoside
Patented product
Fundamental
Studies
Formulation of
products
Product testing
Scale-up
Branched Chain Guerbet
Glycosides Summary
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Liquid crystal at RT for branched glycosides of Guerbet
Guerbet chains give better hydrophobicity
Chain branching support non-lamellar curved phases
Chain asymmetry leads to denser packing hydration
OH’s stabilize the lamellar arrangement
Possible different bilayer structures
Sugar stereochemistry plays subtle role in self-assembly
Liquid Crystals,39 (1), 1-17, 2012
Guerbet Materials
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Guerbet glycoside literatures
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prepared using a glycosidation described elsewhere.
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Rauzah Hashim*, et al. Invited Article Liquid Crystals, 2012, 39 (1), 1-17
Rauzah Hashim*, et al. Thin Solid Films, 2006, 509, 27-35
Guerbet alcohol, was first synthesized by Marcel Guerbet (1899).
Guerbet alcohol contains two asymmetric chains differ by two methylene
units, and the two chains branch at the ß-carbon position, which is also chiral.
Guerbet glycoside series is a Guerbet sugar,
Other Guerbet materials
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alcohol, ester, and acid,
all of which have been used in many industrial applications.
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O’Lenick, A. J., Jr. Guerbet Chemistry. J. Surfactants Deterg. 2001, 4, 311-315
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Our Competitors
Commercialization Roadmap
Upstream
→ Resources
Present Product
Downstream
→ Applications
Cosmetic Creams
HO
HO
OH
OH
O
CnH2n+1
O
HO
O
HO
O
CmH2m+1
OH
Liposome
Palm Oil Derived
Branched Alcohols
April 2015
The Product
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Specialty Chemical
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Low Market Volume (no Bulk-Material)
Target Market Industry
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Cosmetic and Pharmaceutical Industry
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(Patent evaluated)
Example DDS, Diagnostic
Bio- & Med-Tech Companies
Material for Product-Development
April 2015
Economic Analysis
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MY Cosmetic Market
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Volume:
Annual Growth:
Skin Care:
(Data: 2003)
~ RM 2.8 billion
~ 3-5 %
~ ¼ of total Volume
Glycoside based delivery system
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Market Novelty: target liquid crystal delivery
system
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April 2015
Hexasome
Liposome
Cubosome
Commercialization Status Quo
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Established Product Preparation
Basic Product Characterization
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Patent
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April 2015
MY PI 20051074
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Compound Class
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Application of Compound Properties
List of patent approved
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Singapore Patent No. 200706665/7, Oct. 31, 2008
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South Africa Patent No. 2007/8477, Jul. 30, 2008
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Malaysia Patent No. MY-138164-A, Apr. 30, 2009
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U.S. Patent No. US8,304,525, Nov. 6, 2012
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China Patent No. CN 200680008448, Jun. 12, 2013
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Japan Patent No. 5392467, Oct. 25, 2013
Application Development Cycle
Compatibility
Lyotropic
Systems
(Water)
Synthesis
Optimization
Prod.-Property
April 2015
Physical Characterization
Protein
Crystals
Formulation
Liposome
Guerbet
Glycoside
Toxicity
(Creams)
Product
Biological Tests
Cosmetics
Chemical
Analysis
Application Development
Lyotropic
Systems
(Water)
Formulation
Cosmetics
(Creams)
Liposome
Protein
Crystallization
Physical Characterization (OPM, SWAX, Densiometry …)
•
•
•
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CMC
Surface Tension
Phase Analysis
Water Swelling …
April 2015
• Rheology
• ThermoStability
• Encapsultn.
Efficiency
• Vesicle
Stability
• Phase
Stability
• Filtering
Efficiency
Commercialization Ways
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HIR 2
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Other Government Grant (EPU)
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Industrial Partners
Missing Industrial Input
Limited Resources
Product Licensing
Industrial Grant (?)
April 2015
Update 2015: Publication
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2014, Influence of nonionic branched-chain alkyl glycosides on a model
nano-emulsion for drug delivery systems, Colloids and Surfaces B:
Biointerfaces,115: 267 274
2014, Lyotropic Phase Behaviour and Structural Parameters of
Monosaccharide and Disaccharide Guerbet Branched-chain β-D-glycosides.
Advanced Materials Research Vol. 895, 111-115
2014. Amphiphilic designer nano- carriers for controlled release, from drug
delivery to diagnostics, Med. Chem. Commun., 5 (11): 1602 – 1618
2013, Effect of vesicles membrane packing behaviour on skin penetration of
model lipophilic drug, Journal of Microencapsulation, 30(3):265-273
2012, Physico- Chemical Characterization of Natural-Like Branched- Chain
Glycosides towards Formation of Hexosomes and Vesicles, Langmuir, 2012,
28(5), 2395-2403
April 2015
Update 2015
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Testing for Field effect study
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Dielectric measurements
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Pyroelectricity
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2006, Liquid Crystals, 33(3): 361-366.
2006, Phys. Rev. E 73: 011916
2014. Phase sensitive molecular dynamics of self-assembly
glycolipid thin films: A dielectric spectroscopy investigation.J.
Chem. Phys. 141, 085101
Thin Solid Films (2010), 518 4412 4416
Simulation studies
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April 2015
2014. Conformational Dynamics of Dry Lamellar Crystals of Sugar
Based Lipids: An Atomistic Simulation Study, PLOS One : June 30,
2014DOI: 10.1371/journal.pone.0101110
Physical Chemistry Chemical Physics, 2014, 16, 324-334
2012, Journal of Physical Chemistry B, 116(38), 11626-11634
Thank You.
April 2015