1. Commercialization Development of Consumer Products Guerbet Glycosides
Rauzah Hashim
April 2015

2. Project Background MOSTI Strategic Research Top-Down
Glycolipids as Functional Material
High Impact Research- MOHE
Fundamental Science in Self-Assembly
Understanding Guerbet glycosides self-assembly structures and dynamics for functional nano-biotechnology
April 2015

3. Mimicking Natural Products
Branched Chain Glycosides
Branched Chain Glycosides
Phospholipids
Glycolipids
Phosphotidyl-choline
Sphingo-
myline
Glucosyl-
cerebroside
Synthetic Glycolipids
Alkylpolyglucoside
MGDG
Ease of Preparation

4. 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.
One of best manuscripts Liquid Crystals 2012
Success in Geneva
Gold Medal, I.TEX Geneva, 2005
Special Award,
The Mayor of Taipei and
Taiwan ProvincialGovernment, 2005
Gold Medal
2005
4/26/2017 4

5. Glycolipids Self-Assembly Structural Determination

8. Gurbert Glycoside
Patented product
Fundamental Studies
Formulation of products
Product testing
Scale-up

9. Branched Chain Guerbet Glycosides Summary
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

10. Guerbet Materials prepared using a glycosidation described elsewhere.
Guerbet glycoside literatures
Rauzah Hashim*, et al. Invited Article Liquid Crystals, 2012, 39 (1), 1-17
prepared using a glycosidation described elsewhere.
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
alcohol, ester, and acid,
all of which have been used in many industrial applications.
O’Lenick, A. J., Jr. Guerbet Chemistry. J. Surfactants Deterg. 2001, 4,

11. Our Competitors

12. Commercialization Roadmap
Upstream
→ Resources
Palm Oil Derived
Branched Alcohols
Downstream
→ Applications
Present Product
Cosmetic Creams
Liposome
April 2015

13. The Product Specialty Chemical (Patent evaluated)
Low Market Volume (no Bulk-Material)
Target Market Industry
Cosmetic and Pharmaceutical Industry
Example DDS, Diagnostic
Bio- & Med-Tech Companies
Material for Product-Development
April 2015

14. Economic Analysis MY Cosmetic Market (Data: 2003)
Volume: ~ RM 2.8 billion
Annual Growth: ~ 3-5 %
Skin Care: ~ ¼ of total Volume
Glycoside based delivery system
Market Novelty: target liquid crystal delivery system
Hexasome
Liposome
Cubosome
Estimated glycoside content based on MISNI (DDM): ~ 5 g/L cream (= 0.5 %)
Productivity based on estimated synthesis upscaling: > 6 L cream /man-d = turnover RM 10,000 /man-d
April 2015

15. Commercialization Status Quo
Established Product Preparation
Basic Product Characterization
Patent
MY PI
Compound Class
Application of Compound Properties
List of patent approved
Singapore Patent No /7, Oct. 31, 2008
South Africa Patent No. 2007/8477, Jul. 30, 2008
Malaysia Patent No. MY A, Apr. 30, 2009
U.S. Patent No. US8,304,525, Nov. 6, 2012
China Patent No. CN , Jun. 12, 2013
Japan Patent No , Oct. 25, 2013
April 2015

16. Application Development Cycle
Chemical
Analysis
Biological Tests
Toxicity
Compatibility
Formulation
Cosmetics
(Creams)
Liposome
Protein Crystals
Product
Guerbet Glycoside
Lyotropic Systems
(Water)
Synthesis
Optimization Prod.-Property
Physical Characterization
April 2015

17. Application Development
Lyotropic Systems
(Water)
Formulation
Cosmetics
(Creams)
Liposome
Protein
Crystallization
CMC
Surface Tension
Phase Analysis
Water Swelling …
Rheology
Thermo- Stability
Encapsultn. Efficiency
Vesicle Stability
Phase Stability
Filtering Efficiency
Physical Characterization (OPM, SWAX, Densiometry …)
April 2015

18. Commercialization Ways
HIR 2
Industrial Partners
Other Government Grant (EPU)
Missing Industrial Input
Limited Resources
Product Licensing
Industrial Grant (?)
April 2015

19. Update 2015: Publication
2014, Influence of nonionic branched-chain alkyl glycosides on a model nano-emulsion for drug delivery systems, Colloids and Surfaces B: Biointerfaces,115:
2014, Lyotropic Phase Behaviour and Structural Parameters of Monosaccharide and Disaccharide Guerbet Branched-chain β-D-glycosides. Advanced Materials Research Vol. 895,
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):  
2012, Physico- Chemical Characterization of Natural-Like Branched- Chain Glycosides towards Formation of Hexosomes and Vesicles, Langmuir, 2012, 28(5),
April 2015

20. Update 2015 Simulation studies Testing for Field effect study
Dielectric measurements
2006, Liquid Crystals, 33(3):
2006, Phys. Rev. E 73:
2014. Phase sensitive molecular dynamics of self-assembly glycolipid thin films: A dielectric spectroscopy investigation.J. Chem. Phys. 141,  
Pyroelectricity
Thin Solid Films (2010),  
Simulation studies
2014. Conformational Dynamics of Dry Lamellar Crystals of Sugar Based Lipids: An Atomistic Simulation Study, PLOS One : June 30, 2014DOI: /journal.pone
Physical Chemistry Chemical Physics, 2014, 16,
2012, Journal of Physical Chemistry B, 116(38),
April 2015

21. Thank You.
April 2015