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

Project Background n MOSTI Strategic Research Top-Down ¡ ¡ n Glycolipids as Functional Material Project Background n MOSTI Strategic Research Top-Down ¡ ¡ n Glycolipids as Functional Material 2002 -2006 High Impact Research- MOHE ¡ ¡ ¡ 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 Mimicking Natural Products Phospholipids Phosphotidyl- Sphingomyline choline Glycolipids MGDG Glucosylcerebroside Branched Chain Glycosides Synthetic Glycolipids Alkylpolyglucoside Ease of Preparation

Guerbet Glycosides at Geneva ITEX 2005 Nature-Like Synthetic Alkyl Branched-Chain Glycolipids: A Review on 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 Provincial. Government, 2005 Gold Medal One of best manuscripts Liquid Crystals 2012 3/19/2018 2005 4

Glycolipids Self-Assembly Structural Determination Glycolipids Self-Assembly Structural Determination

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

Branched Chain Guerbet Glycosides Summary n n n n Liquid crystal at RT for Branched Chain Guerbet Glycosides Summary n n n n Liquid crystal at RT for branched glycosides of 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 n Guerbet glycoside literatures n n prepared using a glycosidation described elsewhere. Guerbet Materials n Guerbet glycoside literatures n n prepared using a glycosidation described elsewhere. n n n 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 n alcohol, ester, and acid, all of which have been used in many industrial applications. n O’Lenick, A. J. , Jr. Guerbet Chemistry. J. Surfactants Deterg. 2001, 4, 311 -315 n

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

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

Economic Analysis n MY Cosmetic Market n n Volume: Annual Growth: Skin Care: (Data: Economic Analysis n MY Cosmetic Market n n Volume: Annual Growth: Skin Care: (Data: 2003) ~ RM 2. 8 billion ~ 3 -5 % ~ ¼ of total Volume Glycoside based delivery system n Market Novelty: target liquid crystal delivery system ¡ ¡ ¡ April 2015 Hexasome Liposome Cubosome

Commercialization Status Quo n Established Product Preparation Basic Product Characterization n Patent n ¡ Commercialization Status Quo n Established Product Preparation Basic Product Characterization n Patent n ¡ ¡ April 2015 MY PI 20051074 n Compound Class n Application of Compound Properties List of patent approved n Singapore Patent No. 200706665/7, Oct. 31, 2008 n South Africa Patent No. 2007/8477, Jul. 30, 2008 n Malaysia Patent No. MY-138164 -A, Apr. 30, 2009 n U. S. Patent No. US 8, 304, 525, Nov. 6, 2012 n China Patent No. CN 200680008448, Jun. 12, 2013 n Japan Patent No. 5392467, Oct. 25, 2013

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

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

Update 2015: Publication n n 2014, Influence of nonionic branched-chain alkyl glycosides on a Update 2015: Publication n n 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 n Testing for Field effect study ¡ Dielectric measurements n n n Update 2015 n Testing for Field effect study ¡ Dielectric measurements n n n ¡ Pyroelectricity n n 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 ¡ ¡ ¡ April 2015 2014. Conformational Dynamics of Dry Lamellar Crystals of Sugar Based Lipids: An Atomistic Simulation Study, PLOS One : June 30, 2014 DOI: 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 Thank You. April 2015