Linnaeus Plant Sciences. Optimizing Oil Seed Potential for Industrial Applications

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1 Linnaeus Optimizing Oil Seed Potential for Industrial Applications Jack Grushcow

2 Overview Plant Bio-technology overview Castor Case Study HFY Applications Production Issues Future Directions

3 Executive Summary There have been dramatic improvements in biotech methods and tools Systems exist to efficiently clone genes of interest Patents allow control of novel materials Regulatory approvals increasing It is possible to own a feed stock Petroleum supply/cost/environment issues

4 Plant Bio-technology Overview

5 Interesting Genes have been Cloned Fatty acid type Hydroxy Species Ricinus communis (Castor bean) Lesquerella fendleri Ricinoleic acid Ricinoleic/Linoleic (Hydroxy fatty acid elongated to Lesquerolic acid) Product 12-OH-18:1 ( 9cis, 12-OH) Bifunctional enzyme 12-OH-18:1 ( 9cis, 12cis) and 18:2 ( 9cis, 12-OH) Acetylenic Crepis alpina Crepenynic acid 12-ynoic-18:1 Epoxy Crepis palaestina Vernolic acid 12,13-epoxy-18:1 Vernonia galamensis Conjugated Momordica charantia α-eleostearic acid ( 9cis, 11trans, 13trans) 18:3 Impatients balsamina Aleurites fordii (Tung) α-parinaric acid 18:4 Trichosanthes kirilowii Punicic acid ( 9cis, 11trans, 13cis) 18:3 Punicia granatum (Pomegranate) Calendula officinalis Calendic acid ( 8trans, 10trans, 12cis) 18:3 (Marigold) Dimorphotheca sinuata Dimorphecolic 9-OH-18:2 ( 10trans, 12trans) ( 9cis, 12-ynoic) ( 9cis, epoxy) ( 9cis, 11trans, 13trans, 15cis)

6 TAG Assembly (Simple Version) TAG is synthesized by the sequential addition of fatty acids to a glycerol backbone. Expression levels and packaging key. CH2 OH CH OH CH 2 PO 4 CH 2 O R CH OH CH 2 PO 4 CH 2 O R CH O R CH 2 PO 4 CH 2 O R CH O R CH 2 OH TAG CH 2 O R CH O R CH 2 O R

7 Ricinoleic Acid OH Ricinoleic acid: a reactive fatty acid capable of numerous oleochemical conversions

8 Industrial Applications of Castor Oil Over 1,000 patented industrial applications Industrial chemistry established since 1900 s Long recognized for outstanding properties including oxidative stability and lubricity US Strategic stockpile up to 70 s Only commercial source of HFA There are issues..

9 Linnaeus Hydroxy Fatty Acid (HFA) Technology Hydroxylase Gene Expression in Model Expression in Conventional Oilseeds Ricinus communis (Castor) Arabidopsis thaliana

10 Advantages of (GM) Approach Conventional Approach GM Approach Conventional Oils Canola, Soybean, Corn Industrial Oils Lesquerella (Castor) Vernonia Combine Conventional and Industrial Oils High oleic oils, Castor Goals High oleic Low saturates Low polyunsaturates Limited profiles Goals Agronomics Infrastructure Limited regions Goals Higher functionality High oleic Low polyunsaturates Multiple crops

11 Results to Date

12 Four different hydroxy fatty acids can be made in Arabidopsis. Oleic acid (18:1 c9) HYDROXYLATION Ricinoleic acid (12OH-C18:1 9c) Desaturation Densipolic acid (12OH-C18:2 9c,15c) Elongation Elongation Lesquerolic acid (14OH-C20:1 c11) Auricolic acid (14OH-C20:2 c11,c17)

13 Comparison of Fatty Acid Profiles The HFA clearly replaces oxidatively unstable polyunsaturates Hyroxy Fatty Acid (HFA) Hydroxy Fatty Acid Fatty Acid Linnaeus Canola Castor Name Oil* Oil Oil % Fatty Acid Ricinoleic & Others C16:1 Palmitoleic 0.3 C18:1 Oleic C18:2 Linoleic C18:3 Linolenic C20:1 Gadoleic 1.0 C22:1 Erucic 0.7 C12:0 Lauric 0.0 C16:0 Palmitic C18:0 Stearic *Expressed in Brassica napus (hydroxy fatty acids include ricinoleic and densipolic acid)

14 Industrial Applications For Linnaeus HFA Technology HFA Vegetable Oils Base Oil Feedstock Reactive Component Lubricants* Fuels* Paints, Coatings and Inks Functional Fluids Oleochemicals Polymers and Foams* Process Oils * Initial focus areas

15 What is the potential U.S. motor oil market? Replacing 10% of 1.1 billion gallons Automotive Other Bio potential 110 million 50 gallons/acre would require 2.2 million acres!

16 Value Proposition Canola oil $.30 CDN per pound Motor oil $1.25 USD per pound based on $2.50 quart Add pour point and anti-oxidant package What about emission credits?

17 Additional Lubricant Markets Hydraulic oils 210 Metalworking Lubricants 68 *Diesel additive 66 Two-stroke oils 19 Chain bar lubricants US Market in Million gallons National Petroleum Refiners Association *Canadian market estimates based on 2005 mandate

18 Towards Commercialization

19 Where Oil Seeds are Grown

20 Average Seed Production Since ,000,000 Tonnes Canadian Canola Production '000 Tonnes 12,000 10,000 8,000 6,000 4,000 2,

21 Average Canola Oil Prices $0.30 lb. Canola Oil Prices $CDN/MT $CDN/MT

22 Feasibility of Production Canada produces 10 Million acres of Oil seeds Oil yield typically 50 gallons per acre If half acreage is planted yield 250MM Gallons Average commodity price.30 cdn per pound USA and Australia produce large acreages

23 IP Freedom to operate Production Issues Building a real business Closed loop system required Regulations evolving - must manage Stakeholder support key engagement This is a process

24 Target Crops Non-food preferred Specific oil profiles required Agronomics still key Infrastructure must exist FTO considerations Transformation capable

25 Relevance New genes will continue to be cloned and engineered Patents will control new materials Competitive advantages will be conferred Regulations evolving

26 Summary Oil seeds are future factories Petroleum feed stock replacement key Need to step up expression levels Marketing and regulatory strategies needed Plants allow costs to be managed and scaled