Trans FAT LABELING an Industry Perspective

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Trans FAT LABELING an Industry Perspective National Nutrition Database Conference 28 th Edition June 24-26, 2004 Iowa City, IA

Trans FAT LABELING an Industry Perspective Christine Wold QRO Product Labeling General Mills Inc. Jonathan W. DeVries, PhD Technical Manager Medallion Laboratories

Trans Fat Labeling Regulation Issued July 9, 2003 by FDA Made Trans Fat is a mandatory label nutrient Set a compliance date of January 1, 2006 Did not include a Trans Fat Daily Value (DV) Does not permit Trans Fat Claims Does not require a Warning Footnote Intake of trans fat should be as low as possible

What Does This Mean For General Mills?

GMI Must Provide Trans Fat Information for Every Product Over 5,000 retail and 850 foodservice product labels need to be changed Remaining (> 4000) foodservice products need to include Trans Fat in nutrient data shared with our customers

Thank Goodness for 2 Years (Really!!) July 10, 2003 Action Started Inquiries from Consumers Inquiries from Customers Inquiries from Product Developers Identified need to develop a coordinated corporate plan to implement trans fat labeling Address FDA regulated products vs USDA regulated products

GMI Developed a Coordinated Corporate Timeline for Label Changes Prioritization given to: Products with high consumer requests Products with complete, accurate ingredient information and resource availability Foodservice key accounts Leveraged Timing Opportunistic planned label changes Business reformulation plans

Labeling Plan Addressed Consumers, Shelf Life and Logistics Product Categories with Frequent Consumer Inquiries Completed 5/03 Canned Vegetables and Dry Goods Targeted completion 1/05 Longer Shelf Life Simpler distribution Refrigerated/Frozen Foods Targeted completion September, 2005 Complex Distribution Limited Shelf Life

Trans Fat Timeline Highlights Trans Fat labeling rolled out by product category. Cereals, Yogurts and Fruit Snacks were the first product categories to include trans fat on label. All Foodservice work will be completed by 1/1/05 to allow our customers to label their products by 1/1/06. Goal is to have all packages changed by 9/1/05. Totino s and Lloyd s predominately USDA regulated products will change labels last.

How will trans fat labeling be implemented?

Trans Fat Labeling Implementation Requires Cross-Functional Resources Analytical Ingredients Finished Products Logistics Coordinate timing of label changes with business Assure all products shipped after 1/1/06 include trans fat values

Trans Fat Labeling Implementation Requires Cross-Functional Resources Labeling Manage label change process Assure every package is touched Brand Design Manage package design process Plant Quality Compare new packages coming into the plants with approved keylines

How will trans fat be labeled?

Trans Fat is a mandatory nutrient Trans Fat must appear on every Nutrition Facts Panel As a separate line listing g/serving In the Not a significant source footnote if: Trans Fat = <0.5g/serving Total Fat = 0g/serving No fat claims

Why is Trans fat labeling a complex consumer issue?

Consumers Are Looking For Trans Fat Information On The: Ingredient Statement vs Nutrition Facts Panel Partially Hydrogenated Oil = Trans Fat Products with <0.5g trans fat/serving may label 0g trans fat

Dairy fats Consumers are Looking for Trans Fat Information on the: Animal fats Ingredient Statement vs Nutrition Facts Panel Processing/oxidation Low levels of hydrogenation (<0.5 g trans)

There will be more to come on Trans Fat Trans fat claims first round of comments to ANPR submitted early October. Trans fat footnote comments submitted early October. Trans Fat DV timing may be with other nutrient DV changes implemented 2008.

Methods of Analysis and Related Issues Discussion

Structures and Properties of Fatty Acids Methods of Analysis Wrap Up Q & A

Fat is a Chemical Compound Fat is made up of: Glycerol Fatty Acids There are 4 categories of fatty acids differentiated by the types of chemical bonds Fatty acid type determines functionality and health affect

Trans Fat is a Type of Fatty Acid with 1 or more Trans Double Bonds Saturated Fatty Acids (no double bonds) HO O Coconut, Palm kernel, Palm oil (tropical oils), Butter, Hydrogenated Oils and Shortenings Raise LDL cholesterol, and increase risk of cardiovascular disease Mono and Polyunsaturated Fatty Acids ( 1 cis double bond) HO O cis Liquid oils including Canola, Soybean, Olive, Sunflower and Corn oils. Lower LDL cholesterol, associated with reduced risk of cardiovascular disease. Trans Fatty Acids ( 1 trans double bond) HO O trans Partially Hydrogenated Oils, Shortenings, Margarines, Roll-ins, & Chips Raise LDL cholesterol like saturated fat, may also lower HDL. Associated with increased risk of cardiovascular disease and possibly type II diabetes.

TYPES OF FATTY ACIDS Saturated Fats- No Double Bonds Monounsaturates- One Double Bond Cis Configuration Trans Configuration Polyunsaturates-Multiple Double Bonds Cis CH 2 -Cis Configuration Numerous Cis and Trans Configurations

Defining trans Fatty Acids for Labeling Purposes trans fat defined as the sum of all unsaturated fatty acids that contain one or more isolated (i.e., nonconjugated) double bonds in a trans configuration

Saturated Chain

Cis Unsaturated Chain

Trans Unsaturated Chain

Saturated Fatty Acid-Stearic Acid Melting Point: 69.6 o C Boiling Point: 383 o C Sources: Animal Fats and Cocoa Butter

Coupling of Stearic Acid (Saturated Fat) - High Melting Point - Crystallizes

Cis Unsaturated Fatty Acid-Oleic Melting Point: 13.6 o C Boiling Point: 286 o C Sources: Animal & Vegetable Oils, Cocoa Butter, Olive Oil

Coupling of Oleic Acid Lower Melting Point Less crystallization

Trans Unsaturated Fatty Acid-Elaidic Melting Point: 43.7 o C Boiling Point: 288 o C Sources: Hydrogenated Vegetable Oils And Processed Food

Coupling of Elaidic Acid Crystallizes

C22:6 Acid

Functionality Impact Functionality in Food Formulation Blending Effects Oxidation Resistance Leavening/Structure Melting Point Differences Texture Mouth Feel

SOURCES of Trans Fat Hydrogenated Vegetable Oils Animal Fats Dairy Products Result of Fat Oxidation

Analysis Trans Fats in Foods AOAC International 996.06 Total, Saturated and Unsaturated Fatty Acids Add C-11 fatty acid as internal standard Extraction-1 of 3 methods (Pyrogallic acid added-eliminates oxidation and isomerization) Foods except dairy and cheese-acid hydrolysis Dairy-Ammonium Hydroxide hydrolysis Cheese-Combination of Ammonium Hydroxide hydrolysis followed by Acid hydrolysis

Analysis Trans Fats in Foods AOAC International 996.06 (cont) Methylation with BF 3 -Methanol GC Capillary Column (SP2560, 100m x 0.25 mm, 0.2um coating Resolve doublet C18:3, C20:1 Resolve triplet C22:1, C20:3, and C20:4 58 individual fatty acids quantitated 9 trans fatty acids Conjugated linoleic acid

Fatty Acids Included in AOAC 996.06 FATTY ACID RT RRT (C11=1.0) 4:0 Butyric 10.49 0.46 6:0 Caproic 12.36 0.54 8:0 Caprylic 15.69 0.68 10:0 Capric 20.39 0.89 11:0 Undecanoic 22.99 1.00 12:0 Lauric 25.58 1.11 13:0 Tridecanoic 28.15 1.22 14:0 Myristic 30.65 1.33

Fatty Acids Included in AOAC 996.06 FATTY ACID RT RRT (C11=1.0) 14:1 Myristoleic 32.63 1.42 14:1 trans-myristelaidic 32.01 1.39 15:0 Pentadecanoic 33.04 1.44 15:1 Pentadecenoic 34.98 1.52 16:0 Palmitic 35.41 1.54 16:1 trans-palmitelaidic 36.39 1.58 16:1 Palmitoleic 36.88 1.60 17:0 Margaric 37.54 1.63

Fatty Acids Included in AOAC 996.06 FATTY ACID RT RRT (C11=1.0) 17:1 Margaroleic 38.92 1.69 18:0 Stearic 39.78 1.73 18:1 trans 6-Petroselenic 40.50 1.76 18:1 trans-elaidic 40.61 1.77 18:1 trans 11-Vaccenic 40.72 1.77 18:1 Petroselenic 40.90 1.78 18:1 Oleic 40.99 1.78

Fatty Acids Included in AOAC 996.06 FATTY ACID RT RRT (C11=1.0) 18:1 Oleic 40.99 1.78 18:1 Vaccenic 41.18 1.79 18:1 Octadecenoic 41.54 1.81 18:2 trans-linolelaidic 41.69 1.81 18:2 trans 9-Linolelaidic 42.11 1.83 18:2 trans 12-Linolelaidic 42.53 1.85 18:2 Linoleic 42.87 1.86 20:0 Arachidic 43.75 1.90 18:3 g-linolenic 44.25 1.92

Fatty Acids Included in AOAC 996.06 FATTY ACID RT RRT (C11=1.0) 20:1 Eicosenic cis 5 44.42 1.93 20:1 Eicosenic trans 11 44.45 1.93 20:1 Eicosenic cis 8 44.67 1.94 20:1 Eicosenic cis 11 44.82 1.95 20:1 Eicosenic cis 13 44.99 1.96 18:3 Linolenic 45.02 1.96 18:2 Linoleic conjugated 45.35 1.97 18:2 Linoleic conjugated 45.40 1.97 21:0 Heneicosanoic 45.69 1.99

Fatty Acids Included in AOAC 996.06 FATTY ACID RT RRT (C11=1.0) 18:2 Linoleic conjugated 46.18 2.01 18:4 Octadectetraenoic 46.39 2.02 20:2 Eicosadienoic 46.65 2.03 22:0 Behenic 47.46 2.06 20:3 g-eicosatrienoic 47.94 2.09 22:1 Cetoleic 48.27 2.10 22:1 Erucic 48.50 2.11 20:3 Eicosatrienoic 48.68 2.12 20:4 Arachidonic 48.94 2.13

Fatty Acids Included in AOAC 996.06 FATTY ACID RT RRT (C11=1.0) 23:0 Tricosanoic 49.22 2.14 22:2 Docosadienoic 50.17 2.18 24:0 Lignoceric 50.79 2.21 20:5 Eicosapentaenoic 50.96 2.22 24:1 Nervonic 51.92 2.26 22:3 Docosatrienoic 51.98 2.26 22:4 Docosatetraenoioc 52.28 2.27 22:5 Docosapentaenoic 54.75 2.38 22:6 Docosahexaenoic 55.82 2.43

Fatty Acids Included in AOAC 996.06 Performance Specifications Separate Pairs- C20:1 and C18:3 (Rt s = 44.99 and 45.02 respectively) Separate trio C22:1, C20:3, and C20:4 (Rt s = 48.50, 48.68 and 48.94 respectively)

STANDARD FATTY ACID STANDARD FATTY ACID Methyl Esters 15 20 25 30 35 40 45 50 55 Elution Time(min) Detector Response(mV) 0 100 200 300 400 500 4:0 Butyric 6:0 Caproic 8:0 Caprylic 10:0 Capric 11:0 Undecanoic 12:0 Lauric 13:0 Tridecanoic 14:0 Myristic 8:0 Caprylic 12:0 Lauric 10:0 Capric 12:0 Lauric 14:0 Myristic > 14:1 t-tetradecenoic 14:1 Myristoleic 15:0 Pentadecanoic 15:1 Pentadecenoic 16:0 Palmitic > 16:1 t-hexadecenoic 16:1 Palmitoleic > 16:1 16:1 t-hexadecenoic Palmitoleic > 17:0 Margaric > 17:0 Margaric > 17:1 Margaroleic 18:0 Stearic > 17:1 Margaroleic 18:0 Stearic 18:1 trans Elaidic 18:1 trans Elaidic > 18:1 Oleic> > > > > 18:2 t-octadecadienoic 18:1 Oleic > 18:2 t-octadecadienoic > 18:2 Linoleic > 18:2 Linoleic > 20:0 Arachidic > 20:0 Arachidic > 18:3 g-linolenic 18:3 g-linolenic > 20:1 18:3 Gadoleic Linolenic > 20:1 18:3 Gadoleic Linolenic 21:0 Heneicosanoic 20:2 Eicosadienoic 22:0 Behenic 20:3 g-eicosatrienoic > 22:1 20:3 Erucic Eicosatrienoic 20:4 Arachiodonic > 22:2 Docosadienoic 24:1 Nervonic 20:2 Eicosadienoic 22:0 Behenic 20:3 Eicosatrienoic > 22:1 Erucic 23:0 Tricosanoic 22:2 Docosadienoic 24:0 Lignoceric24:0 Lignoceric 20:5 Eicosapentaenoic 24:1 Nervonic 22:3 Docosatrienoic 22:3 Docosatrienoic 22:4 Docosatetraenoic 11:0 Undecanoic 16:0 Palmitic 18:1 Oleic 18:2 Linoleic 22:6 Docosahexaenoic 22:5 Docosapentaenoic 22:6 Docosahexaenoic

Soybean Oil Soybean Oil 43.3 43.4 43.5 43.6 43.7 43.8 43.9 44.0 44.1 44.2 44.3 Elution Time(min) Detector Response(mV) 0 50 100 150 200 > > > > 18:1 trans Elaidic 18:1 Oleic

Hydrogenated Soy Oil Hydrogenated Soy Oil 43.243.343.443.543.643.743.843.944.044.144.244.344.444.544.644.7 Elution Time( min) Detector Response(mV) 0 50 100 150 200 250 > > > 18:1 trans Elaidic 18:1 Oleic

Commercial Vegetable Shortening Commercial Vegetable Shortening > > > Detector Response(mV) 50 100 150 200 18:1 trans Elaidic 18:1 Oleic 43.2 43.4 43.6 43.8 44.0 44.2 44.4 44.6 Elution Time(min)

Margarine 43.4 43.6 43.8 44.0 44.2 44.4 44.6 44.8 45.0 Elution Time(min) Detector Response(mV) 500 1000 1500 2000 > > > 18:1 trans Elaidic 18:1 Oleic

Normalized by Weight % (w/w) as Triglyceride in Product Saturated Fatty Acids Monounsaturated Fatty Acids cis-cis Polyunsaturated Fatty Acids trans Fatty Acids 4:0 Butyric 1.203% 0.097 0.085 6:0 Caproic 0.682% 0.055 0.050 8:0 Caprylic 0.385% 0.031 0.028 10:0 Capric 0.868% 0.070 0.065 12:0 Lauric 0.980% 0.079 0.074 13:0 Tridecanoic 0.037% 0.003 0.003 14:0 Myristic 4.068% 0.328 0.311 14:1 t-tetradecenoic 0.285% 0.023 0.022 14:1 Myristoleic 0.471% 0.038 0.036 15:0 Pentadecanoic 0.459% 0.037 0.035 15:1 Pentadecenoic 16:0 Palmitic 21.248% 1.713 1.632 16:1 t-hexadecenoic 0.360% 0.029 0.028 16:1 Palmitoleic 1.823% 0.147 0.140 17:0 Margaric 0.695% 0.056 0.053 17:1 Margaroleic 18:0 Stearic 12.850% 1.036 0.992 18:1 trans Elaidic 8.546% 0.689 0.659 18:1 Oleic 32.089% 2.587 2.476 18:2 t-octadecadienoic 1.761% 0.142 0.136 18:2 Linoleic 9.092% 0.733 0.701

18:0 Stearic 12.850% 1.036 0.992 18:1 trans Elaidic 8.546% 0.689 0.659 18:1 Oleic 32.089% 2.587 2.476 18:2 t-octadecadienoic 1.761% 0.142 0.136 18:2 Linoleic 9.092% 0.733 0.701 20:0 Arachidic 0.223% 0.018 0.017 18:3 g-linolenic 0.037% 0.003 0.003 20:1 Gadoleic 0.558% 0.045 0.043 18:3 Linolenic 0.744% 0.060 0.057 21:0 Heneicosanoic 18:2 conj-linoleic 0.050% 0.004 0.004 18:4 Octadecatetraenoic 20:2 Eicosadienoic 0.025% 0.002 0.002 22:0 Behenic 0.161% 0.013 0.013 20:3 g-eicosatrienoic 0.062% 0.005 0.005 22:1 Erucic 20:3 Eicosatrienoic 20:4 Arachiodonic 0.087% 0.007 0.007 23:0 Tricosanoic 0.037% 0.003 0.003 22:2 Docosadienoic 24:0 Lignoceric 0.074% 0.006 0.006 20:5 Eicosapentaenoic 24:1 Nervonic 22:3 Docosatrienoic 22:4 Docosatetraenoic 22:5 Docosapentaenoic 0.037% 0.003 0.003 22:6 Docosahexaenoic Totals 100.0% 8.06 3.37 2.70 0.78 0.85 Percent of Fatty Acid Components based on Total Fat 43.79% 35.05% 10.12% 11.04%

Butter Trans 42.7 42.8 42.9 43.0 43.1 43.2 43.3 43.4 43.5 43.6 43.7 43.8 43.9 44.0 44.1 44.2 Elution Time(min) Detector Response(mV) 20 40 60 80 100 120 > > > 18:1 trans Elaidic 18:1 Oleic >

Tallow 42.642.742.842.943.043.143.243.343.443.543.643.743.843.944.0 44.1 Elution Time(min) Detector Response(mV) 0 50 100 150 200 250 > > 18:1 trans Elaidic 18:1 Oleic >

Commercial Vegetable Shortening Commercial Vegetable Shortening > > > Detector Response(mV) 50 100 150 200 18:1 trans Elaidic 18:1 Oleic 43.2 43.4 43.6 43.8 44.0 44.2 44.4 44.6 Elution Time(min)

Trans FATS Effect of Processing Trans Fats levels can change with processing especially if oxidation can occur, e.g. where no antioxidants are being used. Therefore it is recommended that the finished product be analyzed

Method Precautions Avoid all traces of water in the BF 3 Methanol Can make 3-5% difference Assure sample size is small enough to provide approximately 1:1 ratios with standards for largest peaks Assure all reaction times are closely followed

AOCS Efforts GC Columns determined to be best: CP Sil88 SP 2560 Adjusted Area Normalized approach desired for convenience of fats/oil suppliers Proposals for faster procedures

AOCS Efforts Proposals for faster procedures Silliker Laboratories Cargill Ingredients Nestle QA Will not change results, just less analyst time

Updates to Official Method 996.06 AOAC International Thus far there have been no formal approaches to AOACI regarding an update

Summary Trans fat is now a mandatory nutrient required for all FDA regulated products All package labels will need to change January 1, 2006 is the compliance date

Summary Method AOAC 996.06 is effective for all foods analyses Skilled analysts are necessary for accurate data Method streamlining is being investigated.

NLEA Nutrition Labeling Education Act

Trans Fat Labeling Activities NLEA Non cis Fatty Acids Less than Easy to Analyze

NLEA Need Lotsa Excellent Analysts

Questions?