Hydrocolloid Consultant Rutgers Adjunct Professor
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- Annabella King
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1 CARBYDRATES Basic Theory Alan H. King, Ph.D. Hydrocolloid Consultant Rutgers Adjunct Professor Rutgers ffice: Rm #321A, (848) Home ffice: (908) ;
2 utline Introduction CH Structure Reactions of CHs Function of Simple CHs in Foods
3 Introduction Definition/Nomenclature CH Classification CH Metabolism Carbohydrates in Foods CHs = Aliphatic polyhydroxy compounds which carry a carbonyl group.
4 Carbohydrate = Carbon Hydrate i.e., C(H 2 ) or C n (H 2 ) n, or C 6 (H 2 ) 6 = C 6 H 12 6 C 2 +H 2 Sugar + 2
5 Simple Sugar Nomenclature -SE = free sugar, esp. aldose sugar -URNIC = -C (carboxyl) group at 1 o carbon -SIDE = substitution at anomeric carbon = glycoside -AN = polymer. E.g., glucan = glucose polymer Introduction to Food Science ISMERS = compounds with same chemical composition but different structures. (general term) STEREISMERS = isomers differing only in spacial arrangement of groups (e.g., - groups) ENANTIMERS = mirror image isomers (e.g., D- vs L- sugars) ANMERS = isomers differing only in position of anomeric carbon groups EPIMERS = Stereoisomers differing only in position of last asymmetric carbon groups
6 CH Classification I Monosaccharides ligosaccharides Polysaccharides
7 CH Classification II Monosaccharides pen chain Cyclic forms Planar, Haworth projection 3-dimensional 5 and 6 carbon most common
8 Glucose & -D-glucopyranose H C CH 2 H C C H H C H C CH 2 Fischer Projection (straight chain) Haworth Projection
9 -D-glucopyranose
10 CH Classification III Introduction to Food Science Monosaccharides pen chain Cyclic forms Planar, Haworth projection 3-dimensional 5 and 6 carbon most common
11 CH Classification IV ligosaccharides (2 20 monos) Disaccharides Sucrose Maltose Lactose Higher ligosaccharides
12 CH Classification V Polysaccharides > 20 monosaccharide units Homo- and heteroglycans Linear Branched
13 Linear vs Branched Polymers linear Mannose backbone RE branched RE RE = reducing end Substituted Galactose side groups
14 CH Metabolism I Contributions to diet Major source of calories 4 Kcal/g Texture, sweetness Simple vs complex CHs
15 CH Metabolism II Enzyme activity Main means of digestion n specific sugars
16
17 CH Metabolism III Dietary fiber Indigestible polysaccharides Function of Sweetness Positives Negatives
18
19 Carbohydrates in Foods Naturally present 3/4 of dry weight Sucrose Fruit Cereals Animal products Added CHs Introduction to Food Science
20 Free Sugars in Fruit (% Fresh vs (Dry) Basis) Introduction to Food Science Fruit D-Glucose D-Fructose Sucrose % H 2 Apple 1.17 (7.5) 6.04 (38.7) 3.8 (24.2) 84.4 Grape 6.86 (37.3) 7.84 (42.6) 2.2 (12.2) 81.6 Peach 0.91 (8.3) 1.18 (10.8) 6.9 (63.5) 89.1 Pear 0.95 (5.7) 6.77 (40.3) 1.6 (9.6) 83.2 Cherry 6.49 (33.1) 7.38 (37.7) 0.22 (1.1) 80.4 Strawberry 2.09 (20.7) 2.4 (23.8) 1.03 (10.2) 89.9
21 Free Sugars in Vegetables (% Fresh vs (Dry) Basis Basis) Vegetable D-Glucose D-Fructose Sucrose % H 2 Beet 0.18 (1.4) 0.16 (1.3) 6.1 (48.1) 87.3 Carrot 0.85 (7.2) 0.85 (7.2) 4.2 (35.9) 88.2 nion 2.07 (19) 1.1 (10) 0.9 (8.2) 89.1 Spinach 0.09 (1) 0.04 (0.4) 0.06 (0.6) 90.7 Sweet corn 0.34 (1.2) 0.3 (1.1) 3.0 (11.1) 72.7 Tomato 1.1 (17.2) 1.3 (20.6) 0.01 (0.2) 93.5
22 Sugars in Common Foods Food Sugar present(%) Soft Drinks 9 Cracker 12 Ice cream 18 Ready-to-eat cereals (dry) 1-50 range juice 10 Catsup 29 Cake (dry mix) 36 Jello (dry) 83
23 Carbohydrate Structure I Monosaccharides Glycosides ligosaccharides Polysaccharides
24 Carbohydrate Structure II Monosaccharides Important ones D-glyceraldehyde source
25 = CH = CH 2 D-Glycerose D-Triose Aldoses D-Tetroses = D-Erythrose D-Pentoses D-Threose D-Ribose D-Arabinose D-Xylose D-Lyxose D-Hexoses D-Allose D-Altrose D-Glucose D-Mannose D-Gulose D-Idose D-Galactose D-Talose
26 Carbohydrate Structure III Monosaccharides Important ones D-glyceraldehyde source Straight chain does not explain all Rxs Ring formation Mutarotation Haworth projection
27 H 1 C RING FRMATIN 2 4 C C C 3 5 C 6 CH CH
28 Glucose Anomers: Hemiacetals Reducing sugars Mutarotate C C C C C CH Ring opens here - Mutarotation 6 CH 2 Ring here for furanose -D-Glucose (m.p. 146 o, [ ] = +112 o ) -D-Glucose (m.p. 150 o, [ ] = +19 o ) or
29 HAWRTH PRJECTIN D- L- 4 6 CH { L-) D-) { D-) L-) D-GLUCSE D-Glucopyranose)
30 Carbohydrate Structure IV Glycosides Alcohol + acid - H 2 Physiological function Base stable, acid labile Rx with other sugars
31 Glycosides CH 2 CH 2 aglycon + R H + R + H 2 D-glucose alkyl D-glucopyranoside
32 Carbohydrate Structure V ligosaccharides Disaccharides Homogeneous Heterogeneous
33 H CH 2 CH 2 D glucopyranosyl-(1 4)- D glucopyranose Maltose H CH 2 CH 2 H D glucopyranosyl-(1 6)- D glucopyranose Isomaltose Disaccharides of Glucose H CH 2 CH 2 H D glucopyranosyl-(1 4)- D glucopyranose Cellobiose CH 2 H CH 2 D glucopyranosyl-(1 6)- D glucopyranose Gentiobiose CH 2 H 2 HC H D glucopyranosyl-(1 1)- L glucopyranoside Trehalose
34 Heterogeneous Disaccharides CH 2 CH 2 H hemiacetal -Lactose -D-galactopyranosyl (1-4)- -D-glucopyranose CH 2 1 H 1 CH H 4 CH Sucrose -D-glucopyranosyl-(1-2)- -D-fructofuranoside
35 Carbohydrate Structure VI ligosaccharides Disaccharides Homogeneous Heterogeneous Reducing vs Non-reducing Higher ligosaccharides
36 Heterogeneous Disaccharides CH 2 CH 2 H hemiacetal -Lactose -D-galactopyranosyl (1-4)- -D-glucopyranose CH 2 1 H 1 CH H 4 CH Sucrose -D-glucopyranosyl-(1-2)- -D-fructofuranoside
37 Carbohydrate Structure VII Polysaccharides General Starch (I) Source Composition Amylose Amylopectin Structure
38 Starch Granules I Introduction to Food Science Tapioca Granules Wheat Granules Potato Granules
39 Starch Granules II Rice Granules Corn Granules
40 Carbohydrate Structure VIII Polysaccharides General Starch (I) Source Composition Amylose (linear) Amylopectin (branched)
41 Amylose Introduction to Food Science Amylose The Helical Structure Amylose Fractions Showing the Helical Structure
42 1,6 Linkage Amylopectin 1,4 Linkage ^^^ Amylopectin Amylopectin Branching
43 Starch Source Amylose % Amylopectin % Corn Tapioca Waxy maize Nil 99+
44 Carbohydrate Structure IX Polysaccharides Starch (II) Granules Gelatinization Rx with Iodine
45 Structrue of molecules in layer of a starch granule. Thickened areas represent micelles produced by association of chains
46 Carbohydrate Structure X Polysaccharides Starch (II) Granules Gelatinization Rx with Iodine
47 Starch Granules III Introduction to Food Science Micrograph of Potato Starch Granules Micrograph of Potato Starch Granules (polarized light shows Maltese Cross) A B
48 Brabender Swelling Profiles at 6% Solids
49 Starch Rx w/ I 2 Clathrates Model of an iodine-filled amylose helix (Rundle, Foster, and Baldwin, 1944)
50 Polysaccharides Starch (III) Modification Why? Crosslinking Stabilization Retrogradation Freeze/Thaw stability Introduction to Food Science Carbohydrate Structure XI
51
52 Starch granule structure Introduction to Food Science X = Cross-linking; H = Hydrogen bonding Gel phase Micelles Cross-linking to supplement hydrogen bonding in a starch granule Stabilization> > (Complements of NATINAL STARCH) ^ = Blocking action =Stabilizing agent
53 Reactions of Carbohydrates I Hydrolysis Acyclic CH Reactions CH Dehydration/Thermal degradation Browning Reactions - nonenzymatic
54 Reactions of Carbohydrates II Hydrolysis Mechanism Products of hydrolysis Corn Syrups Compositions DE (dextrose equivalents)
55 Reactions of Carbohydrates III Hydrolysis Starch (Amylose), considered as a condensation polymer of glucose
56 Typical, Commercial HFCS Products Components Normal 55% Fructose 90% Fructose Glucose Fructose ligosaccharides Relative sweetness
57 Reactions of Carbohydrates IV Acyclic CH Reactions Ring size transitions Mutarotation Enolization - Lobry de Bruyn- Alberda van Ekenstein Rx
58 Glucose Equilibrium Cpds -D-glucofuranose 0.003% -D-glucopyranose D-glucose (aldehydo-dglucose) -D-glucofuranose -D-glucopyranose Interconversion of D-glucose isomers in aqueous solution
59 Reactions of Carbohydrates VI D-glucose enediol D-glucose, D-mannose D-fructose Lobry de Bruyn-Alberda van Ekenstein reaction of D-glucose.
60 Reactions of Carbohydrates VII CH Dehydration/Thermal degradation Browning Reactions - non-enzymatic Caramelization Enolization Dehydration Polymerization
61 hydroxyacetylfuran enediol 3-deoxyosone 3,4-dideoxyosone hydroxymethylfurfural (HMF) Formation of hydroxymethylfurfural by dehydration of a hexose enediol
62 Reactions of Carbohydrates VIII Browning Reactions - non-enzymatic Caramelization Maillard reaction Amino groups Reducing sugar Water Positive vs negative effects Controlling the Rx
63
64 Function of Simple CHs in Foods I Reactions with other Ingredients Water Flavors Sweeteners Alcohols Bulking Agents
65 = 6 Glu = 7 Glu = 8 Glu Host Molecule Guest Molecule Schardinger dextrin Bacillus macerans amylase
66 Sugar Alcohols; Sweetness Sugar alcohol Relative sweetness Xylitol 90 Sorbitol 63 Galactitol 58 Maltitol 68 Lactitol 35 Sugar alcohols in tap water at 25 o C Sucrose = 100
67 Function of Simple CHs in Foods II Bulking Agents Maltodextrins Polydextrose
68 Dietary Fiber NEW DIETARY FIBER DEFINITIN - Dietary fiber is the edible parts of plants or analogous carbohydrates that are resistant to digestion and absorption in the human small intestine with complete or partial fermentation in the large intestine. Dietary fiber includes polysaccharides, oligosaccharides, lignin, and associated plant substances. Dietary fibers promote beneficial physiological effects including laxation, and/or blood cholesterol attenuation, and/or blood glucose attenuation.
69 Polydextrose Composition % Polymer Glucose Sorbitol Levoglucosan Water Sulphated ash
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