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Appendix 1: Chemical and Physical Characteristics of Vitamins

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Appendix 1: Chemical and Physical Characteristics of Vitamins Appendix 1: Chemical and physical characteristics of vitamins Vitamin A Structuralformula eM, o Principal commercialforms Vitamin A acetate R=COCH3 Vitamin A palmitate R = CO(CH2)14CH3 Empirical formula Molecular weight Retinol C2oH300 286.45 Vitamin A acetate C22H3202 328.50 Vitamin A palmitate C36H6002 524.90 Standardisation 1 Ilg retinol equivalent corresponds to 3.33 international units (IV) ofvitamin A activity. I international unit corresponds to the activity of 0.344 Ilg of pure crystalline vitamin A acetate. The US Pharmacopoeia Unit (USP unit) is the same as the international unit. The biological activity ofpure vitamin A acetate is 6 2.904 x 10 IU/g and ofpure vitamin A palmitate is 6 1.817 x 10 IU/g APPENDIX 1 247 Solubility Retinol is soluble in fats and oils and practically insoluble in water and glycerol. Vitamin A esters are readily soluble in fats, oils, ether, acetone and chloroform. They are soluble in alcohol but insoluble in water. Melting point Vitamin A acetate Vitamin A palmitate Absorption spectrum Vitamin A esters show a characteristic absorption spectrum, the position of the maxima depending on the solvent used: in cyclohexane the maxima is at 328 DID and in isopropanol it is at 326 DID. p-Carotene Structuralformula CH 3 I3-carotene R CH3 CH3 CH3 Apocarotenal: R=CHO Apocarotenoic ester: R=COOC2Hs Principal commercialforms p-Carotene p- Apo - 8' - carotenal Apocarotenoic ester 248 THE TECHNOLOGY OF VITAMINS IN FOOD Empirical fonnula Molecular weight ~-Carotene C40H56 536.9 Apocarotenal C30H400 416.6 Apocarotenoic ester C32H4402 460.7 Standardisation There have been a number ofconventions to establish the relationship between the provitamin activity of~-carotene and vitamin A. The vitamin A equivalents based on retinol equivalents can be calculated as follows: I retinol equivalent = I j.lg retinol = 6 j.lg ~-carotene = 12 j.lg other provitamin A carotenoids = 3.33 IV vitamin A activity from retinol = 10 IV vitamin A activity from ~-carotene. Solubility ~-Carotene is insoluble in water, sparingly soluble in alcohol, fats and oils. Apocarotenal and apocarotenoic ester are insoluble in water and sparingly soluble in fats, oils and alcohol. Melting point ~-Carotene 176-182°C Apocarotenal 136-140°C Apocarotenoic ester I 34-138°C Absorption spectrum Solutions in cyclohexane exhibit the following maxima: ~-Carotene about 456 and 484 nm Apocarotenal about 461 and 488 nm Apocarotenoic ester about 134 and 138 nm Vitamin D Structuralformulae CH, HO Vitamin 02 APPENDIX 1 249 HO VitaminD3 Principal commercialforms VitaminDz: ergocalciferol VitaminD3: cholecalciferol Empirical formula Molecular weight Ergocalciferol (Dz) CZSH440 396.63 Cholecalciferol (D3) C27H440 384.62 Standardisation One international unit (IV) corresponds to the activity of0.025 Ilg ofeither pure crystalline vitamin Dz or D3. The US Pharmacopoeia Unit of vitamin D corre­ sponds to, the international unit. Solubility Soluble in fats and oils, insoluble in water, Melting point Ergocalciferol (Dz) 113-118°C Cholecalciferol (D3) 82-88°C Specific rotation Ergocalciferol (Dz): [a]~ = +102.5° to +107.5° (c = 4 in absolute ethanol) Cholecalciferol (D3): [a]~ = +105° to +112° (c = 5 in absolute ethanol) Absorption spectrum Vitamins Dz and D3 exhibit an absorption maxima at 265 nm in alcoholic solution. 250 THE TECHNOLOGY OF VITAMINS IN FOOD VitaminE Structuralformula CH3 RO dl-a-tocopherol: R =H dl-a-tocopheryl acetate: R = CH3 co Principal commercialforms Empirical formula Molecular weight d-a-Tocopherol C29Hso02 430.7 dl-a-Tocopherol C29Hso02 430.7 d-a-Tocopheryl ~';etate C31Hs203 472.7 dl-a-Tocopheryl acetate C31Hs203 472.7 d-a-Tocopheryl succinate C33Hs40S 530.8 Standardisation The selected international unit (IU) ofvitamin E is the biological activity of I mg ofsynthetic dl-a-tocopheryl acetate. The equivalents ofthe other forms ofvitamin E are related to this standard. The relative activities ofthe most common forms of vitamin E are given below. I IU ofvitamin E is equivalent to: I mg dl-a-tocopheryl acetate 0.909 mg dl-a-tocopherol (1.l0 IU / mg) 1.12 mg dl-a-tocopheryl succinate (0.89 IU / mg) 0.826 mg d-a-tocopheryl acid succinate (1.21 IU / mg) 0.735 mg d-a-tocopheryl acetate (1.36 IU / mg) 0.671 mg d-a-tocopherol (1.49 IU / mg) 1.75 mg d-~-tocopherol (0.57 IU / mg) 7.0 mg d-y-tocopherol (0.14 IU / mg) Solubility Tocopherols and their esters are insoluble in water but readily soluble in vegetable oils, alcohol and organic solvents. APPENDIX 1 251 Refractive index a-Tocopherol 1.5030 - 1.5070 at 20°C a-Tocopheryl acetates 1.4940 - 1.4985 at 20°C Absorption spectrum a-Tocopherol (in alcohol solution) maximum at 292 nm, minimum at 255 nm. a-Tocopheryl acetate (in alcohol solution) maximum at 284-285 nm, minimum at 254nm. VitaminKl Structuralformula Principal commercialforms Empirical formula Molecular weight Vitamin Kl (phytomenadione, phytonadione) 450.68 Standardisation Analytical results are usually expressed as weight units ofpure vitamin Kl as no international standard for the biological activity ofvitamin K has been defmed. Solubility Vitamin Kl is insoluble in water and sparingly soluble in alcohol. It is readily soluble in fats and oils. Refractive index [n]if = 1.525 - 1.528 Absorption spectrum Vitamin Kl shows maxima at 243,249,261 and 270 nm and minima of254 and 285 nm in cyclohexane. 252 THE TECHNOLOGY OF VITAMINS IN FOOD Thiamin (Vitamin Bl) Structuralformula Principal commercialforms Thiamin chloridehydrochloride x=cr,HCl (Thiamin hydrochloride) Thiamin mononitrate Empirical formula Molecular weight Thiamin hydrochloride CI2HI7ClN40S.HCl 337.27 Thiamin mononitrate CI2H1704NsS 327.36 Standardisation To calculate the amount of thiamin cation from the salts (molecular weight of thiamin cation is 265.4): From hydrochloride: divide the amount ofhydrochloride by 1.271 From mononitrate: divide the amount ofmononitrate by 1.234. Solubility Hydrochloride: readily soluble in water (about 1 g / ml), sparingly soluble in alcohol. Mononitrate: slightly soluble in water (about 2.7 g / 100 ml) sparingly soluble in alcohol Melting point Hydrochloride: 250°C (decomposition) Mononitrate: 19Q-200°C Absorption spectrum Thiamin shows a characteristic absorption spectrum in the region of20Q-300 TIm. In 0.1 N hydrochloric acid solution the absorption maxima of thiamin is around 245 nm. The positions ofthe maxima depend on the solvent and pH ofthe solutions. APPENDIX 1 253 Riboflavin (vitamin B2) Structuralformula Principal commercialforms Riboflavin: R = OH .--" ONa Sodium riboflavin-5'-phosphate: R=-O-P, \OH o Empirical formula Molecular weight Riboflavin C17H2006N4 376.36 Sodium riboflavin-5'-phosphate C17H2009N4PNa 478.34 Standardisation 1 g ofsodium riboflavin-5' -phosphate = 0.730 g ofriboflavin. Solubility Riboflavin: sparingly soluble in water (1 g dissolves in from 3000 to 15000 ml water depending on crystal structure). Readily soluble in dilute alkalis. Very sparingly soluble in alcohol. Sodium riboflavin-5' -phosphate: soluble in water (112 mg / ml at pH 6.9, 68 mg / ml at pH 5.6 and 43 mg / ml at pH 3.8). Very sparingly soluble in alcohol. Melting point Riboflavin: decomposition at 280 - 290°C Specific rotation Riboflavin: [a]ijl = -122° to -136° (c = 0.25 in 0.05 N NaOH) Sodium riboflavin-5'-phosphate : [a]ijl = +38° to +42° (c = 1.5 in 20% HCl) 254 THE TECHNOLOGY OF VITAMINS IN FOOD Absorption spectrum In 0.1 N HCl solutions riboflavin and riboflavin phosphate show absorption maxima at about 223, 267, 374 and 444 nm. VitaminB6 Structuralformula CHzOH HO~I CHzOH ~••) ·HCI CH3 N Pyridoxine hydrochloride Principal commercialforms Empirical formula Molecular weight Pyridoxine hydrochloride CgHl2ClN03 205.64 Standardisation 1 mg ofpyridoxine hydrochloride is equivalent to 0.82 mg pyridoxine or pyridox­ amine and 0.81 mg pyridoxal. Solubility Readily soluble in water (about 1g / 4.5 ml). Sparingly soluble in alcohol, soluble in propylene glycol. Melting point Decomposition with browning 205-212°C. Absorption spectrum In aqueous solution the absorption maxima are: at acid pH: 291 nm at neutral pH: 254 and 324 nm at alkaline pH: 245 and 309 nm APPENDIX 1 255 Vitamin B12 Structuralformula NH2-CO-CH2-CH2 CH3 CH3 CH2-CO-NH2 CH2-CH2-CO-NH2 CH3 CH2-CH2-CO-NH2 Principal commercialform Empirical formula Molecular weight Cyanocobalamin C63Hss014N14PCO 1355.42 Standardisation Analytical results are usually expressed as weight units ofcyanocobalamin. Solubility Slightly soluble in water (about 1.25 g /100 ml), soluble in alcohol. Melting point Cyanocobalamin chars at 210 -220°C without melting. Absorption spectrum The aqueous solution shows absorption maxima at 278,361 and 550 nm. 256 THE TECHNOLOGY OF VITAMINS IN FOOD Niacin Structural formula Niacin Niacinamide (nicotinic acid) (nicotinamide) Principal commercialforms Empirical formula Molecular weight Niacin (nicotinic acid) C6HsN02 123.11 Niacinamide (nicotinamide) C6H6N20 122.13 Standardisation Analytical results are normally expressed as weight units of niacinamide. Both forms possess the same vitamin activity. As the human body is capable offorming niacin from the amino acid tryptophan, niacin is often quoted in units of 'niacin equivalent' on the basis that 60 mg oftryptophan equals 1mg ofniacin equivalent. Solubility Niacin (nicotinic acid) is sparingly soluble in water (about 1.6 g / 100 ml) and alcohol (about 1g / 100 ml). Readily soluble in alkali. Niacinamide (nicotinamide) is very soluble in water (about 1 g / ml), slightly soluble in alcohol, soluble in glycerol. Melting point Niacin (nicotinic acid) 234-237°C (sublimation) Niacinamide (nicotinamide) 128-131 oC Absorption spectrum The acid and amide both show similar absorption spectra in aqueous solution with a maximum at about 261 om and an extinction dependent on pH. APPENDIX 1 257 Pantothenic acid Structuralformula CH20H-C(CH3h-CHOH-CO-NH-CH2-CH2-R Pantothenic acid: R= COOH Panthenol: R = CHzOH Principal commercialforms Empirical fonnula Molecular weight ~alcium pantothenate (~91I16()5~)2~a 476.53 Sodium pantothenate ~91I16()5~a 241.20 Panthenol ~91I19()4~ 205.25 Standardisation Pantothenic acid is optically active with only the dextro-rotatory fonns having vitamin activity.
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