Beruflich Dokumente
Kultur Dokumente
vitamins
Vitamin A
Structuralformula
eM,
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) of vitamin 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 of pure vitamin A acetate is
2.904 x 106 IU/g
and of pure vitamin A palmitate is
1.817 x 106 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
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
Standardisation
There have been a number of conventions 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:
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 of 0.025 Ilg of either 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) of vitamin 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 of the most common forms of
vitamin E are given below.
I IU of vitamin 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 of pure vitamin Kl as no
international standard for the biological activity of vitamin 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
Structuralformula
Principal commercialforms
Thiamin chloridehydrochloride x=cr,HCl
(Thiamin hydrochloride)
Thiamin mononitrate
Standardisation
To calculate the amount of thiamin cation from the salts (molecular weight of
thiamin cation is 265.4):
From hydrochloride: divide the amount of hydrochloride by 1.271
From mononitrate: divide the amount of mononitrate 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
Structuralformula
Principal commercialforms
Riboflavin: R = OH .--" ONa
Sodium riboflavin-5'-phosphate: R=-O-P,
\OH
o
Standardisation
1 g of sodium riboflavin-5' -phosphate = 0.730 g of riboflavin.
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 of pyridoxine hydrochloride is equivalent to 0.82 mg pyridoxine or pyridox-
amine and 0.81 mg pyridoxal.
Solubility
Readily soluble in water (about 1 g / 4.5 ml). Sparingly soluble in alcohol, soluble
in propylene glycol.
Melting point
Decomposition with browning 205-2 12°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-N H2
CH2-CH2-CO-NH2
CH3
CH2-CH2-CO-NH 2
Principal commercialform
Empirical formula Molecular weight
Cyanocobalamin C63Hss014N14PCO 1355.42
Standardisation
Analytical results are usually expressed as weight units of cyanocobalamin.
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 of forming
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 1 g / 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 o C
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
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. Although free pantothenic acid is extremely unstable, results are
expressed in tenns of weight units of pantothenic acid.
I mg calcium pantothenate is equivalent to 0.92 mg pantothenic acid.
I mg sodium pantothenate is equivalent to 0.91 mg pantothenic acid.
1 mg panthenol is equivalent to 1.16 mg calcium D-pantothenate.
Solubility
Calcium pantothenate is readily soluble in water (about 4 g /10 ml), sparingly
soluble in alcohol and soluble in glycerol.
Sodium pantothenate is very soluble in water and slightly soluble in alcohol.
Panthenol is very soluble in water, readily soluble in alcohol and slightly soluble
in glycerol.
Melting point
~alcium pantothenate: decomposition 195-196°~
Sodium pantothenate: 122-124°~
dl-Panthenol: 64.5-68.5°~
Specific rotation
~alcium pantothenate [a]~ = +26.0° to +28.0° (c = 4 in water)
Sodium pantothenate [a]~ = +26.5° to +28.5° (c = 4 in water)
Panthenol [a]~ = +29.5° to +31.5° (c = 5 in water)
258 THE TECHNOLOGY OF VITAMINS IN FOOD
Folic acid
-0-
Structuralformula
OH COOH
I '\
N'
I I
:):
N)CHZ_NH
~
-
CO-NH-!H
I
CHz
HzN
~ N N
~ I
CHz
I
COOH
Principal commercialforms
Empirical fonnula Molecular weight
Folic acid C19H19N706 441.40
Standardisation
Analytical results are generally expressed in weight units of pure folic acid as no
international unit for the biological activity of this vitamin has been defined.
Solubility
Folic acid is sparingly soluble in water, readily soluble in dilute alkali, soluble in
dilute acid and insoluble in alcohol.
Melting point
Darkens at 250°C followed by charring.
Specific rotation
[a]~ = c.+ 20° (c = 0.5 in 0.1 N NaOH)
Absorption spectrum
Folic acid shows a characteristic absorption spectrum which is dependent on the
pH of the solution. In 0.1 N NaOH the maxima are at 256, 283 and 365 nm.
APPENDIX 1 259
Biotin
Structuralformula
Principal commercialform
Empirical formula Molecular weight
d-biotin ClOH1603N2S 244.31
Standardisation
Analytical results are normally expressed as weight units of pure d-biotin.
Solubility
Very sparingly soluble in water (about 20 mg/ 100 ml) and alcohol. Soluble in
dilute alkali.
Melting point
228-232°C with decomposition.
Specific rotation
[a]~ =+90° to +94° (c = 1.0 in 0.1 N NaOH)
VitaminC
Structuralformula
O=C~
J-OH
/I
\
,-OH / 0
H-C--l
Ho-C-H
I
I
CH20H
Ascorbic acid
260 THE TECHNOLOGY OF VITAMINS IN FOOD
Principal commercialforms
Empirical formula Molecular weight
Ascorbic acid C6Hg06 176.13
Sodium ascorbate C6H706Na 198.11
Calcium ascorbate C 12H14CaO12.2HzO 426.35
Standardisation
I mg of sodium ascorbate is equivalent to 0.889 mg of ascorbic acid.
1 mg of calcium ascorbate is equivalent to 0.826 mg of ascorbic acid.
Solubility
Ascorbic acid is readily soluble in water (about 30 g /100 ml), slightly soluble in
alcohol, and sparingly soluble in glycerol.
Sodium ascorbate is very soluble in water (about 90 g /100 ml) and almost
insoluble in alcohol.
Calcium ascorbate is soluble in water and slightly soluble in alcohol.
Specific rotation
Ascorbic acid: [a]~ = _22 0 to _23 0 (c = 2 in water)
Sodium ascorbate: [a]~ =+103 0 to +106 0 (c = 5 in water)
Calcium ascorbate: [a]~ = +95 to +97
0 0
(c = 2.4 in water)
Absorption spectrum
Ascorbic acid in strongly acid solution shows an absorption maxima of about 245
nm which shifts at neutrality to 365 nm and at pH 14 to about 300 nm in UV light.
Appendix 2: Recommended nutrient reference values
for food labelling purposes
Recommended dietary intakes in different countries. Adapted from FAO / WHO Joint Expert Consultation on Recommended
Allowances ofNutrients for Food Labelling Purposes, Helsinki, 12-16 September, 1988.
Thiamin Riboflavin
(Bl) (B2) B6 Niacin Bl2 Folate Pant. Biotin C A D E K
Units mg mg mg mg J.lg mg mg mg mg J.lg J.lg mg mg
Argentina 1.3 1.9 - 21 2 0.2 - - 30 750 2.5
Australia 1.0 1.2 1.3 16 2 0.2 - - 30 750
Belgium 1.5 1.7 2.0 18 3 0.4 5.0 0.2 60 1000 7.5 10 0.10
Bolivia 1.1 1.5 2.2 18 3 0.4 4.0 0.1 60 750 5.0 10 0.70
Brazil 1.0 1.5 2.0 17 2 1.0 3.0 - 70 1500 10.0 5
Bulgaria 1.5 1.8 - 19 - - - - 85 1200
Canada 0.4 0.5 0.2 7 2 0.2 5.0 - 60 1000 2.5 10 0.03
Caribbean 1.2 1.7 2.0 20 2 0.2 - - 30 750 2.5 15
Chile 1.1 1.5 - 18 - - - - 45 750
China (PR) 1.5 1.5 - 15 - - - - 75 1300 10.0
Colombia 0.9 1.2 2.3 14 3 0.2 6.0 0.2 40 1600 5.0 10 0.10
Czechoslovakia 1.2 1.8 1.9 20 - 0.2 8.0 - 60 1000 - 12
Denmark 1.4 1.6 2.2 18 - - - - 60 1000 5.0
Finland 0.5 0.7 1.1 7 - - - - 33 440
France 1.5 1.8 2.2 18 3 0.4 7.0 0.1 80 1000 10.0 10
Germany (FR) 1.3 1.7 1.8 18 5 0.4 8.0 - 75 1000 5.0 12
Hungary 1.4 1.8 2.2 18 3 0.4 8.0 - 60 1000 5.0 12
India 1.4 1.5 - 19 1 0.1 - - 50 750 5.0
Indonesia 1.0 1.4 - 17 - - - - 30 1200
Ireland 1.2 1.6 2.2 18 3 0.3 - - 60 750 7.5 10
Israel 1.0 1.6 1.8 17 - - - - 70 1500 10.0
Italy 1.2 1.8 1.4 19 2 0.2 - - 45 700 2.5 10
Japan 1.2 1.7 - 20 - - - - 50 600 2.5
Korea (south) 1.3 1.5 - 17 - - - - 55 750 10.0
Malaysia 1.0 1.4 - 16 2 0.2 - - 30 .750 2.5
Mexico 1.3 1.5 - 23 - - - - 50 1000
Netherlands 1.4 1.6 2.0 18 3 0.4 - - 50 1000 5.0 10
New Zealand 1.2 1.7 2.0 18 3 0.2 - - 60 750 10.0 14
Norway 1.4 1.6 2.2 18 - - - - 60 1000 5.0
Philippines 1.2 1.2 - 16 - - - - 75 650
Poland 1.7 1.7 2.0 17 5 0.4 - - 75 1500 10.0 30
Continued.
FAO/WHO
Codex reference Bl B2 B6 Niacin B12 Folate Pant. Biotin C A D E K
Portugal 1.5 1.8 2.2 18 3 - - - 75 1500
Singapore 0.5 0.8 1.0 6 - - 3.5 0.1 - 360 5.0 10
South Africa 1.5 1.7 2.2 19 3 0.4 7.0 0.2 60 1000 10.0 10
Spain 1.2 1.8 - 20 2 0.2 - - 45 750 2.5
Sweden 1.4 1.6 2.2 18 - - - - 60 1000 5.0
Switzerland 1.2 1.8 1.6 15 1 0.1 10.0 - 75 1650 11.0 10
Taiwan 1.4 1.5 2.0 18 3 0.4 - - 60 750 2.5 10
Thailand 1.0 1.4 - 16 - - - - 30 750 10.0
Turkey 1.2 1.8 - 17 - 0.2 - - 50 750
United Kingdom 1.2 1.6 - 18 - 0.3 - - 30 750 10.0
Uruguay 1.2 1.6 2.0 19 2 0.2 - - 30 750 2.5 10
USA 1.4 1.6 2.2 18 3 0.4 4.0 0.1 60 1000 5.0 10 0.Q7
Venezuela 1.2 1.6 - 20 3 0.2 - - 30 750 2.5
Western Pacific l.i 1.6 - 19 2 0.2 - - 30 750 2.5
Range Minimum 0.4 0.5 0.2 6 1 0.1 3.0 0.1 30 360 2.5 5 0.03
Maximum 1.9 2.2 2.2 23 5 0.4 10.0 0.2 85 1650 11.0 30 0.70
European Community recommended daily allowances for food labelling purposes are expected to be published at the end of 1992. When
accepted by the EC Parliament these will supersede the individual national requirements.
Index
irradiation, deterioration of vitamins 105, stability of vitamins in 92, 96, 97, 131
106 storage of 131
mitochondria
jaundice, vitamin K deficiency 4 modo-reduction in 8
stabilisation oflipid membranes 4
kidney moisture, stability of vitamins 90
pantothenic acid in 97 Mortierella fungus, production of PUFAs 85
provitamins in 94 muscle weakness
riboflavin storage in 5 ascorbic acid deficiency 14
vitamin D conversion in 3 pantothenic acid deficiency 12
vitamin K deficiency in 5 vitamin D deficiency 3