Antioxidants

Living organisms acquire energy by bringing oxygen into their bodies. However, they can also be damaged by oxidative stress. Hence they maintain complex chemical systems of multiple types of antioxidants, which are chemical substances that protect biological materials against the effects of this stress. Human beings utilize antioxidants in a daily life as food additives to avoid their deterioration. Antioxidants in pharmacology are studied, particularly as treatments of stroke and nerve atrophy diseases. Antioxidants are also widely used as ingredients of functional foods. However, some clinical trials suggested that getting antioxidants during athletic exercise might be harmful. Functioning of the antioxidants remains to be investigated.

■Functions of Antioxidants
(1) Scavenging of active oxygen species and radicals
Scavenging of hydrogen peroxide (H2O2), free radicals such as the hydroxyl radical (•OH), the superoxide anion (O2), and the radicals they produce with biological molecules.
(2) Metal inactivation
Chelating metals to inactivate a metal such as iron which promotes oxidation
(3) Oxidase inhibition
(4) Protection of disulfide bond
Inhibition of the oxidative cleavage of disulfide bonds in the proteins.

■Classification of Antioxidants
Antioxidants are classified according to their solubility.
(1) Water-soluble antioxidants
Ascorbic acid (Vitamin C), Glutathione, Lipoic acid.
Typical properties: (a) Neutralization of reactive oxygen species, (b) Inhibition of the cleaving reaction of disulfide bonds.
(2) Fat-soluble antioxidants
α-Tocopherol (Vitamin E), gallates, resveratrol, polyphenols (e.g. ubiquinone, or coenzyme Q10), polyene compounds (e.g. β-Carotene).
Typical properties: Antioxidation of lipids through radical scavenging activity

■Storage Precautions
Solid antioxidants can be stored in a cool and dry place, unless otherwise specified. After opening, they should be stored under inert gases such as nitrogen or argon to prevent their oxidation. Since oily antioxidants can deteriorate faster than solids, they should be stored under an inert gas in a refrigerator. Refrigerated antioxidants should be warmed in a desiccator at room temperature under ambient atmosphere just before use without opening the cap. This operation can avoid moisture uptake of the reagents.

Antioxidant

Antioxidant

A0905 A0905 A0648 A0648 A0296 A0296
A0537 A0537 B0460 B0460 B3773 B3773
C0002 C0002 C2488 C2488 C0560 C0560
C0181 C0181 C1971 C1971 C0393 C0393
C2302 C2302 C0434 C0434 C0515 C0515
C0517 C0517 D0228 D0228 D3908 D3908
D1320 D1320 E0375 E0375 E0890 E0890
E0694 E0694 E0237 E0237 A0232 A0232
H0267 H0267 G0011 G0011 G0074 G0074
G0371 G0371 M0121 M0121 H0049 H0049
H0726 H0726 I0496 I0496 I0822 I0822
I0804 I0804 K0018 K0018 L0124 L0124
L0058 L0058 L0207 L0207 M1105 M1105
H0216 H0216 D0800 D0800 O0180 O0180
O0373 O0373 P1928 P1928 P1878 P1878
G0018 G0018 P1924 P1924 R0071 R0071
R0089 R0089 S0442 S0442 S0418 S0418
S0508 S0508 A0539 A0539 T2682 T2682
T0251 T0251 T2309 T2309 T0252 T0252
T2322 T2322 T2650 T2650
A0905 N-Acetyl-L-cysteine
A0648 2-Aminoethanethiol
A0296 2-Aminoethanethiol Hydrochloride
A0537 L-Ascorbic Acid
B0460 Bilirubin
B3773 4-Butylresorcinol
C0002 Caffeic Acid
C2488 Carnosic Acid
C0560 beta-Carotene
C0181 Chlorogenic Acid Hydrate
C1971 Coenzyme Q10
C0393 trans-p-Coumaric Acid
C2302 Curcumin (Synthetic)
C0434 Curcumin (Natural)
C0515 L-Cysteine
C0517 L-Cysteine Hydrochloride Monohydrate
D0228 2,6-Di-tert-butyl-p-cresol
D3908 Diosmin
D1320 Dithioerythritol
E0375 Ellagic Acid Dihydrate
E0890 (-)-Epicatechin Gallate
E0694 (-)-Epigallocatechin Gallate Hydrate
E0237 6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline [Antioxidant for rubber]
A0232 Eugenol
H0267 trans-Ferulic Acid
G0011 Gallic Acid Hydrate
G0074 Glutathione reduced form
G0371 Gnetol
M0121 Guaiacol
H0049 Hesperidin
H0726 6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic Acid
I0496 3-Indolemethanol
I0822 Isoliquiritigenin
I0804 Isorhapontigenin
K0018 Kaempferol Hydrate
L0124 Linoleic Acid
L0058 DL-alpha-Lipoic Acid
L0207 (R)-alpha-Lipoic Acid
M1105 Melatonin
H0216 Methyl 4-Hydroxybenzoate
D0800 Nordihydroguaiaretic Acid
O0180 Oleic Acid
O0373 Oxyresveratrol
P1928 Piceatannol
P1878 Piceid
G0018 Propyl Gallate
P1924 Pterostilbene
R0071 Resveratrol
R0089 Rhapontigenin
S0442 L-Selenomethionine
S0418 Sesamol
S0508 Silybin (mixture of Silybin A and Silybin B)
S0271 Sodium Copper Chlorophyllin
A0539 Sodium L-Ascorbate
T2682 3',4',5,7-Tetrahydroxyflavone
T0251 DL-alpha-Tocopherol
T2309 D-alpha-Tocopherol
T0252 DL-alpha-Tocopherol Acetate
T2322 D-alpha-Tocopherol Acetate
T2650 3,4,5-Trihydroxybenzaldehyde

Literature

1) E. T. Denisov, I. B. Afanas’ev, in Oxidation and Antioxidants in Organic Chemistry and Biology, Taylor & Francis, New York, 2005; S. I. Baskin, H. Salem, in Oxidants, Antioxidants, and Free Radicals, Taylor & Francis, New York, 1997, p. 1.
2) M. Ristow, K. Zarse, A. Oberbach, N. Klöting, M. Birringer, M. Kiehntopf, M. Stumvoll, C. R. Kahn, M. Blüher, Proc. Natl. Acad. Sci. USA 2009, 106, 8665 [DOI].


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