《Inhibition of the autoxidation of fats and oils. IX. Antioxidant activity of some 4-alkylcatechols》 was published in Nippon Nogei Kagaku Kaishi in 1954. These research results belong to Tamura, Saburo; Okubo, Hide; Kaneta, Hiroshi. Computed Properties of C10H14O2 The article mentions the following:
cf. C.A. 50, 6403b. 4-Alkylcatechols, 1,2,4-(HO)2C6H3R (I), were synthesized and studied for the relationship between the antioxidant property and chem. structure. Veratrole (20 g.) and 13 g. Ac2O in PhNO2 with 26 g. AlCl3 below 0° gave 19 g. 4-acetylveratrole, b15 170-5°, 13 g. of which was hydrogenated with 40 g. Zn amalgam to 6 g. 4-ethylveratrole, b55 150°, which was demethylated with HI to 60% I (R = Et) (II), b9 130-2°. Similar processes gave: I (R = Bu) (III), b5 143-8°, m. 42-3°, from 4-butylveratrole, b8 128-35° (prepared from 4-butyroylveratrole, b9 175°, m. 52-3°); I (R = hexyl) (IV), b5 164-70°, from 4-hexylveratrole, b11 155-60° (prepared from 4-hexanoylveratrole, b17 176-8°); I (R = decyl) (V), m. 73-4°, from 4-decylveratrole, m. 25-6° (prepared from 4-decanoylveratrole, m. 60-1°); and I (R = dodecyl) (VI), m. 75-6°, from 4-dodecylveratrole, m. 39-40° (prepared from 4-dodecanoylveratrole, m. 57°). Guaiacol propionate, b8 115-18°, prepared from guaiacol and propionic acid in the presence of SOCl2, was treated with AlCl3 and CS2 to obtain 4-propionylguaiacol, b15 182-7°, which was converted to 4-propylguaiacol, b15 130-6°, and then to I (R = Pr) (VII), b12 155-7°. Other I were prepared from catechol esters: 4-valeroylcatechol, b10 245-55°, gave I (R = pentyl) (VIII), b7 155-60°; and 4-octanoylcatechol, b4 210-20°, gave I (R = octyl) (IX), b5 175-80°. The relative antioxidant activity was expressed as in Part V (C.A. 50, 6402b). At 0.01% on a molar basis, the results by the active O method (hrs.) and the inhibitor ratio, resp., were: lard (no antioxidant), 4.5, -; dihydronorguaiaretic acid (IXa), 28.0, 0.53; catechol, 26.0, 0.48; II, 61.0, 1.25 (the most active); VII, 52.0, 1.07; III, 51.0, 1.05; VIII, 48.0, 0.98; IV, 47.0, 0.96; IX, 40.5, 0.81; V, 50.0, 1.00; VI, 42.0, 0.84; propionylcatechol, 8.0, 0.05; and dodecanoylcatechol, 8.0, 0.08. However, most of these alkylcatechols were apt to produce eczema on human skin and discolored the product. In the experiment, the researchers used many compounds, for example, 4-Butylbenzene-1,2-diol(cas: 2525-05-5Computed Properties of C10H14O2)
4-Butylbenzene-1,2-diol(cas: 2525-05-5) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. Organoboron compounds are less toxic than organostannane reagents, and unlike alkynylzinc and magnesium, many organoboron compounds possess remarkable oxidative and thermal stabilities. Computed Properties of C10H14O2
Referemce:
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