ステロイド系ホルモンの誘導体の研究 (第7報)

17位に水酸基を有するステロイドの呈色反応について その2

抄録

Relationship between coloration reaction and chemical structure was examined in various steroids by heating in 85% formic acid. The condition for coloration seems to be the presence of a hydroxyl in 3-position and a double bond in 5-position or a radical in 5-position which tends to undergo dehydration to form a double bond, with a hydroxyl or carbonyl in 17- or 20-position. When the substituent in 3-position is a carbonyl and there is a double bond in 4-position, or the A-ring is an aromatic ring with hydroxyl in 3-position, presence of a tertiary hydroxyl in 17-position (excluding the case where carbonyl is present in 20-position) and a secondary hydroxyl in 17α-position required.
It was found that by heating a steroid with 85% formic acid and heating glacial acetic acid solution of bromine, only the steroid with tertiary hydroxyl in 17-position shows coloration while other steroids are colored by heating with 85% formic acid but the color fades on addition of glacial acetic acid solution of bromine. The color developed in compounds of 5-en-3β-ol type is bluish violet and that of compounds of 4-en-3-one type is yellowish red, with absorption maximum at 540-560mμ in the former and at 420-440mμ in the latter.