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PHTHIOCEROL, a characteristic constituent of the waxes of human and bovine strains of tubercle bacilli1–3, was found by Stodola and Anderson1 in 1936 to be a methoxy-glycol with the formula
C34H67(OH)2OCH3 or C35H69(OH)2OCH3. About ten years ago it was shown that phthiocerol has a long-chain structure with a methyl branch in position 4 4–6. More recently the presence of a
β-glycol grouping was demonstrated7,8, and several structural formulæ have been suggested on the basis of degradation experiments (for a review see ref. 9). Definite evidence that the
methoxyl group is attached to carbon atom 3 adjacent to the methyl group was first obtained by a mass spectrometric study of phthiocerol10,11, and this was afterwards confirmed by chemical
studies12–14. The mass-spectrometric results also indicated the presence of a hydroxyl group in position 22 from the straight-chain end of the molecule. The mass spectrum of a purified
sample of phthiocerane, the hydrocarbon obtained by reduction of phthiocerol15, showed this compound to consist mainly of 4-methyltetratriacontane11. Structure (I) for phthiocerol was
suggested on the basis of the mass spectrometric study11.
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