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ABSTRACT 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. Access through your institution Buy or subscribe This is a preview of subscription content, access via your institution ACCESS
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_AURANTIOCHYTRIUM_ Article Open access 25 March 2021 BIOACTIVE AMBUIC ACID CONGENERS FROM ENDOPHYTIC FUNGUS _PESTALOTIOPSIS TRACHICARPICOLA_ SC-J551 Article 13 November 2023 NEW NAPHTHYL
DERIVATIVES FROM _ASPERGILLUS CALIFORNICUS_ Article 01 October 2020 REFERENCES * Stodola, F. H., and Anderson, R. J., _J. Biol. Chem._, 114, 467 (1936). CAS Google Scholar * Reeves, R. E.,
and Anderson, R. J., _J. Biol. Chem._, 119, 535 (1937). CAS Google Scholar * Cason, J., and Anderson, R. J., _J. Biol. Chem._, 119, 549 (1937); 126, 527 (1938) CAS Google Scholar *
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stenhagen, E., _J. Biol. Chem._, 173, 383 (1948). PubMed Google Scholar * Ställberg-Stenhagen, S., and Stenhagen, E., _J. Biol. Chem._, 183, 223 (1950) Google Scholar *
Demarteau-Ginsburg, H., and Lederer, E., _C.R. Acad. Sci._, _Paris_, 240, 815 (1955). CAS Google Scholar * Hall, J. A., Lewis, J. W., and Polgar, N., _J. Chem. Soc._, 3971 (1955). *
Demarteau-Ginsburg, H., thesis, Paris (1958). * Ryhage, R., Stenhagen, E., and von Sydow, E., _Acta Chem. Scand._, 10, 158 (1956). Article CAS Google Scholar * Ryhage, R., Stenhagen, E.,
and von Sydow, E., _Acta Chem. Scand._, 11, 180 (1957). Article CAS Google Scholar * Demarteau-Ginsburg, H., _C.R. Acad. Sci._, _Paris_, 243, 2169 (1956). CAS Google Scholar * Lewis, J.
W., and Polgar, N., _J. Chem. Soc._, 102 (1958). * Drayson, P. K., Lewis, J. W., and Polgar, N., _J. Chem. Soc._, 430 (1958). * Ginger, L. G., and Anderson, R. J., _J. Biol. Chem._, 157,
213 (1945) CAS Google Scholar * Hall, J. A., and Polgar, N., _Chem. and Indust._, 1293 (1954). * Ryhage, R., Stenhagen, E., and von Sydow, E. (to be publihed). * Demarteau-Ginsburg, H.,
Ginsburg, A., and Lederer, E., _Biochim. Biophys. Acta_, 12, 587 (1953). Article CAS Google Scholar * Ahlquist, L., Ryhage, R., Stenhagen, E., and von Sydow, E., _Arkiv za Kemi._ (to be
published). Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Institut de Biologie physico-chimique, Paris H. DEMARTEAU-GINSBURG & E. LEDERER * Laboratory for Mass
Spectrometry, Karolinska Institutet, Stockholm R. RYHAGE * Institute of Medical Biochemistry, University of Gothenburg, S. STÄLLBERG-STENHAGEN * Institute of Medical Chemistry, University of
Uppsala, E. STENHAGEN Authors * H. DEMARTEAU-GINSBURG View author publications You can also search for this author inPubMed Google Scholar * E. LEDERER View author publications You can also
search for this author inPubMed Google Scholar * R. RYHAGE View author publications You can also search for this author inPubMed Google Scholar * S. STÄLLBERG-STENHAGEN View author
publications You can also search for this author inPubMed Google Scholar * E. STENHAGEN View author publications You can also search for this author inPubMed Google Scholar RIGHTS AND
PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE DEMARTEAU-GINSBURG, H., LEDERER, E., RYHAGE, R. _et al._ Structure of Phthiocerol. _Nature_ 183, 1117–1119 (1959).
https://doi.org/10.1038/1831117a0 Download citation * Issue Date: 18 April 1959 * DOI: https://doi.org/10.1038/1831117a0 SHARE THIS ARTICLE Anyone you share the following link with will be
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