Letter | Published:

Structure of -Boswellinic Acid

Nature volume 140, page 467 (11 September 1937) | Download Citation

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Abstract

THE investigations of Ruzicka, and of Winterstein and their co-workers, have shown that the majority of the triterpene acids (hederagenin, gypsogenin, oleanolic acid, sia- and suma-resinolic acids) are in all probability θ-hydroxy-γ: δunsaturated mono-basic acids, as indicated in the accompanying formula1. Onthe other hand, β-boswellinic acid, C29H46(OH)COOH, one of the principal triterpene constituents of frankincense, evidently possesses a somewhat different constitution, for on mild oxidation with chromic anhydride this acid is converted into a monoketone C29H46O, m.p. 196° (found: C, 84·53; H, 11·11. C29H46O requires C, 84·80 ; H, 11·30 per cent), which has been characterized by the preparation of an oxime. Oxidation under similar conditions of β-boswellinic methyl ester, however, furnishes the corresponding keto-ester, m.p. 160° (found: C, 79·12 ; H, 10·20. C31H48O3 requires C, 79·41 ; H, 10·33 per cent), which forms an oxime, m.p. 200°.

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References

  1. 1.

    , , and , Helv. chim. Acta, 20, 325 (1937).

  2. 2.

    and , J. Biol. Chem., 69, 641 (1926).

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Affiliations

  1. King's College, London. July 26.

    • J. C. E. SIMPSON

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DOI

https://doi.org/10.1038/140467a0

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