1. APIs
  2. Levonorgestrel
  3. Impurities
  4. Methoxydienone

Methoxydienone

Structure

MOL SDF CML

Other Names & Identifiers

  • BP Levonorgestrel Impurity R
  • 13-Ethyl-3-methoxygona-2,5(10)-dien-17-one
  • Methoxygonadiene

CASRN

2322-77-2

Notes

Anabolic steroid.

Molecular Formula

C20H28O2

References

Molecular Weight

300.44 g/mol

References

Reaxys ID Number

2996354

References

Source of Impurity

Synthetic side product formed during the ethinylation step

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References

  1. Horvath PB, G.; Brlik, J.; Csehi, A.; Dravecz, F.; Halmos, Z.; Lauko, A.; Renyei, M.; Varga, K.; Gorog, S. Estimation of impurity profiles of drugs and related materials .16. Identification of the side-products of the ethinylation step in the synthesis of contraceptive gestogens. Journal of Pharmaceutical and Biomedical Analysis. 1997; 15:1343-9.
    2. (View all citations for this reference)

Melting Point

184-185° C in methanol, 152-160° C in methanol

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References

  1. Rufer CK, H.; Schroder, E.; Kieslich, K.; Gibian, H. Totalsynthese optisch aktiver steroide. 3. Totalsynthese von optisch aktiven 13-athyl-gonan-derivaten. Annalen Der Chemie-Justus Liebig. 1967; 702:141-+.
    2. (View all citations for this reference)
  2. Smith HP, P. C.; Smith, L. L.; Gadsby, B.; Hartley, D.; Ledig, K.; Herbst, D.; Wendt, G. R.; Fisher, J.; Pattison, T. W.; Watson, D. H. P.; Siddall, J.; McLoughlin, B. J.; Tokolics, J.; Siuda, J.; Rees, R.; McMenamin, J.; Douglas, G. H.; Foell, T.; Edgren, R. A.; Buzby, G. C.; Jansen, A. B. A.; Hughes, G. A. Totally synthetic steroid hormones. 2. 13β-alkylgona-1,3,5(10)-trienes 13β-alkylgon-4-en-3-ones + related compounds. Journal of the Chemical Society. 1964:4472-&.
    3. (View all citations for this reference)

Structural Difference from API

no ethynyl group at C17; double bonds between C2 & C3 and C5 & C10 instead of between C4 & C5; methoxy group at C3 instead of carbonyl; carbonyl on C17 instead of hydroxy and ethynl

References

Circular Dichroism

270-320 nm in dioxane

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References

  1. Baier HD, G.; Quinkert, G. TOTAL SYNTHESIS VON (-)-NORGESTREL. Helvetica Chimica Acta. 1985; 68:1054-68.
    2. (View all citations for this reference)

Optical Rotary Power

156.2 -158 at 589 nm, 20° C

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References

  1. Baier HD, G.; Quinkert, G. TOTAL SYNTHESIS VON (-)-NORGESTREL. Helvetica Chimica Acta. 1985; 68:1054-68.
    2. (View all citations for this reference)
  2. Rufer CK, H.; Schroder, E.; Kieslich, K.; Gibian, H. Totalsynthese optisch aktiver steroide. 3. Totalsynthese von optisch aktiven 13-athyl-gonan-derivaten. Annalen Der Chemie-Justus Liebig. 1967; 702:141-+.
    3. (View all citations for this reference)

Spectra

NMR, IR

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References

  1. Baier HD, G.; Quinkert, G. TOTAL SYNTHESIS VON (-)-NORGESTREL. Helvetica Chimica Acta. 1985; 68:1054-68.
    2. (View all citations for this reference)
  2. Smith H, Phillips PC, Smith LL, Gadsby B, Hartley D, Ledig K, Herbst D, Wendt GR, Fisher J, Pattison TW, Watson DHP, Siddall J, McLoughlin BJ, Tokolics J, Siuda, J Rees R, McMenamin J, Douglas GH, Foell T, Edgren RA, Buzby GC, Jansen ABA, Hughes GA; Totally synthetic steroid hormones. 2. 13β-alkylgona-1,3,5(10)-trienes 13β-alkylgon-4-en-3-ones + related compounds. Journal of the Chemical Society, 1964 (4472-4481)
    3. (View all citations for this reference)

Limits

0.1%

References

  1. British Pharmacopoeia 2017: Levonorgestrel monograph.
    2. (View all citations for this reference)
  2. Wikipedia: Methoxydienone. (View all citations for this reference)