1. APIs
  2. Levonorgestrel
  3. Impurities
  4. 13-Ethylgon-4-ene-3,17-dione

13-Ethylgon-4-ene-3,17-dione

Structure

MOL SDF CML

Other Names & Identifiers

  • BP Levonorgestrel Impurity L

CASRN

21800-83-9

Notes

BP 2017/EP 8.2 for Levonorgestrel says this impurity is also called levodione; however, sources such as PubChem and ChEBI demonstrate that the name levodione actually applies to a non-steroidal cyclohexane derivative.

Molecular Formula

C19H26O2

References

Molecular Weight

286.41 g/mol

References

Reaxys ID Number

2221392

References

Structural Difference from API

hydroxy & ethynyl groups on C17 replaced by carbonyl

References

Optical Rotary Power

97.8-98° at 589 nm in chloroform, 24-25° C

library_books

References

  1. Micheli RAH, Z. G.; Cohen, N.; Parrish, D. R.; Portland, L. A.; Sciamanna, W.; Scott, M. A.; Wehrli, P. A. Total synthesis of optically-active 19-norsteroids - (+)-estr-4-ene-3,17-dione and (+)-13β-ethylgon-4-ene-3,17-dione. Journal of Organic Chemistry. 1975; 40:675-81.
    2. (View all citations for this reference)
  2. Rao PNC, J. W.; Kim, H. K. Preparative chemical methods for aromatization of 19-nor-δ(4)-3-oxosteroids. Steroids. 1994; 59:621-7.
    3. (View all citations for this reference)

Melting Point

174.5-175.5° C in acetone

library_books

References

  1. Micheli RAH, Z. G.; Cohen, N.; Parrish, D. R.; Portland, L. A.; Sciamanna, W.; Scott, M. A.; Wehrli, P. A. Total synthesis of optically-active 19-norsteroids - (+)-estr-4-ene-3,17-dione and (+)-13β-ethylgon-4-ene-3,17-dione. Journal of Organic Chemistry. 1975; 40:675-81.
    2. (View all citations for this reference)

Spectra

NMR, IR

library_books

References

  1. Rao PNC, J. W.; Kim, H. K. Preparative chemical methods for aromatization of 19-nor-δ(4)-3-oxosteroids. Steroids. 1994; 59:621-7.
    2. (View all citations for this reference)

Spectra

UV-Vis Absorption

library_books

References

  1. Micheli RAH, Z. G.; Cohen, N.; Parrish, D. R.; Portland, L. A.; Sciamanna, W.; Scott, M. A.; Wehrli, P. A. Total synthesis of optically-active 19-norsteroids - (+)-estr-4-ene-3,17-dione and (+)-13β-ethylgon-4-ene-3,17-dione. Journal of Organic Chemistry. 1975; 40:675-81.
    2. (View all citations for this reference)

Limits

0.1%

References

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