1. APIs
  2. Levonorgestrel
  3. Impurities
  4. 13β-Ethyl-17α-ethinyl-17β-hydroxy-5α-gonan-3-one

13β-Ethyl-17α-ethinyl-17β-hydroxy-5α-gonan-3-one

Structure

MOL SDF CML

CASRN

78088-19-4

Notes

Not identified in pharmacopoeias. Result of photolysis of norgestrel in methanol. Photodegrades further to LNG Impurities 6 and 7.

ID in reference

3b

library_books

References

  1. Williams, J. R.; Mattei, P. L.; Abdel-Magid, A.; Blount, J. F., Photochemistry of estr-4-en-3-ones: 17.beta.-hydroxy-4-estren-3-one, 17.beta.-acetoxy-4,9-estradien-3-one, 17.beta.-hydroxy-4,9,11-estratrien-3-one, and norgestrel. Photochemistry of 5.alpha.-estran-3-ones. The Journal of Organic Chemistry 1986, 51 (6), 769-773. (View all citations for this reference)

Reaxys ID Number

5570508

References

Molecular Formula

C21H30O2

References

Molecular Weight

314.47 g/mol

References

Structural Difference from API

no double bond between C4 & C5, hydrogen on C5 is in the α position

References

Melting Point

199-200 deg C

library_books

References

  1. Williams, J. R.; Mattei, P. L.; Abdel-Magid, A.; Blount, J. F., Photochemistry of estr-4-en-3-ones: 17.beta.-hydroxy-4-estren-3-one, 17.beta.-acetoxy-4,9-estradien-3-one, 17.beta.-hydroxy-4,9,11-estratrien-3-one, and norgestrel. Photochemistry of 5.alpha.-estran-3-ones. The Journal of Organic Chemistry 1986, 51 (6), 769-773. (View all citations for this reference)

Source of Impurity

Product of photolysis in polar solvent (methanol)

library_books

References

  1. Williams, J. R.; Mattei, P. L.; Abdel-Magid, A.; Blount, J. F., Photochemistry of estr-4-en-3-ones: 17.beta.-hydroxy-4-estren-3-one, 17.beta.-acetoxy-4,9-estradien-3-one, 17.beta.-hydroxy-4,9,11-estratrien-3-one, and norgestrel. Photochemistry of 5.alpha.-estran-3-ones. The Journal of Organic Chemistry 1986, 51 (6), 769-773. (View all citations for this reference)

References

  1. Williams, J. R.; Mattei, P. L.; Abdel-Magid, A.; Blount, J. F., Photochemistry of estr-4-en-3-ones: 17.beta.-hydroxy-4-estren-3-one, 17.beta.-acetoxy-4,9-estradien-3-one, 17.beta.-hydroxy-4,9,11-estratrien-3-one, and norgestrel. Photochemistry of 5.alpha.-estran-3-ones. The Journal of Organic Chemistry 1986, 51 (6), 769-773. (View all citations for this reference)