Chemistry:Allenolic acid

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Allenolic acid
Allenolic acid.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC13H12O3
Molar mass216.236 g·mol−1
3D model (JSmol)

Allenolic acid, or allenoic acid, is a synthetic,[1] nonsteroidal estrogen discovered in 1947 or 1948 that, although studied clinically,[2] was never marketed.[3][4][5] It is an open-ring or seco-analogue of steroidal estrogens like estrone and equilenin.[6][7][8] The compound was named after Dr. Edgar Allen, one of the pioneers in estrogen research.[9][10] Although described as an estrogen, allenolic acid probably is totally inactive at the receptor, whereas a derivative, allenestrol (α,α-dimethyl-β-ethylallenolic acid), is reported to be a potent estrogen.[11] Another derivative of allenolic acid (specifically 6-methoxy-allenestrol), methallenestril (brand name Vallestril), is also a potent estrogen and, in contrast to allenolic acid and allenestrol, has been marketed.[12][13][14][15]

See also

References

  1. The Menopause and Postmenopause: The Proceedings of an International Symposium held in Rome, June 1979. Springer Science & Business Media. 6 December 2012. pp. 110–. ISBN 978-94-011-7230-1. https://books.google.com/books?id=wZF9CAAAQBAJ&pg=PA110. 
  2. American Practitioner and Digest of Treatment. Lippincott.. January 1951. p. 443. https://books.google.com/books?id=px8gAQAAMAAJ. 
  3. Reversibility of Chronic Degenerative Disease and Hypersensitivity, Volume 1: Regulating Mechanisms of Chemical Sensitivity. CRC Press. 18 June 2010. pp. 464–. ISBN 978-1-4398-1345-4. https://books.google.com/books?id=--U8r_WYVIcC&pg=PA464. 
  4. "Estrogens and antiestrogens". Gynecologic Investigation 3 (1): 2–29. 1972. doi:10.1159/000301742. PMID 4347198. 
  5. "Experimental and clinical studies on a new synthetic estrogen, an allenolic acid derivative, vallestril". American Journal of Obstetrics and Gynecology 74 (3): 635–50. September 1957. doi:10.1016/0002-9378(57)90519-7. PMID 13458265. 
  6. Indian Journal of Chemistry: Organic including medicinal. Council of Scientific & Industrial Research.. 1980. p. 886. https://books.google.com/books?id=7ZdVAAAAMAAJ. 
  7. Endocrines, Vitamins, and Some Common Metabolic Disorders. Dar al-Maaref. 1963. p. 194. https://books.google.com/books?id=xXhFAAAAYAAJ. 
  8. Morrison, James D. (November 1983). Stereodifferentiating addition reactions. Academic Press. p. v. ISBN 978-0-12-507702-6. https://books.google.com/books?id=Iw3wAAAAMAAJ. 
  9. Thompson, Willard Owen (1953). The Year Book of Endocrinology. Year Book Medical Publishers. p. 292. https://books.google.com/books?id=vUtEAQAAIAAJ. 
  10. American Practitioner and Digest of Treatment. Lippincott.. January 1956. https://books.google.com/books?id=DiggAQAAMAAJ. 
  11. "753. Oestrogenic carboxylic acids. Part II. Open-chain analogues of doisynolic acid". Journal of the Chemical Society (Resumed): 3714. 1959. doi:10.1039/jr9590003714. ISSN 0368-1769. 
  12. Journal of the Japanese Obstetrical & Gynecological Society. 1958. p. 83. https://books.google.com/books?id=tRcHAQAAIAAJ. 
  13. Steroid Biochemistry. Academic Press. 1970. p. 144. ISBN 9780123366504. https://books.google.com/books?id=gAlrAAAAMAAJ. 
  14. The Effects of the Sulfonylureas and Related Compounds in Experimental and Clinical Diabetes. The Academy. 1957. p. 681. https://books.google.com/books?id=b64PAAAAIAAJ. 
  15. Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. 27 November 2013. pp. 106–. ISBN 978-3-642-65806-8. https://books.google.com/books?id=aU_oCAAAQBAJ&pg=PA106.