Wikipedia

Allenolic acid

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 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]

Allenolic acid
Identifiers
  • 3-(6-Hydroxynaphthalen-2-yl)propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H12O3
Molar mass216.236 g·mol−1
3D model (JSmol)
  • C1=CC2=C(C=CC(=C2)O)C=C1CCC(=O)O
  • InChI=1S/C13H12O3/c14-12-5-4-10-7-9(2-6-13(15)16)1-3-11(10)8-12/h1,3-5,7-8,14H,2,6H2,(H,15,16)
  • Key:NHGXZNWPADXVOA-UHFFFAOYSA-N

See also

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References

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  1. ^ Paoletti R, Pasetto N, Ambrus JL (6 December 2012). The Menopause and Postmenopause: The Proceedings of an International Symposium held in Rome, June 1979. Springer Science & Business Media. pp. 110–. ISBN 978-94-011-7230-1.
  2. ^ American Practitioner and Digest of Treatment. Lippincott. January 1951. p. 443.
  3. ^ Rea WJ, Patel K (18 June 2010). Reversibility of Chronic Degenerative Disease and Hypersensitivity, Volume 1: Regulating Mechanisms of Chemical Sensitivity. CRC Press. pp. 464–. ISBN 978-1-4398-1345-4.
  4. ^ Geynet C, Millet C, Truong H, Baulieu EE (1972). "Estrogens and antiestrogens". Gynecologic Investigation. 3 (1): 2–29. doi:10.1159/000301742. PMID 4347198.
  5. ^ Furuya H, Deguchi K, Shima M (September 1957). "Experimental and clinical studies on a new synthetic estrogen, an allenolic acid derivative, vallestril". American Journal of Obstetrics and Gynecology. 74 (3): 635–50. 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.
  7. ^ Ghalioungui P, Ghareeb A (1963). Endocrines, Vitamins, and Some Common Metabolic Disorders. Dar al-Maaref. p. 194.
  8. ^ Morrison JD (November 1983). Stereodifferentiating addition reactions. Academic Press. p. v. ISBN 978-0-12-507702-6.
  9. ^ Thompson WO (1953). The Year Book of Endocrinology. Year Book Medical Publishers. p. 292.
  10. ^ American Practitioner and Digest of Treatment. Lippincott. January 1956.
  11. ^ Clark ER, Robson RD (1959). "753. Oestrogenic carboxylic acids. Part II. Open-chain analogues of doisynolic acid". Journal of the Chemical Society (Resumed): 3714. doi:10.1039/jr9590003714. ISSN 0368-1769.
  12. ^ Journal of the Japanese Obstetrical & Gynecological Society. 1958. p. 83.
  13. ^ Heftmann E (1970). Steroid Biochemistry. Academic Press. p. 144. ISBN 9780123366504.
  14. ^ The Effects of the Sulfonylureas and Related Compounds in Experimental and Clinical Diabetes. The Academy. 1957. p. 681.
  15. ^ Sartorelli AC, Johns DG (27 November 2013). Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. pp. 106–. ISBN 978-3-642-65806-8.
 

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