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
IUPAC name
  • 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)
SMILES
  • C1=CC2=C(C=CC(=C2)O)C=C1CCC(=O)O
InChI
  • 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

References
  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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