Allenolic acid

Allenolic acid

Identifiers
IUPAC name 3-(6-Hydroxynaphthalen-2-yl)propanoic acid
CAS Number	553-39-9
PubChem (CID)	96227
ChemSpider	86868
UNII	I2MQT1CC3H
ChEBI	CHEBI:34529
Chemical and physical data
Formula	C13H12O3
Molar mass	216.23258 g/mol
3D model (Jmol)	Interactive image
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

Allenolic acid, or allenoic acid, is a synthetic,^[1] non-steroidal 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] The methyl ether of allenolic acid, methallenestril (brand name Vallestril), is also an estrogen and, in contrast to allenolic acid, has been marketed.^{[11][12][13][14]}

See also

• Bisdehydrodoisynolic acid
• Doisynoestrol
• Doisynolic acid

References

1. Rodolfo Paoletti; N. Pasetto; J.L. Ambrus (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. William J. Rea; Kalpana Patel (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, E.E. (1972). "Estrogens and Antiestrogens". Gynecologic and Obstetric Investigation. 3 (1-4): 1–29. doi:10.1159/000301742. ISSN 1423-002X.
5. Furuya, Hiroshi; Deguchi, Keiji; Shima, Motowo (1957). "Experimental and clinical studies on a new synthetic estrogen, an allenolic acid derivative, vallestril". American Journal of Obstetrics and Gynecology. 74 (3): 635–650. doi:10.1016/0002-9378(57)90519-7. ISSN 0002-9378.
6. Indian Journal of Chemistry: Organic including medicinal. Council of Scientific & Industrial Research. 1980. p. 886.
7. Paul Ghalioungui; Ahmed Ghareeb (1963). Endocrines, Vitamins, and Some Common Metabolic Disorders. Dar al-Maaref. p. 194.
8. James D. Morrison (November 1983). Stereodifferentiating addition reactions. Academic Press. p. v. ISBN 978-0-12-507702-6.
9. Willard Owen Thompson (1953). The Year Book of Endocrinology. Year Book Medical Publishers. p. 292.
10. American Practitioner and Digest of Treatment. Lippincott. January 1956.
11. Journal of the Japanese Obstetrical & Gynecological Society. 1958. p. 83.
12. Erich Heftmann (1970). Steroid Biochemistry. Academic Press. p. 144.
13. The Effects of the Sulfonylureas and Related Compounds in Experimental and Clinical Diabetes. The Academy. 1957. p. 681.
14. Alan C. Sartorelli; David G. Johns (27 November 2013). Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. pp. 106–. ISBN 978-3-642-65806-8.