Title: Doisynolic Acid
CAS Registry Number: 109784-48-7
CAS Name: 1-Ethyl-1,2,3,4,4a,9,10,10a-octahydro-7-hydroxy-2-methyl-2-phenanthrenecarboxylic acid
Additional Names: 3-hydroxy-16,17-secoestra-1,3,5(10)-trien-17-oic acid
Molecular Formula: C18H24O3
Molecular Weight: 288.38
Percent Composition: C 74.97%, H 8.39%, O 16.64%
Literature References: Prepd by alkali fusion of estrone: MacCorquodale et al., J. Biol. Chem. 99, 327 (1933); 101, 753 (1933); Heer, Miescher, Helv. Chim. Acta 28, 156 (1945). Sixteen isomers are possible. If the hydrogen atom at position 4a is a- and the hydrogen atom at position 10a is b-, the acid belongs to the A series. If the hydrogen at 4a is b- and the hydrogen at 10a is a-, the acid belongs to the B series. If both hydrogens are a-, the acid belongs to the C series. If both hydrogens are b-, the acid belongs to the D series: Miescher, Chem. Rev. 43, 367 (1948). If the hydrogen atom at position 1 and the methyl group at position 2 have either the a,a- or b,b-orientation, the acid is designated cis; if they are a,b- the acid is designated trans: L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) pp 487-495. Synthesis of dl-cis and dl-trans of the A series and dl-cis of the B series: Anner, Miescher, Helv. Chim. Acta 29, 1889 (1946); 30, 1422 (1947). Synthesis of dl-cis of the C series: Jilck, Protiva, Collect. Czech. Chem. Commun. 23, 692 (1958). Stereochemistry of d-cis-form: Iriarte, Crabbe, Chem. Commun. 1972, 1110. Reviews: Shoppee, Annu. Rep. Prog. Chem. 44, 190 (1948); Miescher in Recent Progress in Hormone Research vol. 3, G. Pincus Ed. (Academic Press, New York, 1948) pp 47-69.
Derivative Type: dl-cis Acid of the A series
Properties: Crystals from methanol, mp 181-182°. Appears to have the highest estrogenic potency.
Melting point: mp 181-182°
Derivative Type: dl-trans Acid of the A series
Properties: Plates from methanol, mp 175-177°.
Melting point: mp 175-177°
Derivative Type: dl-cis Acid of the B series
Properties: Crystals from methanol, mp 212-214°.
Melting point: mp 212-214°
Derivative Type: dl-cis Acid of the C series
Properties: Crystals from methanol, mp 113-117°.
Melting point: mp 113-117°
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