3616. 16-Epiestriol

Nomenclature

CAS number: 547-81-9
(16β,17β)-Estra-1,3,5(10)-triene-3,16,17-triol; Δ1,3,5-estratriene-3,16β,17β-triol; 16-epioestriol; Actriol (Organon).
C18H24O3; mol wt 288.38.
C 74.97%, H 8.39%, O 16.64%.

Description and references

Isoln from urine of pregnant women: Marrian, Bauld, Biochem. J. 59, 136 (1955); Watson, Marrian, ibid. 63, 64 (1956). From human placenta: Diczfalusy, Halla, Acta Endocrinol. 27, 303 (1958). Prepn by reduction of 3,16β-diacetoxy-1,3,5(10)-estratrien-17-one: Biggerstaff, Gallagher, J. Org. Chem. 22, 1220 (1957).

Chemical structure

Properties

Crystals from methanol + benzene, mp 289-291°. [α]D15 +76° (c = 0.297 in ethanol).

Derivative

Epiestriol-3-allyl ether.

Description and references

Prepn: Huffman, US 3002009 (1961 to Lasdon Found).

Properties

Crystals, mp 156-156.5°.