Anol, also known as p-hydroxypropenylbenzene,[1] is a simple
phenol that was derived via
demethylation from
anethole, an
estrogenic constituent of
anise and
fennel, by
Sir Charles Dodds in 1937.[2][3] It was reported to possess extremely potent estrogenic activity on par with that of
steroidal estrogens like
estrone, with a dose of 1 μg inducing
estrus in rats.[2] However, subsequent studies with different preparations of anol failed to confirm these findings, and it was found that
dimerization of anol into
dianol and
hexestrol can rapidly occur and that the latter impurity was responsible for the highly potent estrogenic effects.[4][2][3][5][6] Dodds later synthesized the structurally related and extremely potent estrogen
diethylstilbestrol in 1938.[2][5]
^Campbell NR, Dodds EC, Lawson W (1940). "The nature of the oestrogenic substances produced during the demethylation of anethole". Proceedings of the Royal Society of London. Series B, Biological Sciences. 128 (851): 253–262.
Bibcode:
1940RSPSB.128..253C.
doi:
10.1098/rspb.1940.0009.
ISSN2053-9193.
S2CID98223820.
^Solmssen UV (December 1945). "Synthetic estrogens and the relation between their structure and their activity". Chemical Reviews. 37 (3): 481–598.
doi:
10.1021/cr60118a004.
PMID21013428.