8-Prenyl-naringenin
8-prenyl-naringenin, the hop estrogen, also known as HOPEIN

8-Prenylnaringenin (8-PN) is found almost exclusively in hops. It is located in the glandular parts of the cones of the female hop plant and can probably also be produced during the drying process of the cones.
8-PN is an estrogen that has the highest potency of all plant metabolites. Compared to the most effective estrogen in humans, 17ß-estradiol, it is 70 times less effective and about half as effective as estriol.
8-PN is a pure estrogen, so it does not bind to any other than the estrogen receptors.
The structural elucidation of the substance took place in 1997. The structure was already known, but not its hormonal properties.

However, this hormonal effect has long been known from hops and hopped beer. The Munich beer drivers experienced signs of feminization, even gynecomastia, and the female hop pickers experienced irregularities in their menstrual cycle during the harvest season, which resulted in many unexpected pregnancies.

The brewing processes have now been changed and most types of beer available on the market are no longer brewed only with hops or alcoholic hop extracts. Instead, CO2 extracts are produced from hops in which the bitter substances but no longer 8-PN are present.
The use of 8-PN for medicine is possible in many ways, as the substance is very suitable for local drug targeting (dermal and vaginal use), has clear tissue specificity (bone > uterus) and therefore enables a new treatment regime in the HRT. Also, as a dietary supplement 8-PN can compensate for estrogen deficiencies in older men.