Chemical Properties
There are multiple isomers: 3R, 4R type: CAS number [26614-21-1], melting point 80°C, [α]17/D+17.6° (5% ethanol); 3S, 4S type: CAS number [26614-22-2]; 3RS, 4RS type: CAS number [5776-72-7], crystalline (benzene/petroleum ether), melting point 128°C, low activity; 3RS, 4RS type: CAS number [84-16-2], needle-shaped crystals (benzene), melting point 185-186°C, the strongest activity, animal experiments show teratogenic and fertility-affecting effects, exercise experiments show hepatotoxic and hemolytic effects.
Uses
Vitestrol can be used in methods related to bioactive agents that convert from anions to molecules
Definition
ChEBI: Hexestrol is a stilbenoid.
World Health Organization (WHO)
Hexestrol is a stilbene derivative. See WHO comment for
diethylstilbestrol.
(Reference: (WHODI) WHO Drug Information, 77.1, 16, 1977)
Purification Methods
Crystallise meso-Hexestero from *benzene or aqueous EtOH (m 185-188o). The meso-dibenzoyl derivative has m 236-237o. The 3RS,4RS(±)-racemate [5776-72-7] crystallises from pet ether, *C6H6/pet ether, Et2O/pet ether, or MeOH/H2O and has m 128-129o . The (±)-dibenzoyl derivative has m 123-124o . The 3R,4R(+)-isomer [26614-21-1] and 3S,4S(-)-isomer [26614-22-2] crystallise from Et2O/pet ether with m 80 -80.5o and have [] D (+) and (-) 17.7o (c 5, EtOH). Their dibenzoyl derivatives have m 116.5o .[Beilstein 6 III 5503, 6 IV 6761.] They have estrogenic activity where optically active forms are more potent and they have antineoplastic activity. [Aboul-Enein et al. Anal Profiles Drug Subst 11 347 1982, J Am Chem Soc 65 4911941.]
