1.0 2010-04-08 22:07:38 UTC 2019-11-26 03:01:41 UTC FDB007498 Diethylstilbesterol Diethylstilbestrol is a synthetic estrogen that was developed to supplement a woman's natural estrogen production. In 1971, the Food and Drug Administration (FDA) issued a Drug Bulletin advising physicians to stop prescribing DES to pregnant women because it was linked to a rare vaginal cancer in female offspring. Diethylstilbesterol is found in gram bean. (E)-3,4-bis(4-hydroxyphenyl)-3-hexene (E)-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol 4,4'-Dihydroxy-a,b-diethylstilbene 4,4'-dihydroxy-alpha,beta-diethylstilbene 4,4'-Dihydroxy-α,β-diethylstilbene a,Alpha'-diethyl-(e)-4,4'-stilbenediol alpha,alpha'-diethyl-(E)-4,4'-stilbenediol DES Diethylstilbestrol Diethylstilbestrol bp Diethylstilbestrolum Diethylstilboesterol Dietilestilbestrol Distilbene Percutatrine oestrogenique iscovesco Rcra waste number u089 trans-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol trans-Diethylstilbesterol trans-Diethylstilbestrol trans-Diethylstilboesterol α,alpha'-diethyl-(e)-4,4'-stilbenediol C18H20O2 268.3502 268.146329884 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol Stil 56-53-1 CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1 InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3 RGLYKWWBQGJZGM-UHFFFAOYSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Hydrocarbon derivatives Organooxygen compounds Phenylpropanes 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenylpropane Stilbene Solid logp 4.62 ALOGPS logs -4.39 ALOGPS solubility 1.09e-02 g/l ALOGPS melting_point 170.5 oC logp 5.19 ChemAxon pka_strongest_acidic 9.13 ChemAxon pka_strongest_basic -6 ChemAxon iupac 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol ChemAxon average_mass 268.3502 ChemAxon mono_mass 268.146329884 ChemAxon smiles CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1 ChemAxon formula C18H20O2 ChemAxon inchi InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3 ChemAxon inchikey RGLYKWWBQGJZGM-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 83.24 ChemAxon polarizability 30.69 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14239 Specdb::CMs 40306 Specdb::CMs 157079 Specdb::MsMs 105882 Specdb::MsMs 105883 Specdb::MsMs 105884 Specdb::MsMs 172500 Specdb::MsMs 172501 Specdb::MsMs 172502 Specdb::MsMs 2450896 Specdb::MsMs 2450897 Specdb::MsMs 2450898 Specdb::MsMs 2487381 Specdb::MsMs 2487382 Specdb::MsMs 2487383 HMDB14400 4531 DES #<Reference:0x000055ce31dac438> #<Reference:0x000055ce31dac280> #<Reference:0x000055ce31dac0c8> #<Reference:0x000055ce31dabee8> #<Reference:0x000055ce31dabd30> Gram bean Type 1 specific Vigna mungo 3915 0.0018 0.0018 0.0018 mg/100 g Estrogen receptor P03372 ESR1 Estrogen receptor beta Q92731 ESR2