CAS 2408-40-4

Diethylstilbestrol monoglucuronide

Description:

Diethylstilbestrol monoglucuronide is a chemical compound that is a glucuronide conjugate of diethylstilbestrol, a synthetic nonsteroidal estrogen. This compound is characterized by its structure, which includes a stilbene backbone with two ethyl groups and a glucuronic acid moiety attached, enhancing its solubility and facilitating excretion. Diethylstilbestrol itself was historically used in medicine, particularly for hormone replacement therapy and to prevent pregnancy complications, but its use has declined due to associated health risks. The monoglucuronide form is typically more polar than its parent compound, which affects its pharmacokinetics and biological activity. It is important in the context of drug metabolism, as glucuronidation is a major pathway for the detoxification and elimination of various drugs and endogenous compounds. The compound is of interest in pharmacological and toxicological studies, particularly regarding its potential effects and the implications of estrogenic activity in various biological systems.

Formula: C₂₄H₂₈O₈

InChI: InChI=1S/C24H28O8/c1-3-17(13-5-9-15(25)10-6-13)18(4-2)14-7-11-16(12-8-14)31-24-21(28)19(26)20(27)22(32-24)23(29)30/h5-12,19-22,24-28H,3-4H2,1-2H3,(H,29,30)/b18-17+/t19-,20-,21+,22-,24+/m0/s1

InChI key: InChIKey=LJMPVHCKUXKZAV-PDSLVOJVSA-N

SMILES: C(=C(/CC)\C1=CC=C(O)C=C1)(\CC)/C2=CC=C(O[C@@H]3O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]3O)C=C2

Synonyms:

• (E)-4-(1-Ethyl-2-(4-hydroxyphenyl)but-1-enyl)phenyl-beta-D-glucopyranosiduronic acid
• 4-[(1E)-1-Ethyl-2-(4-hydroxyphenyl)-1-buten-1-yl]phenyl β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid
• 4-[(1E)-1-ethyl-2-(4-hydroxyphenyl)but-1-en-1-yl]phenyl D-glucopyranosiduronic acid
• Diethylstilbestrol monoglucuronide
• Glucopyranosiduronic acid, p-(α,β-diethyl-p-hydroxystyryl)phenyl, (E)-, β-<span class="text-smallcaps">D</span>-
• Stilbestrol monoglucuronide
• β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, 4-[(1E)-1-ethyl-2-(4-hydroxyphenyl)-1-buten-1-yl]phenyl
• β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, 4-[(1E)-1-ethyl-2-(4-hydroxyphenyl)-1-butenyl]phenyl
• β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, 4-[1-ethyl-2-(4-hydroxyphenyl)-1-butenyl]phenyl, (E)-
• β-D-Glucopyranosiduronic acid, 4-[(1E)-1-ethyl-2-(4-hydroxyphenyl)-1-buten-1-yl]phenyl
• β-D-Glucopyranosiduronic acid, 4-[1-ethyl-2-(4-hydroxyphenyl)-1-butenyl]phenyl, (E)-
• 4-[(1E)-1-Ethyl-2-(4-hydroxyphenyl)-1-buten-1-yl]phenyl β-D-glucopyranosiduronic acid
• β-D-Glucopyranosiduronic acid, 4-[(1E)-1-ethyl-2-(4-hydroxyphenyl)-1-butenyl]phenyl

Diethyl stilbestrol b-D-glucuronide

CAS: 2408-40-4

Ref: 7W-GC2661

Diethyl Stilbestrol β-D-Glucuronide

Controlled Product

CAS: 2408-40-4

Stability Hygroscopic
Applications A metabolite of Fosfestrol.
References Vanluchene, E., et al.: J. Steroid Biochem., 16, 701 (1982), Fodey, T., et al.: Food Agric. Immunol., 8, 157 (1996),

Formula: C₂₄H₂₈O₈

Color and Shape: Neat

Molecular weight: 444.47

Ref: TR-D445020

Diethyl stilbestrol β-D-glucuronide

CAS: 2408-40-4

Diethylstilbestrol (DES) is an endogenous substance that has been shown to be a potent estrogen. It is metabolized in the body to form stilbestrol glucuronide, which is excreted in the urine. Radiolabeling studies have shown that DES has a chemical structure similar to estradiol, although its pharmacologic effects are not as potent. Diethylstilbestrol glucuronide can be used for the diagnosis of cancer and other diseases by using nuclear medicine techniques such as positron emission tomography (PET) and single-photon emission computed tomography (SPECT). Studies have also demonstrated that DES can induce erythropoietic protoporphyria in animals.

Formula: C₂₄H₂₈O₈

Purity: Min. 95%

Color and Shape: White to off-white powder.

Molecular weight: 444.47 g/mol

Ref: 3D-MD10197