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Purity: ≥98%
Diethylstilbestrol (also called Stilbestrol; DES; Distilbene) is a synthetic non-steroidal form of estrogen that can be used to prevent miscarriage and other pregnancy complications as well as in the treatment of menopausal and postmenopausal disorders. Diethylstilbestrol is a well-known teratogen and carcinogen, that inhibits the hypothalamic-pituitary-gonadal axis, thereby blocking the testicular synthesis of testosterone, lowering plasma testosterone, and inducing a chemical castration. Diethylstilbestrol promotes coactivator release from orphan nuclear receptor ERR beta and inhibits its transcriptional activity in trophoblast stem cells.
| ln Vitro |
Diethylstilbestrol (0-100 µM) activates CatSper, enhances Ca2+ influx into human sperm, and interferes with progesterone actions in human sperm [5]. Diethylstilbestrol (0-10 µM, 1 hour) produces oxidative damage to DNA and promotes death in spermatogonial stem cells [7].
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| ln Vivo |
In mouse seminal vesicles, diethylstilbestrol (2 μg/day, subcutaneous injection) alters target gene methylation patterns and epigenetic modifiers (DNMT3A, MBD2, and HDAC2) while promoting ERα-mediated hormonal toxicity [3]. In rats, diethylstilbestrol (340 μg/kg, PO, every 2 days for 2 weeks) lowers corticosterone and adrenal cholesterol [4]. In adult mice, diethylstilbestrol (5 μg/kg, intraperitoneal injection) can cause thymocyte autophagy and decrease thymocyte count [6]. In both rat and human placentas, diethylstilbestrol (0.5 mg/kg, oral) lowers HSD11B2 activity [8].
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| Animal Protocol |
Animal/Disease Models: Adult mice[6]
Doses: 5 μg/kg Route of Administration: ip Experimental Results: decreased number of thymocytes, and induced autophagy in thymocytes. Increased expression of Becn1, LC3 I and LC3 II. |
| References |
[1]. Troisi, R., et al., Medical conditions among adult offspring prenatally exposed to diethylstilbestrol. Epidemiology, 2013. 24(3): p. 430-8.
[2]. Kebir, O. and M.O. Krebs, Diethylstilbestrol and risk of psychiatric disorders: a critical review and new insights. World J Biol Psychiatry, 2012. 13(2): p. 84-95. [3]. Li Y, et al. Diethylstilbestrol (DES)-stimulated hormonal toxicity is mediated by ERα alteration of target gene methylation patterns and epigenetic modifiers (DNMT3A, MBD2, and HDAC2) in the mouse seminal vesicle. Environ Health Perspect. 2014 Mar;122(3):262-8. [4]. Haeno S, et al. Diethylstilbestrol decreased adrenal cholesterol and corticosterone in rats. J Endocrinol. 2014 Apr 22;221(2):261-72. [5]. Zou QX, et al. Diethylstilbestrol activates CatSper and disturbs progesterone actions in human spermatozoa. Hum Reprod. 2017 Feb;32(2):290-298. [6]. Singh NP, et al. Diethylstilbestrol (DES) induces autophagy in thymocytes by regulating Beclin-1 expression through epigenetic modulation. Toxicology. 2018 Dec 1;410:49-58. [7]. Habas K, et al. Diethylstilbestrol induces oxidative DNA damage, resulting in apoptosis of spermatogonial stem cells in vitro. Toxicology. 2017 May 1;382:117-121. [8]. Wang Y, et al. Diethylstilbestrol inhibits human and rat 11β-hydroxysteroid dehydrogenase 2. Endocr Connect. 2019 Jul;8(7):1061-1069. |
| Molecular Formula |
C18H20O2
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| Molecular Weight |
268.35
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| CAS # |
56-53-1
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| Related CAS # |
Diethylstilbestrol-d8;91318-10-4;Diethylstilbestrol-d3;58322-36-4
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| SMILES |
O([H])C1C([H])=C([H])C(=C([H])C=1[H])/C(/C([H])([H])C([H])([H])[H])=C(/C1C([H])=C([H])C(=C([H])C=1[H])O[H])\C([H])([H])C([H])([H])[H]
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| InChi Key |
RGLYKWWBQGJZGM-ISLYRVAYSA-N
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| InChi Code |
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/b18-17+
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| Chemical Name |
4-[(E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.7265 mL | 18.6324 mL | 37.2648 mL | |
| 5 mM | 0.7453 mL | 3.7265 mL | 7.4530 mL | |
| 10 mM | 0.3726 mL | 1.8632 mL | 3.7265 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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