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Quinestrol

CAS# 152-43-2

Quinestrol

2D Structure

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Quinestrol

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Chemical Properties of Quinestrol

Cas No. 152-43-2 SDF Download SDF
PubChem ID 9046 Appearance Powder
Formula C25H32O2 M.Wt 364.5
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 24 mg/mL (65.84 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
SMILES CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC5CCCC5
Standard InChIKey PWZUUYSISTUNDW-VAFBSOEGSA-N
Standard InChI InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Quinestrol Dilution Calculator

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Preparing Stock Solutions of Quinestrol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7435 mL 13.7174 mL 27.4348 mL 54.8697 mL 68.5871 mL
5 mM 0.5487 mL 2.7435 mL 5.487 mL 10.9739 mL 13.7174 mL
10 mM 0.2743 mL 1.3717 mL 2.7435 mL 5.487 mL 6.8587 mL
50 mM 0.0549 mL 0.2743 mL 0.5487 mL 1.0974 mL 1.3717 mL
100 mM 0.0274 mL 0.1372 mL 0.2743 mL 0.5487 mL 0.6859 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Quinestrol

Degradation Kinetics and Transformation Products of Levonorgestrel and Quinestrol in Soils.[Pubmed:30900888]

J Agric Food Chem. 2019 Apr 2.

Levonorgestrel (LNG) and Quinestrol (QUN) are typical endocrine disruptors that enter the soil via sewage irrigation and sludge return. However, the fates of both compounds in soil are not well-understood. Laboratory microcosm studies were conducted to fill the gap of understanding of LNG and QUN behavior in soils. High values of goodness-of-fit indices (GFIs) were obtained using the double-first-order in parallel (DFOP) model and the single-first-order (SFO) model to fit the degradation kinetics of LNG and QUN in soils, respectively. The end-points (DT50 and DT90) of LNG and QUN were positively correlated with soil total organic carbon (TOC). Soil water content and temperature were observed to be critical factors in degradation of LNG and QUN. The degradation rates of LNG and QUN were very slow under sterile and flooded conditions, indicating that the aerobic microbial degradation was dominant in the degradation of LNG and QUN. Moreover, major transformation products were identified, and biodegradation pathways of LNG and QUN were proposed. The present study is expected to provide basic information for ecological risk assessment of LNG and QUN in the soil compartment.

The accumulation, transformation, and effects of quinestrol in duckweed (Spirodela polyrhiza L.).[Pubmed:29660861]

Sci Total Environ. 2018 Sep 1;634:1034-1041.

Potential risk of endocrine disrupting compounds on non-target organisms has received extensive attentions in recent years. The present work aimed to investigate the behavior and effect of a synthetic steroid estrogen Quinestrol in duckweed Spirodela polyrhiza L. Experimental results showed that Quinestrol could be uptaken, accumulated, and biotransformed into 17 alpha-ethynylestradiol in S. polyrhiza L. The accumulation of Quinestrol had a positive relation to the exposure concentration. The bioaccumulation rate was higher when the duckweed was exposed to Quinestrol solutions at low concentrations than at high concentration. While the transformation of Quinestrol showed no concentration-dependent manner. Quinestrol reduced the biomass and pigment content and increased superoxide dismutase and catalase activities and malondialdehyde contents in the duckweed. The results demonstrated that Quinestrol could be accumulated and biotransformed in aquatic plant S. polyrhiza L. This work would provide supplemental data on the behavior of this steroid estrogen compound in aquatic system.

Effect of synthetic hormones on reproduction in Mastomys natalensis.[Pubmed:29367841]

J Pest Sci (2004). 2018;91(1):157-168.

Rodent pest management traditionally relies on some form of lethal control. Developing effective fertility control for pest rodent species could be a major breakthrough particularly in the context of managing rodent population outbreaks. This laboratory-based study is the first to report on the effects of using fertility compounds on an outbreaking rodent pest species found throughout sub-Saharan Africa. Mastomys natalensis were fed bait containing the synthetic steroid hormones Quinestrol and levonorgestrel, both singly and in combination, at three concentrations (10, 50, 100 ppm) for 7 days. Consumption of the bait and animal body mass was mostly the same between treatments when analysed by sex, day and treatment. However, a repeated measures ANOVA indicated that Quinestrol and Quinestrol + levonorgestrel treatments reduced consumption by up to 45%, particularly at the higher concentrations of 50 and 100 ppm. Although there was no clear concentration effect on animal body mass, Quinestrol and Quinestrol + levonorgestrel lowered body mass by up to 20% compared to the untreated and levonorgestrel treatments. Quinestrol and Quinestrol + levonorgestrel reduced the weight of male rat testes, epididymis and seminal vesicles by 60-80%, and sperm concentration and motility were reduced by more than 95%. No weight changes were observed to uterine and ovarian tissue; however, high uterine oedema was observed among all female rats consuming treated bait at 8 and 40 days from trial start. Trials with mate pairing showed there were significant differences in the pregnancy rate with all treatments when compared to the untreated control group of rodents.

Responses in reproductive organs, steroid hormones and CYP450 enzymes in female Mongolian gerbil (Meriones unguiculatus) over time after quinestrol treatment.[Pubmed:29183580]

Pestic Biochem Physiol. 2017 Nov;143:122-126.

The aim of this study was to assess the effects and reversibility of the synthetic estrogen compound, Quinestrol, on the reproductive organs, steroid hormones, and drug-metabolizing enzymes CYP3A4 and CYP1A2 in liver and kidney over time after two Quinestrol treatments in female Mongolian gerbils (Meriones unguiculatus). Female gerbils were treated with 4mg/kg Quinestrol (9 gerbils/group, 3 treated group) (1 control group, 0mg/kg) for 3days and treated again after 25days. Animals were killed for collection of samples at 5, 10 and 15days after the second treatment ending. Two interval Quinestrol treatments significantly increased uterine weight, with trend of increase over time, but no change could be detected in ovarian weights. Quinestrol treatment increased progesterone and estradiol levels, both with trend of decline over time. Quinestrol increased liver and kidney weights and total enzyme content of CYP3A4 and CYP1A2, with trend of decline over time. On the basis of reversible changes of detoxification enzymes or organs, interval Quinestrol treatment effectively and reversibly influenced the reproductive hormone and organ to some extent.

Quinestrol induces spermatogenic apoptosis in vivo via increasing pro-apoptotic proteins in adult male mice.[Pubmed:25038589]

Tissue Cell. 2014 Oct;46(5):318-25.

The effects of Quinestrol on spermatogenesis were investigated in adult male mice by daily intragastric administration of Quinestrol with various doses of 5, 10, 50 and 100mg/kg body weight for 10 days. The sperm counts declined while the number of abnormal spermatozoa went up in mice treated with Quinestrol. The testicular weight and seminiferous tubular area gradually declined with increasing dosages of Quinestrol to 50 and 100mg/kg. Rarefied germ cells showed irregular distributions in the seminiferous tubules of mice treated with 50 and 100mg/kg Quinestrol. Apoptosis was highly pronounced in spermatogonia, spermatocytes, spermatids and Leydig cells. Antioxidant enzyme activities - superoxide dismutase and glutathione peroxidase - as well as total antioxidant capacity significantly reduced, while malondialdehyde contents increased. The number of germ cells expressing caspase-3, p53, Bax and FasL significantly increased whereas cells expressing Bcl-2 significantly decreased in groups treated with 50 and 100mg/kg Quinestrol compared with the control. The concentration of nitrogen monoxidum also increased significantly under these dosages. The results suggest that Quinestrol stimulates oxidative stress to induce apoptosis in spermatogenic cells through the mitochondrial and death receptor pathways in adult male mice.

Description

Quinestrol is a synthetic estrogen, used in hormone replacement therapy, and occasionally to treat breast cancer and prostate cancer

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