Estrone

Estrogenic hormone CAS# 53-16-7

Estrone

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Quality Control of Estrone

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Chemical structure

Estrone

3D structure

Chemical Properties of Estrone

Cas No. 53-16-7 SDF Download SDF
PubChem ID 5870 Appearance Powder
Formula C18H22O2 M.Wt 270.37
Type of Compound Steroids Storage Desiccate at -20°C
Solubility DMSO : 33.33 mg/mL (123.28 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
SMILES CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O
Standard InChIKey DNXHEGUUPJUMQT-CBZIJGRNSA-N
Standard InChI InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/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.

Biological Activity of Estrone

DescriptionEstrone,a steroid known to play an important role as precursor of 17 beta-estradiol,especially in postmenopausal women, it inhibits the BCRP-mediated drug efflux and overcome drug resistance.The widely distributed estrone esters in food and their relatively high concentrations may result in high free hormone intakes in humans, the continued and massive intake of estrone may enhance tissue deposition and lead to obesity.
TargetsEstrogen receptor | Progestogen receptor
In vitro

The effect of particle size on sorption of estrogens, androgens and progestagens in aquatic sediment.[Pubmed: 26094244]

J Hazard Mater. 2015 May 29;299:112-121.

There is growing concern about the biologic effects of steroid hormones in impacted waterways. There is increasing evidence of enhanced transport and biological effects stemming from steroid hormones associated with soils or sediments; however, there are limited studies evaluating how steroid hormone distribution between various particle sizes within whole sediments affects steroid fate.
METHODS AND RESULTS:
In this study, sorption of 17β-estradiol, Estrone, progesterone, and testosterone was evaluated to different size fractions of two natural sediments, a silty loam and a sandy sediment, to determine the steroid sorption capacity to each fraction and distribution within the whole sediment. Sorption isotherms for all steroid hormones fit linear sorption models. Sorption capacity was influenced more by organic carbon content than particle size. Interactions between size fractions were found to affect the distribution of steroids within the whole sediments. All four steroids preferentially sorbed to the clay and colloids in the silty loam sediment at the lowest aqueous concentration (1 ng/L) and as aqueous concentration increased, the distribution of sorbed steroid was similar to the distribution by weight of each size fraction within the whole sediment.
CONCLUSIONS:
In the sandy sediment, preferential sorption to fine particles was observed.

Estrone and 17beta-estradiol reverse breast cancer resistance protein-mediated multidrug resistance.[Pubmed: 11927002]

Jpn J Cancer Res. 2002 Mar;93(3):231-5.

Breast cancer resistance protein (BCRP), an adenosine triphosphate-binding cassette transporter, confers resistance to a series of anticancer reagents, including mitoxantrone, SN-38 and topotecan.
METHODS AND RESULTS:
In the present study, we found that Estrone and 17beta-estradiol potentiated the cytotoxicity of mitoxantrone, SN-38 and topotecan in BCRP-transduced K562 cells (K562 / BCRP). These estrogens showed only a marginal effect, or none, in parental K562 cells. Estrone and 17beta-estradiol increased the cellular accumulation of topotecan in K562 / BCRP cells, but not in K562 cells, suggesting that these estrogens inhibit the BCRP-mediated drug efflux and overcome drug resistance.

In vivo

Estrone in food: a factor influencing the development of obesity?[Pubmed: 10654162]

Eur J Nutr. 1999 Oct;38(5):247-53.

Estrone is a relatively abundant hormone widely distributed in tissues of animal and plant origin. It is a mild estrogen that induces increases in body weight in experimental animals. The relative abundance of Estrone esters in animal tissues suggests that it may also be found in foods, from which it may alter the mechanisms of body weight control. To measure the total Estrone content in food and to determine whether this may affect body weight.
METHODS AND RESULTS:
In the first part of the study, a method was devised for the measurement of total Estrone content in food. This was applied to the analysis of Estrone content in a variety of food. Finally, hyperlipidic diets (18.6 MJ/kg) with a total Estrone content 0.89 +/- 0.21 mumol/kg (control group) and 1.37 +/- 0.13 mumol/kg (laced with Estrone fatty esters) were given to rats during 15 days, in order to determine the influence of dietary Estrone on the body mass. Zucker lean (Fa/?) rats weighing initially 200-215 g were used. The total Estrone (essentially as fatty esters) content of food was investigated by combining a dried methanol extraction with saponification and measurement of the free Estrone evolved through radioimmunoassay. The content of Estrone was zero in some vegetables, but significant in fruits, meats, and especially fats, both of plant and animal origin. The application of these analyses to a standard recommended diet for humans may result in intakes of more than 1 mumol of Estrone per day, a figure comparable to the estrogen production by women. When rats were exposed to a raised Estrone content in a fat-rich diet, they significantly increased their body weights, doubling their rate of growth (1.99 g/day) compared with controls (0.81 g/day), but maintaining their plasma composition and the proportions of lipid, water, and protein in their carcasses.
CONCLUSIONS:
The widely distributed Estrone esters in food and their relatively high concentrations may result in high free hormone intakes in humans. The continued and massive intake of Estrone may enhance tissue deposition and lead to obesity.

Protocol of Estrone

Animal Research

Inhibitory effect of a steroidal antiestrogen (EM-170) on estrone-stimulated growth of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary carcinoma in the rat.[Pubmed: 7749151]

Breast Cancer Res Treat. 1995 Mar;33(3):237-44.

Recently, compounds having pure antiestrogenic activity have become available.
METHODS AND RESULTS:
In this study, we examined the activity of the new steroidal antiestrogen EM-170 (N-n-butyl, N-methyl-11-(16' alpha-chloro-3',17' alpha-dihydroxy-estra-1',3',5'-(10')-trien-7' alpha-yl) undecanamide) on the growth of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary carcinoma stimulated by treatment with Estrone (E1), a steroid known to play an important role as precursor of 17 beta-estradiol (E2), especially in postmenopausal women. Twenty-five days after ovariectomy (OVX), tumor volume in control OVX animals decreased to 51.4 +/- 11% of the initial volume; treatment with E1, administered by Silastic implants, stimulated tumor growth to 179 +/- 21%. Treatment with the antiestrogen EM-170 at a dose of 200 micrograms (twice daily) not only completely reversed the stimulatory effect of E1, but also inhibited tumor growth to 30.5 +/- 9.6%, an effect that is 41% (P < 0.01 vs OVX control) greater than that of ovariectomy alone. At a relatively low dose of 40 micrograms (twice daily), 20 days of treatment with EM-170 reversed by 55% the stimulatory effect of E1 (1.0 micrograms, subcutaneously, twice daily) on tumor growth in OVX animals. On the other hand, the antiestrogen also induced a significant inhibitory effect on 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) activity in the DMBA-induced mammary tumors, an effect that is in agreement with the marked reduction caused by the same treatment on tumor estradiol (E2) levels in E1-treated OVX animals.

Estrone Dilution Calculator

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Estrone Molarity Calculator

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Preparing Stock Solutions of Estrone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6986 mL 18.4932 mL 36.9864 mL 73.9727 mL 92.4659 mL
5 mM 0.7397 mL 3.6986 mL 7.3973 mL 14.7945 mL 18.4932 mL
10 mM 0.3699 mL 1.8493 mL 3.6986 mL 7.3973 mL 9.2466 mL
50 mM 0.074 mL 0.3699 mL 0.7397 mL 1.4795 mL 1.8493 mL
100 mM 0.037 mL 0.1849 mL 0.3699 mL 0.7397 mL 0.9247 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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Background on Estrone

Estrone (E1, and also oestrone) is an estrogenic hormone secreted by the ovary as well as adipose tissue with the chemical name of 3-hydroxyestra-1,3,5(10)-triene-17-one and the chemical formula C18H22O2. Estrone is an odorless, solid crystalline powder, white in color with a melting point of 254.5 °C and a specific gravity of 1.23. Estrone is one of several natural estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones; estradiol is present almost always in the reproductive female body, and estriol is abundant primarily during pregnancy.

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References on Estrone

The effect of particle size on sorption of estrogens, androgens and progestagens in aquatic sediment.[Pubmed:26094244]

J Hazard Mater. 2015 Dec 15;299:112-21.

There is growing concern about the biologic effects of steroid hormones in impacted waterways. There is increasing evidence of enhanced transport and biological effects stemming from steroid hormones associated with soils or sediments; however, there are limited studies evaluating how steroid hormone distribution between various particle sizes within whole sediments affects steroid fate. In this study, sorption of 17beta-estradiol, Estrone, progesterone, and testosterone was evaluated to different size fractions of two natural sediments, a silty loam and a sandy sediment, to determine the steroid sorption capacity to each fraction and distribution within the whole sediment. Sorption isotherms for all steroid hormones fit linear sorption models. Sorption capacity was influenced more by organic carbon content than particle size. Interactions between size fractions were found to affect the distribution of steroids within the whole sediments. All four steroids preferentially sorbed to the clay and colloids in the silty loam sediment at the lowest aqueous concentration (1 ng/L) and as aqueous concentration increased, the distribution of sorbed steroid was similar to the distribution by weight of each size fraction within the whole sediment. In the sandy sediment, preferential sorption to fine particles was observed.

Inhibitory effect of a steroidal antiestrogen (EM-170) on estrone-stimulated growth of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary carcinoma in the rat.[Pubmed:7749151]

Breast Cancer Res Treat. 1995 Mar;33(3):237-44.

Recently, compounds having pure antiestrogenic activity have become available. In this study, we examined the activity of the new steroidal antiestrogen EM-170 (N-n-butyl, N-methyl-11-(16' alpha-chloro-3',17' alpha-dihydroxy-estra-1',3',5'-(10')-trien-7' alpha-yl) undecanamide) on the growth of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary carcinoma stimulated by treatment with Estrone (E1), a steroid known to play an important role as precursor of 17 beta-estradiol (E2), especially in postmenopausal women. Twenty-five days after ovariectomy (OVX), tumor volume in control OVX animals decreased to 51.4 +/- 11% of the initial volume; treatment with E1, administered by Silastic implants, stimulated tumor growth to 179 +/- 21%. Treatment with the antiestrogen EM-170 at a dose of 200 micrograms (twice daily) not only completely reversed the stimulatory effect of E1, but also inhibited tumor growth to 30.5 +/- 9.6%, an effect that is 41% (P < 0.01 vs OVX control) greater than that of ovariectomy alone. At a relatively low dose of 40 micrograms (twice daily), 20 days of treatment with EM-170 reversed by 55% the stimulatory effect of E1 (1.0 micrograms, subcutaneously, twice daily) on tumor growth in OVX animals. On the other hand, the antiestrogen also induced a significant inhibitory effect on 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) activity in the DMBA-induced mammary tumors, an effect that is in agreement with the marked reduction caused by the same treatment on tumor estradiol (E2) levels in E1-treated OVX animals.(ABSTRACT TRUNCATED AT 250 WORDS)

Estrone and 17beta-estradiol reverse breast cancer resistance protein-mediated multidrug resistance.[Pubmed:11927002]

Jpn J Cancer Res. 2002 Mar;93(3):231-5.

Breast cancer resistance protein (BCRP), an adenosine triphosphate-binding cassette transporter, confers resistance to a series of anticancer reagents, including mitoxantrone, SN-38 and topotecan. In the present study, we found that Estrone and 17beta-estradiol potentiated the cytotoxicity of mitoxantrone, SN-38 and topotecan in BCRP-transduced K562 cells (K562 / BCRP). These estrogens showed only a marginal effect, or none, in parental K562 cells. Estrone and 17beta-estradiol increased the cellular accumulation of topotecan in K562 / BCRP cells, but not in K562 cells, suggesting that these estrogens inhibit the BCRP-mediated drug efflux and overcome drug resistance.

Description

Estrone is an estrogenic hormone.

Keywords:

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