Estrone 3-methyl ether
(Synonyms: 3-甲氧基雌酮) 目录号 : GC45451
A synthetic estrogen
Cas No.:1624-62-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Estrone 3-methyl ether is a synthetic estrogen and derivative of estrone .1 It stimulates proliferation of estrogen-dependent MCF-7 breast cancer cells in vitro when used at concentrations ranging from 0.16 to 20 μM but lacks estrogen receptor (ER) binding activity (IC50s = >100 μM for ERα and ERβ). Estrone 3-methyl ether has been used in the synthesis of various estrogen receptor modulators.2
References
1. Alsayari, A., Kopel, L., Ahmed, M.S., et al. Design, synthesis, and biological evaluation of steroidal analogs as estrogenic/anti-estrogenic agents. Steroids 118, 32-40 (2017).
2. Kuznetsov, Y.V., Levina, I.S., Scherbakov, A.M., et al. New estrogen receptor antagonists. 3,20-Dihydroxy-19-norpregna-1,3,5(10)-trienes: Synthesis, molecular modeling, and biological evaluation. Eur. J. Med. Chem. 143, 670-682 (2018).
| Cas No. | 1624-62-0 | SDF | |
| 别名 | 3-甲氧基雌酮 | ||
| Canonical SMILES | O=C1CC[C@@]2([H])[C@]3([H])CCC4=CC(OC)=CC=C4[C@@]3([H])CC[C@@]21C | ||
| 分子式 | C19H24O2 | 分子量 | 284.4 |
| 溶解度 | Chloroform: 30 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.5162 mL | 17.5809 mL | 35.1617 mL |
| 5 mM | 0.7032 mL | 3.5162 mL | 7.0323 mL |
| 10 mM | 0.3516 mL | 1.7581 mL | 3.5162 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2
Sci Rep 2019 Jul 24;9(1):10734.PMID:31341201DOI:10.1038/s41598-019-47225-1.
Estrone, estradiol, ethynylestradiol and Estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transformed to D-ring lactone. Ethynylestradiol was coupled with methylglucoside and 6β-hydroxyderivative was obtained. Estrone 3-methyl ether was not transformed indicating that a free hydroxyl group at C-3 is necessary for glycosylation. Baeyer-Villiger oxidation combined with hydroxylation and glycosylation was observed. All glycosides obtained in this study are 3-O-β-methylglucosides.
Lumi-mestranol and epi-lumi-mestranol
Steroids 1979 Mar;33(3):287-94.PMID:442124DOI:10.1016/0039-128x(79)90005-9.
Treatment of lumi-estrone 3-methyl ether (I) with acetylene gave the C-17-epimeric compounds lumi-mestranol (3-methoxy-17 alpha-ethynyl-13 alpha-estra-1,3,5(10)-trien-17 beta-ol, III ) and epi-lumi-mestranol (3-methoxy-17 beta-ethynyl-13 alpha-estra-1,3,5(10)-trien-17 alpha-ol, IV). The structures of the two isomers were assigned on the basis of their molecular rotations and shift-reagent experiments in the NMR. The irradiation of Estrone 3-methyl ether (II) to provide compound I was investigated in two solvent systems. Minor products of these reactions were the seco-steroids VII, VIII and X.
Manganese-Catalyzed Hydrogen-Autotransfer C-C Bond Formation: α-Alkylation of Ketones with Primary Alcohols
Angew Chem Int Ed Engl 2016 Nov 21;55(48):14967-14971.PMID:27785889DOI:10.1002/anie.201607072.
A novel catalytic hydrogen-autotransfer protocol for the atom-efficient α-alkylation of ketones with readily available alcohols is presented. The use of manganese complexes bearing non-innocent PNP pincer ligands enabled the functionalization of a broad range of valuable ketones, including 2-oxindole, Estrone 3-methyl ether, and testosterone. Mechanistic investigations suggest the participation of an intramolecular amidate-assisted alcohol-dehydrogenation process.
Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series
Molecules 2019 Feb 4;24(3):569.PMID:30720767DOI:10.3390/molecules24030569.
Microwave-assisted syntheses of novel ring d-condensed 2-pyrazolines in the estrone series were efficiently carried out from steroidal ,-enones and hydrazine derivatives. The ring-closure reaction of 16-benzylidene Estrone 3-methyl ether with hydrazine in acetic acid resulted in a 2:1 diastereomeric mixture of two 16,17-cis fused pyrazolines, which is contrary to the former literature data for both stereoselectivity and product structure. However, the cyclization reactions of a mestranol-derived unsaturated ketone with different arylhydrazines in acidic ethanol furnished the heterocyclic products in good to excellent yields independently of the substituents present on the aromatic ring of the reagents applied. The MW conditions also permitted the ring-closure reaction with p-nitrophenylhydrazine which is unfavorable under conventional heating. Moreover, the transformations led to the heterocyclic compounds stereoselectively with a 16,17-cis ring junction without being susceptible to spontaneous and promoted oxidation to pyrazoles.
Structure-effect relationship in the induction of mitotic phase-specific abnormality of centrosome integrity and multipolar spindles by steroidal estrogens and their derivatives in cultured mammalian cells
J Steroid Biochem Mol Biol 2001 Aug;78(2):113-22.PMID:11566435DOI:10.1016/s0960-0760(01)00084-x.
In order to determine the structure-effect relationship in the induction of centrosome disintegrity (abnormality of gamma-tubulin signals) and multipolar spindles in a cultured fibroblast cell line V79 by steroidal estrogens, the activities of various estrogens and their derivatives were investigated. Induction of centrosome disintegrity by estrogens was specific in cells in the mitotic phase and was not observed in interphase cells. The centrosome disintegrity induced 24 h after exposure to estrogens was accompanied by the appearance of multinucleated cells, but the microtubule network was organized. The rank order of potency of estrogens in inducing mitotic phase-specific centrosome disintegrity and multipolar spindles was as follows: 2-methoxyestradiol>dihydroequilin 3-methyl ether=equilin 3-methyl ether>17alpha-estradiol>17beta-estradiol 3-methyl ether=17beta-estradiol>dihydroequilin>Estrone 3-methyl ether. Equilin and estrone were not effective in causing centrosome disintegrity. These results suggest that the 17-hydroxyl group, irrespective of whether it is the sterically alpha or beta form, is necessary for estradiol and dihydroequilin to cause centrosome disintegrity and that O-methylation at the C-3 position was effective for equilin and dihydroequilin in enhancing the centrosome abnormality. 2-Methoxyestradiol was the most potent inducer of the centrosome disintegrity among the tested compounds and caused the induction of multiple signals of gamma-tubulin, including more than five signals.