(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

• ChemBase编号: 663
• 分子式: C18H24O2
• 平均质量: 272.38196
• 单一同位素质量: 272.17763001
• SMILES: O[C@@H]1[C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(O)cc2)CC1)C
• Canonical SMILES: Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1
• InChIKey: VOXZDWNPVJITMN-ZBRFXRBCSA-N

名称和登记号

名称

• IUPAC标准名: (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol; (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,14-diol; (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol; (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol
• IUPAC传统名: estradiol; (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol; (-)-estradiol
• 商标名: Aerodiol; Agofollin; Alora; Altrad; Amnestrogen; Aquadiol; Bardiol; Climaderm; Climara; Combipatch; Compudose; Compudose 200; Compudose 365; Corpagen; Delestrogen; Depo-Estradiol; Dermestril; Dihydromenformon; Dihydrotheelin; Dimenformon; Dimenformon Prolongatum; Diogyn; Diogynets; Divigel; Encore; Esclim; Estinyl; Estrace; Estraderm; Estraderm Tts; Estradurin; Estrasorb; Estreva; Estrifam; Estring; Estring Vaginal Ring; Estroclim; Estroclim 50; Estrofem 2; Estrofem Forte; Estrogel; Estrogens, Esterified; Estrovite; Evorel; Extrasorb; Femestral; Femestrol; Feminone; Femogen; Fempatch; Femring; Femtrace; Femtran; Follicyclin; Ginedisc; Ginosedol; Gynergon; Gynestrel; Gynodiol; Gynoestryl; Gynpolar; Nordicol; Oestergon; Oestradiol; Oestradiol R; Oestrogel; Oestroglandol; Oestrogynal; Ovahormon; Ovasterol; Ovastevol; Ovociclina; Ovocyclin; Ovocycline; Ovocylin; Perlatanol; Primofol; Profoliol; Profoliol B; Progynon; Progynon Dh; Progynon-Dh; Ricifon; Ritsifon; Sandrena Gel; Sisare Gel; Sk-Estrogens; Soldep; Sotipox; Syndiol; Systen; Tradelia; Trial Sat; Trocosone; Vagifem; Vivelle; Zerella; Zumenon; Elestrin; Evamist; Vivelle-DOT; Innofem; Lamdiol; Lynoral; Macrodiol; Macrol; Menest; Menorest; Menostar; Microdiol; Climara, Menostar
• 别名: β-雌二醇; 雌二醇; 3,17β-二羟基-1,3,5(10)-雌三烯; β-雌二醇 半水合物; 1,3,5-雌甾三烯-3,17β-二醇; 17β-雌二醇; 3,17β-二羟基-1,3,5(10)-雌甾三烯; 雌二醇; β-雌二醇; D-Estradiol; D-Oestradiol; Estradiol-17beta; Estradiol Valerate; Estradiol Cypionate; Dihydroxyestrin; Dihydroxyoestrin; Dihydroxyesterin; Dihydrofollicular Hormone; Dihydrofolliculin; Cis-Estradiol; Cis-Oestradiol; Beta-Estradiol; estradiol; 17-beta; Estradiol; ESTRADIOL,U.S.P.; (8''R'',9''S'',13''S'',14''S'',17''S'')-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[''a'']phenanthrene-3,17-diol; Estradiol; β-Estradiol hemihydrate; 1,3,5-Estratriene-3,17β-diol; 3,17β-Dihydroxy-1,3,5(10)-estratriene; (17β)-Estra-1,3,5(10)-triene-3,17-diol; 3,17-Epidihydroxyestratriene; Cimara; Estrace; Estraderm; Estradot; Estring; Estrofem; Estrogel; Evorel; 17β-Estradiol; beta-Estradiol; (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol; β-Estradiol; 17β-estradiol; oestradiol; 17β-Oestradiol

登记号

• CAS号: 50-28-2; 35380-71-3
• EC号: 200-023-8
• MDL号: MFCD00003693
• Beilstein号: 1914275
• PubChem SID: 160964126; 24278426; 24894483; 24894380; 24870281; 24894389; 24894462; 46508115
• PubChem CID: 5757
• CHEBI ID: 16469
• ATC码: G03CA03
• CHEMBL: 135
• Chemspider ID: 5554
• DrugBank ID: DB00783
• IUPHAR配体索引: 1012
• KEGG ID: D00105
• 美国药典/FDA物质标识码: 4TI98Z838E
• 维基百科标题: Estradiol

理论计算性质

JChem

• Acid pKa: 10.327061
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 3.7454948
• LogD (pH = 7.4): 3.7449908
• Log P: 3.7455013
• 摩尔折射率: 79.9047 cm^3
• 极化性: 31.30958 Å^3
• 极化表面积: 40.46 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.57
• LOG S: -4.11
• 溶解度: 2.13e-02 g/l

分子性质

理化性质

• 溶解度: 3.6 mg/L; Acetone; Dioxane; DMSO; Ethanol
• 外观: powder; White Solid
• 熔点: 173-179°C; 176-180 °C; 176-180 °C(lit.)
• 比旋光度: [α]20/D +79±2°, c = 1% in dioxane; [α]20/D +80.4°, c = 1 in dioxane
• 疏水性(logP): 3.784; 4.2

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: KG2975000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 45; 60-63-40-64
• 安全公开号: 53-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H350; H351-H360Fd-H362
• GHS警示性声明: P201-P263-P281-P308 + P313; P201-P308 + P313
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral, transdermal
• 生物利用度: 97–99% is bound
• 排泄: Urine, and sweat glands
• 半衰期: ~13-17 hours
• 代谢: Liver
• 法定药品分级: S4 (Au), POM (UK), ?-only (U.S.)
• 妊娠期药物分类: X (USA)
• 相关基因信息: human ... ESR1(2099), ESR2(2100), ESRRA(2101), ESRRB(2103), GPER(2852), SERPINA6(866)mouse ... Esr1(13982), Esr2(13983), Esrra(26379)rat ... Afp(24177), Ar(24208), Esr1(24890), Esr2(25149), Shbg(24775); human ... ESR1(2099), ESR2(2100), ESRRB(2103), GPER(2852), SERPINA6(866)mouse ... Esr1(13982), Esr2(13983), Esrra(26379)rat ... Afp(24177), Ar(24208), Esr1(24890), Esr2(25149), Shbg(24775)
• 生物活性机理: Estradiol enters cells freely and interacts with a cytoplasmic target cell receptor.; The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell.; When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA.

产品相关信息

• 纯度: ≥97.0% (HPLC); ≥98%; 95%; 97%
• 级别: analytical standard; purum; USP; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 药效: 0.2-10 ng/mL
• 包装: vial of 250 mg
• 适用性: meets USP testing specifications; suitable for cell culture
• 生物来源: Isol. from ovaries and pregnancy urine. Sex pheromone for mallard ducks
• 无菌消毒: γ-irradiated
• 应用领域: Estradiol (and its semisynthetic esters) are used in estrogen replacement therapy; The most potent of the natural estrogens
• Empirical Formula (Hill Notation): C18H24O2; C18H24O2 · 0.5H2O

详细说明

MP Biomedicals - 05203747

MP Biomedicals Rare Chemical collection

DrugBank - DB00783

• Drug Groups: approved; investigational
• Description: Generally refers to the 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Various isomers can be synthesized. [PubChem]
• Indication: For the treatment of urogenital symptoms associated with post-menopausal atrophy of the vagina (such as dryness, burning, pruritus and dyspareunia) and/or the lower urinary tract (urinary urgency and dysuria).
• Pharmacology: Estradiol, the principal intracellular human estrogen, is substantially more active than its metabolites, estrone and estriol, at the cellular level.
• Toxicity: Can cause nausea and vomiting, and withdrawal bleeding may occur in females.
• Affected Organisms: Humans and other mammals
• Biotransformation: Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450.
• Absorption: 43%
• Half Life: 36 hours
• Protein Binding: >95%
• Elimination: Estradiol, estrone and estriol are excreted in the urine along with glucuronide and sulfate conjugates.
• References: Pentikainen V, Erkkila K, Suomalainen L, Parvinen M, Dunkel L: Estradiol acts as a germ cell survival factor in the human testis in vitro. J Clin Endocrinol Metab. 2000 May;85(5):2057-67. [Pubmed] ; Sharpe RM, Skakkebaek NE: Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet. 1993 May 29;341(8857):1392-5. [Pubmed] ; Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. [Pubmed] ; Carani C, Qin K, Simoni M, Faustini-Fustini M, Serpente S, Boyd J, Korach KS, Simpson ER: Effect of testosterone and estradiol in a man with aromatase deficiency. N Engl J Med. 1997 Jul 10;337(2):91-5. [Pubmed] ; Behl C, Widmann M, Trapp T, Holsboer F: 17-beta estradiol protects neurons from oxidative stress-induced cell death in vitro. Biochem Biophys Res Commun. 1995 Nov 13;216(2):473-82. [Pubmed] ; Schmidt JW, Wollner D, Curcio J, Riedlinger J, Kim LS: Hormone replacement therapy in menopausal women: Past problems and future possibilities. Gynecol Endocrinol. 2006 Oct;22(10):564-77. [Pubmed] ; Foresta C, Zuccarello D, Biagioli A, De Toni L, Prana E, Nicoletti V, Ambrosini G, Ferlin A: Oestrogen stimulates endothelial progenitor cells via oestrogen receptor-alpha. Clin Endocrinol (Oxf). 2007 Oct;67(4):520-5. Epub 2007 Jun 15. [Pubmed] ; Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1709

Research Area: Endocrinology
Biological Activity:
Estradiol is the predominant sex hormone present in females. It is also present in males, being produced as an active metabolic product of testosterone. It represents the major estrogen in humans. Estradiol has not only a critical impact on reproductive and sexual functioning, but also affects other organs including the bones. [1]

Sigma Aldrich - E2257

Application
β-雌二醇可用于研究细胞分化和转化（肿瘤发生）。
Reconstitution
要制备 20μg/mL 的储存液，可加入 1mL 无水乙醇，温和搅拌使之溶解，在搅拌下加入 49mL 无菌培养基。
Physical form
室温下为粉末状；分成小份冻存，以避免使用时反复冷冻/解冻
Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。

Sigma Aldrich - E125

Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。

Sigma Aldrich - E2758

Application
β-Estradiol is used to study cell differentiation and transformations (tumorigenicity).
Reconstitution
To prepare a 20 μg/ml stock solution, add 1 ml absolute ethanol to 1 mg β-estradiol; gently swirl to dissolve; add 49 ml sterile medium while mixing.
Physical form
powder-RT; stock-frozen in working aliquots, avoid repeated freeze/thaw
Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。

Sigma Aldrich - E8875

包装
1, 5, 25, 100 g in glass bottle
250 mg in glass bottle
Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E8875.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - E1024

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。

Sigma Aldrich - E1132

包装
Supplied in amber screw-cap vials
Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。

Sigma Aldrich - 250155

Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。

Sigma Aldrich - 31734

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 75262

Biochem/physiol Actions
由绝经前卵巢分泌的主要雌激素。雌激素在胚胎形成中以及在青春期，通过调控基因转录，并因此调控蛋白合成，从而指导女性表型的发展。它还可诱导促性腺激素的生成，继而诱导排卵。暴露于雌二醇将增加乳腺癌的发病率以及增加增生。

Toronto Research Chemicals - E888000

Estradiol is the major estrogen secreted by the premenopausal ovary.

参考文献

• Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. Pubmed
• Pentikainen V, Erkkila K, Suomalainen L, Parvinen M, Dunkel L: Estradiol acts as a germ cell survival factor in the human testis in vitro. J Clin Endocrinol Metab. 2000 May;85(5):2057-67. Pubmed
• Sharpe RM, Skakkebaek NE: Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet. 1993 May 29;341(8857):1392-5. Pubmed
• Carani C, Qin K, Simoni M, Faustini-Fustini M, Serpente S, Boyd J, Korach KS, Simpson ER: Effect of testosterone and estradiol in a man with aromatase deficiency. N Engl J Med. 1997 Jul 10;337(2):91-5. Pubmed
• Behl C, Widmann M, Trapp T, Holsboer F: 17-beta estradiol protects neurons from oxidative stress-induced cell death in vitro. Biochem Biophys Res Commun. 1995 Nov 13;216(2):473-82. Pubmed
• Schmidt JW, Wollner D, Curcio J, Riedlinger J, Kim LS: Hormone replacement therapy in menopausal women: Past problems and future possibilities. Gynecol Endocrinol. 2006 Oct;22(10):564-77. Pubmed
• Foresta C, Zuccarello D, Biagioli A, De Toni L, Prana E, Nicoletti V, Ambrosini G, Ferlin A: Oestrogen stimulates endothelial progenitor cells via oestrogen receptor-alpha. Clin Endocrinol (Oxf). 2007 Oct;67(4):520-5. Epub 2007 Jun 15. Pubmed
• Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. Pubmed
• http://en.wikipedia.org/wiki/Estradiol
• Salole, E.G., et al.: Anal. Profiles Drug Subs., 15, 283 (1986)
• Lievertz, R.W., et al.: Am. J. Obstet. Gynecol., 156, 1289 (1986)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1055C, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 565A; 589B; 600B, (nmr)
• Marker, R.E., J.A.C.S., 1938, 60, 2927, (synth)
• Miki, T. et al., Proc. Chem. Soc., London, 1963, 139, (synth)
• Ohrt, J.M. et al., Acta Cryst., 1964, 17, 1611, (cryst struct, derivs)
• Gibson, H. et al., Tet. Lett., 1966, 2321, (synth)
• Tsukuda, Y. et al., J.C.S.(B), 1968, 1387, (cryst struct)
• Wittstruck, T.A. et al., J.O.C., 1973, 38, 1542, (cmr)
• Ponold, K. et al., Pharmazie, 1973, 28, 371; 1977, 32, 598; 1979, 34, 2050, (STS 153)
• Busetta, B. et al., Acta Cryst. B, 1976, 32, 1290, (cryst struct)
• Eder, U. et al., Chem. Ber., 1976, 109, 2948, (synth)
• IARC Monog., 1979, 21, 279, (tox, rev)
• Quinkert, G. et al., Annalen, 1981, 2335; 1982, 1999, (synth)
• Hylarides, M.D. et al., J.O.C., 1984, 49, 2744, (synth)
• Larner, J.M. et al., Endocrinology (Baltimore), 1985, 117, 1209, (metab)
• Salole, E.G. et al., Anal. Profiles Drug Subst., 1986, 15, 283, (rev)
• Schneider, G. et al., Annalen, 1988, 679, (3-Me ether, synth, pmr, cmr, ir)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 6627, (synonyms)
• Collins, M.A. et al., Tet. Lett., 1995, 36, 4467, (synth)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1455
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BFV325; EDO000; EDP000; EDR000; EDS100; DAZ115; EDO500; EDR500