(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 ID: 663
• Molecular Formular: C18H24O2
• Molecular Mass: 272.38196
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: 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
• Brand Name: 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
• Synonyms: 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; 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

Database IDs

• CAS Number: 50-28-2; 35380-71-3
• EC Number: 200-023-8
• MDL Number: MFCD00003693
• Beilstein Number: 1914275
• PubChem SID: 24894380; 24894389; 160964126; 24894462; 24894483; 24870281; 24278426; 46508115
• PubChem CID: 5757
• CHEBI ID: 16469
• ATC CODE: G03CA03
• CHEMBL: 135
• Chemspider ID: 5554
• DrugBank ID: DB00783
• IUPHAR ligand ID: 1012
• KEGG ID: D00105
• Unique Ingredient Identifier: 4TI98Z838E
• Wikipedia Title: Estradiol

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.327061
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.7454948
• LogD (pH = 7.4): 3.7449908
• Log P: 3.7455013
• Molar Refractivity: 79.9047 cm^3
• Polarizability: 31.30958 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.57
• LOG S: -4.11
• Solubility (Water): 2.13e-02 g/l

PROPERTIES

Physical Property

• Solubility: 3.6 mg/L; Acetone; Dioxane; DMSO; Ethanol
• Apperance: powder; White Solid
• Melting Point: 173-179°C; 176-180 °C; 176-180 °C(lit.)
• Optical Rotation: [α]20/D +79±2°, c = 1% in dioxane; [α]20/D +80.4°, c = 1 in dioxane
• Hydrophobicity(logP): 3.784; 4.2

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: KG2975000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45; 60-63-40-64
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350; H351-H360Fd-H362
• GHS Precautionary statements: P201-P263-P281-P308 + P313; P201-P308 + P313
• Personal Protective Equipment: 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
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral, transdermal
• Bioavailability: 97–99% is bound
• Excretion: Urine, and sweat glands
• Half Life: ~13-17 hours
• Metabolism: Liver
• Legal Status: S4 (Au), POM (UK), ?-only (U.S.)
• Pregnancy Category: X (USA)
• Gene Information: 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)
• Mechanism of Action: 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.

Product Information

• Purity: ≥97.0% (HPLC); ≥98%; 95%; 97%
• Grade: analytical standard; purum; USP; VETRANAL™, analytical standard
• Salt Data: Free Base
• Potency: 0.2-10 ng/mL
• Packaging: vial of 250 mg
• Suitability: meets USP testing specifications; suitable for cell culture
• Biological Source: Isol. from ovaries and pregnancy urine. Sex pheromone for mallard ducks
• Sterility: γ-irradiated
• Application(s): 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

DETAILS

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
The major estrogen secreted by the premenopausal ovary. Estrogens direct the development of the female phenotype in embryogenesis and during puberty by regulating gene transcription and, thus, protein synthesis. It also induces the production of gonadotropins which, in turn, induce ovulation. Exposure to estradiol increases breast cancer incidence and proliferation.

Sigma Aldrich - 31734

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 75262

Biochem/physiol Actions
The major estrogen secreted by the premenopausal ovary. Estrogens direct the development of the female phenotype in embryogenesis and during puberty by regulating gene transcription and, thus, protein synthesis. It also induces the production of gonadotropins which, in turn, induce ovulation. Exposure to estradiol increases breast cancer incidence and proliferation.

Toronto Research Chemicals - E888000

Estradiol is the major estrogen secreted by the premenopausal ovary.

REFERENCES

• 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