Estradiol

Base Information

• Chemical Name: Estradiol
• CAS No.: 50-28-2
• Deprecated CAS: 873662-39-6,1050677-52-5,1206475-11-7,1050677-52-5,1206475-11-7
• Molecular Formula: C18H24O2
• Molecular Weight: 272.387
• Hs Code.: 29372390
• European Community (EC) Number: 200-023-8
• NSC Number: 9895
• UNII: 4TI98Z838E
• DSSTox Substance ID: DTXSID0020573
• Nikkaji Number: J4.100I
• Wikipedia: Estradiol
• Wikidata: Q422416
• NCI Thesaurus Code: C478,C2295
• RXCUI: 4083
• Pharos Ligand ID: M3TNLZD5Z8Y9
• Metabolomics Workbench ID: 35273
• ChEMBL ID: CHEMBL135
• Mol file: 50-28-2.mol

Synonyms:17 beta Estradiol;17 beta Oestradiol;17 beta-Estradiol;17 beta-Oestradiol;Aerodiol;Delestrogen;Estrace;Estraderm TTS;Estradiol;Estradiol 17 alpha;Estradiol 17 beta;Estradiol 17beta;Estradiol Anhydrous;Estradiol Hemihydrate;Estradiol Hemihydrate, (17 alpha)-Isomer;Estradiol Monohydrate;estradiol valerate;estradiol valeriante;Estradiol, (+-)-Isomer;Estradiol, (-)-Isomer;Estradiol, (16 alpha,17 alpha)-Isomer;Estradiol, (16 alpha,17 beta)-Isomer;Estradiol, (17-alpha)-Isomer;Estradiol, (8 alpha,17 beta)-(+-)-Isomer;Estradiol, (8 alpha,17 beta)-Isomer;Estradiol, (9 beta,17 alpha)-Isomer;Estradiol, (9 beta,17 beta)-Isomer;Estradiol, Monosodium Salt;Estradiol, Sodium Salt;Estradiol-17 alpha;Estradiol-17 beta;Estradiol-17beta;Oestradiol;Ovocyclin;Progynon Depot;Progynon-Depot;Progynova;Vivelle

Chemical Property of Estradiol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 9.82E-09mmHg at 25°C
• Melting Point: 178-179 °C(lit.)
• Refractive Index: 80.4 ° (C=1, Dioxane)
• Boiling Point: 445.917 °C at 760 mmHg
• PKA: pKa 10.71±0.02(H2O(0.1% p-dioxane) t=25±0.1 I=0.03(KCl))(Approximate)
• Flash Point: 209.634 °C
• PSA: 40.46000
• Density: 1.17 g/cm³
• LogP: 3.60920
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent), slightly soluble in methylene chloride.
• Water Solubility.: Soluble in dimethyl sulfoxide, ethanol , water, phosphate buffer saline, dimethyl formamide, acetone, dioxane and alkali hydroxi
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 272.177630004
• Heavy Atom Count: 20
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

Estradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn,F
• Statements: 60-61-45-63-64-40-36-20/21/22-11-48
• Safety Statements: 53-22-36/37/39-45-36/37-26-16-36-20

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O
• Recent ClinicalTrials: Treating Postmenopausal Dyspareunia Where it Hurts
• Recent EU Clinical Trials: The effect of low-dose rhythmic 17-β-estradiol administration on bone turnover in postmenopausal women
• Recent NIPH Clinical Trials: Clinical trial of the Estrogen replacement effect on Physical Performance to muscle resistance exercise for elderly with Osteoarthritis of Knee joint.
• Natural Production and Functions: Estradiol is a hormone naturally produced in the human body by the ovaries. It plays a crucial role in regulating various physiological processes such as the menstrual cycle, cardiovascular system, neurologic system, skeletal system, and vascular system.; Estradiol is the most potent and abundant estrogen (E2) during a woman's reproductive years.
• Types of Estrogen: There are four different kinds of estrogen: estrone (E1), estradiol (E2), estriol (E3), and estetrol (E4). Estradiol (E2) is particularly important and serves as a key indicator in gonadal hormone detection.
• Clinical Uses: Estradiol is primarily used to alleviate menopausal symptoms such as hot flashes, vaginal changes, and vulvovaginal symptoms. It is also employed to prevent osteoporosis in menopausal women.
• Mechanism of Action: Estradiol is a steroidal estrogen with two types, α and β, with the α type exhibiting strong physiological effects. It is synthesized by the enzyme aromatase, which is involved in various neuroendocrine events, reproduction, neural development, synaptic plasticity, and cell survival. Aromatase is expressed in neurons and a subpopulation of astrocytes in the brain.
• Effect on Libido: Estradiol plays a role in regulating libido in males, acting at various levels of regulation, including direct effects in the brain. It influences sexual behavior by affecting areas of the brain involved in sexual arousal and mood regulation.; The effect of estradiol on libido is influenced by testosterone levels, with different outcomes observed at low and normal testosterone levels.

Technology Process of Estradiol

There total 189 articles about Estradiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

estrone acetate (901-93-9) → estradiol (50-28-2)

Guidance literature:

With diisobutylaluminium hydride; nickel dichloride; In dichloromethane; toluene; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.3184/174751911X13050949941793

Reference yield: 97.5%

3-O-methyl-17β-oestradiol (1035-77-4) → estradiol (50-28-2)

Guidance literature:

With aluminium trichloride; In ethanethiol; for 0.5h; Ambient temperature;

DOI:10.1021/jo01310a003

Reference yield: 97.0%

Estrone (53-16-7) → estradiol (50-28-2)

Guidance literature:

Estrone; With sodium tetrahydroborate; sodium hydroxide; In methanol; water; for 0.75h;

With hydrogenchloride; In methanol; water;

DOI:10.1021/ol101154h

upstream raw materials:

quinoline

1-dehydrotestosterone

1,3,5-trinitrobenzene

Estrone

Downstream raw materials:

estradiol 17-decanoate

2-(17β-hydroxy-estra-1,3,5(10)-trien-3-yloxy)-5-nitro-benzophenone

2-Iodoestradiol

Estra-1,3,5(10)-trien-3,17β-diol 3-propionate ester

Refernces

• 1、 MacCorquodale,Thayer,Doisy. "-". . p. 435,438. Retrieved 1936.
• 2、 Gibb,Lavoie. "Substrate specificity of the placental microsomal aromatase". . p. 507 - 519. Retrieved 1980.
• 3、 Byrns, Michael C.,Duan, Ling,Lee, Seon Hwa,Blair, Ian A.,Penning, Trevor M.. "Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer". . p. 177 - 187. Retrieved 2010.
• 4、 Albers,Muller. "Complexation of steroid hormones with cyclodextrin derivatives: Substituent effects of the guest molecule on solubility and stability in aqueous solution". . p. 756 - 761. Retrieved 1992.
• 5、 Oppolzer, Wolfgang,Roberts, David Anthony. "177. The Enantioselective Synthesis of (+)-Estradiol from 1,3-Dihydrobenzothiophene-2,2-dioxide by Successive Thermal SO2-Extrusion and Cycloaddition Reactions". . p. 1703 - 1705. Retrieved 1980.
• 6、 Hall, Peter F.,Chen, Shiuan,Nakajin, Shizuo,Shinoda, Masato,Shively, John E.. "Purification and characterization of aromatase from human placenta". . p. 37 - 50. Retrieved 1987.
• 7、 Bain, J. D.,Kasman, L. H.,Bercovitz, A. B.,Lasley, B. L.. "A COMPARISON OF THREE METHODS OF HYDROLYSIS FOR ESTROGEN CONJUGATES". . p. 603 - 620. Retrieved 1984.
• 8、 Kellis, James T.,Vickery, Larry E.. "6α-Fluorotestosterone: a nonaromatizable androgen inhibitor of aromatase cytochrome P450". . p. 242 - 246. Retrieved 1990.
• 9、 Llabrés i Xamena, F. X.,Mautschke, H.-H.. "One-Step Chemo-, Regio- and Stereoselective Reduction of Ketosteroids to Hydroxysteroids over Zr-Containing MOF-808 Metal-Organic Frameworks". . p. 10766 - 10775. Retrieved 2021/06/15.
• 10、 Adriano, Natalie,Ahearn, Ceilidh,Black, Cory,Cracchiolo, Michael,Ghere, Daniel,Hare, Patrick M.,Nu?ez, Alexandra,Olivan, Lars,Patel, Raj,Saner, Stephanie,Smith, Krista R.,Watkins, Barbie. "Solvent- and Wavelength-Dependent Photolysis of Estrone". . . Retrieved 2021/11/08.