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:

17β-oestradiol diacetate

17-β-estradiol 17-acetate

2-iodo-17β-oestradiol

2-bromo-17β-oestradiol

Refernces

Estradiol-16alpha-carboxylic acid esters as locally active estrogens.

10.1021/jm000523h

The research aimed to design and synthesize estradiol analogues, specifically 16R-carboxylic acid esters, to function as locally active estrogens with minimal systemic effects, thereby addressing issues related to hormone replacement therapy (HRT) in menopausal women. The study involved synthesizing a series of 16R-carboxylic acid substituted steroids and their esters, including methyl, ethyl, propyl, and butyl esters, and testing their estrogenic activity through various assays such as estrogen receptor (ER) binding and alkaline phosphatase induction in Ishikawa cells. The findings revealed that while the parent carboxylic acids lacked estrogenic activity, many of the esters exhibited significant potency, particularly the methyl, ethyl, and fluoroethyl esters, which showed a divergence between systemic and local estrogenic actions. The research concluded that these metabolically labile estrogens could be beneficial for treating vaginal dyspareunia in women for whom systemic estrogens are contraindicated, highlighting the potential of using steroidal carboxylic acid esters as effective local estrogen therapies.

Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation

10.1016/j.bmc.2008.05.051

The research investigates the isolation, chemical modification, and estrogenic activity evaluation of diarylheptanoids from the rhizomes of Curcuma comosa. The study identified three new diarylheptanoids, a mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one (15), along with other known diarylheptanoids. The absolute stereochemistry of the isolated compounds was determined using the modified Mosher’s method. The compounds were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. The study found that some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. The research highlights the potential health benefits of these compounds, particularly for postmenopausal women. Key chemicals involved in the research include the isolated diarylheptanoids, their chemically modified analogues, and the reagents used for chemical modification and analysis, such as methyl iodide, acetic anhydride, palladium on carbon, and various solvents like pyridine, ethanol, and benzene.