113680-55-0

Basic information

• Product Name: 3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL
• Synonyms: 3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL;(17)-3,17-Bis(methoxymethoxy)estra-1,3,5(10)-triene;3,172-O-Bis(methoxymethyl)estradiol
• CAS NO: 113680-55-0
• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.48708
• Product Categories: Steroids
• Mol File: 113680-55-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 463.574°C at 760 mmHg
• Flash Point: 117.61°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.544
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL(113680-55-0)
• EPA Substance Registry System: 3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL(113680-55-0)

Safety Data

• Hazardous Substances Data: 113680-55-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

An analog of 2-Methoxyestradiol as antitumor agents.

InChI:InChI=1/C22H32O4/c1-22-11-10-18-17-7-5-16(25-13-23-2)12-15(17)4-6-19(18)20(22)8-9-21(22)26-14-24-3/h5,7,12,18-21H,4,6,8-11,13-14H2,1-3H3/t18-,19-,20+,21+,22+/m1/s1

Upstream product

• 791-69-5 9⁽¹¹⁾-Dehydroestradiol 
• 107-30-2 chloromethyl methyl ether 
• 50-28-2 estradiol 

Downstream Products

• 159143-74-5 3,17β-bis(benzyloxy)estra-1,3,5(10)-triene-2-carbaldehyde 
• 159143-75-6 3,17β-bis(benzyloxy)-2-hydroxyestra-1,3,5(10)-triene 
• 1382488-48-3 3,17β-O,O-bis(benzyloxy)estradiol-2-yl formate 
• 1382488-49-4 2-triisopropylsilyloxy-3,17β-O,O-bis(benzyloxy)estradiol 
• 401600-86-0 2-methoxyestradiol 3,17-O,O-bis-sulfamate 
• 22145-26-2 (17β)-2-benzyloxy-1,3,5(10)-estratriene-3,17-diol 
• 1356544-09-6 2-hydroxyestradiol-3,17β-O,O-bis(N-trityl)sulfamate 
• 1356544-08-5 2-O-benzyloxyestradiol-3,17β-O,O-bis(N-trutyl)sulfamate 
• 1356544-11-0 2-O-benzyloxyestradiol-3,17β-O,O-bissulfamate 
• 15833-07-5 2-bromoestradiol 
• 161762-38-5 [3-((8R,9S,13S,14S,17S)-3,17-Bis-methoxymethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl)-propyl]-carbamic acid benzyl ester 
• 161762-39-6 [2-((8R,9S,13S,14S,17S)-3,17-Bis-methoxymethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl)-ethyl]-carbamic acid benzyl ester 
• 24381-12-2 2-Iodoestradiol 
• 791595-66-9 3-benzyloxy-2-methoxy-17α-trifluoromethyl-1,3,5(10)-estratriene-17β-trimethylsilane 

Relevant articles and documents

Synthesis of 2-[11C]methoxy-3,17β-estradiol to measure the pharmacokinetics of an antitumor drug candidate, 2-methoxy-3,17β-estradiol

2-Methoxy-3,17β-estradiol, an endogenous estrogen metabolite, showed cytotoxicity in various cancer cell lines and also has antiangiogenic and proapoptotic activities. Clinical I and II trials of 2-methoxy-3,17β- estradiol for multiple myeloma, advanced solid tumors, metastatic breast and prostate cancer are underway. We prepared 2-[11C]methoxy-3,17β- estradiol to measure the pharmacokinetics and organ distribution of 2-methoxy-3,17β-estradiol in clinical trials. 2-[11C]Methoxy-3, 17β-estradiol was synthesized from a precursor, 2-hydroxy-3,17β-O- bis(methoxymethyl)estradiol, in two steps with over 99% radiochemical purity. The overall reaction time was 45 min and the decay-corrected radiochemical yield was 32.9%. The distribution coefficient (logP7.4) of 2-[ 11C]methoxy-3,17β-estradiol at pH 7.4 was measured as 2.95. Copyright

A short, economical synthesis of 2-methoxyestradiol, an anticancer agent in clinical trials

(Chemical Equation Presented) 2-Methoxyestradiol, a natural metabolite of estradiol and potential therapeutic agent for many types of cancers, has been synthesized successfully in three steps, starting from estradiol and cumyl methyl peroxide.

Design, synthesis and biological evaluation of novel 2-methoxyestradiol analogs as dual selective estrogen receptor modulators (SERMs) and antiangiogenic agents

2-methoxyestradiol is a novel agent showing both anti-angiogenic and vascular disrupting properties. In this study, a series of 11α-substituted 2-methoxyestradiol analogs have been designed and synthesized targeting dual ERα and microtubulin. Biological e

STEROIDAL COMPOUND AND MEDICINE COMPRISING THE SAME

PROBLEM TO BE SOLVED: To provide a new steroidal compound useful as a medicine for diagnosis and a medicine comprising the same. SOLUTION: The present invention provides a steroidal compound represented by formula (1) (where R1 is a hydroxy gro

Synthesis of 2-[11C]methoxy-3,17β-O,O-bis(sulfamoyl) estradiol as a new potential PET agent for imaging of steroid sulfatase (STS) in cancers

Steroid sulfatase (STS) catalyzes the hydrolysis of steroid sulfates to estrones, the main source of estrogens in tumors. Carbonic anhydrase II (CAII) is highly expressed in red blood cells through a coordination of the monoanionic form of the sulfamate moiety to the zinc atom in the enzyme active site, and CAII is highly expressed in several tumors. 2-Methoxy-3,17β-O,O- bis(sulfamoyl)estradiol (5) is a dual-function STS-CAII inhibitor inhibited STS with 39 nM IC50 value selectively over CAII with 379 nM IC 50 value. This compound exhibited potent antiproferative activity with mean graph midpoint value of 87 nM in the NCI 60-cell-line panel, and antiangiogenic in vitro and in vivo activity in an early-stage Lewis lung model as well. The compound has been recently developed as a multitargeted anticancer agent. Both STS and CAII are over-expressed in cancers and have become attractive targets for cancer treatment and molecular imaging of cancer. Here we report the first design and synthesis of 2-[11C]methoxy-3,17β- O,O-bis(sulfamoyl)estradiol ([11C]5) as a new potential imaging agent for biomedical imaging technique positron emission tomography (PET) to image STS in cancers. The authentic standard 5 was synthesized from 17β-estradiol by published procedures in 5 steps with 40% overall chemical yield. The precursor 2-hydroxy-3,17β-O,O-bis(sulfamoyl)estradiol (14a) for radiolabeling was synthesized from 17β-estradiol in 10 steps with 5% overall chemical yield. The target tracer [11C]5 was prepared from the precursor 14a with [11C]CH3OTf through O-[ 11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) purification in 40-50% radiochemical yields based on [ 11C]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB.