28336-31-4

Basic information

• Product Name: Estratetraenol Methyl Ether
• Synonyms: Estratetraenol Methyl Ether;3-Methoxy-estra-1,3,5(10),16-tetraene
• CAS NO: 28336-31-4
• Molecular Formula: C₁₉H₂₄O
• Molecular Weight: 268.39326
• Mol File: 28336-31-4.mol

Chemical Properties

• Boiling Point: 385.7°Cat760mmHg
• Flash Point: 155.4°C
• Appearance: /
• Density: 1.054g/cm³
• Vapor Pressure: 8.29E-06mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: Estratetraenol Methyl Ether(CAS DataBase Reference)
• NIST Chemistry Reference: Estratetraenol Methyl Ether(28336-31-4)
• EPA Substance Registry System: Estratetraenol Methyl Ether(28336-31-4)

Safety Data

• Hazardous Substances Data: 28336-31-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H24O/c1-19-10-3-4-18(19)17-7-5-13-12-14(20-2)6-8-15(13)16(17)9-11-19/h3,6,8,10,12,16-18H,4-5,7,9,11H2,1-2H3/t16-,17-,18+,19+/m1/s1

Upstream product

• 28336-32-5 16α,17α-Epoxy-3-methoxyestra-1,3,5(10)-triene 
• 1091-94-7 3-methoxy-estra-1,3,5⁽¹⁰⁾-trien-17-one 
• 95667-45-1 Trifluoro-methanesulfonic acid 3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl ester 
• 50304-31-9 3-methoxy-17β-hydroxyestra-1,3,5(10)-triene-17α-carbonitrile 
• 50304-38-6 (8S,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene-17-carbonitrile 
• 1637747-50-2 3-methoxyestra-1,3,5(10)-trien-17α-iodide 
• 1035-77-4 3-O-methyl-17β-oestradiol 
• 124-63-0 methanesulfonyl chloride 
• 105663-60-3 3-Methoxy-estra-1,3,5⁽¹⁰⁾-trien-17-on-hydrazone 
• 1624-62-0 estrone 3-methyl ether 
• 53-16-7 Estrone 
• 201230-82-2 carbon monoxide 
• 105644-55-1 (8R,9S,13S,14S)-17-iodo-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene 
• 32164-54-8 Oestronmethylaether-tosylhydrazon 

Downstream Products

• 1624-73-3 3-methoxy-19-norpregna-1,3,5⁽¹⁰⁾-trien-20-one 
• 1667-98-7 3-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾-trien-20-one 
• 74111-56-1 16α-Hydroxy-oestratrien-3-methylether 
• 1229-33-0 16β-hydroxy-3-methoxyestra-1,3,5(10)-triene 

Relevant articles and documents

New estrogen receptor antagonists. 3,20-Dihydroxy-19-norpregna-1,3,5(10)-trienes: Synthesis, molecular modeling, and biological evaluation

New estrogen receptor α (ERα) antagonists – 3,20-dihydroxy-19-norpregna-1,3,5(10)-trienes containing an additional carbocyclic ring D′ at the 16α,17α positions – were synthesized. The effects of the new compounds on the MCF-7 breast cancer cells and ERα activation were investigated. All the steroids studied were synthesized starting from estrone methyl ether. The scaffold of compounds containing the six-membered ring D′ was constructed via the Diels–Alder reaction of butadiene with 3-methoxy-19-norpregna-1,3,5(10),16-tetraen-20-one 5. The hydrogenation of primary 16α,17α-cyclohexeno-adduct 7 followed by 3-demethylation (by HBr–AcOH) and reduction of 20-oxo group (by LiAlH4) or in one step by DIBAH gave target mono- and dihydroxy steroids 9–11. The Corey–Chaykovsky reaction of the same 3-methoxy-19-norpregna-1,3,5(10),16-tetraen-20-one 5 gave 16α,17α-methylene-substituted compound. The reaction of the latter with DIBAH immediately yielded 3,20-dihydroxy-16α,17α-methyleno-19-norpregna-1,3,5(10)-triene 13. The same procedures using 3-methoxy-19-norpregna-1,3,5(10),16-tetraen-20-one 5 produced corresponding 3,20-dihydroxy-16,17-19-norpregna-1,3,5(10)-triene 16 and 3,20-dihydroxy-19-norpregna-1,3,5(10),16-tetraene 17. All compounds were fully characterized by 1D and 2D NMR, HRMS, and X-ray diffraction. The molecular docking showed that the target compounds can bind to ER, their binding mode being similar to that of natural estradiol. 16α,17α-Methylene- or unsubstituted compounds exhibit the highest cytotoxicity against MCF-7 cells, being simultaneously relatively weak ERα inhibitors. 3,20-Dihydroxy steroids containing the six-membered ring D′ proved to be the most effective ERα inhibitors. These compounds displayed moderate cytotoxicity comparable of that of tamoxifen and showed no toxic effect on MCF-10A normal, nontumorigenic epithelial cells. The new ER antagonists were found to be good candidates for further testing as agents for the treatment and prevention of ERα-positive breast cancers.

Synthesis of novel 17-(5′-iodo)triazolyl-3-methoxyestrane epimers via Cu(I)-catalyzed azide-alkyne cycloadditon, and an evaluation of their cytotoxic activity in vitro Dedicated to Professor Irén Vincze on the occasion of her 85th birthday

The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of 3-methoxyestrane 17α- and 17β-azide epimers (3 and 5) with different terminal alkynes afforded novel 1,4-substituted triazolyl derivatives (8a-f and 11a-f). If the Ph3P in the clas

E-Ring extended estrone derivatives: introduction of 2-phenylcyclopentenone to the estrone D-ring via an intermolecular Pauson-Khand reaction

An expedient synthetic route to E-ring extended estrone derivatives is reported. Estrone-derived cyclopentenones were accessed by an intermolecular Pauson-Khand (PK) cycloaddition. It was found that electron donating and withdrawing substituents in the arylalkyne increased and decreased the yields of PK products, respectively. The stereochemistry of the products was elucidated by X-ray and NMR studies.

Androstane steroids as neurochemical initiators of change in human hypothalamic function and related pharmaceutical compositions and methods

The invention relates to a method of altering hypothalamic function in an individual. The method comprises nasally administering a human semiochemical, e.g. an Androstane steroid, or a pharmaceutical composition containing a semiochemical, such that the ligand semiochemical binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers. Other embodiments of the invention include pharmaceutical compositions containing the steroids.

17-Methyleneandrostan-3alpha-ol analogs as CRH inhibitors

17-Methyleneandrostan-3α-ol analogs are useful as corticotropin releasing hormone (CRH) inhibitors, and especially as anti-depressants, when administered to the vomeronasal organ. An improved synthesis of 17-methylenandrost-4-en-3α-ol is disclosed.

19-nor-cholane steroids as neurochemical initators of change in human hypothalamic function

The invention relates to a method of altering hypothalamic function in an individual. The method comprises nasally administering a human vomeropherin, e.g. a 19-nor cholane steroid, or a pharmaceutical composition containing a vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers. Other embodiments of the invention include pharmaceutical compositions containing the steroids.

Facile synthesis of 17-formyl steroids via palladium-catalyzed homogeneous carbonylation reaction.

17-formyl-androst-16-ene and its analogues were synthesized from the corresponding 17-iodo-16-ene derivatives in palladium-catalyzed formylation reaction using tributyltin hydride as hydrogen source under mild reaction conditions. The formation of androst-16-ene and its isomerization products, as well as that of analogous steroidal olefins as side-products, was found to be dependent on the reaction conditions. The formylation reaction tolerates various functional groups on the A and B rings of the steroids. Copyright 2002 Elsevier Science Inc.

Steroids as neurochemical stimulators of the VNO to alleviate pain

The invention relates to a method of alleviating pain. The method comprises nasally administering a steroid which is a human vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers.

Steroids as neurochemical stimulators of the VNO to alleviate symptoms of PMS and anxiety

The invention relates to a method of alleviating the symptoms of PMS and anxiety. The method comprises nasally administering a steroid which is a human vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers.

Steroids as neurochemical stimulators of the VNO to treat paroxistic tachycardia

The invention relates to a method of alleviating the symptoms of PMS and anxiety. The method comprises nasally administering a steroid which is a human vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers.