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M6383 Sigma-Aldrich

2-Methoxyestradiol

powder

Synonym: 1,3,5(10)-Estratriene-2,3,17-triol 2-methyl ether, 2,3,17β-Trihydroxy-1,3,5(10)-estratriene 2-methyl ether, 2-Hydroxyestradiol 2-methyl ether, 3,17β-Dihydroxy-2-methoxy-1,3,5(10)-estratriene

  • CAS Number 362-07-2

  • Empirical Formula (Hill Notation) C19H26O3

  • Molecular Weight 302.41

  •  MDL number MFCD00010489

  •  PubChem Substance ID 24278561

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Properties

Related Categories Angiogenesis, Angiogenesis Inhibitors, Anti-proliferative Agents, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   200
assay   ≥98% (HPLC)
  ≥98% (TLC)
form   powder
color   white to faint yellow
mp   189-190  °C
solubility   DMSO: 10 mg/mL
  ethanol: 10 mg/mL
  H2O: insoluble
shipped in   ambient
storage temp.   room temp
SMILES string   OC1=C(C=C(C2=C1)[C@]3([H])[C@](CC2)([H])[C@]4([H])CC[C@H](O)[C@](C)4CC3)OC
InChI   1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
InChI key   CQOQDQWUFQDJMK-SSTWWWIQSA-N
Gene Information   human ... ESR1(2099), ESR2(2100)

Description

General description

2-Methoxyestradiol (2-ME) is a metabolite, derived from estradiol. It is usually seen at high levels in the normal follicle.

Application

2-Methoxyestradiol has been used:
• as hypoxia-inducible factor 1-alpha (HIF-1α) inhibitor to treat microglia to test whether hypoxia leads to cell death
• to determine the anticancer potential in L-lactate-activated osteosarcoma cells
• as a reference chemical and angiogenesis inhibitor to assess the performance of in vitro angiogenesis assay

Packaging

5, 10, 50 mg in glass bottle

Biochem/physiol Actions

2-Methoxyestradiol (2-ME) is a potent inhibitor of endothelial cell proliferation and angiogenesis.It has little affinity for classical estrogen receptors.

2-Methoxyestradiol plays a key role in the apoptosis of tumor cells. It also participates in microtubule stabilization. It exhibits cardioprotective activity and acts as an anticancer agent.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M6383.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Respiratory system
RIDADR 
UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
WGK Germany 
WGK 3
RTECS 
KG7537500
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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