M6383

2-Methoxyestradiol

powder

• Synonym(s): 3,17β-Dihydroxy-2-methoxy-1,3,5(10)-estratriene, 2,3,17β-Trihydroxy-1,3,5(10)-estratriene 2-methyl ether, 1,3,5(10)-Estratriene-2,3,17-triol 2-methyl ether, 2-Hydroxyestradiol 2-methyl ether
• Empirical Formula (Hill Notation): C₁₉H₂₆O₃
• CAS Number: 362-07-2
• Molecular Weight: 302.41
• MDL number: MFCD00010489
• PubChem Substance ID: 24278561

Properties

• Quality Level: 200
• sterility: non-sterile
• 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 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.

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

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 Information

• Pictograms: GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301 + H311 + H331 - H315 - H319 - H335 - H350 - H360 - H372 - H410
• Precautionary Statements: P273 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338
• Target Organs: Respiratory system
• Personal Protective Equipment: dust mask type N95 (US),Eyeshields,Gloves
• RIDADR: UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
• WGK Germany: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable