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M6383

Sigma-Aldrich

2-Methoxyestradiol

powder

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Synonym(s):
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
Empirical Formula (Hill Notation):
C19H26O3
CAS Number:
Molecular Weight:
302.41
MDL number:
PubChem Substance ID:

sterility

non-sterile

Quality Level

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

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This Item
E8750SMB01382K1001
2-Methoxyestradiol powder

M6383

2-Methoxyestradiol

α-Estradiol powder, ≥98% (TLC)

E8750

α-Estradiol

2-Methoxyestrone ≥95% (HPLC), from synthetic, solid

SMB01382

2-Methoxyestrone

β-Estradiol-6-one

K1001

β-Estradiol-6-one

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

room temp

storage temp.

room temp

storage temp.

2-8°C

storage temp.

room temp

solubility

DMSO: 10 mg/mL, H2O: insoluble, ethanol: 10 mg/mL

solubility

ethanol: 50 mg/mL, clear, colorless

solubility

-

solubility

chloroform: methanol (1:1): 19.60-20.40 mg/mL, clear, colorless to faintly yellow

shipped in

ambient

shipped in

ambient

shipped in

-

shipped in

ambient

color

white to faint yellow

color

white to slight yellow

color

-

color

-

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

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.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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N Klauber et al.
Cancer research, 57(1), 81-86 (1997-01-01)
2-Methoxyestradiol (2-ME), an endogenous estrogen metabolite which disrupts microtubule function, has been shown to inhibit proliferating cells in vitro and suppress certain murine tumors in vivo. In vitro screening has determined that breast cancer cell lines are most sensitive to
R K Dubey et al.
Hypertension (Dallas, Tex. : 1979), 31(1 Pt 2), 522-528 (1998-02-07)
Postmenopausal women (PMW) have increased incidence of cardiovascular disease, and estrogen substitution therapy has been shown to have cardioprotective effects. Since abnormal growth of cardiac fibroblasts (CFs) is associated with hypertension and myocardial infarction and estrogen inhibits vascular smooth muscle
The effect of steroid hormones on ovarian follicle development
Vitamins and Hormones, 107, 155-175 (2018)
Hypoxia Induces autophagic cell death through hypoxia-inducible factor 1alpha in microglia
Yang Z, et al.
Testing, 9(5), e96509-e96509 (2014)
2-Methoxyestradiol reverses the pro-carcinogenic effect of L-lactate in osteosarcoma 143B cells
Gorska-PM, et al.
Cancer, Genomics, and Proteomics, 14(6), 483-493 (2017)

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