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M6383

Sigma-Aldrich

2-Methoxyestradiol

powder

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C19H26O3
Číslo CAS:
362-07-2
Molekulová hmotnost:
302.41
MDL number:
MFCD00010489
UNSPSC Code:
51111800
PubChem Substance ID:
24278561
NACRES:
NA.77

sterility

non-sterile

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)

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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

Osvědčení o analýze (COA)

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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)
Intra-Laboratory Pre-Validation of a Human Cell Based in vitro Angiogenesis Assay for Testing Angiogenesis Modulators
Sarkanen JR, et al.
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