A natural metabolite of estradiol
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2-Methoxyestradiol

Item No. 13021

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methoxy-estra-1,3,5(10)-triene-3,17β-diol
CAS Number
362-07-2
Synonyms
  • 2-Hydroxyestradiol 2-methyl ether
  • 2-ME2
  • NSC 659853
  • Panzem
Molecular Formula
C19H26O3
Formula Weight
302.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 1 mg/ml
λmax
209, 287 nm
SMILES
COC1=C(O)C=C(CC[C@]2([H])[C@]3([H])CC[C@@]4(C)[C@@]2([H])CC[C@@H]4O)C3=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    2-methoxy Estradiol (2-ME2) is a natural metabolite formed by CYP450-mediated hydroxylation followed by catechol-O-methyltransferase (COMT) methylation of estradiol. Administration of 2-hydroxy estradiol (2-HE2) to rats results in formation and clearance of 2-ME2 with t½ values of 7.9 and 24.9 minutes, respectively.1 2-ME2 exhibits no affinity for estrogen receptors. 2-ME2 has achieved considerable attention as an anti-cancer agent acting as an angiogenesis inhibitor via the HIF-1α pathway.2,3,4 The levels of COMT and 2-ME2 are significantly lower in women with severe pre-eclampsia.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zacharia, L.C., Piché, C.A., Fielding, R.M., et al. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. J. Pharmacol. Exp. Ther. 309(3), 1093-1097 (2004).

    2. Mooberry, S.L. New insights into 2-methoxyestradiol, a promising antiangiogenic and antitumor agent. Curr. Opin. Oncol. 15(6), 425-430 (2003).

    3. Mooberry, S.L. Mechanism of action of 2-methoxyestradiol: New developments. Drug Resist. Updat. 6(6), 355-361 (2003).

    4. Becker, C.M., Rohwer, N., Funakoshi, T., et al. 2-methoxyestradiol inhibits hypoxia-inducible factor-1α and suppressess growth of lesions in a mouse model of endometriosis. Am. J. Pathol. 172(2), 534-544 (2008).

    5. Kanasaki, K., Palmsten, K., Sugimoto, H., et al. Deficiency in catechol-O-methyltransferase and 2-methoxyoestradiol is associated with pre-eclampsia. Nature 453, 1117-1123 (2008).