A natural metabolite of estradiol
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2-Hydroxyestradiol

Item No. 13019

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
estra-1,3,5(10)-triene-2,3,17β-triol
CAS Number
362-05-0
Synonyms
  • 2-HE2
  • NSC 61711
Molecular Formula
C18H24O3
Formula Weight
288.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/mlEthanol: 25 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
289 nm
SMILES
OC1=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/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
InChi Key
DILDHNKDVHLEQB-XSSYPUMDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    2-Hydroxyestradiol (2-HE2) is a cytochrome P450 metabolite of estradiol with low affinity for estrogen receptors. 2-HE is rapidly metabolized by catechol-O-methyltransferase (COMT) to form 2-methoxy estradiol (2-ME2) with a half-life of approximately ten minutes in rat.1 2-ME2 has achieved considerable attention as an anti-cancer agent acting as an angiogenesis inhibitor via the HIF-1a pathway.2,3,4 Due to the rapid metabolism of 2-HE2, the effects attributed to 2-HE2, may actually be those of 2-ME2.1

    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).