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Structure Database (LMSD)

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Common Name

Estradiol valerate

Systematic Name

17-pentanoyl-estra-1,3,5(10)-triene-3,17β-diol

Synonyms

LM ID

LMST02010039

Formula

C₂₃H₃₂O₃

Exact Mass

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356.235146

Sum Composition

ST 23:4;O3

Status

Curated

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Classification

Biological Context

β-Estradiol 17-valerate is a synthetic estrogen.^1,2,3 It increases estrogen receptor β (ERβ), but not ERα, levels in the hippocampus and cortex of ovariectomized rats when administered at a dose of 0.3 mg/day.¹ Intradermal administration of β-estradiol 17-valerate (5 µg/animal) induces transient permanent diestrus and decreases litter size in rats.² β-Estradiol 17-valerate has been used to induce polycystic ovarian syndrome in rats.³ It has been found in wastewater effluent.⁴ Formulations containing β-estradiol 17-valerate have been used in hormone replacement therapy and in the treatment of menopausal symptoms, as well as in oral contraceptives in combination with dienogest.

This information has been provided by Cayman Chemical

References

1. Jin, M., Jin, F., Zhang, L., et al. Two estrogen replacement therapies differentially regulate expression of estrogen receptors alpha and beta in the hippocampus and cortex of ovariectomized rat. Brain Res. Mol. Brain Res. 142(2), 107-114 (2005).

2. Seidman, D.S., Itsekson, A., Alesker, M., et al. Estradiol valerate as a possible endocrine reproductive disruptor: Evidence from an in vivo rat model. Fertil. Steril. 91(4 Suppl), 1510-1512 (2009).

3. Dikmen, A., Ergenolglu, A.M., Yeniel, A.O., et al. Evaluation of glycemic and oxidative/antioxidative status in the estradiol valerate-induced PCOS model of rats. Eur. J. Obstet. Gynecol. Reprod. Biol. 160(1), 55-59 (2012).

4. Zhou, Y., Zha, J., Xu, Y., et al. Occurrences of six steroid estrogens from different effluents in Beijing, China. Environ. Monit. Assess. 184(3), 1719-1729 (2012).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Esters of unsaturated polyhydroxy estrane

String Representations

InChiKey (Click to copy)

RSEPBGGWRJCQGY-RBRWEJTLSA-N

InChi (Click to copy)

InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1

SMILES (Click to copy)

[C@]12(CC[C@H](OC(=O)CCCC)[C@@]1(C)CC[C@@]1(C3C=CC(O)=CC=3CC[C@@]21[H])[H])[H]