Estradiol Benzoate

Cayman Chemical Item Number 10006487

17β-Oestradiol Benzoate; β-Estradiol Benzoate; 17β-Estradiol 3-Benzoate; E2 Benzoate (CAS 50-50-0)

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Description

Estrogens direct the development of the female genotype in embryogenesis and at puberty. Estradiol is the major estrogen secreted by the premenopausal ovary.1,2 Estradiol benzoate is an estradiol analog which contains a benzyl ester at the C-3 position. It is often used in combination with a progestin to induce estrus in domestic livestock.3 Estradiol benzoate binds to the human and murine estrogen receptor α (ERα), and chicken ER with IC50 values in the range of 22-28 nM.4 This reflects a 6-10 fold reduction in binding affinity compared to estradiol.4

1. Miller, W.L., and Tyrrell, J.B. The adrenal cortex. 3rd edition 555-711 (1995).

2. Vance, D.E. Cholesterol and related derivatives. 2nd ed. 725-748 (1988).

3. Cavalieri, J., Hepworth, G., and Macmillan, K.L. Ovarian follicular development in Holstein cows following synchronisation of oestrus with oestradiol benxoate and an intravaginal progesterone releasing insert for 5-9 days and duration of the oestrous cycle and concentrations of progesterone following ovulation. Anim Reprod Sci 81 177-193 (2004).

4. Matthews, J., Celius, T., Halgren, R., et al. Differential estrogen receptor binding of estrogenic substances: A species comparison. J Steroid Biochem Mol Biol 74 223-234 (2000).

Synonyms
  • 17β-Oestradiol Benzoate
  • β-Estradiol Benzoate
  • 17β-Estradiol 3-Benzoate
  • E2 Benzoate
Formal Name estra-​1,​3,​5(10)-​triene-​3,​17β-​diol 3-​benzoate
CAS Number 50-50-0
Molecular Formula C25H28O3
Formula Weight 376.5
Formulation A crystalline solid
Purity ≥98%
λmax 202, 230 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(Oc1ccc2c(CC[C@@H]​3[C@@H]​2CC[C@]​2(C)​[C@@H]​(O)​CC[C@@H]​32)​c1)​c1ccccc1
InCHI Code
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​1S/C25H28O3/c1-25-14-13-20-19-10-8-18(28-24(27)​16-5-3-2-4-6-16)​15-17(19)​7-9-21(20)​22(25)​11-12-23(25)​26/h2-6,8,10,15,20-23,26H,7,9,11-14H2,1H3/t20-,21-,22+,23+,25+/m1/s1
InCHI Key
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UYIFTLBWAOGQBI-BZDYCCQFSA-N

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Size Price Quantity Subtotal
500 mg $25.00 $0.00
1 g $45.00 $0.00
5 g $138.00 $0.00
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