ESTETROL
ESTETROL Basic information
- Product Name:
- ESTETROL
- Synonyms:
-
- 1,3,5(10)-ESTRATRIEN-3,15-ALPHA, 16-ALPHA, 17-BETA-TETROL
- 15-ALPHA-HYDROXYESTRIOL
- E 4
- ESTETROL
- (15a,16a,17)-Estra-1,3,5(10)-triene-3,15,16,17-tetrol
- 15a-Hydroxyestriol
- 3,15a,16a,17-Tetrahydroxyestra-1,3,5(10)-triene
- Estra-1,3,5(10)-triene-3,15a,16a,17-tetrol
- CAS:
- 15183-37-6
- MF:
- C18H24O4
- MW:
- 304.38
- Product Categories:
-
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Steroids
- Mol File:
- 15183-37-6.mol
ESTETROL Chemical Properties
- Melting point:
- 233-236°C
- Boiling point:
- 491.9±45.0 °C(Predicted)
- Density
- 1.343±0.06 g/cm3(Predicted)
- storage temp.
- -20°C Freezer
- solubility
- DMSO: soluble20mg/mL, clear
- pka
- 10.22±0.70(Predicted)
- form
- powder
- color
- white to beige
- optical activity
- [α]/D +125 to +135, c = 1 in ethanol
- InChI
- InChI=1/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/s3
- InChIKey
- AJIPIJNNOJSSQC-VRHMYLLRNA-N
- SMILES
- [C@@]12([H])CCC3C=C(O)C=CC=3[C@@]1([H])CC[C@]1(C)[C@H]([C@H](O)[C@H](O)[C@@]21[H])O |&1:0,11,15,17,18,20,22,r|
ESTETROL Usage And Synthesis
Chemical Properties
Off-White Solid
Uses
Estetrol is an estrogen steroid hormone exclusively produced by fetal liver from estradiol and estriol during pregnancy. It binds to estrogen receptors (ERs) with 4-fold higher affinity for ERα over ERβ and exhibits estrogenic effects in most tissues expressing ERs (bone, brain, vagina, and endometrium). In breast tumors, however, estetrol acts as an estrogen antagonist in the presence of estradiol, preventing tumor growth.
Uses
A metabolite of Estradiol. It is an estrogenic steroid synthesized exclusively by the fetal liver during human pregnancy and reaching the maternal circulation through the placenta.
Definition
ChEBI: Estetrol is a 3-hydroxy steroid that is 17beta-estradiol which has been substituted at the 15alpha and 16alpha positions by two additional hydroxy groups. It is a natural estrogen produced exclusively during pregnancy by the fetal liver. It has a role as an estrogen, an estrogen receptor agonist, a human metabolite, a human xenobiotic metabolite and an oral contraceptive. It is a 3-hydroxy steroid, a 17beta-hydroxy steroid, a 16alpha-hydroxy steroid, a 15alpha-hydroxy steroid and a steroid hormone. It derives from a hydride of an estrane.
in vivo
Estetrol (0.6 and 6 mg/kg/day, mixed in diet, 12 weeks) induces an atheroprotective effect in mice, with an ERα‐dependent manner[3].
Estetrol (0.03-3.0 mg/kg, p.o., twice daily for four consecutive days) inhibits ovulation in rats[5].
| Animal Model: | Four‐week‐old ovariectomized ERα+/+LDL‐r?/? or ERα?/?LDL‐r?/? mice were switched to atherogenic diet from the age of 6-18 weeks[1] |
| Dosage: | 0.6 or 6 mg/kg/day |
| Administration: | mixed in atherogenic diet, 12 weeks |
| Result: | Decreased total plasma cholesterol at 6 mg/kg/day in ERα+/+LDLr?/? but not in ERα?/?LDLr?/? mice. Prevented lipid deposition in ovariectomized ERα+/+LDLr?/? mice. |
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