ESTETROL

Product NameESTETROL
CAS15183-37-6
MFC18H24O4
MW304.38
EINECS
MOL File15183-37-6.mol

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\|

Usage And Synthesis

Chemical Properties

Off-White Solid

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.

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.

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.

ESTETROL

Chemical Properties

Usage And Synthesis

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