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Estriol

CAT: 0804-HY-B0412-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-B0412-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Estriol (Oestriol), an orally active estrogen, is a ERα and ERβ agonist. Estriol is a potent GPR30 antagonist in estrogen receptor-negative breast cancer cells. Estriol can ameliorate disease severity through immunomodulatory mechanisms that decrease tissue inflammation. Estriol has powerful proconvulsant effects[1][2][3].
CAS Number
50-27-1
Product Name Alternative
Oestriol
UNSPSC
12352005
Hazard Statement
H351, H360, H362
Target
Endogenous Metabolite; Estrogen Receptor/ERR
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease; Vitamin D Related/Nuclear Receptor
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Estriol.html
Purity
98.47
Solubility
DMSO : 250 mg/mL (ultrasonic) |H2O : < 0.1 mg/mL (ultrasonic; warming; heat to 80°C)
Smiles
C[C@@]1([C@H]2O)[C@](C[C@H]2O)([H])[C@@](CCC3=C4C=CC(O)=C3)([H])[C@]4([H])CC1
Molecular Formula
C18H24O3
Molecular Weight
288.39
Precautions
H351, H360, H362
References & Citations
[1]Rosamaria Lappano, et al. Estriol acts as a GPR30 antagonist in estrogen receptor-negative breast cancer cells. Mol Cell Endocrinol. 2010 May 14;320 (1-2) :162-70.|[2]Rainer Girgert, et al. Inhibition of GPR30 by estriol prevents growth stimulation of triple-negative breast cancer cells by 17β-estradiol. BMC Cancer. 2014 Dec 11:14:935. |[3]Aakifa Ahmad, et al. Proconvulsant effects of estriol, the third estrogen, in the mouse PTZ-kindling model. Neurol Sci. 2014 Oct;35 (10) :1561-6.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
Launched
Isoform
Human Endogenous Metabolite

Chemical Information

Estriol

Estriol is a 3-hydroxy steroid that is estra-1,3,5(10)-trien-3-ol substituted by additional hydroxy groups at positions 16 and 17 (16alpha,17beta-stereoisomer). It has a role as an estrogen, a mouse metabolite, a human xenobiotic metabolite and a human metabolite. It is a 16alpha-hydroxy steroid, a 17beta-hydroxy steroid and a 3-hydroxy steroid. It derives from a hydride of an estrane.

CAS Number50-27-1
PubChem CID5756
IUPAC Name(8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
Molecular FormulaC18H24O3
Molecular Weight288.4
XLogP2.5
Topological Polar Surface Area60.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count21
Formal Charge0
Complexity411
SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
InChI
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
InChIKey
PROQIPRRNZUXQM-ZXXIGWHRSA-N
Chemical Structure
2D Structure
2D structure of Estriol
CAS: 50-27-1
CID: 5756
Formula: C18H24O3
MW: 288.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight288.4
XLogP32.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass288.17254462
Monoisotopic Mass288.17254462
Topological Polar Surface Area60.7 Ų
Heavy Atom Count21
Formal Charge0
Complexity411
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

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367429Estriol 3 (Estriol-3, Estriol) discontinued
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E02390-01Estriol

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