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50-27-1

Basic Information
CAS No.: 50-27-1
Name: Estriol
Article Data: 44
Cas Database
Molecular Structure:
Molecular Structure of 50-27-1 (Estriol)
Formula: C18H24O3
Molecular Weight: 288.387
Synonyms: 1,3,5-Oestratriene-3beta,16alpha,17beta-triol;NSC-12169;1,3,5(10)-Estratriene-3,16-alpha,17beta-triol;(16.alpha.,17.beta.)-Oestra-1,3,5(10)-triene-3,16,17-triol;16.alpha.-Hydroxyestradiol;16.alpha.,17.beta.-Estriol;1,3,5-Estratriene-3beta,16alpha,17beta-triol;1,3, 5(10)-Estratriene-3,16.alpha., 17.beta.-triol;Estra-1,3,5(10)-triene-3,16,17-triol,(16R,17a)-;Estra-1,3,5(10)-trien-3, 16.alpha., 17.beta.-triol;16-alpha-Hydroxyoestradiol;16.alpha.-Estriol;16alpha-Hydroxy-17beta-estradiol;Triovex;Ovestrion;Oestra-1,3,5(10)-triene-3,16alpha,17beta-triol;3, 16.alpha.,17.beta.-Estriol;Synapause;Klimoral;Folicular hormone;16-alpha-Hydroxyestradiol;3,16.alpha., 17.beta.-Trihydroxy-1,3,5(10)-estratriene;Hemostyptanon;Estra-1,3,5(10)-triene-3,16,17-triol, (16alpha,17beta)-;Estra-1,3,5(10)-trien-3,16alpha,17beta-triol;Estriolo [Italian];Tridestrin;Estra-1,3,5(10)-trien-3,16.alpha., 17.beta.-triol;3,16-alpha,17-beta-Oestriol;3,16-alpha,17-beta-Estriol;Oestra-1,3,5(10)-triene-3,16.alpha., 17.beta.-triol;Aacifemine;16.alpha.,17.beta.-Oestriol;Deuslon-A;Oestratriol;3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene;3,16.alpha., 17.beta.-Trihydroxy-.delta.-1,3,5-oestratriene;16.alpha.-Hydroxyoestradiol;3,16alpha,17beta-Trihydroxy-delta-1,3,5-oestratriene;A 13610;Oestriolum;Trihydroxyoestrin;Holin V;Thulol;Triodurin;Orestin;Estra-1,3,5(10)-triene-3,16.alpha.,17.beta.-triol;Oestriol [Steroidal oestrogens];Overstin;Orgastyptin;Ovestin;Estriel;(16alpha,17beta)-estra-1,3,5(10)-triene-3,16,17-triol;Theelol;Stiptanon;(16alpha,17beta)-Oestra-1,3,5(10)-triene-3,16,17-triol;
EINECS: 200-022-2
Density: 1.255 g/cm3
Melting Point: 280-282 °C(lit.)
Boiling Point: 469 °C at 760 mmHg
Flash Point: 220.8 °C
Solubility: 3.2mg/L(25 oC)
Appearance: White crystalline powder
Hazard Symbols: ToxicT
Risk Codes: 60-61-40-45
Safety: 53-22-36/37/39-45-36/37
Transport Information: N/A
PSA: 60.69000
LogP: 2.58000
Synthetic route
79258-14-3

2,4-dibromo-3,16α-dihydroxy-1,3,5(10)-estratrien-17-one

50-27-1

Estriol

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium dichloride In methanol at 0℃; for 2h;96%
With sodium borodeuteride; palladium dichloride In deuteromethanol at 0℃; for 1h;92%
Multi-step reaction with 4 steps
1: 85 percent / Ag2CO3 / benzene / 72 h / Ambient temperature
2: 95 percent / NaBH4, PdCl2 / methanol / 2 h / 0 °C
3: 65 percent / aq. 2M NaOH / methanol / Ambient temperature
4: 24 h / 38 °C / beef-liver β-glucuronidase, 0.1M acetate buffer (pH 4.6)
View Scheme
566-76-7

16α-hydroxyestrone

50-27-1

Estriol

Conditions
ConditionsYield
With methanol; sodium tris(acetoxy)borohydride In 1,4-dioxane at 20 - 25℃;94%
123715-88-8

estra-1,3,5(10)-triene-3,16α,17β-triol 3-methoxyethyl ether

50-27-1

Estriol

Conditions
ConditionsYield
With sec.-butyllithium In tetrahydrofuran; N,N-dimethyl-formamide at -78℃;90%
53-16-7

Estrone

A

50-28-2

estradiol

B

50-27-1

Estriol

Conditions
ConditionsYield
Isolierung aus dem Harn von Maennern nach Injektion von (+)-O-Acetyl-oestron;
1474-53-9

3-methoxy-estra-1,3,5(10)-triene-16α,17β-diol

50-27-1

Estriol

Conditions
ConditionsYield
With hydrogen bromide; acetic acid
1247-71-8

3,16α-diacetoxy-1,3,5(10)-estratrien-17-one

50-27-1

Estriol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether; benzene
1247-71-8

3,16α-diacetoxy-1,3,5(10)-estratrien-17-one

A

50-27-1

Estriol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
69744-63-4

3,17β-diacetoxy-16α,17α-epoxy-estra-1,3,5(10)-triene

50-27-1

Estriol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether; benzene
472-57-1

3-Hydroxyestra-1,3,5(10)-triene 16β,17β-Oxide

A

50-27-1

Estriol

B

793-89-5

16,17-Epiestriol

Conditions
ConditionsYield
With acetic acid Erwaermen des Reaktionsprodukts mit aethanol. KOH;
50-28-2

estradiol

A

53-16-7

Estrone

B

50-27-1

Estriol

C

2487-49-2

3,7α-dihydroxy-estra-1,3,5(10)-trien-17-one

D

1476-78-4

6α-hydroxyestrone

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; D-glucose; oxygen; sodium chloride; calcium chloride; magnesium chloride at 37℃; for 0.166667h; Kinetics; Product distribution; Mechanism; <6,7-3H>-labeled, metabolism in uterine tissue from 6 months old prepubertal pigs;
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    Name:Estriol The alias:E 3;ESTRIOL;ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL; CAS NO:50-27-1 EINECS NO:200-022-2 Molecular formula:C18H24O3 Molecular weight:288.38 Product Quality 12 years of chemical raw materials Mature operation of the indu

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Consensus Reports

IARC Cancer Review: Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 327.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 327.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 , 1974,p. 117.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .

Specification

1. Introduction of Estriol
Estriol Estriol is one of the three major naturally occurring estrogens. Its IUPAC Name is (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. Estriol is only produced in significant amounts during pregnancy as it is made by the placenta from 16-hydroxydehydroepiandrosterone sulfate (16-OH DHEAS), an androgen steroid made in the fetal liver and adrenal glands

2. Properties of Estriol
Index of Refraction: 1.624 
Molar Refractivity: 81.09 cm3 
Molar Volume: 229.6 cm3 
Surface Tension:  53.8 dyne/cm 
Density: 1.255 g/cm3 
Flash Point: 220.8 °C 
Enthalpy of Vaporization: 77.05 kJ/mol 
Boiling Point: 469 °C at 760 mmHg 
Vapour Pressure: 1.34E-09 mmHg at 25°C 
XLogP3-AA: 2.5
H-Bond Donor: 3
H-Bond Acceptor: 3
Structure Descriptors of Estriol (CAS NO.50-27-1):

3. Structure Descriptors of Estriol
Canonical SMILES: CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
Isomeric 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

4. Toxicity of Estriol

1.    

cyt-ham:ovr 50 µmol/L

    TOLED5    Toxicology Letters. 29 (1985),201.
2.    

imp-gpg TDLo:20 mg/kg:ETA,TER

    RBBIAL    Revista Brasileira de Biologia. 5 (1945),1.
5. Safety Information of Estriol
Suspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Other experimental reproductive effects. Mutation data reported. A steroid drug for the treatment of menopause. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes : T (Toxic)Toxic
Risk Statements : 
R60-61-40-45 (May impair fertility;May cause harm to the unborn child;Limited evidence of a carcinogenic effect;May cause cancer)
Safety Statements : 
S53-22-36/37/39-45-36/37 (Avoid exposure - obtain special instruction before use;Do not breathe dust;Wear suitable protective clothing, gloves and eye/face protection;In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);Wear suitable protective clothing and gloves)
WGK Germany : 3

6. Preparation of Estriol
Estriol is only produced in significant amounts during pregnancy as it is made by the fetal liver from 16-OHDHEAS, an androgen steroid made in the fetal adrenal glands.

7. Use of Estriol
According to researchers at UCLA's Geffen Medical School,In pregnant women with multiple sclerosis (MS), estriol reduces the disease's symptoms noticeably. Estriol can be measured in maternal blood or urine,then it can be used as a marker of fetal health and wellbeing. Estriol also can be used in the treatment of prostate disease,it also have certain curative effect for leukopenia and prostate hypertrophy.