Estriol

Modify Date: 2024-01-02 12:13:14

Estriol Structure
Estriol structure
 Common Name Estriol
CAS Number 50-27-1 Molecular Weight 288.381
Density 1.3±0.1 g/cm3 Boiling Point 469.0±45.0 °C at 760 mmHg
Molecular Formula C18H24O3 Melting Point 280-282 °C(lit.)
MSDS Chinese USA Flash Point 220.8±23.3 °C
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Estriol


Estriol is an antagonist of the G-protein coupled estrogen receptor in estrogen receptor-negative breast cancer cells.Target: Estrogen Receptor/ERRA recent study shows that estrogen (estrone, estradiol, and estriol) inhibits Alzheimer's disease-associated low-order Aβ oligomer formation, and among them, estriol shows the strongest in vitro activity [1]. In mPTEN+/- mice, estriol treatments resulted in a 187.54% gain in the relative ratio of uterine wet weight to body weight; estriol also increases the ratio to 176.88% in wild-type mice [2]. Estriol treatment (20 mg/kg ip), in vivo, sensitizes Kupffer cells to LPS via mechanisms dependent on an increase in CD14 by elevated portal blood endotoxin caused by increased gut permeability in rats; while one-half of the rats given estriol intraperitoneally 24 hours before an injection of a sublethal dose of LPS (5 mg/kg) died within 24 hours [3].

 Names

Name estriol
Synonym More Synonyms

 Estriol Biological Activity

Description Estriol is an antagonist of the G-protein coupled estrogen receptor in estrogen receptor-negative breast cancer cells.Target: Estrogen Receptor/ERRA recent study shows that estrogen (estrone, estradiol, and estriol) inhibits Alzheimer's disease-associated low-order Aβ oligomer formation, and among them, estriol shows the strongest in vitro activity [1]. In mPTEN+/- mice, estriol treatments resulted in a 187.54% gain in the relative ratio of uterine wet weight to body weight; estriol also increases the ratio to 176.88% in wild-type mice [2]. Estriol treatment (20 mg/kg ip), in vivo, sensitizes Kupffer cells to LPS via mechanisms dependent on an increase in CD14 by elevated portal blood endotoxin caused by increased gut permeability in rats; while one-half of the rats given estriol intraperitoneally 24 hours before an injection of a sublethal dose of LPS (5 mg/kg) died within 24 hours [3].
Related Catalog
Target

Human Endogenous Metabolite

References

[1]. Morinaga, A., et al., Effects of sex hormones on Alzheimer's disease-associated beta-amyloid oligomer formation in vitro. Exp Neurol, 2011. 228(2): p. 298-302.

[2]. Begum, M., et al., Neonatal estrogenic exposure suppresses PTEN-related endometrial carcinogenesis in recombinant mice. Lab Invest, 2006. 86(3): p. 286-96.

[3]. Hewitt, S.C. and K.S. Korach, Estrogenic activity of bisphenol A and 2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane (HPTE) demonstrated in mouse uterine gene profiles. Environ Health Perspect, 2011. 119(1): p. 63-70.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 469.0±45.0 °C at 760 mmHg
Melting Point 280-282 °C(lit.)
Molecular Formula C18H24O3
Molecular Weight 288.381
Flash Point 220.8±23.3 °C
Exact Mass 288.172546
PSA 60.69000
LogP 2.94
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.624
Storage condition -20°C Freezer

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KG8225000
CHEMICAL NAME :
Estriol
CAS REGISTRY NUMBER :
50-27-1
BEILSTEIN REFERENCE NO. :
2508172
LAST UPDATED :
199612
DATA ITEMS CITED :
31
MOLECULAR FORMULA :
C18-H24-O3
MOLECULAR WEIGHT :
288.42
WISWESSER LINE NOTATION :
L E5 B666TTT&J E1 FQ GQ OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
26 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - uterine tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
480 mg/kg/64W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
34 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
17500 ug/kg
SEX/DURATION :
female 35 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3 mg/kg
SEX/DURATION :
female 1-4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
577 ug/kg
SEX/DURATION :
female 16-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8440 ng/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5 mg/kg
SEX/DURATION :
female 5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
250 ug/kg
SEX/DURATION :
female 4-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
50 ug/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
350 ug/kg
SEX/DURATION :
female 7 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
500 ug/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
400 ug/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
85 ug/kg
SEX/DURATION :
female 7 day(s) pre-mating female 1-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
105 ug/kg
SEX/DURATION :
female 1-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intrauterine
DOSE :
1500 ng/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
100 mg/kg
SEX/DURATION :
male 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
60 ug/kg
SEX/DURATION :
female 1-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
25 ug/kg
SEX/DURATION :
female 1-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intrauterine
DOSE :
760 ng/kg
SEX/DURATION :
female 28 day(s) pre-mating female 1-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
3200 ug/kg
SEX/DURATION :
female 2-5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

MUTATION DATA

TYPE OF TEST :
Sex chromosome loss and nondisjunction
TEST SYSTEM :
Rodent - hamster Fibroblast
DOSE/DURATION :
75 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 171,31,1986 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 21,327,1979 TOXICOLOGY REVIEW CANCAR Cancer (Philadelphia). (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1948- Volume(issue)/page/year: 40,1825,1977 TOXICOLOGY REVIEW CLECAP Clinical Endocrinology (Oxford). (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1972- Volume(issue)/page/year: 4,551,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80409 No. of Facilities: 68 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 2770 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80409 No. of Facilities: 316 (estimated) No. of Industries: 3 No. of Occupations: 7 No. of Employees: 3694 (estimated) No. of Female Employees: 2675 (estimated)

 Safety Information

Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H351-H360
Precautionary Statements P201-P281-P308 + P313
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R60
Safety Phrases S53-S22-S36/37/39-S45-S36/37
RIDADR 2811.0
WGK Germany 3
RTECS KG8225000
Hazard Class 6.1

 Synthetic Route

 Articles131

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 Synonyms

16α-Estriol
OVESTIN
TRIOVEX
(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triol
16a-Hydroxyestradiol
Tridestrin
Oestriol
Thulol
Ovo-Vinces
Colpogyn
Orestin
MFCD00003691
oekolp
Estra-1,3,5(10)-triene-3,16,17-triol, (16α,17β)-
Theelol
E 3
Estriol
16α,17β-Estriol
OE3
(16α,17β)-Oestra-1,3,5(10)-triene-3,16,17-triol
16α-Hydroxyestradiol
Aacifemine
Holin
Ortho-Gynest
16a-Estriol
Estriol (JP15/USP)
Estratriol
Estra-1,3,5(10)-triene-3,16α,17β-triol
Gynasan
Klimax E
trans-Estriol
Estra-1,3,5(10)-triene-3,16a,17b-triol
(16α,17β)-Estra-1,3,5(10)-triene-3,16,17-triol
3,16α,17β-Trihydroxyestra-1,3,5(10)-triene
3,16a,17b-Trihydroxyestra-1,3,5(10)-triene
Estriol [USAN:JAN]
16a,17b-Estriol
EINECS 200-022-2
3,16a,17b-Trihydroxy-D1,3,5-estratriene
Hormomed
Ovesterin
1,3,5-Estratriene-3b,16a,17b-triol
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