Natural hormone Pharmacokinetics Indications Side effects Determination of estriol content Purpose and Function Precautions Drug Interactions Storage Chemical Properties Uses Production method
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Estriol

Natural hormone Pharmacokinetics Indications Side effects Determination of estriol content Purpose and Function Precautions Drug Interactions Storage Chemical Properties Uses Production method
Product Name
Estriol
CAS No.
50-27-1
Chemical Name
Estriol
Synonyms
E 3;OVESTIN;16α-Estriol;ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL;(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol;1,3,5(10)-Estratriene-3,16α,17β-triol, 16α-Hydroxyestradiol, 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene;Estriol,1,3,5(10)-Estratriene-3,16α,17β-triol, 16α-Hydroxyestradiol, 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene;(8R,9S,13S,14S,16R,17R)-13-Methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol;OE3;Holin
CBNumber
CB1687589
Molecular Formula
C18H24O3
Formula Weight
288.38
MOL File
50-27-1.mol
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Estriol Property

Melting point:
280-282 °C(lit.)
alpha 
D25 +58° ±5° (0.04 g in 1 ml dioxane)
Boiling point:
370.61°C (rough estimate)
Density 
1.27
refractive index 
58 ° (C=0.4, Dioxane)
Flash point:
9℃
storage temp. 
2-8°C
solubility 
Practically insoluble in water, sparingly soluble in ethanol (96 per cent).
pka
pKa 10.38±0.02(H2O t=23±2 Iunspeci?ed) (Uncertain)
form 
Solid
color 
White to Off-White
optical activity
+6127 (95% ethanol)
Water Solubility 
3.2mg/L(25 ºC)
Merck 
3707
BRN 
2508172
InChIKey
PROQIPRRNZUXQM-ZXXIGWHRSA-N
CAS DataBase Reference
50-27-1(CAS DataBase Reference)
NIST Chemistry Reference
Estriol(50-27-1)
EPA Substance Registry System
Estriol (50-27-1)
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Safety

Hazard Codes 
T,F
Risk Statements 
60-61-40-45-39/23/24/25-23/24/25-11
Safety Statements 
53-22-36/37/39-45-36/37-16
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
3
RTECS 
KG8225000
8-10
HS Code 
29072990
Hazardous Substances Data
50-27-1(Hazardous Substances Data)
Toxicity
LD50 oral in rat: > 2gm/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H351Suspected of causing cancer

H362May cause harm to breast-fed children

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2800
Product name
Estriol
Purity
certified reference material, pharmaceutical secondary standard
Packaging
200MG
Price
$243
Updated
2024/03/01
Sigma-Aldrich
Product number
E-074
Product name
Estriol solution
Purity
1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
BP752
Product name
Estriol
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$257
Updated
2024/03/01
Sigma-Aldrich
Product number
1254508
Product name
Estriol
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
100mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
46565
Product name
Estriol
Purity
VETRANAL
Packaging
100mg
Price
$95.4
Updated
2022/05/15
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Estriol Chemical Properties,Usage,Production

Natural hormone

Estriol belongs to natural hormone and is the metabolite of estradiol in vivo. It is mainly presented in the urine. Estrogen has a relative small activity with the oral activity being 6 times as high as estrone but being weaker than estradiol with non-carcinogenic effects. After its administration, the in vivo estradiol levels did not change. Estriol has selective action on the vaginal and cervical canal but has no effect on the uterus and endometrium entity. Animal experiments have shown that estriol has a stronger effect on vaginal epithelial keratosis than estradiol, thus being able to promote vaginal epithelial hyperplasia, superficial cells keratosis, mucosal angiogenesis and vaginal epithelial wound healing, but having a weak effect on the weight gain of mouse uterus. At the same time, estriol can enhance the function of cervix cell, causing the cervix muscle fiber hyperplasia and increasing the cervical elasticity and softness. In addition, estriol has feedback inhibition on the hypothalamus and pituitary but does not inhibit ovulation while only having significant impact on the corpus luteum and therefore can be used as the auxiliary drug in the medium-term labor induction and artificial abortion and for the treatment of various kinds of menopathy. Estriol also has significant effect on the hematopoietic system and can reduce vascular permeability and fragility. Therefore, it can be used for the treatment of various kinds of hemorrhage. It also has effect of rapidly increasing the peripheral leukocytes and generally begins to take effect at 1 to 3 days after treatment but with a shorter duration of action and is effective in treatment the leukopenia induced by radiotherapy and chemotherapy.

Figure 1 is the formula of estriol

Pharmacokinetics

It can be absorbed from the gastrointestinal tract and skin but is susceptible to damage upon oral administration and is therefore mainly subject to intramuscular injection and topical usage. It is metabolized in the body to less-active estrone and estriol and can be inactivated when being combined with glucuronic acid and sulfuric acid and further excreted in urine.

Indications

It can be used for treating cervicitis, especially suitable for treating menopausal syndrome and senile vaginitis. It can also be used as the adjuvant drug for middle-term labor induction and artificial abortion. It can also be used for treating prostatic hypertrophy and prostate cancer. In addition, it still has a rapid role in increasing the peripheral leukocytes. It generally takes effect at 1 to 3 days after the treatment but with a short duration period. It also has efficacy in treating leukopenia caused by chemotherapy or radiotherapy as well as reducing the vascular permeability and fragility and can be used for the treatment of various kinds of hemorrhage. It also has quick hemostasis effect on menorrhagia, hysterectomy or tonsillectomy.

Side effects

There are temporary breast swelling or lumps, menstrual disorders which can self-limiting and recovery after discontinuing the drug. In oral administration, it has been occasionally observed of loss of appetite, nausea, vomiting, abdominal pain and so on.

Determination of estriol content

Estriol is produced through the hydroxylation of carbon 16 in dehydroepiandrosterone at fetal adrenal; it further enters into the placenta and the metabolism by the placental syncytiotrophoblast cells. It is then released into the maternal blood with the free estriol absorbed by the maternal liver and further combined into glucuronic acid or sulfuric acid estriol that are further excreted by the kidneys. Therefore, the estriol in the urine is all in the form of conjugated estriol while the estriol in the blood contains both free type and bound type with free form accounting for about 10 to 30% and the rest being in bound form. Determination of estriol in the urine of pregnant women with a spectrophotometer has been widely used clinically. There are other common methods including radioimmunoassay. Estriol is not contained in the blood of non-pregnant women. According to the measurement of the Shanghai Second Medical Ruijin Hospital, upon 26 weeks of pregnancy, the plasma free estriol is 4~6ng/ml while upon 36 weeks, it is 10~12ng/ml and it is 19ng/ml or more in full term but with large individual differences. The total plasma estriol value, at 25 weeks of gestation, is 50ng/ml and is 200ng/ml at 40 weeks of pregnancy. At 24h, the urine estriol was 8.12 ± 0.28mg at 28 weeks of pregnancy and was 19.81 ± 8.28 mg in full term. It is generally believed that after 36 weeks of pregnancy, if the urine content at 24 h > 15mg, the value is normal; 12~10mg is alert value while <10mg is dangerous values. Since the major precursor of estriol during pregnancy comes from fetus, being different from the estrone and estradiol that is from the mother, the determination of estriol may reflect the condition of fetal development. When some fetal malformations and maternal or fetal diseases affect fetal development or cause fetal asphyxia, it is always accompanied of decrease of estriol. However, due to the great daily fluctuations of estriol level, it is generally measured for 4 to 5 times at least for some time in order to determine whether the level of estriol is really low. The estriol level in mild hypertension of pregnancy are often normal before 34 weeks while is maintained at low level after 34 weeks while the level significantly drops upon severe pregnancy-induced hypertension. For pregnant women upon exceeding the expected date, you can continuously measure the urinary estriol in 24h. If it is always higher than 25mg, you can still wait under close observation; if it is less than 10mg, the fetus is at risk and should be subject to positive treatment. Owing to lack of hypothalamus, non-brain child has pituitary hypoplasia and small adrenal gland. Since the supply of the raw material for the placental synthesis of estriol, 16-hydroxy isopropyl DHEA is in insufficient amount, the estriol in urine of pregnant women is very low with most being below the normal 10%.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Purpose and Function

1. It can be used for treating cervicitis and especially suitable for treating menopausal syndrome and senile vaginitis.
2. It can also be used as the adjuvant drug for middle-term labor induction and artificial abortion. 3. It can also be used for treating prostatic hypertrophy and prostate cancer.
4. It still has a rapid role in increasing the peripheral leukocytes. It generally takes effect at 1 to 3 days after the treatment but with a short duration period. It also has efficacy in treating leukopenia caused by chemotherapy or radiotherapy.
5. It can be used for reducing the vascular permeability and fragility and can be used for the treatment of various kinds of hemorrhage. It also has quick hemostasis effect on menorrhagia, hysterectomy or tonsillectomy.

Precautions

1. Pregnant and lactating women, patients of breast hyperplasia, breast lumps, gynecological cancer, and aplastic anemia patients should be disabled with minor patients being not suitable for using it.
2. Patients of heart (liver, kidney) disease, hypertension, diabetes, epilepsy, migraine (including medical history), endometriosis, fibrocystic breasts, porphyria, hyperlipidemia or having history of pregnancy itching and herpes should take with caution.
3. If prescribed therapy doesn’t work, it is not suitable for increasing the dose or extending the usage time.

Drug Interactions

It can be used in combination with estradiol with competitive antagonism.

Storage

It should be sealed upon shading for storage.

Chemical Properties

It is white crystalline powder with the M.p. being 283 ℃, relative density being 1.27, and the specific rotation being [α] 25D + 34.4°(pyridine) and 25D + 58°± 5°(4%, dioxane). Its ethanol solution has maximum absorption at the wavelength of 280 nm. The crystal is insoluble in water, slightly soluble in ethanol (1: 500), diethyl ether, chloroform, dioxane and vegetable oil and easily soluble in pyridine and alkali hydroxide solution.

Uses

It belongs to estrogen drug. It can be used for treating leukopenia, various kinds of menopathy, senile vaginitis, and menopausal syndrome. You may also get temporary breast swelling and lumps, menstrual cycle disorders with self-recovery after stopping the drug for about 1 month. Patients of breast hyperplasia, breast lumps, and cancer potentially being related to female hormone-related cancer, aplastic anemia and liver disease patients should be disabled.

Production method

Take estrone as raw material; go through acetylation, epoxidation, and reduction to obtain the estriol products.
Estrone [acetylation] → [16, 17-epoxidation] → [rearrangement] → [Restore] → [hydrolysis] → finished product of estriol.
Estrone acetate successively goes through followed enolization, acetylation, epoxidation and reduction to obtain it.

Description

Estriol is significantly less active than estradiol; however, it has a selective ability to stimulate blood flow and restoration of genital epithelium. In addition, using this drug reduces mental symptoms of menopausal syndrome. It is used in the premenopausal and menopausal periods, for skin atrophy and signs of genital degeneration, and so on.

Description

Estriol is a metabolite of estradiol and a major estrogen produced in the later stages of pregnancy. In a longitudinal study in healthy pregnant women, total plasma estriol levels increased from <10 ng/ml at 8-10 weeks gestation to approximately 150 ng/ml at week 38. The majority of the estriol synthesized in the later stages of pregnancy originates from fetal dehydroepiandrosterone sulfate (DHEAS) and serves as a direct marker of fetal adrenal gland activity. Saliva contains primarily unbound and unconjugated estriol and is commonly used for monitoring estriol levels. Plasma levels of estriol in males and non-pregnant females is less than 2 ng/ml.

Chemical Properties

White or almost white, crystalline powder.

Uses

17b-estradiol metabolite, primary estrogen in urine

Uses

A metabolite of Estradiol. An estrogenic metabolite considerably less potent than the hormone Estradiol

Uses

A metabolite of Estradiol (E888000). An estrogenic metabolite considerably less potent than the hormone Estradiol (E888000).

Definition

ChEBI: 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).

brand name

Theelol (Parke-Davis).

General Description

Estriol, estra-1,3,5(10)-triene-3,16 ,17 -triol, is available for compounding into several differentformulations for use in HRT. It can be used alone or in combinationswith estradiol (Bi-Est) or with estradiol and estrone(Tri-Est).

Hazard

A carcinogen (OSHA).

Safety Profile

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.

Synthesis

Estriol, estra-1,3,5(10)-trien-3,16|á,17|?-triol (28.1.25), is proposed to be synthesized from the methyl ester of estrone (28.1.8). Methyl ester of estrone is reacted with isopropenylacetate in the presence of p-toluenesulfonic acid, forming the corresponding enolacetate (28.1.23). The resulting enolacetate is oxidized to an epoxide using perbenzoic acid. The resulting epoxide (28.1.24) undergoes reduction by lithium aluminum hydride to.

Purification Methods

Crystallise estriol from EtOH/ethyl acetate. Also purify it by countercurrent distribution with cyclohexane/EtOAc (1:1) and EtOH/H2O (1:1). The UV (EtOH) has max at 280nm ( 2,090 M-1cm-1). [Huffmann & Lott 71 719 1949, Leeds et al. J Am Chem Soc 76 2943 1954, Beilstein 6 IV 7550.]

Estriol Preparation Products And Raw materials

Raw materials

Preparation Products

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Estriol Suppliers

Wuhan Senwayer Century Chemical Co.,Ltd
Tel
027-86652399 13627115097;
Fax
86-27-59707018
Email
sales@senwayer.com
Country
China
ProdList
267
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55
Jiangxi ravel Biotechnology Co.,Ltd
Tel
400-880-2824 15608648206
Email
1987516016@qq.com
Country
China
ProdList
2816
Advantage
58
Wuhan Dingxintong Pharmaceutical Co. , Ltd.
Tel
027-027-83984790 17720532645
Fax
027-83984790
Email
t17720532645@163.com
Country
China
ProdList
971
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58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
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69
future industrial shanghai co., ltd
Tel
400-0066400 13621662912
Fax
021-55660885
Email
sales@jonln.com
Country
China
ProdList
1995
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65
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
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61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
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81
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
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View Lastest Price from Estriol manufacturers

Dorne Chemical Technology co. LTD
Product
Estriol 50-27-1
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
1000kg
Release date
2024-03-26
Sinoway Industrial co., ltd.
Product
Estriol 50-27-1
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
99% up, High Density
Supply Ability
20 tons
Release date
2021-08-04
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Estriol 50-27-1
Price
US $0.00/g
Min. Order
10g
Purity
97.0-102.0%,USP39
Supply Ability
50kg/month
Release date
2021-06-19

50-27-1, EstriolRelated Search:


  • E 3
  • ESTRIOL
  • ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL
  • ESTRA-1,3,5(10)-TRIENE-3,16ALPHA,17BETA-TRIOL
  • TRIDESTRIN
  • ESTRIOL(P)
  • Estriol,1,3,5(10)-Estratriene-3,16α,17β-triol, 16α-Hydroxyestradiol, 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene
  • Estriol (100 mg)
  • 1,3,5(10)-Estratriene-3,16α,17β-triol, 16α-Hydroxyestradiol, 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene
  • Estriol, Micronized
  • 1,3,5-estratriene-3β,16α,17β-triol
  • 16a-Hydroxyestradiol
  • 3,16ALPHA,17BETA-TRIHYDROXY-1,3,5[10]-ESTRATRIENE
  • 16ALPHA-HYDROXYESTRADIOL
  • 16-ALPHA-HYDROXY 17-BETA-ESTRADIOL
  • 1,3,5-ESTRATRIENE-3,16ALPHA, 17BETA-TRIOL
  • 1,3,5[10]-ESTRATRIENE-3,16ALPHA,17BETA-TRIOL
  • 1,3,5(10)-estratriene-3,16a,17b-triol
  • 1,3,5(10)-ESTRATRIEN-3,16A,17BETA-TRIOL
  • 1,3,5(10)-ESTRATRIEN-3, 16ALPHA, 17BETA-TRIOL
  • Estriol Estratriol
  • (16a,17)-Estra-1,3,5[10]-triene-3,16,17-triol
  • Acifemine
  • 16-alpha,17-beta-oestriol
  • 16alpha,17beta-Oestriol
  • 16alpha-Estriol
  • 16-alpha-hydroxyoestradiol
  • 16alpha-Hydroxyoestradiol
  • 3,16-alpha,17-beta-estriol
  • 3,16alpha,17beta-Estriol
  • 3,16-alpha,17-beta-Oestriol
  • 3,16-alpha,17-beta-trihydroxy-delta-1,3,5-estratriene
  • 3,16alpha,17beta-Trihydroxy-delta-1,3,5-estratriene
  • 3,16-alpha,17-beta-trihydroxy-delta-1,3,5-oestratriene
  • 3,16alpha,17beta-Trihydroxy-delta-1,3,5-oestratriene
  • 3,16-alpha,17-beta-trihydroxyestra-1,3,5(10)-triene
  • Holin
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  • Klimoral
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