1,3,5(10)-Estratriene-3,16alpha,17beta-triol

Base Information

• Chemical Name: 1,3,5(10)-Estratriene-3,16alpha,17beta-triol
• CAS No.: 50-27-1
• Molecular Formula: C18H24O3
• Molecular Weight: 288.387
• Hs Code.: 29072990
• Mol file: 50-27-1.mol

Synonyms:3,16.alpha.,17.beta.-Estriol;Estra-1,3,5(10)-triene-3,16,17-triol, (16.alpha.,17.beta.)-;3,16-.alpha.,17-.beta.-Oestriol;1,3,5(10)-Estratrien-3,16.alpha.,17.beta.-triol;1,3,5(10)-Estratriene-3,16.alpha.,17.beta.-triol;Estra-1,3,5(10)-trien-3,16.alpha.,17.beta.-triol;Estra-1,3,5(10)-triene-3,16.alpha.,17.beta.-triol;1,3,5-Estratriene-3.beta.,16-.alpha.,17-.beta.-triol;1,3,5-Oestratriene-3-.beta.,16.alpha.,17.beta.-triol;3,16.alpha.,17.beta.-Trihydroxy-1,3,5(10)-estratriene;3,16.alpha.,17.beta.-Trihydroxyestra-1,3,5(10)-triene;Estra-1,3,5(10)-triene-3,16-.alpha., l7-.beta.-triol;Oestra-1,3,5(10)-triene-3,16.alpha., 17.beta.-triol;3,16-.alpha.,17-.beta.-Trihydroxyoestra-1,3,5(10)-triene;3,16.alpha.,17.beta.-Trihydroxy-.delta.-1,3,5-estratriene;3,16.alpha.,17.beta.-Trihydroxy-.delta.-1,3,5-oestratriene;(16.alpha.,17.beta.)-Estra-1,3,5(10)-triene-3,16,17-triol;(16.alpha.,17.beta.)-Oestra-1,3,5(10)-triene-3,16,17-triol;SCHEMBL13970720;PROQIPRRNZUXQM-SBZGPEHISA-N

Chemical Property of 1,3,5(10)-Estratriene-3,16alpha,17beta-triol

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.34E-09mmHg at 25°C
• Melting Point: 280-282 °C(lit.)
• Refractive Index: 58 ° (C=0.4, Dioxane)
• Boiling Point: 469 °C at 760 mmHg
• PKA: pKa 10.38±0.02(H2O t=23±2 Iunspeci?ed) (Uncertain)
• Flash Point: 220.8 °C
• PSA: 60.69000
• Density: 1.255 g/cm³
• LogP: 2.58000
• Storage Temp.: -20°C Freezer
• Solubility.: Practically insoluble in water, sparingly soluble in ethanol (96 per cent).
• Water Solubility.: 3.2mg/L(25 oC)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 288.17254462
• Heavy Atom Count: 21
• Complexity: 411

Purity/Quality:

98% ^*data from raw suppliers

Estriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 60-61-40-45-39/23/24/25-23/24/25-11
• Safety Statements: 53-22-36/37/39-45-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
• Isomeric SMILES: CC12CCC3C(C1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O
• 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.
• Drug Interactions: It can be used in combination with estradiol with competitive antagonism.
• 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. 17b-estradiol metabolite, primary estrogen in urine A metabolite of Estradiol. An estrogenic metabolite considerably less potent than the hormone Estradiol A metabolite of Estradiol (E888000). An estrogenic metabolite considerably less potent than the hormone Estradiol (E888000).
• 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. 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.

Technology Process of 1,3,5(10)-Estratriene-3,16alpha,17beta-triol

There total 40 articles about 1,3,5(10)-Estratriene-3,16alpha,17beta-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2,4-dibromo-3,16α-dihydroxyestra-1,3,5(19)-trien-17-one (79258-14-3) → Estriol (50-27-1,300853-07-0)

Guidance literature:

With sodium tetrahydroborate; palladium dichloride; In methanol; at 0 ℃; for 2h;

Reference yield: 94.0%

16α-hydroxyestrone (566-76-7) → Estriol (50-27-1,300853-07-0)

Guidance literature:

With methanol; sodium tris(acetoxy)borohydride; In 1,4-dioxane; at 20 - 25 ℃;

Reference yield: 90.0%

estra-1,3,5(10)-triene-3,16α,17β-triol 3-methoxyethyl ether (123715-88-8) → Estriol (50-27-1,300853-07-0)

Guidance literature:

With sec.-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide; at -78 ℃;

upstream raw materials:

Estrone

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

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

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

Downstream raw materials:

Oestriol-3-benzoat

2-methoxyestriol

Estrone

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

Refernces

• 1、 Lim, Young-Ran,Hong, Myoung-Ki,Kim, Jin-Kwang,Doan, Thanh Thi Ngoc,Kim, Dong-Hyun,Yun, Chul-Ho,Chun, Young-Jin,Kang, Lin-Woo,Kim, Donghak. "Crystal structure of cytochrome P450 CYP105N1 from Streptomyces coelicolor, an oxidase in the coelibactin siderophore biosynthetic pathway". . p. 111 - 117. Retrieved 2013/02/23.
• 2、 Yamazaki, Hiroshi,Shaw, Peter M.,Guengerich, F. Peter,Shimada, Tsutomu. "Roles of cytochromes P450 1A2 and 3A4 in the oxidation of estradiol and estrone in human liver microsomes". . p. 659 - 665. Retrieved 2007/10/03.