Estra-1,3,5(10)-trien-17-one, 3-hydroxy-
Estrone
CAS: 53-16-7
Molecular Formula: C18H22O2
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Names and Identifiers
| Name | Estrone |
| Synonyms | Estrol OESTRON Estrone Oestrin Oestrone folliculin beta-Estrone Estrone (200 mg) ketohydroxyestrin Estropipate (Estrone) Estrone, Plant Base, USP 1,3,5(10)-estratrien-3-ol-17-one ESTRA-1,3,5(10)-TRIEN-3-OL-17-ONE 3-Hydroxy-1,3,5(10)-estratrien-17-one 3-hydroxyestra-1,3,5(10)-trien-17-one Estra-1,3,5(10)-trien-17-one, 3-hydroxy- 3beta-Hydroxyestra-1,3,5(10)-trien-17-one 1,3,5(10)-Estratrien-3-ol-17-one, 3-Hydroxy-1,3,5(10)-estratrien-17-one, Folliculin 3-Hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one Estrone,1,3,5(10)-Estratrien-3-ol-17-one, 3-Hydroxy-1,3,5(10)-estratrien-17-one, Folliculin (8R,13S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one |
| CAS | 53-16-7 |
| EINECS | 200-164-5 |
| InChI | InChI=1/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14?,15-,16?,18+/m1/s1 |
| InChIKey | DNXHEGUUPJUMQT-CBZIJGRNSA-N |
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Physico-chemical Properties
| Molecular Formula | C18H22O2 |
| Molar Mass | 270.37 |
| Density | 1.2360 |
| Melting Point | 258-260°C(lit.) |
| Boling Point | 353.48°C (rough estimate) |
| Specific Rotation(α) | 158 º (c=1, dioxane) |
| Flash Point | 9℃ |
| Water Solubility | 0.03 g/L |
| Solubility | Soluble in ethanol, propanol, ether, chloroform, dioxane, vegetable oil and sodium hydroxide solution, almost insoluble in water. No smell. |
| Vapor Presure | 1.54E-08mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White to almost white |
| Merck | 3708 |
| BRN | 1915077 |
| pKa | pKa 10.77±0.02(H2O)(Approximate) |
| Storage Condition | room temp |
| Refractive Index | 165 ° (C=1, Dioxane) |
| MDL | MFCD00003620 |
| Physical and Chemical Properties | Melting point 258-261°C specific optical rotation 158 ° (c = 1, dioxane) water-soluble 0.03g/L |
| Use | Is an intermediate in the synthesis of medicinal ethinyl estradiol |
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Risk and Safety
| Risk Codes | R45 - May cause cancer R60 - May impair fertility R61 - May cause harm to the unborn child R64 - May cause harm to breast-fed babies R40 - Limited evidence of a carcinogenic effect R63 - Possible risk of harm to the unborn child R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. |
| UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 3 |
| RTECS | KG8575000 |
| HS Code | 29335995 |
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Reference
| Reference Show more | 1. Zhou Xueyan, Chen Renguo, Wei Qunli, Zhang Bei, Li Zhiyong, Yin Jiale, Yin Xiaoming. Determination of estrone and estradiol in human serum by liquid chromatography-tandem mass spectrometry [J]. Journal of Clinical Laboratory, 2015,33(05):328-332. 2. Sha haolei, Zhang Zhiyan, Xia Jingfen, et al. Detection and risk assessment of typical environmental estrogens in Dongqian Lake, Ningbo [J]. Sichuan environment, 2015, 34(06):10-14. 3. Liu, Mengue, et al. "A high throughput screening method for endocreine disruption chemicals in tap water and milk samples based on estrogen receptor alpha and gold nanoparticles." Analytical Methods 12.2 (2020): 200-204.DOI https://doi.org/10.1039/C9AY02179E 4. [IF = 6.057] Xuemei Wang et al."Enhanced in-out-tube solid-phase microextraction by molecularly imprinted polymers-coated capillary followed by HPLC for Endocrine Disrupting Chemicals analysis."Talanta. 2019 Mar;194:7 5. [IF=7.086] Xiaoqi Li et al."Screening of estrogenic endocrine-disrupting chemicals in meat products based on the detection of vitellogenin by enzyme-linked immunosorbent assay."Chemosphere. 2021 Jan;263:128251 |
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Nature
Open Data Verified Data
This product is white to milky white crystalline powder, odorless, tasteless, melting point 280 ℃ (decomposition), than the rotation of 158.~165. (Dioxane). Almost insoluble in water, soluble in ethanol, chloroform, boiling ethanol, acetone, oxane, vegetable oil, slightly soluble in anhydrous ethanol, ether, alkali. Estrone is a kind of estrogen secreted by mature ovarian follicles (mainly the theca cells) and the corpus luteum. Its effect is the same as that of estradiol, which can promote and regulate the development of female sexual organs, and promote the appearance of female sexual characteristics. Estrone has one-tenth the estrogenic activity of estradiol, but is three times stronger than estriol. Oral is more easily inactivated, so the oral dose is about five times more than the injected dose.
Last Update：2024-01-02 23:10:35
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Use
Open Data Verified Data
- mainly used for uterine hypoplasia, menstrual disorders, menopausal disorders.
- the usage and dose of intramuscular injection of 0. 2~1 mg/time; Oral daily 1~12mg, divided into doses. It can be used as an intermediate for the synthesis of ethinyl estradiol.
Last Update：2022-01-01 11:14:17
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Safety
Open Data Verified Data
- may cause Nausea, Vomit, dizziness, etc. Prolonged use can cause excessive endometrial hyperplasia bleeding occurs.
- closed storage in the dark.
Last Update：2022-01-01 11:14:17
Estra-1,3,5(10)-trien-17-one, 3-hydroxy- - Reference Information
| update date: | 2022/11/12 10:05:38 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| description | estrone, also known as female ketone, white crystalline powder, soluble in ethanol, insoluble in water. It is isolated from the urine of a pregnant woman or from the ovary of a livestock. It is a primitive hormone secreted by the ovaries of female animals. It has been used clinically and is an important pharmaceutical intermediate that can be used to synthesize derivatives of ethinylestradiol or estradiol. Estrone (or translated as estrone, estrogen ketone) is a weaker female steroid sex hormone, one of the three main endogenous estrogens, and the other two are estradiol and Estriol. The biosynthesis of estrogens such as estrone starts with cholesterol, most of which is secreted by the gonads, and a small part is the conversion of adipose tissue to androgens from the adrenal glands. Compared with estradiol, the activity of estrone and estriol is very small. Estrone can be converted to estradiol and is the main precursor of estradiol metabolism. |
| use | estrone is a key intermediate for the synthesis of estrogens and 19-demethylsteroid compounds. Block estriol and its ethers, estradiol and its esters or estriol and its derivatives synthesized from estrone are the main drugs for oral contraceptives or menopausal hormone supplement therapy in women, respectively. Biochemical research, female hormone drugs. It is an intermediate for the synthesis of pharmaceutical ethinylestradiol It is mainly used for uterine hypoplasia, menstrual disorders and menopausal disorders. It is an intermediate for the synthesis of ethinylestradiol drugs. Can cause nausea, vomiting, dizziness, etc. Long-term use can cause excessive hyperplasia of endometrium and hemorrhage. This product is an intermediate of the hormonal drug ethinylestradiol for contraceptives No. 1. |
| synthesis | domestic use of geoo compounds as starting materials, through 11 steps of reaction synthesis 3. Foreign natural sterols are used to remove the 17-position edge chain by microbial action to obtain androstene-1, 4-ethylene-3, 17-dione (ADD,1), and synthesize 3 from 1, and then further form a series of estrogen drugs. This synthetic route has development prospects in technology. |
| Production method | It is obtained by oxidation of 4-estrene-19-alkol-3, 17-dione by fermentation. Using dehydroepiandrosterone acetate as raw material, after addition, epoxidation, ring opening, and A ring dehydrogenation, a finished product of estradione is prepared. Dehydroepiestrone acetate [hypochlorous acid] → 5 α-chloroandrostane -3 β, 6 β-diol -17-one -3-acetate [HgO, I2]→ C- 19, C- 6 oxygen ring compound [NaOH]→ 5 α-chloro -6 β, 19-epoxy -17-one -3 alcohol [Zn powder] → [chromic acid oxidation, elimination] 19-hydroxyandrost-4-ene-3, 17-dione [microorganism] → oestrone finished product. estradione is brominated by hydrogen bromide to obtain dibromo compound, which is refluxed in 2,4, 6-trimethylpyridine solution to obtain crude product, and then recrystallized and refined by methanol or acetone. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:54:55
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