(10R,13S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Base Information

• Chemical Name: (10R,13S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS No.: 57-83-0
• Molecular Formula: C21H30O2
• Molecular Weight: 314.468
• Hs Code.: 29372390
• NSC Number: 759615
• Mol file: 57-83-0.mol

Synonyms:(10R,13S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;Spectrum_000864;Spectrum2_001299;Spectrum3_000558;Spectrum4_000490;Spectrum5_001401;BSPBio_002235;KBioGR_000979;KBioSS_001344;DivK1c_000445;SPECTRUM1500508;SPBio_001337;SCHEMBL7900795;HMS501G07;KBio1_000445;KBio2_001344;KBio2_003912;KBio2_006480;KBio3_001735;NINDS_000445;HMS1920L12;HMS2092C13;Pharmakon1600-01500508;CCG-39237;NSC759615;AKOS022902507;NSC-759615;IDI1_000445;NCGC00178747-01;SBI-0051494.P003;AB00052081_02;EN300-27144436;SR-05000001705;SR-05000001705-1;BRD-A67479912-001-02-6;(1S,9aR,11aS)-1-acetyl-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

Chemical Property of (10R,13S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Chemical Property:

• Appearance/Colour: Crystalline powder
• Vapor Pressure: 5.44E-10mmHg at 25°C
• Melting Point: 128-132 °C(lit.)
• Refractive Index: 182 ° (C=2, Dioxane)
• Boiling Point: 447.2 °C at 760 mmHg
• Flash Point: 166.7 °C
• PSA: 34.14000
• Density: 1.08 g/cm³
• LogP: 4.72350
• Storage Temp.: Store at RT
• Solubility.: H2O: 25 mg/mL, may be clear to slightly hazy
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 589

Purity/Quality:

99% ^*data from raw suppliers

Progesterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T,F
• Statements: 40-45-62-36-20/21/22-11
• Safety Statements: 36/37-45-53-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
• Isomeric SMILES: CC(=O)[C@H]1CCC2[C@@]1(CCC3C2CCC4=CC(=O)CC[C@]34C)C
• Description: Progesterone is a hormone released by luteal cells in the ovaries which contains 21 Carbon Atoms. Progesterone is also a crucial metabolic intermediate in the production of other endogenous steroids. There are two crystal forms of progesterone, that are type-α and type-β, the two types have similar physiological activity. Type-α is precipitated from dilute ethanol as orthorhombic white prismatic crystal, while type-β is orthorhombic white needle crystal, they are both insoluble in water, but soluble in ethanol, ethyl ether, chloroform, acetone, dioxane and concentrated sulfuric acid. Progesterone can be released by the ovary, placenta and adrenal cortex. Its physiological function mainly manifests in promoting estrogen treated over thicken lining of the uterus to continue the development, proliferation and thickening and hypertrophy, soften and secretion of mucus in order to make good condition for implantation of the fertilized egg. After the implantation, early stage survival and development of fertilized egg is also under the control of the high progesterone release. As a result, progesterone is a very important hormone in the female reproductive system, and it is also an important intermediate in the biosynthesis of steroid hormones. All steroid hormone releasable glands can produce progesterone, but only ovarian and placenta can release progesterone as the main hormone. Ovarian will release large amount of progesterone in the luteal phase after ovulation by granulose luteal cells, so progesterone is also named as progestin. Progesterone will decrease in result of corpus luteum atrophy. For normal women, placenta will becomes the main organ maintain progesterone after 8 to 9 weeks of pregnancy, accompany with the ovary releasing until the end of pregnancy. Progesterone, along with pregnenolone, is the biosynthetic precursor of all other steroid hormones. Progesterone is synthesized from cholesterol by the sequential action of desmolase in the mitochondria, which produces pregnenolone, followed by Δ4,5-isomerase in the outer mitochondrial membrane and smooth endoplasmic reticulum of steroid-secreting cells. Progesterone activates the human progesterone receptor with an EC50 value of 0.5 nM.
• Uses: The main physiological effects of progesterone: 1. Progesterone can maintain the female animal pregnancy, and cause a series of physiological changes, such as inhibition of female estrus. 2. Progesterone has the power to promote the thickening of the lining of the uterus, promote the bending of the gland and to increase secretion function. 3. Progesterone can inhibit the peristalsis of the uterus, and contribute to the cervix contraction, secretion of mucus, etc.. These physiological changes provide suitable environment for the operation, growth and development of early embryos, as well as the continued growth of the fetus. 4. Small amount of progesterone is also used in combination with the hormone estrogen to promote female estrus. The synergy between progesterone and prolactin can promote the development of mammary glands. 5. Progesterone is involved in the feedback regulation of the hypothalamus and anterior pituitary, which makes the balance of the animal reproductive hormones. In vivo, progesterone content of all sorts of livestock follicular phase is below 1 ng/ml, while in bovine corpus luteum period is approximately 4 ng/ml, pregnancy period is about 18 ng/ml. 6. Formerly biochemical study shows that progesterone modulates action as progestogens, clinical for the treatment of habitual abortion, dysmenorrhea, amenorrhea and other symptoms. One of progesterone's most important functions is as hormone drugs, to promote and maintain the uterine changes in the early stage of pregnancy, used in habitual abortion, irregular menstruation, etc.. In addition, progesterone also behaves as steroid hormone drug as well as progestogens, which is used in treatment of threatened abortion. Progesterone is used as a contraceptive, for amenorrhea, for premenopausal syndrome, infertility, incomplete pregnancies, and anovulatory uterine bleeding. Steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.This compound is a contaminant of emerging concern (CECs).
• Biological Functions: Progesterone is a hormone, produced primarily by the corpus luteum of the ovary but also by the placenta, that prepares the inner lining of the uterus for implantation ofa fertilized egg cell. If implantation fails, the corpus luteum degenerates and progesterone production ceases accordingly. If implantation occurs,the corpus luteum continues to secrete progesterone, under the influence of luteinizing hormone and prolactin, for several months of pregnancy,by which time the placenta has taken over this function. Duringpregnancy, progesterone maintains the constitution of the uterus and prevents further release of eggs from the ovary. Small amounts of progesterone are produced by the testes.

Technology Process of (10R,13S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

There total 270 articles about (10R,13S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one 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: 99.0%

(20S)-21-hydroxy-20-methylpregn-4-en-3-one (60966-36-1) → Progesterone (57-83-0)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; acetylacetone copper; N,N-diethylaniline; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 0 ℃; for 2h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 99.0%

16-dehydroprogesterone (1096-38-4) → Progesterone (57-83-0)

Guidance literature:

With phenylsilane; isopropyl alcohol; Mn(dpm)3; at 23 ℃;

DOI:10.1016/S0040-4039(00)01728-7

Reference yield: 97.0%

6-dehydroprogesterone (1162-56-7) → Progesterone (57-83-0)

Guidance literature:

With formic acid; In isopropyl alcohol; at 76 - 80 ℃; for 6h; Inert atmosphere;

upstream raw materials:

16-dehydroprogesterone

diazomethane

diethyl ether

17β-androstane-4-ene-3-keto-17-formaldehyde

Downstream raw materials:

deoxycorticosterone acetate

pregnenolone methyl ether

6-Methylene Progesterone

3-Ethylendioxy-pregnen-⁽⁴⁾-on-⁽²⁰⁾

Refernces

• 1、 Qujeq, Durdi. "Development of a quantitative assay method for 3 beta-hydroxy-delta 5-steroid dehydrogenase in the rat testis.". . p. 1071 - 1077. Retrieved 2002.
• 2、 Wiebe, J. P.. "IDENTIFICATION OF A UNIQUE SERTOLI CELL STEROID AS 3α-HYDROXY-4-PREGNEN-20-ONE (3α-DIHYDROPROGESTERONE: 3α-DHP)". . p. 259 - 278. Retrieved 1982.
• 3、 Spielman,Meyer. "-". . p. 893. Retrieved 1939.
• 4、 Sholl, Samuel A.. "3β-HYDROXYSTEROID DEHYDROGENASE/Δ5-4ISOMERASE ACTIVITY IN THE RHESUS MONKEY PLACENTA AND FETAL ADRENAL, TESTIS AND OVARY DURING LATE GESTATION". . p. 757 - 768. Retrieved 1983.
• 5、 Peng, Haidong,Wang, Yaya,Jiang, Kai,Chen, Xinru,Zhang, Wenlu,Zhang, Yanan,Deng, Zixin,Qu, Xudong. "A Dual Role Reductase from Phytosterols Catabolism Enables the Efficient Production of Valuable Steroid Precursors". supporting information. p. 5414 - 5420. Retrieved 2021/02/05.
• 6、 -. "Preparation method of progesterone". Paragraph 0052-0081. . Retrieved 2021/04/26.