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  • Lutein Lutein Good Quality Eyesight Protection Marigold Flower Extract Powder 20% Lutein Zeaxanthin

    Cas No: 57-83-0

  • USD $ 30.0-40.0 / Kilogram

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  • 1 Metric Ton/Day

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  • 57-83-0 Structure
  • Basic information

    1. Product Name: Progesterone
    2. Synonyms: PROGESTERONE-WATER SOLUBLE;progestin;PROGESTERONE;PRIMOLUT;17alpha-Hydroxy-6alpha-methylpregn-4-ene-3,20-dione;17alpha-Progesterone;3,20-Pregnene-4;4-Pregnen-3,20-dion
    3. CAS NO:57-83-0
    4. Molecular Formula: C21H30O2
    5. Molecular Weight: 314.46
    6. EINECS: 200-350-6
    7. Product Categories: MI;FINISHED MEDICINE;Steroids;ketone;Biochemistry;Steroids (Others);Intermediates & Fine Chemicals;Pharmaceuticals;Intracellular receptor;Steroid and Hormone;API;ENDOMETRIN;Plant extract;Pharma material;Inhibitors
    8. Mol File: 57-83-0.mol
    9. Article Data: 95
  • Chemical Properties

    1. Melting Point: 128-132 °C(lit.)
    2. Boiling Point: 394.13°C (rough estimate)
    3. Flash Point: 2℃
    4. Appearance: Yellow to yellow-brown/powder
    5. Density: d23 1.166; d20 1.171
    6. Vapor Pressure: 5.44E-10mmHg at 25°C
    7. Refractive Index: 182 ° (C=2, Dioxane)
    8. Storage Temp.: Store at RT
    9. Solubility: H2O: 25 mg/mL, may be clear to slightly hazy
    10. Water Solubility: <0.1 g/100 mL at 19℃
    11. Stability: Stable. Incompatible with strong oxidizing agents.
    12. Merck: 7773
    13. BRN: 1915950
    14. CAS DataBase Reference: Progesterone(CAS DataBase Reference)
    15. NIST Chemistry Reference: Progesterone(57-83-0)
    16. EPA Substance Registry System: Progesterone(57-83-0)
  • Safety Data

    1. Hazard Codes: Xn,T,F
    2. Statements: 40-45-62-36-20/21/22-11
    3. Safety Statements: 36/37-45-53-16
    4. RIDADR: UN 1648 3 / PGII
    5. WGK Germany: 3
    6. RTECS: TW0175000
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 57-83-0(Hazardous Substances Data)

57-83-0 Usage

Description

Progesterone, also known as pregn-4-en-3,20-dione, is a C21-steroid hormone that plays a crucial role in the female reproductive system. It is synthesized from cholesterol and is a biosynthetic precursor of all other steroid hormones. Progesterone is involved in the menstrual cycle, pregnancy, and embryogenesis in humans and other species. It is a white powder with a melting point of 121°C, stable in air, and has low toxicity. There are two crystal forms of progesterone, type-α and type-β, both insoluble in water but soluble in ethanol, ethyl ether, chloroform, acetone, dioxane, and concentrated sulfuric acid.

Uses

Used in Pharmaceutical Industry:
Progesterone is used as a hormone drug for promoting and maintaining uterine changes in the early stage of pregnancy. It is used in the treatment of habitual abortion, irregular menstruation, threatened abortion, amenorrhea, and premenopausal syndrome. It also plays a role in the feedback regulation of the hypothalamus and anterior pituitary, balancing animal reproductive hormones.
Used in Contraceptive Applications:
Progesterone is used as a contraceptive drug, working alongside estrogen to promote female estrus and inhibit ovulation.
Used in Gynecological Treatments:
Progesterone is used to treat dysmenorrhea, amenorrhea, and other symptoms related to the female reproductive system. It is also used in combination with other hormones to promote the development of mammary glands.
Used in Research and Development:
Progesterone is used as a progesterone receptor agonist and a mouse and human metabolite in research and development for understanding its role in various physiological processes.
Progesterone is also implicated in the etiology of breast cancer and is considered a contaminant of emerging concern (CECs). It is available in various forms, including oral micronized progesterone (Prometrium), intramuscular injections, and vaginal gels containing 4% or 8% progesterone. It was originally obtained from animal ovaries but is now prepared synthetically from plant sterol precursors. The discovery of 19-nortestosterones with progesterone activity has led to the development of synthetically modified progestins with significant therapeutic importance. However, progesterone is light-sensitive and should be protected from light.

Preparation

Progesterone can be obtained by oxidation of the pregnenolone. Dry toluene was added to a oven dried reaction kettle, and then cyclohexanone and pregnenolone were added in order with vigorous stirring to dissolve. Side product H2O was removed by Soxhlet extraction with toluene steam, aluminium isopropoxidequickly was added flowingly, the oxidation reaction was hold on at 115 oC for 2h, cooling to 80 oC, add 5% dilute sulfuric acid under stirring then stand by until water and toluene separated, the toluene layer was extracted with water to neutrality and then distillation off toluene and cyclohexanone. Cooling, filtering, filter cake was beated with petroleum, filtering, washing with petroleum, dried as crude progesterone. The crude product was dissolved in ethanol, decolorized by activated carbon, recrystallized to get the final product, yield 80%. Another way to produce progesterone is choosing the 16-Dehydropregnenolone acetate as start material, treated consecutively by catalytic hydrogenation, alkali hydrolysis, oxidation by aluminum isopropoxide, to get the progesterone as final product.

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Progesterone is sensitive to light .

Hazard

A carcinogen (OSHA).

Health Hazard

ACUTE/CHRONIC HAZARDS: Progesterone may be absorbed through the skin.

Fire Hazard

Flash point data for Progesterone are not available; however, Progesterone is probably combustible.

Biological Activity

Endogenous progesterone receptor (PR) agonist (EC 50 = 0.5 nM).

Biochem/physiol Actions

Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.

Pharmacology

During the second half of the menstrual cycle, progesterone promotes glandular growth in the endometrium, hyperemia of the uterus, thickening of the endometrium in preparation for implantation of a fertilized egg, and reduces the excitability of the uterus during pregnancy, inhibiting its activity and relaxing smooth muscles , allowing the embryo to grow safely. Under the joint action of estrogen, progesterone promotes the development of breast lobules and glands, so that the breasts can fully develop and prepare for lactation. Progesterone closes the cervix, reduces and thickens the mucus, and makes it difficult for sperm to penetrate; in large doses, it inhibits the secretion of pituitary gonadotropin through a negative feedback effect on the hypothalamus, resulting in the inhibition of ovulation. After ovulation, on the basis of the action of progesterone hormone, the endometrium continues to thicken and hyperemia, the glands proliferate and branch, from the proliferative phase to the secretory phase, which is conducive to the implantation and embryonic development of pregnant eggs. Progesterone inhibits uterine contractions and reduces the sensitivity of the uterus to oxytocin, allowing the fetus to grow safely. Progesterone competes against aldosterone, thereby promoting Na and Cl excretion and diuresis. Progesterone can slightly increase body temperature in normal women, so the basal body temperature in the luteal phase of the menstrual cycle is higher than that in the follicular phase.

Safety Profile

NTP 10th Report on Carcinogens. IARC Cancer Review: Animal Lirmted Evidence IMEMDT 21,491,79; Animal Sufficient Evidence IMEMDT 6,135,74. EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory. SAFETY PROFILE: Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Poison by intravenous and intraperitoneal routes. Human teratogenic effects by ingestion and parenteral routes: developmental abnormalities of the urogenital system. Human male reproductive effects by intramuscular route: changes in spermatogenesis, the prostate, seminal vesicle, Cowper's gland and accessory glands, impotence, and breast development. Human female reproductive effects by ingestion, parenteral, and intravaginal routes: ferthty changes; menstrual cycle changes and disorders; uterus, cervix, and vagina changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Progesterone, pregn-4-en-3,20-dione (28.3.1), is made by oxidizing pregnenolon with aluminum isopropylate in the presence of cyclohexanone as a proton acceptor (Oppenauer oxidation). Pregnenolon itself is made by subsequent oxidation and further cleavage of the side chain of stigmasterin, a sterin of plant origin that is isolated from soybeans.

Carcinogenicity

Progesterone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Purification Methods

The form crystallises from EtOH with m 127-131o. The -form crystallises from pet ether or aqueous pet ether/aqueous Et2O with m 119-120o or 121o. It also crystallises from Et2O, Me2CO/EtOAc, MeOH, aqueous Et2O, aqueous MeOH, wet pet ether, Et2O/pet ether, pet ether/*C6H6, Et2O/pentane and isopropyl ether. The is at 240nm with log 4.25 (EtOH). [Wintersteiner & Allen J Biol Chem 107 max 321 1934, Beilstein 7 III 3648, 7 IV 2395.]

Check Digit Verification of cas no

The CAS Registry Mumber 57-83-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 57-83:
(4*5)+(3*7)+(2*8)+(1*3)=60
60 % 10 = 0
So 57-83-0 is a valid CAS Registry Number.
InChI:InChI=1/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1

57-83-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (P0478)  Progesterone  >98.0%(HPLC)

  • 57-83-0

  • 5g

  • 185.00CNY

  • Detail
  • TCI America

  • (P0478)  Progesterone  >98.0%(HPLC)

  • 57-83-0

  • 25g

  • 450.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001666)  Progesterone for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 57-83-0

  • Y0001666

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001665)  Progesterone for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 57-83-0

  • Y0001665

  • 1,880.19CNY

  • Detail
  • Sigma

  • (P0130)  Progesterone  ≥99%

  • 57-83-0

  • P0130-25G

  • 1,535.04CNY

  • Detail
  • Sigma

  • (P0130)  Progesterone  ≥99%

  • 57-83-0

  • P0130-100G

  • 5,499.00CNY

  • Detail

57-83-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name progesterone

1.2 Other means of identification

Product number -
Other names Luteol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Veterinary Drug: PRODUCTION_AID
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57-83-0 SDS

57-83-0Synthetic route

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With phenylsilane; isopropyl alcohol; Mn(dpm)3 at 23℃;99%
With hydrogen; palladium on activated charcoal In ethyl acetate for 0.75h; Ambient temperature;89%
With potato dextrose broth medium In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436;8%
With Lindlar's catalyst Hydrogenation;
C25H36O4
60037-01-6

C25H36O4

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With perchloric acid In 1,4-dioxane Ambient temperature;99%
(20S)-21-hydroxy-20-methylpregn-4-en-3-one
60966-36-1

(20S)-21-hydroxy-20-methylpregn-4-en-3-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
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;99%
6-dehydroprogesterone
1162-56-7

6-dehydroprogesterone

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With formic acid In isopropyl alcohol at 76 - 80℃; for 6h; Inert atmosphere;97%
With palladium on activated charcoal Hydrogenation;
21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With methanol; trimethylsilyl iodide In chloroform for 2h; Ambient temperature;96%
With trimethylsilyl iodide In chloroform for 2h; Ambient temperature;90%
With trimethylsilyl iodide In chloroform for 2h; Ambient temperature;90%
3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>pregna-3,5-diene-20-one
112251-19-1

3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>pregna-3,5-diene-20-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; ethanol at 60℃; for 24h;95%
21-trityloxy-pregn-4-ene-3,20-dione
26623-68-7

21-trityloxy-pregn-4-ene-3,20-dione

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With methanol; trimethylsilyl iodide In acetonitrile for 1.3h; Ambient temperature;94%
C25H36O4

C25H36O4

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide In acetonitrile for 2h; Ambient temperature;94%
11-deoxy-21-iodocorticosterone
20576-46-9

11-deoxy-21-iodocorticosterone

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With mercaptoacetic acid In various solvent(s) for 0.166667h; Ambient temperature;93.8%
Pregnenolone
145-13-1

Pregnenolone

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With bromopentacarbonylmanganese(I); N-methyl-N,N-di(2-pyridylmethyl)amine; acetone; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique; Darkness;93%
With <(C4Ph4COHOCC4Ph4)(μ-H)><(CO)4Ru2>; acetone at 56℃; for 12h;90%
Stage #1: Pregnenolone With cyclohexanone In toluene for 2h; Oppenauer Oxidation;
Stage #2: With aluminum isopropoxide In toluene for 1.5h; Oppenauer Oxidation; Reflux;
90%
pregn-4-ene-3,20-diol
15780-23-1

pregn-4-ene-3,20-diol

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane for 0.5h;93%
3β-ethylether-3,5-androstadiene-17,20-epoxy-20-methyl carboxylic acid ethyl ester

3β-ethylether-3,5-androstadiene-17,20-epoxy-20-methyl carboxylic acid ethyl ester

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With lithium chloride In dimethyl sulfoxide at 130 - 140℃; for 12h; Inert atmosphere;92.86%
17β-cyano-4-androsten-3-one
63079-23-2

17β-cyano-4-androsten-3-one

methylmagnesium bromide
75-16-1

methylmagnesium bromide

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
In tetrahydrofuran at 65℃; for 3h;90.7%
17β-cyano-4-androsten-3-one
63079-23-2

17β-cyano-4-androsten-3-one

methyllithium
917-54-4

methyllithium

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
In benzene at -10 - -5℃; for 2h; Solvent; Temperature;90.6%
17β-cyano-4-androsten-3-one
63079-23-2

17β-cyano-4-androsten-3-one

methylmagnesium chloride
676-58-4

methylmagnesium chloride

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
In tetrahydrofuran at 65℃; for 4h;90.5%
(20S)-3-oxopregn-4-ene-20-carboxaldehyde
3986-89-8

(20S)-3-oxopregn-4-ene-20-carboxaldehyde

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; [2,2]bipyridinyl; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 40℃; for 22h;90%
With sodium acetate; acetic anhydride Ozonisieren des Reaktionsprodukts;
methanol
67-56-1

methanol

C20H27NO

C20H27NO

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
Stage #1: C20H27NO With magnesium In tetrahydrofuran; dichloromethane for 1h; Reflux;
Stage #2: methanol With hydrogenchloride In water at 40℃; for 3h; Reagent/catalyst;
90%
C30H39NO3S

C30H39NO3S

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 20℃; for 1h;90%
21-methoxyprogesterone
20380-14-7

21-methoxyprogesterone

A

Progesterone
57-83-0

Progesterone

B

21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

Conditions
ConditionsYield
With methanol; trimethylsilyl iodide In chloroform for 12h; Ambient temperature;A 89%
B 6%
With methanol; trimethylsilyl iodide In chloroform for 12h; Product distribution; Mechanism; Ambient temperature; other solvent, other 21-alkoxy-20-keto corticoid steroids;A 89%
B 6%
20-ethylenedioxy-4-pregnen-3-one
978-98-3

20-ethylenedioxy-4-pregnen-3-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide In acetonitrile for 15h; Ambient temperature;89%
With hydrogenchloride In methanol at 25℃; for 6h; Industrial scale;8.7 kg
20β-carboxyaldehyde-4-pregnen-3-one
24254-01-1

20β-carboxyaldehyde-4-pregnen-3-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With air; tetrapropanesulfonatehexamethylenetetramine[(1/2Cu2+)SO42-]4 In N,N-dimethyl-formamide at 45℃; for 6h; Temperature; Reagent/catalyst;87.8%
With morpholine; 1,10-Phenanthroline; neon; nitrogen; oxygen; copper(II) formate In dimethyl sulfoxide; 1,2-dichloro-ethane at 50℃; Reagent/catalyst; Temperature; Solvent;83.2%
Stage #1: 20β-carboxyaldehyde-4-pregnen-3-one With piperidine; copper(l) chloride In acetonitrile
Stage #2: With sulfuric acid; oxygen In water; acetonitrile at 30℃; for 7.5h; Solvent; Reagent/catalyst; Temperature;
18 g
4-pregnen-3-ol-20-one
566-66-5, 25680-68-6, 104528-39-4

4-pregnen-3-ol-20-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With nickel(II) triflate; cyclohexanone; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 110℃; for 12h; Schlenk technique;86%
(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1Hcyclopenta[a]phenanthren-17-yl methyl oxalate

(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1Hcyclopenta[a]phenanthren-17-yl methyl oxalate

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With 2-(2'-pyridyl)benzimidazole; diphenylsilane; magnesium chloride; nickel dichloride; zinc In N,N-dimethyl acetamide at 40℃; Inert atmosphere; Schlenk technique;86%
3,20-dioxopregn-4-en-11α-yl Se-phenyl selenocarbonate

3,20-dioxopregn-4-en-11α-yl Se-phenyl selenocarbonate

A

Progesterone
57-83-0

Progesterone

B

11-alpha-hydroxyprogesterone
80-75-1

11-alpha-hydroxyprogesterone

C

3,20-dioxopregn-4-en-11α-yl formate
115459-64-8

3,20-dioxopregn-4-en-11α-yl formate

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In xylene at 144℃;A 83%
B 3%
C 8%
3-cycloethylenedioxy-pregn-5-ene-20-one
1051-35-0

3-cycloethylenedioxy-pregn-5-ene-20-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In chloroform for 24h; Heating;83%
3,3-ethanediyldimercaptopregn-4-en-20-one
63883-02-3

3,3-ethanediyldimercaptopregn-4-en-20-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In benzene for 14h; Heating;83%
20-methylpregna-4,20-dien-3-one
23638-55-3

20-methylpregna-4,20-dien-3-one

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With potassium permanganate; sodium periodate In acetone at 60℃; for 1h; Reagent/catalyst; Solvent; Temperature;81%
With tetrachloromethane; ozone at 0℃; anschliessend Erwaermen mit Essigsaeure und Zink-Pulver und Behandeln des in 1.2-Dichlor-aethan geloesten Reaktionsprodukts mit CrO3 in wss. Essigsaeure bei 0grad;
Progesterone dibromide
111439-11-3

Progesterone dibromide

Progesterone
57-83-0

Progesterone

Conditions
ConditionsYield
With copper; copper(II) perchlorate In methanol at 0℃; for 8h;80%
Pregnenolone
145-13-1

Pregnenolone

A

Progesterone
57-83-0

Progesterone

B

pregnane-3,20-dione
7350-00-7

pregnane-3,20-dione

Conditions
ConditionsYield
aluminum oxide; copper In toluene at 60℃;A 5%
B 72%
Cortexolone
152-58-9

Cortexolone

A

Progesterone
57-83-0

Progesterone

B

21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

Conditions
ConditionsYield
With trimethylsilyl iodide In acetonitrile for 3h; Ambient temperature;A 5%
B 72%
With trimethylsilyl iodide In acetonitrile for 3h; Ambient temperature;A 5%
B 72%
With trimethylsilyl iodide In chloroform for 3h; Ambient temperature;A 53%
B 10%
With trimethylsilyl iodide In chloroform for 3h; Ambient temperature;A 38%
B 48%
Progesterone
57-83-0

Progesterone

pregn-4-ene-3,20-diol
15780-23-1

pregn-4-ene-3,20-diol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 2h;100%
With methanol; sodium tetrahydroborate at 0℃; for 2h;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;90%
With lithium borohydride In diethyl ether for 2h; Heating; Yield given;
With methanol; sodium tetrahydroborate at 0℃; for 2h;
Progesterone
57-83-0

Progesterone

ethylene glycol
107-21-1

ethylene glycol

20-ethylenedioxy-4-pregnen-3-one
978-98-3

20-ethylenedioxy-4-pregnen-3-one

Conditions
ConditionsYield
With tetraethoxy orthosilicate; toluene-4-sulfonic acid at 20℃; for 5h;100%
With tetraethoxy orthosilicate; toluene-4-sulfonic acid at 20℃; for 5h;95.52%
With tetraethoxy orthosilicate; toluene-4-sulfonic acid at 25℃; for 5h;83%
With toluene-4-sulfonic acid
oxalic acid In benzene for 48h; Reflux;
morpholine
110-91-8

morpholine

Progesterone
57-83-0

Progesterone

3-morpholinopregna-3,5-dien-20-one

3-morpholinopregna-3,5-dien-20-one

Conditions
ConditionsYield
With o-toluenesulfonic acid In toluene Heating;98%
indole
120-72-9

indole

Progesterone
57-83-0

Progesterone

C29H37NO2
1233478-23-3

C29H37NO2

Conditions
ConditionsYield
With rhodium(III) chloride hydrate In methanol for 0.0833333h; Michael addition; Reflux; diastereoselective reaction;98%
Progesterone
57-83-0

Progesterone

ethylene glycol
107-21-1

ethylene glycol

5-pregnene-3,20-dione-3,20-bisethyleneketal
7093-55-2

5-pregnene-3,20-dione-3,20-bisethyleneketal

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Product distribution / selectivity; Reflux;98%
With acetyl chloride; trimethyl orthoformate In tetrahydrofuran at 35℃; for 2h; Solvent; Large scale;91%
Progesterone
57-83-0

Progesterone

2-(methylamino)benzenethiol
21749-63-3

2-(methylamino)benzenethiol

C28H37NOS

C28H37NOS

Conditions
ConditionsYield
In ethanol for 24h; Heating;97%
Progesterone
57-83-0

Progesterone

3,20-dioximinoprogesterone
26144-38-7

3,20-dioximinoprogesterone

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In pyridine; methanol for 3h;96%
Progesterone
57-83-0

Progesterone

6β,11α-dihydroxyprogesterone
600-48-6

6β,11α-dihydroxyprogesterone

Conditions
ConditionsYield
With Mucor 881 fungal culture In tetrahydrofuran; aq. phosphate buffer for 288h; pH=7; Microbiological reaction;96%
(microbiological transformation);
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 216 h / 37 °C / Microbiological reaction
2: dimethyl sulfoxide / 216 h / 37 °C / Microbiological reaction
View Scheme
Multi-step reaction with 3 steps
1: dimethyl sulfoxide / 216 h / 37 °C / Microbiological reaction
2: potassium hydroxide / methanol
3: dimethyl sulfoxide / 216 h / 37 °C / Microbiological reaction
View Scheme
Progesterone
57-83-0

Progesterone

(E)-(1-((E)-3-hydrazono-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethylidene)hydrazine

(E)-(1-((E)-3-hydrazono-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethylidene)hydrazine

Conditions
ConditionsYield
With hydrazine hydrate; acetic acid In ethanol for 0.5h; Reflux;96%
Progesterone
57-83-0

Progesterone

N-methylhydroxyamine hydrochloride
4229-44-1

N-methylhydroxyamine hydrochloride

C22H33NO2
132734-45-3

C22H33NO2

Conditions
ConditionsYield
In dichloromethane Heating;95%
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

Progesterone
57-83-0

Progesterone

C30H39NO2
1233478-25-5

C30H39NO2

Conditions
ConditionsYield
With rhodium(III) chloride hydrate In methanol for 0.0833333h; Michael addition; Reflux; diastereoselective reaction;95%
1-methylindole
603-76-9

1-methylindole

Progesterone
57-83-0

Progesterone

C30H39NO2
1233478-24-4

C30H39NO2

Conditions
ConditionsYield
With rhodium(III) chloride hydrate In methanol at 50℃; for 0.05h; Michael addition; Microwave irradiation; diastereoselective reaction;95%
Progesterone
57-83-0

Progesterone

ethylene glycol
107-21-1

ethylene glycol

pregn-5-ene-3,20-dione cyclic 20-(1,2-ethanediylacetal)
1427208-28-3

pregn-5-ene-3,20-dione cyclic 20-(1,2-ethanediylacetal)

Conditions
ConditionsYield
With tetraethoxy orthosilicate; toluene-4-sulfonic acid at 20℃; for 5h;95%
Progesterone
57-83-0

Progesterone

testololactone
4416-57-3

testololactone

Conditions
ConditionsYield
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 48h; Enzymatic reaction;94%
With Aspergillus tamarii MRC 72400 In N,N-dimethyl-formamide at 24℃; for 120h; Baeyer-Villiger oxidation; Microbiological reaction;86%
With Aspergillus oryzae
Progesterone
57-83-0

Progesterone

11-alpha-hydroxyprogesterone
80-75-1

11-alpha-hydroxyprogesterone

Conditions
ConditionsYield
With Aspergillus ochraceus NRRL405; Kinaway's medium; β‐cyclodextrin; potassium dihydrogenphosphate for 48h; Product distribution; Further Variations:; Reagents; pH-values;93.1%
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 216 h / 37 °C / Microbiological reaction
2: potassium hydroxide / methanol
View Scheme
Progesterone
57-83-0

Progesterone

testolactone
968-93-4

testolactone

Conditions
ConditionsYield
With Fusarium oxysporum SC1301 In dimethyl sulfoxide at 30℃; for 11h;93%
With cultures of cylindrocarpone radicola
With cultures of fusarium cancasicum
With cultures of fusarium solani
Progesterone
57-83-0

Progesterone

3,5-seco-4-norpregn-5,20-dion-3-carboxylic acid
3510-20-1

3,5-seco-4-norpregn-5,20-dion-3-carboxylic acid

Conditions
ConditionsYield
With potassium permanganate; sodium periodate; sodium carbonate In water; tert-butyl alcohol Reflux;92.2%
With sodium hydroxide; adogen 464; dihydrogen peroxide; ozone In dichloromethane at -5℃; for 2h;84%
With potassium permanganate; sodium periodate; potassium carbonate In water; tert-butyl alcohol at 50℃; for 1h;80%

57-83-0Relevant articles and documents

Regulation of steroidogenesis in the ovine corpus luteum

Silavin,Moss,Niswender

, p. 229 - 241 (1980)

To examine the factor affecting LH-induced progesterone production in vitro in ovine luteal slices, an experimental procedure was employed wherein each slice served as its own control. The role of microfilaments in steroidogenesis was studied in luteal slices treated with cytochalasin B (an inhibitor of microfilament function). Cytochalasin B treatment resulted in significant reduction of progesterone production by luteal slices in response to LH and the addition of serum to the medium did not alter this effect. The ability of luteal slices to respond to LH with increased progesterone secretion was restored when cytochalasin B was removed from the medium. Further studies indicated that inhibition of LH-induced progesterone production by treatment with cytochalasin B was not a result of a change in: 1) cyclic adenosine 3'-5'-monophosphate production in response to LH; 2) mitochondrial membrane permeability to cholesterol; or 3) activity of 3β-hydroxysteroid dehydrogenase, Δ5, Δ4-isomerase enzyme complex. The possibility existed that microfilaments were necessary for cholesterol transport to mitochondria in response to LH stimulation. However, mitochondrial cholesterol content was unchanged in response to LH in the presence or absence of aminoglutethimide (an inhibitor of cholesterol side-chain cleavage enzyme activity) as determined by uptake of 3H-cholesterol or total content determined by gas-liquid chormatography. Further, treatment with cytochalasin B had no effect on mitochondrial cholesterol content. These results suggest a role for microfilaments in LH-induced progesterone production at a point prior to the conversion of cholesterol to pregnenolone.

Fujimoto,Prager

, p. 3259 (1953)

Soft drugs: Thiazolidine-type derivatives of progesterone and testosterone

Bodor,Sloan

, p. 514 - 520 (1982)

Progesterone and testosterone are natural soft drugs, but to be used as drugs, their fast and facile metabolism must be prevented and their delivery controlled. A prodrug-soft drug combination can serve this purpose. Thiazolidines of testosterone, testosterone 17-proprionate and progesterone were synthesized from the reaction of cysteine alkyl esters, N-methylaminoethanethiol, and mercaptamine and their hydrochlorides with the appropriate steroids. The thiazolidines function as bioreversible derivatives of the parent steroids.

Gut

, p. 906,908 (1953)

The catalytic mechanism of the 3-ketosteroid isomerase of Digitalis lanata involves an intramolecular proton transfer and the activity is not associated with the 3β-hydroxysteroid dehydrogenase activity

Meitinger, Nadine,Munkert, Jennifer,Maia de Pádua, Rodrigo,de Souza Filho, José Dias,Maid, Harald,Bauer, Walter,Braga, Fern?o Castro,Kreis, Wolfgang

, p. 1567 - 1571 (2016)

The isomerization of the Δ5-3-ketosteroid isoprogesterone into the Δ4-3-ketosteroid progesterone has been examined with recombinant 3β-hydroxysteroid dehydrogenase from Digitalis lanata (rDl3βHSD), partially purified 3-ketosteroid isomerase from Digitalis lanata (Dl3KSI) and under non-enzymatic conditions in deuterium oxide (D2O). Studies indicate that the isomerization catalyzed by the Dl3KSI proceeds without significant isotope exchange between the medium and the steroid and thus involves an intramolecular proton transfer consistent with the mechanism of the bacterial 3-ketosteroid isomerase of Pseudomonas testosteroni. For the rDl3βHSD as well as under non-enzymatic conditions deuterium was incorporated from the incubation buffer during isomerization. Together with a comparison of the rate of isomerization under the different conditions, it was demonstrated that rDl3βHSD does not possess 3-ketosteroid isomerase activity.

One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride

Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.

, p. 3768 - 3777 (2021/03/01)

Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Ye, Yang,Ma, Guobin,Yao, Ken,Gong, Hegui

, p. 1625 - 1628 (2021/01/18)

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

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