(8R,9S,10R,13S,14S)-10,13-Dimethyl-17-[1-tripropylsilanyloxy-eth-(Z)-ylidene]-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
Cortexolone
Conditions | Yield |
---|---|
With potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid | 88% |
Conditions | Yield |
---|---|
With water; potassium carbonate In methanol at 20℃; for 3h; Inert atmosphere; | 85% |
With methanol; potassium hydrogencarbonate |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol Ambient temperature; | 80% |
With potassium hydroxide |
Cortexolone
Conditions | Yield |
---|---|
With water; potassium carbonate In acetone at 20℃; for 72h; Inert atmosphere; | 70% |
21-bromo-17α-hydroxy-4-pregnene-3,20-dione
Cortexolone
Conditions | Yield |
---|---|
With potassium carbonate for 0.166667h; Heating; | 68% |
With water; potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; | 57% |
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; potassium dihydrogenphosphate; D-glucose; menadione; corn-steep liquor In water; N,N-dimethyl-formamide at 28℃; for 40h; Rhodococcus sp.; | A 30% B 50% |
Conditions | Yield |
---|---|
mit Hilfe von Trichothecium roseum; |
21-Hydroxyprogesterone
A
Cortexolone
B
6β,21-dihydroxypregna-4-en-3,20-dione
Conditions | Yield |
---|---|
mit Hilfe von Trichothecium roseum; |
17.20βF-dihydroxy-3-oxo-pregnen-(4)-al-(21)
Cortexolone
Conditions | Yield |
---|---|
With pyridine |
Progesterone
A
HYDROCORTISONE
B
17-hydroxyprogesterone
C
21-Hydroxyprogesterone
D
Corticosterone
E
Cortexolone
Conditions | Yield |
---|---|
With glucose-6-phosphate dehydrogenase; phosphate buffer; air; α-D-glucose 6-phosphate; midterm female fetal human adrenal tissue; NADP; magnesium chloride at 37℃; for 2h; Product distribution; <3H>labeled; | A 36.3 % Chromat. B n/a C n/a D 4.7 % Chromat. E n/a |
Progesterone
A
17-hydroxyprogesterone
B
21-Hydroxyprogesterone
C
Corticosterone
D
Cortexolone
Conditions | Yield |
---|---|
With glucose-6-phosphate dehydrogenase; phosphate buffer; air; α-D-glucose 6-phosphate; midterm female fetal human kidney tissue; NADP; magnesium chloride at 37℃; for 2h; Product distribution; <3H>labeled; | A 2.3 % Chromat. B 21.1 % Chromat. C n/a D 32.5 % Chromat. |
17-hydroxyprogesterone
A
HYDROCORTISONE
B
testosterone
C
Androstenedione
D
Cortexolone
Conditions | Yield |
---|---|
With D-glucose 6-phosphate; sporadic adrenal pheochromocytomas; oxygen; NADP; glucose 6-phosphate dehydrogenase at 37℃; for 1h; Product distribution; <4-14C>-labeled; | A 20.6 % Turnov. B 1.1 % Turnov. C 2.3 % Turnov. D 14.8 % Turnov. |
Conditions | Yield |
---|---|
With α-D-glucose 6-phosphate; 21-hydroxylase from human fetal adrenals; glucose-6-phosphate-dehydrogenase; potassium chloride; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride Equilibrium constant; interaction with cytochrome P-450 obtained from microsomes and mitochondria from human fetal adrenals in dependence on conc.; apparent spectral dissociation const.; inhibition by danazol; | |
With CYP21 Enzymatic reaction; | |
With recombinant human cytochrome P450 21A2; water In aq. phosphate buffer at 37℃; Enzymatic reaction; | |
With wild-type human cytochrome P450 21A2 Kinetics; Reagent/catalyst; Enzymatic reaction; |
methanol
16α,17α-epoxyprogesterone
A
Cortexolone
B
20,20-dimethoxy-16α,17α-epoxypregn-4-en-21-ol-3-one
Conditions | Yield |
---|---|
With potassium hydroxide; [bis(acetoxy)iodo]benzene at 20℃; for 7h; | A 0.08 g B 0.15 g |
16α,17α-epoxyprogesterone
A
17-hydroxyprogesterone
B
Cortexolone
C
16α,17α-epoxypregn-4-en-21-ol-3,20-dione
Conditions | Yield |
---|---|
With potassium hydroxide; [bis(acetoxy)iodo]benzene In methanol at 20℃; for 8h; | A 0.02 g B 0.02 g C 0.19 g |
Pregnenolone
A
HYDROCORTISONE
B
testosterone
C
Androstenedione
D
21-Hydroxyprogesterone
E
Corticosterone
F
Cortexolone
Conditions | Yield |
---|---|
With D-glucose 6-phosphate; sporadic adrenal pheochromocytomas; oxygen; NADP; glucose 6-phosphate dehydrogenase at 37℃; for 1h; Product distribution; <4-14C>-labeled; | A 12.6 % Turnov. B 0.9 % Turnov. C 1.9 % Turnov. D 2.4 % Turnov. E 6.8 % Turnov. F 2.3 % Turnov. G n/a |
Cortexolone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent 2: hydrolysis 3: 80 percent / KOH / methanol / Ambient temperature View Scheme |
C28H39NO7
Cortexolone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrolysis 2: 80 percent / KOH / methanol / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 10 percent / CuBr2 / tetrahydrofuran / 2 h / Heating 2: 65 percent / 8 N CrO3 / acetone / 0.08 h 3: 68 percent / aq. K2CO3 / 0.17 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 65 percent / 8 N CrO3 / acetone / 0.08 h 2: 68 percent / aq. K2CO3 / 0.17 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 79 percent / RhCl(PPh3)3 2: 88 percent / mCPBA, KHCO3 View Scheme |
Cortexolone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous methanol.KHCO3 2: pyridine View Scheme |
Progesterone
A
21-Hydroxyprogesterone
B
2β,16β-hydroxyprogesterone
C
Cortexolone
D
16β-hydroxyprogesterone
E
2beta-Hydroxyprogesterone
Conditions | Yield |
---|---|
With Bacillus megaterium cytochrome P450 BM3 monooxygenase (V78L/A82F/F87A)-expressing cells at 25℃; for 24h; diastereoselective reaction; |
Progesterone
A
21-Hydroxyprogesterone
B
Cortexolone
C
16β-hydroxyprogesterone
D
2beta-Hydroxyprogesterone
Conditions | Yield |
---|---|
With Bacillus megaterium cytochrome P450 BM3 monooxygenase (R47Y/T49F/V78T/A82F/F78A)-expressing cells at 25℃; for 24h; diastereoselective reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CYP17A1 / Enzymatic reaction 2: CYP21 / Enzymatic reaction View Scheme |
A
Androstenedione
B
Cortexolone
C
R-16α,17-dihydroxy-pregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium tert-butylate; oxygen / tetrahydrofuran; tert-butyl alcohol / 4.67 h / 20 °C 2: acetic acid / methanol / 3 h / 20 °C 3: 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; zebrafish P450 17A2 enzyme / aq. phosphate buffer; ethanol; dimethyl sulfoxide / 37 °C / pH 7.4 / Enzymatic reaction 4: zebrafish P450 17A1 enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine / aq. phosphate buffer / 37 °C / pH 7.4 / Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium tert-butylate; oxygen / tetrahydrofuran; tert-butyl alcohol / 4.67 h / 20 °C 2: acetic acid / methanol / 3 h / 20 °C 3: 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; zebrafish P450 17A2 enzyme / aq. phosphate buffer; ethanol; dimethyl sulfoxide / 37 °C / pH 7.4 / Enzymatic reaction 4: 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; zebrafish b5 enzyme; NADPH-P450 reductase; zebrafish P450 17A2 enzyme / aq. phosphate buffer / 37 °C / pH 7.4 / Enzymatic reaction View Scheme |
A
Androstenedione
B
Cortexolone
C
R-16α,17-dihydroxy-pregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid / methanol / 3 h / 20 °C 2: 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; zebrafish P450 17A2 enzyme / aq. phosphate buffer; ethanol; dimethyl sulfoxide / 37 °C / pH 7.4 / Enzymatic reaction 3: zebrafish P450 17A1 enzyme; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine / aq. phosphate buffer / 37 °C / pH 7.4 / Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 0.5h; | 100% |
With pyridine |
Cortexolone
Conditions | Yield |
---|---|
With air; copper diacetate In methanol for 5h; | 100% |
Cortexolone
pivaloyl chloride
17-Hydroxy-21-trimethylacetoxy-4-pregnen-3,20-dion
Conditions | Yield |
---|---|
With dmap In pyridine at 0℃; for 2h; | 99% |
With pyridine; dichloromethane |
Cortexolone
methanesulfonyl chloride
17α-hydroxy-21-<(methylsulfonyl)oxy>pregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 97% |
Conditions | Yield |
---|---|
AuCl(xanthphos) In chloroform; N,N-dimethyl-formamide at 50℃; for 6h; | 96% |
Cortexolone
17,21,21-trihydroxy-4-pregnene-3,20-dione
Conditions | Yield |
---|---|
With copper diacetate; air In methanol for 7h; Ambient temperature; | 95% |
Cortexolone
11β,20-dihydroxy-3-oxo-4,cis-17(20)-pregnadien-21-al
Conditions | Yield |
---|---|
With oxone; 2-Iodobenzoic acid In dimethyl sulfoxide at 75℃; for 12h; Inert atmosphere; | 92% |
Cortexolone
20-hydroxy-3,11-dioxo-4,cis-17(20)-pregnadien-21-al
Conditions | Yield |
---|---|
With oxone; 2-Iodobenzoic acid In dimethyl sulfoxide at 75℃; for 12h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With Rhizopus oryzae lipase immobilized on Lewatit 1600 resin In di-isopropyl ether at 55℃; for 48h; regioselective reaction; | 91% |
Cortexolone
20-hydroxy-3-oxo-4,cis-17(20)-pregnadien-21-al
Conditions | Yield |
---|---|
With oxone; 2-Iodobenzoic acid In dimethyl sulfoxide at 75℃; for 12h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.166667h; | 88% |
Cortexolone
methyl 17α-hydroxy-3-oxoandrost-4-ene-17-carboxylate
Conditions | Yield |
---|---|
With sulfuric acid; sodium hydrogencarbonate In methanol | 87% |
Conditions | Yield |
---|---|
In water; acetonitrile at 20℃; Electrochemical reaction; | 86% |
With ammonium hydroxide; iodine In water; acetonitrile at 50℃; for 24h; | 78% |
With manganese(IV) oxide In chloroform for 4h; Heating; | 67.6% |
Cortexolone
Bestmann ylide
4-((8R,9S,10R,13S,14S,17R)-17-Hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-5H-furan-2-one
Conditions | Yield |
---|---|
In benzene for 3h; Heating; | 86% |
Cortexolone
methanesulfonyl chloride
17α-hydroxy-21-chloro-4-pregnene-3,20-dione
Conditions | Yield |
---|---|
With dmap In dichloromethane for 4h; Reflux; | 85% |
Conditions | Yield |
---|---|
With sodium periodate In tetrahydrofuran; methanol at 20℃; for 2h; | 82% |
With methanol; periodic acid | |
With periodic acid In methanol | |
Multi-step reaction with 2 steps 1: TsOH / dioxane; butan-2-one 2: aq. HIO4 / methanol View Scheme | |
With sodium hydroxide; sulfuric acid In methanol; water; acetone |
phthalimide
Cortexolone
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.166667h; | 82% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With hydrogenchloride In chloroform; water at 20℃; for 5h; | 71% |
With hydrogenchloride; chloroform |
Cortexolone
A
20-hydroxy-3-oxo-4,trans-17(20)-pregnadien-21-al
B
20-hydroxy-3-oxo-4,cis-17(20)-pregnadien-21-al
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,4-dioxane Heating; | A 10% B 71% |
With zinc diacetate; acetic acid Heating; | A 6% B 16.6% |
With zinc diacetate; acetic acid Heating; | A 6% B 16.6% |
Cortexolone
17α,21-Dihydroxypregn-4-en-3,20-dione 21-phosphate
Conditions | Yield |
---|---|
With pyridine; 2-cyanoethyl phosphate; dicyclohexyl-carbodiimide | 70% |
Cortexolone
2,2-dimethoxy-propane
17,21-dihydroxy-3-methoxypregna-3,5-dien-20-one 17,21-acetonide
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 6h; Heating; | 61% |
Cortexolone
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester
pregn-4-en-17α,21-diol-3,20-dione-21-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronate)
Conditions | Yield |
---|---|
With silver carbonate In toluene for 6h; Koenigs-Knorr synthesis; Reflux; | 48% |
Cortexolone
A
(8R,9S,10R,13S,14S,17R)-17-((R)-1,2-Dihydroxy-ethyl)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
B
4-pregnen-17α,20β,21-triol-3-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; calcium chloride In water; ethyl acetate at -27℃; | A n/a B 40% |
The Pregn-4-ene-3,20-dione,17,21-dihydroxy- is an organic compound with the formula C21H30O4. The IUPAC name of this chemical is (8R,9S,10R,13S,14S,17R)-17-Hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one. With the CAS registry number 152-58-9, it is also named as 11-Desoxycortisol. The product's categories are Pharmaceutical Raw Materials; Steroids; Biochemistry; Hydroxyketosteroids; Intermediates and Fine Chemicals; Pharmaceuticals. Besides, it is crystalline solid, which should be stored in a sealed place. And it can be used for glucocorticoid receptor binding. This chemical can be prepared by separating extraction of Adrenal.
Physical properties about Pregn-4-ene-3,20-dione,17,21-dihydroxy- are: (1)ACD/LogP: 2.74; (2)#H bond acceptors: 4; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 4; (5)Polar Surface Area: 52.6 Å2; (6)Index of Refraction: 1.577; (7)Molar Refractivity: 94.05 cm3; (8)Molar Volume: 283.4 cm3; (9)Polarizability: 37.28×10-24 cm3; (10)Surface Tension: 52.8 dyne/cm; (11)Density: 1.22 g/cm3; (12)Flash Point: 285.1 °C; (13)Enthalpy of Vaporization: 91.87 kJ/mol; (14)Boiling Point: 524.5 °C at 760 mmHg; (15)Vapour Pressure: 3.41E-13 mmHg at 25 °C.
When you are using this chemical, please be cautious about it as the following:
It is toxic in contact with skin and if swallowed. Besides, this chemical is harmful if swallowed.
You can still convert the following datas into molecular structure:
(1)InChI: InChI=1/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1
(2)InChIKey: WHBHBVVOGNECLV-OBQKJFGGBG
(3)Std. InChI: InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1
(4)Std. InChIKey: WHBHBVVOGNECLV-OBQKJFGGSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04684, |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View