Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
With pyridine at 0 - 25℃; for 24h; | 99% |
With pyridine at 0 - 20℃; | 91% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B In ethyl acetate at 55℃; regioselective reaction; | 92% |
Δ6-hydrocortisone-21-acetate
A
hydrocortisone acetate
Conditions | Yield |
---|---|
With hydrogen; Pd/SrCO3 In ethyl acetate for 0.333333h; atmospheric pressure; | A 42% B 19% |
Conditions | Yield |
---|---|
With acetone |
21-acetoxy-11β-hydroxy-pregna-4,17(20)c-dien-3-one
hydrocortisone acetate
Conditions | Yield |
---|---|
With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene | |
With osmium(VIII) oxide; triethylamine N-oxide; dihydrogen peroxide |
4β-chloro-17-hydroxy-5β-pregnane-3,11,20-trione
hydrocortisone acetate
Conditions | Yield |
---|---|
ueber mehrere Stufen; |
21-acetoxy-11β-hydroxy-pregna-4,17(20)t-dien-3-one
hydrocortisone acetate
Conditions | Yield |
---|---|
With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene | |
With osmium(VIII) oxide; triethylamine N-oxide; dihydrogen peroxide |
RU 18760
hydrocortisone acetate
Conditions | Yield |
---|---|
With bromine dann mit Semicarbazid und anschliessend mit Brenztraubensaeure; |
Conditions | Yield |
---|---|
With Candida antarctica lipase B In tetrahydrofuran at 45℃; for 4h; Yield given; |
22-acetoxy-11β-hydroxy-3-oxo-23,24-dinor-5β-chol-17(20)ξ-ene-21-nitrile
hydrocortisone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: OsO4 2: bromine / dann mit Semicarbazid und anschliessend mit Brenztraubensaeure View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: CrO3; pyridine 3: ueber mehrere Stufen View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tert-butyl hypochlorite; water; tert-butyl alcohol; HCl 2: ueber mehrere Stufen View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CrO3; pyridine 2: ueber mehrere Stufen View Scheme |
20,20-ethanediyldioxy-3α,17-dihydroxy-5β-pregnan-11-one
A
hydrocortisone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: LiAlH4 / folgenden mit wss.HCl 3: CrO3; pyridine 4: ueber mehrere Stufen View Scheme |
21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
chromium(III) chloride
zinc
hydrocortisone acetate
Conditions | Yield |
---|---|
With acetic acid In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone |
21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
hydrocortisone acetate
Conditions | Yield |
---|---|
With zinc In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone |
21-acetoxy-9-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione
hydrocortisone acetate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | |
In N,N-dimethyl-formamide |
hydrocortisone acetate
Conditions | Yield |
---|---|
Stage #1: C25H38N6O6 With hydrogenchloride In chloroform; water at 25 - 30℃; for 0.5h; Stage #2: With sodium nitrite In chloroform; water at 5 - 10℃; for 2h; | 18.1 g |
hydrocortisone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium acetate; acetic acid / acetone / 5 h / Reflux 2.1: hydrogenchloride / water; chloroform / 0.5 h / 25 - 30 °C 2.2: 2 h / 5 - 10 °C View Scheme |
hydrocortisone acetate
Conditions | Yield |
---|---|
Stage #1: C25H38N6O6 With hydrogenchloride In chloroform; water at 25 - 30℃; for 0.5h; Stage #2: With sodium nitrite In chloroform; water at 5 - 10℃; for 2h; |
Conditions | Yield |
---|---|
With rhodium chloride; water In methanol at 20 - 65℃; for 4h; Autoclave; | 85 g |
Multi-step reaction with 2 steps 1: water; tetrafluoroboric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / acetone / -5 °C 2: mercaptoacetic acid; zinc; chromium(III) chloride hexahydrate / dimethyl sulfoxide; 2-methyltetrahydrofuran / -5 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium tert-butylate / tetrahydrofuran / 8 h / 20 - 40 °C 2: dihydrogen peroxide / dichloromethane / 1.5 h / 20 - 40 °C 3: water; rhodium chloride / methanol / 4 h / 20 - 65 °C / Autoclave View Scheme |
21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
hydrocortisone acetate
Conditions | Yield |
---|---|
With hydrogenchloride; chromium chloride; mercaptoacetic acid In tetrahydrofuran; water; N,N-dimethyl-formamide at 10 - 60℃; for 2.5h; Inert atmosphere; | |
With chromium(III) chloride hexahydrate; mercaptoacetic acid; zinc In 2-methyltetrahydrofuran; dimethyl sulfoxide at -5℃; Solvent; Temperature; Inert atmosphere; | 45.5 g |
21-chloro-11,17-dihydroxy-pregn-4-ene-3,20-dione
potassium acetate
hydrocortisone acetate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; | 0.94 g |
9-bromo-21-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione
hydrocortisone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; chromium chloride; zinc / N,N-dimethyl-formamide; water / 0 - 15 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 80 °C View Scheme |
21-chloro-17-hydroxy-pregna-4,9(11)-diene-3,20-dione
hydrocortisone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: perchloric acid; N-Bromosuccinimide / acetone / 5 - 20 °C 2: hydrogenchloride; chromium chloride; zinc / N,N-dimethyl-formamide; water / 0 - 15 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 80 °C View Scheme |
Conditions | Yield |
---|---|
With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 20℃; for 6h; Time; | 14.6 g |
Conditions | Yield |
---|---|
With pyridine; methanesulfonyl chloride In N,N-dimethyl-formamide at 50 - 82℃; for 2h; | 95.85% |
With N,N'-Thionyldiimidazole In tetrahydrofuran for 0.5h; Ambient temperature; | 40% |
With pyridine; methanesulfonyl chloride In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With potassium carbonate In methanol for 1h; | 95% |
With sodium methylate In methanol at 20℃; for 0.5h; | 94.82% |
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 3h; | 91.3% |
hydrocortisone acetate
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; 1,1'-(phenyl-λ3-iodanediyl)bis(2-methoxypyridin-1-ium)trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; Molecular sieve; Inert atmosphere; | 82% |
1. Introduction of Hydrocortisone acetate
Hydrocortisone acetate is one kind of white powder. The IUPAC Name of this chemical is [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate. Besides, Hydrocortisone acetate stability is stable, but may be light or moisture sensitive. It is incompatible with strong oxidizing agents. Hydrocortisone acetate belongs to Biochemistry;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Veterinaries;Steroid and Hormone.
The Classification Code of this chemical is Anti-Inflammatory Agents; Drug / Therapeutic Agent; Glucocorticoid; Mutation data; Reproductive Effect.
2. Properties of Hydrocortisone acetate
Physical properties about Hydrocortisone acetate are:
(1)Nominal Mass: 404 Da; (2)Average Mass: 404.4966 Da; (3)Monoisotopic Mass: 404.219889 Da; (4)Index of Refraction: 1.572; (5)Molar Refractivity: 105.15 cm3; (6)Molar Volume: 319.2 cm3; (7)Surface Tension: 54.6 dyne/cm; (8)Density: 1.26 g/cm3; (9)Flash Point: 196.2 °C; (10)Enthalpy of Vaporization: 99.14 kJ/mol; (11)Boiling Point: 576.6 °C at 760 mmHg; (12)Vapour Pressure: 1.08E-15 mmHg at 25°C; (13)Storage temp: 0-6°C; (14)Decomposition: 223°C.
3. Structure Descriptors of Hydrocortisone acetate
(1)InChI: InChI=1S/C23H32O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-18,20,26,28H,4-9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1
(2)InChIKey: InChIKey=ALEXXDVDDISNDU-JZYPGELDSA-N
(3)Smiles: C1[C@@]2([C@H]([C@H]3[C@H]([C@@]4(C(=CC(=O)CC4)CC3)C)[C@H]1O)CC[C@@]2(C(COC(C)=O)=O)O)C
4. Toxicity of Hydrocortisone acetate
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 2300mg/kg (2300mg/kg) | Compilation of LD50 Values of New Drugs. | |
mouse | LD50 | subcutaneous | 45050ug/kg (45.05mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
rat | LDLo | subcutaneous | 250mg/kg (250mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 2102, 1977. |
RTECS : GM8960000
5. Safety information of Hydrocortisone acetate
Hazard Codes: Xn
Risk Statements: 63
R63: Possible risk of harm to the unborn child
Safety Statements: 36/37
S36/37: Wear suitable protective clothing and gloves
WGK Germany: 3
6. Uses of Hydrocortisone acetate
Hydrocortisone acetate can be used for biochemical research. As a sugar cortical hormone drug, it can anti-inflammatory, anti-allergic, antitoxin, resistance to shock action.
7. Production of Hydrocortisone acetate
Hydrocortisone and Acetic anhydride esterification under the condition of Azabenzene can be used to manufacture Hydrocortisone acetate.
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