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50-24-8

Basic Information
CAS No.: 50-24-8
Name: Prednisolone
Article Data: 60
Cas Database
Molecular Structure:
Molecular Structure of 50-24-8 (Prednisolone)
Formula: C21H28O5
Molecular Weight: 360.45
Synonyms: Predonin;Supercortisol;Codelcortone;Prestwick_404;Precortancyl;Cortalone;Dydeltrone;Fernisolone;Meti-Derm;Donisolone;K 1557;Paracortol;Cotogesic;Paracotol;Precortilon;Sterolone;Delcortol;Rolisone;Precortalon;Hydrodeltalone;Delta-Ef-Cortelan;Delta-cortef (TN);component of Ataraxoid;Prenolone;Cordrol;Hydeltra;(8S,9S,10S,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one;Meticortelone;Deltacortenol;Sterane;Delta F;Precortisyl;Ulacort;Meticortelone;Sterolone;Deltisilone;Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11.beta.)-;Decortin H;1-Dehydrohydrocortisone;Prednis;Pregna-1,4-diene-3,20-dione,11,17,21- trihydroxy-,(11a)-;Predonine;Lentosone;1, 2-Dehydrohydrocortisone;Hydroretrocortin;Deltacortril;Di-Adreson F;Derpo PD;Deltahydrocortisone;Dexa-Cortidelt Hostacortin H;Hostacortin H;Scherisolon;Hydrodeltisone;Metacortandralone;Ultracortene-H;Ultracorten H;Fernisolone P;
EINECS: 200-021-7
Density: 1.31 g/cm3
Melting Point: 240 °C (dec.)(lit.)
Boiling Point: 570.6 °C at 760 mmHg
Flash Point: 313 °C
Solubility: 2.225g/L(25 oC)
Appearance: Crystalline Solid
Hazard Symbols: HarmfulXn, CorrosiveC, FlammableF
Risk Codes: 22-34-11
Safety: 22-45-36/37/39-26-16
Transport Information: N/A
PSA: 94.83000
LogP: 1.55760
Synthetic route
67-56-1

methanol

52-21-1

prednisolone 21-acetate

A

50-24-8

prednisolon

B

79-20-9

acetic acid methyl ester

Conditions
ConditionsYield
With triethylamine at 20℃; under 8250660 Torr; for 2h; Product distribution;A n/a
B 100%
50-23-7

HYDROCORTISONE

50-24-8

prednisolon

Conditions
ConditionsYield
With Rhodococcus coprophilus DSM 43347 In dimethyl sulfoxide at 30℃; for 24h; Reagent/catalyst; Green chemistry; regiospecific reaction;97%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 4h; Reflux;83.33%
With potassium phosphate buffer In methanol at 30℃; free and the urethane prepolymer-entrapped acetone-dried cells of Arthrobacter simplex; effect of gel hydrophobicity; effect of electron acceptors and solvents;
With 3-ketosteroid-Δ1-dehydrogenase from Mycobacterium smegmatis mc2155; phenazine methosulfate In dimethyl sulfoxide at 30℃; for 16h; pH=8; Catalytic behavior; Kinetics; Solvent; Reagent/catalyst; Enzymatic reaction;
67-56-1

methanol

prednisolone 21-isobutyrate

A

50-24-8

prednisolon

B

547-63-7

Methyl isobutyrate

Conditions
ConditionsYield
With triethylamine at 20℃; under 8250660 Torr; for 2h; Product distribution;A n/a
B 96%
52-21-1

prednisolone 21-acetate

50-24-8

prednisolon

Conditions
ConditionsYield
With water; potassium carbonate; sodium hydroxide In methanol at 0 - 10℃; for 2h; Inert atmosphere;92.5%
With methanol; triethylamine for 14h; Ambient temperature;49%
With potassium hydroxide
Stage #1: prednisolone 21-acetate With water; sodium hydroxide In methanol; dichloromethane at 0 - 30℃; for 2.5h; Inert atmosphere;
Stage #2: With acetic acid In methanol; dichloromethane at -12 - -5℃; for 1h; pH=6 - 7; Reagent/catalyst; Reflux;
15.8 g
98523-85-4

prednisolone 11β,21-diacetate

50-24-8

prednisolon

Conditions
ConditionsYield
With di(n-butyl)tin oxide In methanol for 2.5h; Heating;91%

21-<<(6-carboxy-3-cyclohexen-1-yl)carbonyl>oxy>-11β,17α-dihydroxypregna-1,4-diene-3,20-dione

50-24-8

prednisolon

Conditions
ConditionsYield
With methanol; triethylamine for 0.166667h; Ambient temperature; Irradiation;90%

prednisolone 21-[hydrogen (cyclohex-3-ene-1,2-dicarboxylate)]

50-24-8

prednisolon

Conditions
ConditionsYield
With methanol; triethylamine at 20℃; under 8250660 Torr; for 168h; Product distribution; Further Variations:; Reagents; Pressures;81%
67-56-1

methanol

1107-99-9

prednisolone 21-trimethylacetate

A

50-24-8

prednisolon

B

598-98-1

Methyl pivalate

Conditions
ConditionsYield
With triethylamine at 20℃; under 8250660 Torr; for 2h; Product distribution; Further Variations:; Reagents; Pressures;A n/a
B 78%
67-56-1

methanol

104687-90-3

prednisolone 11β-acetate

A

50-24-8

prednisolon

B

79-20-9

acetic acid methyl ester

Conditions
ConditionsYield
With triethylamine at 20℃; under 8250660 Torr; for 168h; Product distribution; Further Variations:; Reagents; Pressures;A 76%
B n/a
50-23-7

HYDROCORTISONE

A

50-24-8

prednisolon

B

15847-24-2

11β,17α,20β,21-tetrahydroxy-1,4-pregnadiene-3-one

Conditions
ConditionsYield
With Rhodococcus erythropholis DSM 43188 In dimethyl sulfoxide at 30℃; for 72h; Green chemistry; regiospecific reaction;A 37%
B 40%
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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The Hydrodeltalone, with the CAS registry number 50-24-8, is also known as 11beta,17alpha,21-Trihydroxypregna-1,4-diene-3,20-dione; 1,4-Pregnadiene-11b,17a,21-triol-3,20-dione. It belongs to the product categories of Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone.This chemical's molecular formula is C21H28O5 and molecular weight is 360.45.Its EINECS number is 200-021-7.What's more,Its systematic name is Prednisolone.It is Crystalline Solid.It is a glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.

Physical properties about Hydrodeltalone are:
(1)ACD/LogP: 1.635; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.64; (4)ACD/LogD (pH 7.4): 1.64; (5)ACD/BCF (pH 5.5): 10.29; (6)ACD/BCF (pH 7.4): 10.29; (7)ACD/KOC (pH 5.5): 184.65; (8)ACD/KOC (pH 7.4): 184.65; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.612; (13)Molar Refractivity: 95.481 cm3; (14)Molar Volume: 274.7 cm3; (15)Surface Tension: 60.7360000610352 dyne/cm; (16)Density: 1.312 g/cm3; (17)Flash Point: 312.953 °C; (18)Enthalpy of Vaporization: 98.3 kJ/mol; (19)Boiling Point: 570.629 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C;

You can still convert the following datas into molecular structure:
(1)SMILES:O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]2[C@@H]4[C@@H](O)C[C@@]3([C@@](O)(C(=O)CO)CC[C@@H]23)C)C;
(2)Std. InChI:InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1;
(3)Std. InChIKey:OIGNJSKKLXVSLS-VWUMJDOOSA-N.

Safety Information of Hydrodeltalone:
The Hydrodeltalone is highly flammable.Keep it far away from sources of ignition - No smoking. It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it ,wear suitable protective clothing, gloves and eye/face protection.In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

The toxicity data of Prednisolone as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 9mg/kg/2W-I (9mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 603, 1984.
mouse LD50 intraperitoneal 65mg/kg (65mg/kg)   Indian Drugs. Vol. 22, Pg. 529, 1985.
mouse LD50 intravenous 180mg/kg (180mg/kg)   Pharmaceutical Chemistry Journal Vol. 16, Pg. 63, 1982.
mouse LD50 oral 1680mg/kg (1680mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 111, 1970.
mouse LD50 subcutaneous > 3500mg/kg (3500mg/kg)   Drugs in Japan Vol. 6, Pg. 710, 1982.
rat LD50 intraperitoneal 2gm/kg (2000mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LD50 intravenous 120mg/kg (120mg/kg)   Pharmaceutical Chemistry Journal Vol. 16, Pg. 63, 1982.
rat LD50 subcutaneous 147mg/kg (147mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 250, 1966.
women TDLo oral 14mg/kg/13D-I (14mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 603, 1984.