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50-23-7

Basic Information
CAS No.: 50-23-7
Name: Hydrocortisone
Molecular Structure:
Molecular Structure of 50-23-7 (Hydrocortisone)
Formula: C21H30O5
Molecular Weight: 362.46
Synonyms: Cortisol(8CI);11b,17,21-Trihydroxypregn-4-ene-3,20-dione;11b,17,21-Trihydroxyprogesterone;11b,17a,21-Trihydroxypregn-4-ene-3,20-dione;11b-Hydroxycortisone;17-Hydroxycorticosterone;4-Pregnene-11b,17a,21-triol-3,20-dione;Acticort;Aeroseb HC;Ala-Cort;Anflam;Anti-inflammatory hormone;CaldeCort Spray;Cetacort;Cobadex;Cortanal;Cortef;Corticreme;Cortiment;Cortispray;Cortril;Dermocortal;Dihydrocostisone;Domolene-HC;DuoCort;Efcorbin;Eldecort;Esiderm H;Evacort;
EINECS: 200-020-1
Density: 1.28 g/cm3
Melting Point: 211-214 °C(lit.)
Boiling Point: 566.4 °C at 760 mmHg
Flash Point: 310.4 °C
Solubility: water: 100 mg/mL
Appearance: crystalline white powder
Hazard Symbols: HarmfulXn
Risk Codes: 63-62-40
Safety: 36/37-45-36-22
Transport Information:
PSA: 94.83000
LogP: 1.78160
Synthetic route
50-03-3

hydrocortisone acetate

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
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%

3,11β,17α,21-tetrahydroxypregn-4-en-20-one

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With [(η5-C5Me5)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)]OTf2 In water; tert-butyl alcohol at 60℃; for 8h; chemoselective reaction;64%
152-58-9

Cortexolone

A

50-23-7

HYDROCORTISONE

B

53-06-5

Cortisone

C

63-05-8

Androstenedione

Conditions
ConditionsYield
at 37℃; for 2h; 17,20-lyase, metyrapone, NAD+, malic acid;A n/a
B n/a
C 17%
With metyrapone; malic acid; 17,20-lyase; NAD at 37℃; for 2h; Product distribution; var. pH, temp., and cofactors;A n/a
B n/a
C 17%
152-58-9

Cortexolone

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
mit Hilfe von Cunninghamella blakesleeana;
mit Hilfe von Curvularia lunata;
With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate; adrenal mitochondrial 11-hydroxylase of squirrel monkey (Saimiri sciureus); 2-amino-2-hydroxymethyl-1,3-propanediol; NADPH; calcium chloride; magnesium chloride at 37℃; for 0.133333h; Product distribution; Kinetics; adrenal 11-hydroxylase of rhesus macaques and cynomolgus monkey, Km, Vmax, influence of metyrapone;
104117-71-7

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-disemicarbazone

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With potassium borohydride anschliessend mit HNO2;
76338-54-0

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17,21-triol

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With sulfuric acid
57-83-0

Progesterone

A

50-23-7

HYDROCORTISONE

B

68-96-2

17-hydroxyprogesterone

C

64-85-7

21-Hydroxyprogesterone

D

50-22-6

Corticosterone

E

152-58-9

Cortexolone

Conditions
ConditionsYield
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
57-83-0

Progesterone

A

50-23-7

HYDROCORTISONE

B

64-85-7

21-Hydroxyprogesterone

C

50-22-6

Corticosterone

Conditions
ConditionsYield
With carbon dioxide; adenomatous adrenal tissue of patients with Cushing's syndrome; Krebs-Ringer bicarbonate solution; oxygen In ethanol at 37℃; for 1h; Product distribution; tritium labeled study;A 34.1 % Chromat.
B n/a
C 16.1 % Chromat.
57-83-0

Progesterone

A

50-23-7

HYDROCORTISONE

B

50-22-6

Corticosterone

Conditions
ConditionsYield
With carbon dioxide; Krebs-Ringer bicarbonate solution; normal adrenal tissue of patients with renal cell carcinoma; oxygen In ethanol at 37℃; for 1h; Product distribution; tritium labeled study;A 35.7 % Chromat.
B 40.6 % Chromat.
With carbon dioxide; Krebs-Ringer bicarbonate solution; surrounding adrenal tissue of patients with primary aldosteronism; oxygen In ethanol at 37℃; for 1h; Product distribution; tritium labeled study;A 16.7 % Chromat.
B 58.0 % Chromat.
68-96-2

17-hydroxyprogesterone

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With carbon dioxide; adenomatous and surrounding adrenal tissue of patients with Cushing's syndrome; Krebs-Ringer bicarbonate solution; primary aldosteronism or renal cell carcinoma; oxygen In ethanol at 37℃; for 1h; Product distribution; tritium labeled study;
68-96-2

17-hydroxyprogesterone

A

50-23-7

HYDROCORTISONE

B

58-22-0

testosterone

C

63-05-8

Androstenedione

D

152-58-9

Cortexolone

Conditions
ConditionsYield
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.
152-58-9

Cortexolone

A

50-23-7

HYDROCORTISONE

B

53-06-5

Cortisone

C

566-35-8

Epicortisol

D

595-18-6

14,17,21-trihydroxy-pregn-4-ene-3,20-dione

E

2899-95-8

(8S,9S,10R,11S,13S,14S,17R)-17-((R)-1,2-dihydroxyethyl)-11,17-dihydroxy-10,13-dimethyl-6,7,8, 9,10,11,12,13,14,15,16, 17-dodecahydro-1H-cyclopenta[a] phenanthrene-3 (2H)-one

Conditions
ConditionsYield
In ethanol Product distribution; culture of Cunningamella urvilaria lunata; also other cultures: C. blakesleeana, Th. hyalospora or Th. hiegemella orchidis were used; different times and temperatures of their preparation before reaction;A 52 % Chromat.
B 6 % Chromat.
C 4 % Chromat.
D 17 % Chromat.
E 1 % Chromat.
566-35-8

Epicortisol

A

50-23-7

HYDROCORTISONE

B

53-06-5

Cortisone

Conditions
ConditionsYield
In ethanol Product distribution; culture of Cunningamella urvilaria lunata; also other cultures: C. blakesleeana, Th. hyalospora or Th. hiegemella orchidis were used; different times and temperatures of their preparation before reaction;A 0.5 % Chromat.
B 0.5 % Chromat.
2203-97-6

hydrocortisone hemisuccinate

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With tetramethyl ammoniumhydroxide; tetrazolium blue In ethanol Rate constant; Ambient temperature; reaction of corticosteroids and their hemisuccinate esters with blue tetrazolium under USP assay conditions, hydrolysis of esters, effect of water content, kinetic study by HPLC;

5'-(Cortisol-21-phosphoryl)-5-fluoro-2'-deoxyuridine ammonium salt

A

50-23-7

HYDROCORTISONE

B

134-46-3

5-fluoro-2'-deoxyuridine-5'-O-monophosphate

Conditions
ConditionsYield
With phosphodiesterase I (EC 3.1.4.1) Product distribution; further: 5'-nucleotidase (EC 3.1.3.5) from C. adamanteus, acid phosphatase (EC 3.1.3.2) from wheat germ;

hydrocortisone sodium succinate

A

50-23-7

HYDROCORTISONE

B

53-06-5

Cortisone

C

382-44-5

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

D

cortisone sodium succinate

Conditions
ConditionsYield
Product distribution; Rate constant; Irradiation; multistep reaction, radiolytic degradation;

3-(4-Methyl-piperazin-1-ylmethyl)-benzoic acid 2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-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)-2-oxo-ethyl ester

A

50-23-7

HYDROCORTISONE

B

514209-42-8

3-[(4-methylpiperazin-1-yl)methyl]benzoic acid

Conditions
ConditionsYield
In water at 37℃; phosphate buffer pH=7.4, human plasma; other N-subst. (aminomethyl)benzoate esters of drugs; variation of the pH; other temperature;

(S)-2,6-Diamino-hexanoic acid 2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-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)-2-oxo-ethyl ester; hydrochloride

A

50-23-7

HYDROCORTISONE

B

56-87-1

L-lysine

C

(S)-2,6-Diamino-hexanoic acid (8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxy-acetyl)-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 ester; hydrochloride

Conditions
ConditionsYield
With actate buffer In water at 25℃; Rate constant; rate constante for the hydrolysis and acyl migration; pH 5; other pH;
Conditions
ConditionsYield
β-glucoronidase I In water at 37℃; for 0.166667h; Product distribution; substrate specifity of enzyme;
β-glucoronidase II In water at 37℃; for 0.166667h; Product distribution; substrate specifity of enzyme;

Hydrocortisone pivalate

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With Curvularia lunata In water at 30℃; for 65h; Yield given;
11β,17,21-trihydroxy-16-tritio-pregn-4-ene-3,20-dione

11β,17,21-trihydroxy-16-tritio-pregn-4-ene-3,20-dione

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Herstellung;
17,21-dihydroxy-pregn-4-ene-3,11,20-trione-3,20-disemicarbazone

17,21-dihydroxy-pregn-4-ene-3,11,20-trione-3,20-disemicarbazone

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With lithium borohydride anschliessend mit Brenztraubensaeure;
145-13-1

Pregnenolone

A

50-23-7

HYDROCORTISONE

B

58-22-0

testosterone

C

63-05-8

Androstenedione

D

64-85-7

21-Hydroxyprogesterone

E

50-22-6

Corticosterone

F

152-58-9

Cortexolone

G

DHEA

DHEA

Conditions
ConditionsYield
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
50-04-4

Cortisone acetate

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: KBH4 / anschliessend mit HNO2
View Scheme
102213-14-9

22-acetoxy-11β-hydroxy-3-oxo-23,24-dinor-5β-chol-17(20)ξ-ene-21-nitrile

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: OsO4
2: bromine / dann mit Semicarbazid und anschliessend mit Brenztraubensaeure
3: KHCO3
View Scheme
64313-94-6

RU 18760

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine / dann mit Semicarbazid und anschliessend mit Brenztraubensaeure
2: KHCO3
View Scheme
566-35-8

Epicortisol

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: benzene; toluene-4-sulfonic acid
2: chromium (VI)-oxide; pyridine
3: sodium borate; aq. NaOH solution
4: aqueous H2SO4
View Scheme
101524-47-4

3,3;20,20-bis-ethanediyldioxy-17,21-dihydroxy-pregn-5-en-11-one

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran; lithium alanate; diethyl ether
2: aqueous H2SO4
View Scheme
Multi-step reaction with 2 steps
1: sodium borate; aq. NaOH solution
2: aqueous H2SO4
View Scheme
102030-55-7

3,20-bis(ethylenedioxy)-11α,17α,21-trihydroxypregn-5-ene

50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: chromium (VI)-oxide; pyridine
2: sodium borate; aq. NaOH solution
3: aqueous H2SO4
View Scheme
50-23-7

HYDROCORTISONE

382-44-5

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

Conditions
ConditionsYield
Stage #1: HYDROCORTISONE With sodium tetrahydroborate In ethanol; dichloromethane for 2h;
Stage #2: With sodium periodate In acetone at 20℃;
100%
In water; acetonitrile at 20℃; Electrochemical reaction;99%
Stage #1: HYDROCORTISONE With sodium tetrahydroborate In ethanol; dichloromethane at 20℃; for 2h;
Stage #2: With sodium periodate In ethanol; dichloromethane; water; acetone at 20℃;
99%
50-23-7

HYDROCORTISONE

108-24-7

acetic anhydride

50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With pyridine at 20℃;100%
With pyridine at 0 - 25℃; for 24h;99%
With pyridine at 0 - 20℃;91%
50-23-7

HYDROCORTISONE

1609-47-8

diethyl dicarbonate

Hydrocortisone-21-ethyl carbonate

Conditions
ConditionsYield
In ethanol for 0.5h; Heating;100%
50-23-7

HYDROCORTISONE

1482-50-4

5β-pregnane-11β,17α,21-triol-3,20-dione

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In N,N-dimethyl-formamide at 30℃; under 2585.81 Torr;100%
With hydrogen; palladium 10% on activated carbon In N,N-dimethyl-formamide at 25 - 35℃; under 3102.97 Torr; for 6h;91.5%
With palladium 10% on activated carbon; hydrogen In N,N-dimethyl-formamide at 25 - 35℃; under 3102.97 Torr; for 6h; Autoclave;91.5%
50-23-7

HYDROCORTISONE

122-51-0

orthoformic acid triethyl ester

C23H32O4

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 40 - 45℃; Reagent/catalyst; Solvent;99.2%
108-30-5

succinic acid anhydride

50-23-7

HYDROCORTISONE

2203-97-6

hydrocortisone hemisuccinate

Conditions
ConditionsYield
With pyridine at 20℃; for 24h;98%
With pyridine for 5h; Heating;94%
Stage #1: succinic acid anhydride; HYDROCORTISONE With dmap In tetrahydrofuran; N,N-dimethyl-formamide at 45℃; for 4h;
Stage #2: In tetrahydrofuran; N,N-dimethyl-formamide; acetone at 0 - 10℃; for 2h;
89%
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;
108-30-5

succinic acid anhydride

50-23-7

HYDROCORTISONE

hydrocortisone-succinate-hydrocortisone

Conditions
ConditionsYield
With pyridine for 4h; Heating;97%
50-23-7

HYDROCORTISONE

21-dehydrohydrocortisone dimer

Conditions
ConditionsYield
With air; copper diacetate In methanol for 5h;97%
108-30-5

succinic acid anhydride

50-23-7

HYDROCORTISONE

hydrocortisone sodium succinate

Conditions
ConditionsYield
Stage #1: succinic acid anhydride; HYDROCORTISONE With dmap In tetrahydrofuran; N,N-dimethyl-formamide at 45℃; for 4h;
Stage #2: In tetrahydrofuran; N,N-dimethyl-formamide; acetone at 0 - 10℃; for 2h;
Stage #3: With sodium hydrogencarbonate In water; acetone at 15 - 25℃; for 3h; Temperature;
97%
50-23-7

HYDROCORTISONE

3597-45-3

cortienic acid

Conditions
ConditionsYield
In tetrahydrofuran; methanol; water96%
In tetrahydrofuran; methanol; water96%
With periodic acid In tetrahydrofuran at 20℃; for 2h;95%
50-00-0

formaldehyd

50-23-7

HYDROCORTISONE

6-methine hydrocortisone

Conditions
ConditionsYield
Stage #1: HYDROCORTISONE With Pyridine hydrobromide; Triethyl orthoacetate In ethanol at 20℃; for 0.166667h;
Stage #2: formaldehyd With N-methylaniline In ethanol; water at 20℃; for 3h; Reagent/catalyst;
95.7%
50-23-7

HYDROCORTISONE

18162-48-6

tert-butyldimethylsilyl chloride

146201-53-8

21-tert-butyldimethylsilyloxy-11β,17-dihydroxypregn-4-ene-3,20-dione

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 0.25h;95%
108-30-5

succinic acid anhydride

50-23-7

HYDROCORTISONE

103242-89-3

21-(3-Carboxy-1-oxopropoxy)-17α-hydroxy-11α-hydroxypregna-4-ene-3,20-dione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In diethyl ether; ethyl acetate; acetonitrile95%
50-23-7

HYDROCORTISONE

124-63-0

methanesulfonyl chloride

77826-00-7

(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2′-oxetane]-3,3′(2H)-dione

Conditions
ConditionsYield
Stage #1: HYDROCORTISONE; methanesulfonyl chloride With pyridine In water at 0℃; for 2h;
Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h;
95%
50-23-7

HYDROCORTISONE

124-63-0

methanesulfonyl chloride

6677-96-9

11β,7α-dihydroxy-21-<(methylsulfonyl)oxy>pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With pyridine at 0℃; for 0.25h;94%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;92%
Stage #1: HYDROCORTISONE With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h;
Stage #2: methanesulfonyl chloride In dichloromethane at 0℃; for 4 - 6h;
82%
50-23-7

HYDROCORTISONE

50-22-6

Corticosterone

Conditions
ConditionsYield
With trimethylsilyl iodide In acetonitrile at 20℃; for 0.333333h;94%
With trimethylsilyl iodide In acetonitrile at 20℃; for 0.333333h;94%
With trimethylsilyl iodide In acetonitrile for 3h; Ambient temperature;71%
With trimethylsilyl iodide In acetonitrile for 3h; Ambient temperature;71%
With trimethylsilyl iodide In acetonitrile at 20℃; for 3h;45%
50-23-7

HYDROCORTISONE

142-62-1

hexanoic acid

3593-96-2

21-hexanoyloxy-11β,17α-dihydroxypregn-4-en-3,20-dione

Conditions
ConditionsYield
With Candida antarctica lipase B In ethanol; toluene at 110℃; regioselective reaction;93%
50-23-7

HYDROCORTISONE

79-20-9

acetic acid methyl ester

50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With Candida antarctica lipase B In ethyl acetate at 55℃; regioselective reaction;92%
50-23-7

HYDROCORTISONE

124-07-2

Octanoic acid

21-octanoyloxy-11β,17α-dihydroxypregn-4-en-3,20-dione

Conditions
ConditionsYield
With Candida antarctica lipase B In ethanol; toluene at 110℃; regioselective reaction;92%
50-23-7

HYDROCORTISONE

382-45-6

adrenosterone

Conditions
ConditionsYield
With dipyridinium dichromate In dichloromethane for 44h; Ambient temperature;91%
With chromium(VI) oxide In acetic acid at 20℃; for 4h; other oxid. reagents;73%
Multi-step reaction with 2 steps
1: aqueous periodic acid
2: CrO3; acetic acid
View Scheme
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / dichloromethane; ethanol / 2 h
1.2: 20 °C
2.1: chromium(VI) oxide / water; acetic acid / 1.5 h
View Scheme
Multi-step reaction with 2 steps
1: acetonitrile; water / 20 °C / Electrochemical reaction
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium carbonate / acetonitrile; water / Electrochemical reaction
View Scheme
50-23-7

HYDROCORTISONE

1070955-54-2

C14H19NO4

1154703-35-1

3-(2-t-butoxycarbonylaminophenyl)propionic acid 2-(11,17-dihydroxy-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)-2-oxo-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane91%
50-23-7

HYDROCORTISONE

106-70-7

methyl hexanoate

3593-96-2

21-hexanoyloxy-11β,17α-dihydroxypregn-4-en-3,20-dione

Conditions
ConditionsYield
With Candida antarctica lipase B In toluene at 110℃; regioselective reaction;90%
50-23-7

HYDROCORTISONE

111-11-5

methyl octanate

21-octanoyloxy-11β,17α-dihydroxypregn-4-en-3,20-dione

Conditions
ConditionsYield
With Candida antarctica lipase B In toluene at 110℃; regioselective reaction;90%
50-23-7

HYDROCORTISONE

1-allyl-1-isopropoxysiletane

(8S,9S,10R,11S,13S,14S,17R)-17-(1,2-dihydroxypent-4-en-2-yl)-11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
In acetonitrile at 80℃; for 8h; Schlenk technique; Inert atmosphere;90%
50-23-7

HYDROCORTISONE

methacrylic anhydride

cortisol 21-monomethacrylate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃; for 48h; Inert atmosphere;89%
50-23-7

HYDROCORTISONE

4-bromocortisol

Conditions
ConditionsYield
With oxone; triethylamine; sodium bromide In tetrahydrofuran; water at 20℃; for 3h;89%
50-23-7

HYDROCORTISONE

108-24-7

acetic anhydride

A

991-08-2

3,11β,17α,21-tetraacetoxy-3,5-pregnadiene-20-one

B

3517-51-9

11β,17α,21-triacetoxy-pregn-4-ene-3,20-dione

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.0833333h; microwave irradiation;A 88%
B n/a
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

1. Introduction of Hydrocortisone
Hydrocortisone is one kind of crystalline white powder. The IUPAC Name of this chemical is (8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one. In addition, the Classification Code of this chemical is Anti-Inflammatory Agents; Drug / Therapeutic Agent; Glucocorticoid; Mutation data; Reproductive Effect. Hydrocortisone is very slightly soluble in water and sparingly soluble in alcohol.

2. Properties of Hydrocortisone
Physical properties about Hydrocortisone are:
(1)Melting point: 211-214 °C(lit.); (2)Storage temp.: -20°C; (3)Solubility: H2O: 100 mg/mL; (4)Index of Refraction: 1.594; (5)Molar Refractivity: 95.57 cm3; (6)Molar Volume: 281.3 cm3; (7)Surface Tension: 58.8 dyne/cm; (8)Density: 1.28 g/cm3; (9)Flash Point: 310.4 °C; (10)Enthalpy of Vaporization: 97.71 kJ/mol; (11)Boiling Point: 566.4 °C at 760 mmHg; (12)Vapour Pressure: 3.44E-15 mmHg at 25 °C; (13)XLogP3-AA: 1.6; (14)H-Bond Donor: 3; (15)H-Bond Acceptor: 5.

3. Structure Descriptors of Hydrocortisone
(1)Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O
(2)Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
(3)InChI: InChI=1S/C21H30O5/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/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1 
(4)InChIKey: JYGXADMDTFJGBT-VWUMJDOOSA-N

4. Toxicity of Hydrocortisone

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 400mg/kg/10D- (400mg/kg) BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS Psychopharmacology Vol. 145, Pg. 260, 1999.
mouse LD50 subcutaneous > 500mg/kg (500mg/kg)   Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 24(3), Pg. 26, 1990.
rat LD50 intraperitoneal 150mg/kg (150mg/kg)   Japanese Journal of Pharmacology. Vol. 21, Pg. 377, 1971.
rat LD50 subcutaneous 449mg/kg (449mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 250, 1966.

5. Safety information of Hydrocortisone
Poison by intraperitoneal route. Moderately toxic by subcutaneous route. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. A steroid. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Hazard Codes: XnHarmful
WGK Germany: 3
Risk Statements: 63-62-40 
R62: Risk of impaired fertility. 
R63: Possible risk of harm to the unborn child. 
R40: Limited evidence of a carcinogenic effect.
Safety Statements of Hydrocortisone: 36/37-45-36-22 
S36/37: Wear suitable protective clothing and gloves. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36: Wear suitable protective clothing. 
S22: Do not breathe dust.

6. Uses of Hydrocortisone
Hydrocortisone (CAS NO.50-23-7) is used to treat a variety of different illnesses. Its synthetic counterpart is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions.

7. Production of Hydrocortisone
Hydrocortisone can be got from the adrenal gland. Or it can be got from 17α- hydroxyprogesterone.