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50-23-7

Basic Information
CAS No.: 50-23-7
Name: Hydrocortisone
Article Data: 65
Cas Database
Molecular Structure:
Molecular Structure of 50-23-7 (Hydrocortisone)
Formula: C21H30O5
Molecular Weight: 362.466
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: N/A
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;
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    Hydrocortisone Basic information Product Name: Hydrocortisone Synonyms: 11,17a,21-Trihydroxy-4-pragnene-3,20-dione;11-beta,17,21-trihydroxypregn-4-ene-3,20-dione;11beta,17,21-Trihydroxyp

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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.