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BLOOM TECH Advanced API/Technology support Hydrocortisone CAS 50-23-7
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50-23-7 Usage

General Description

Hydrocortisone, 11β,17,21-trihydroxypregn-4-ene-3,20-dione, is the primary natural GCin humans. Despite the large number of synthetic GCs, hydrocortisone,its esters, and its salts remain a mainstay ofmodern adrenocortical steroid therapy and the standard forcomparison of all other GCs and MCs . It isused for all the indications mentioned previously.

Definition

ChEBI: A C21-steroid that is pregn-4-ene substituted by oxo groups at positions 3 and 20 and hydroxy groups at positions 11, 17 and 21. Cortisol is a corticosteroid hormone or glucocorticoid produced by zona fasciculata of the adrenal cortex, which is a part of the adrenal gland. It is usually referred to as the "stress hormone" as it is involved in response to stress and anxiety, controlled by corticotropin-releasing hormone (CRH). It increases blood pressure and blood sugar, and reduces immun responses

Brand name

Acticort (Baker Norton); Ala-Cort (Del Ray); Cetacort (Healthpoint); Colocort (Paddock); Cort- Dome (Bayer); Cortef (Pharmacia & Upjohn); Cortenema (Solvay Pharmaceuticals); Cortril (Pfizer); Dermacort (Monarch); Dermacort (Solvay Pharmaceuticals); Eldecort (Valeant); Epicort (Bluline); Flexicort (Westwood- Squibb); Glycort (Heran); Hi-Cor (C & M); Hydro-Rx (X Gen); Hydrocortone (Merck); Hytone (Dermik); Hytone (Sanofi Aventis); Nutracort (Healthpoint); Penecort (Allergan); Proctocort (Monarch); Stie-Cort (Stiefel); Synacort (Medicis); Texacort (Sirius).

Chemical Synthesis

Hydrocortisone, 11β,17α,21-trihydroxypregn-4-en-3,20-dione (27.1.8), is synthesized in various ways and from various compounds containing a steroid skeleton. According to one of them, hydrocortisone is synthesized from dextropregnenolone. The double bond between C16 and C17 of dextropregnenolone is oxidized using hydrogen peroxide in a base, forming an epoxide 27.1.1. Interacting this with hydrobromic acid opens the epoxide ring, forming 16-bromo-17-hydroxydextropregnenolone (27.1.2). The resulting bromo derivative undergoes debromination by hydrogen using a palladium on carbon catalyst, and then the secondary hydroxyl group undergoes esterification using formic acid in the presence of p-toluenesulfonic acid, giving 3-formyloxy-17-hydroxydextropregnenolone (27.1.3). The resulting 3-formyloxy- 17-hydroxydextropregnenolone undergoes bromination by bromine, which results in bromination of the C4–C5 double bond and the methyl group of acetyl moiety, which forms a tribromo derivative 27.1.4. Reacting the product with sodium iodide results in dehalogenation of the resulting vicinal dibromide, during which the double bond is simultaneously shifted into the position between carbon atoms C5 and C6 that gives the bromoketone 27.1.5. This is reacted with potassium acetate and then with acetic anhydride in the presence of p-toluenesulfonic acid, forming a diacetate 27.1.6. Taking into account that unlike acetates, formates are easily oxidized and give exactly the same products as do the corresponding alcohols, the resulting diacetate is oxidized in an Oppenauer oxidation reaction, using aluminum isopropoxide and cyclohexanone as a hydrogen acceptor. During this, isomerization of the double bond into the primary position between C4 and C5 simultaneously takes place, forming a stable, conjugated vinylketone, after which the acetyl protection of both hydroxyl groups is hydrolyzed using potassium hydroxide, giving 17-hydroxy-11-deoxycorticosterone (27.1.7). This undergoes microbiological oxidation at position C1, forming the desired hydrocortisone (27.1.8). Side reactions of microbiological oxidation using the very same microorganisms can cause hydroxylation of steroids in different positions, using easily accessible progesterone as an initial substance.

Uses

glucocorticoid, antiinflammatory

Purification Methods

Recrystallise hydrocortisone from EtOH or isoPrOH. It is bitter tasting and has UV with max at 242 nm (log 4.20). Its solubility at 25o is: H2O (0.28%), EtOH (1.5%), MeOH (0.62%), Me2CO (0.93%), CHCl3 (0.16%), propylene glycol (1.3%) and Et2O (0.35%). It gives an intense green colour with conc H2SO4. [Wendler et al. J Am Chem Soc 72 5793 1950, Beilstein 8 IV 3422.]

Veterinary Drugs and Treatments

Because of its rapid effect and relatively high mineralocorticoid effect, hydrocortisone sodium succinate (Solu-Cortef?) is the most commonly used form of this medication when an acute glucocorticoid/ mineralocorticoid effect is desired (e.g., acute adrenal insufficiency). Corticosteroids have not been shown beneficial in treating hypovolemic shock, but low dose glucocorticoids probably reduce mortality associated with septic shock. Glucocorticoids have been used in an attempt to treat practically every malady that afflicts man or animal, but there are three broad uses and dosage ranges for use of these agents. 1) Replacement of glucocorticoid activity in patients with adrenal insufficiency, 2) as an antiinflammatory agent, and 3) as an immunosuppressive. Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases (e.g., rheumatoid arthritis), collagen diseases (e.g., systemic lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic diseases (e.g., pemphigus, allergic dermatoses), hematologic disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias), neoplasias, nervous system disorders (increased CSF pressure), GI diseases (e.g., ulcerative colitis exacerbations), and renal diseases (e.g., nephrotic syndrome). Some glucocorticoids are used topically in the eye and skin for various conditions or are injected intra-articularly or intra-lesionally. The above listing is certainly not complete.

Uses

Principle glucocorticoid hormone produced by adrenal cortex. An anti-inflammatory hormone.

Safety Profile

Poison by

Originator

Hydrocortone,MSD,US,1952

Mechanism of action

Hydrocortisone exhibits anti-shock, anti-allergy, and anti-inflammatory action. It raises sugar content in the blood, increases potassium secretion, and lowers sodium excretion from the body. It exhibits anti-metabolic action and reduces histamine synthesis in the body.

Health Hazard

Cortisol Increases (1) protein catabolism (excepting liver) gluconeogenesis; (2) carbohydrate anabolism (liver); (3) blood sugar; (4) glucose absorption; (5) brain excitation; (6) spread of infections; (7)urinary glucose and nitrogen; (8) stress tolerance; (9) lactation; (10) water diuresis.Regulates general adaptation syndrome, water balance, blood pressure, and hormone release.Decreases (1) fat anabolism; (2) growth rate; (3) inflammation; (4) eosinophils; (5) lymphocytes; (6) antigen sensitivity; (7) respiratory quotient; (8) ketosis; (9) wound healing; (10) skin pigmentation; (11)RBC hemolysis.

Indications

Hydrocortisone (Cortizone, Cortaid, Anusol-HC, Hytone, LactiCare-HC, Sarnol HC, Penecort, Texacort, and many other branded products) may be purchased as a generic drug.

Therapeutic Function

Glucocorticoid

Uses

Cortisol, or Hydrocortisone, is a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.

Chemical Properties

crystalline white powder

Contact allergens

Hydrocortisone is the principal glucocorticoid hor- mone produced by the adrenal cortex and is used topi- cally or systemically. It belongs to the allergenic A group. Marker of allergy is tixocortol pivalate.

Manufacturing Process

The following example from US Patent 2,602,769 illustrates the preparation of 17-hydroxycorticosterone (compound F) from 11-desoxy-17- hydroxycorticosterone (compound S). A medium was prepared from 0.5% peptone, 2% dextrose, 0.5% soybean meal, 0.5% KH2PO4, 0.5% sodium chloride and 0.3% yeast extract in tap water. To 200 ml of this sterilized medium was added an inoculum of the vegetative mycella of Cunninghamella blakesleeana. The spores had first been transferred from a sport slant to a broth medium and the broth medium was aerobically incubated at 24°C for 24 to 72 hours in a .reciprocating shaker until the development of vegetative growth. The inoculated medium containing added vegetative mycella of Cunninghamella blakesleeana was incubated for 48 hours at 24°C following which was added 66 mg of compound S, 11-desoxy-17-hydroxycorticosterone in solution in a minimum of ethanol, and incubation was maintained for 7 hours at 24°C. The beer containing steroid was diluted with 800 ml of acetone, shaken 1 hour on a reciprocating shaker and filtered. The cake was suspended in 500 ml of acetone, shaken another hour and again filtered. The filtrates were combined and the acetone was volatilized under reduced pressure at 50°C. Acetone was then added, if necessary, to bring the concentration to 20% acetone and this resulting aqueous acetone solution was extracted five times each with one-third volume of Skellysolve B petroleum ether to remove fatty materials. These extracts were back washed two times with one-tenth volume of 20% aqueous acetone and the washings were added to the main acetone extract. The combined acetone extracts were extracted six times with one-fourth volume of ethylene dichloride and the ethylene dichloride extract was evaporated under vacuum to leave the steroid residue. This steroid residue was taken up in a minimum of methylene chloride and applied to the top of a column packed with 30 grams of silica which had been previously triturated with 21 ml of ethylene glycol. Then various developing mixtures, saturated with ethylene glycol, were passed over the column. Cuts were made as each steroid was eluted as determined by the lowering of the absorption of light at 240 nm on the automatic chromatographic fraction cutter. Band Solvent Tube No. (60ml) Crude Solids (mg) 1 Cyclohexane 1-4 11 2 Cyclohexane-methylene chloride 3:1 5-13 6.4 compound S 3 Cyclohexane-methylene chloride 1:1 14-16 3.0 4 Cyclohexane-methylene chloride 2:3 17-23 6.0 compound E 5 Cyclohexane-methylene chloride 1:4 24-38 12.2 compound F 6 Methylene chloride 39-59 4.8 A 7.7 mg portion of band 5 was taken up in a minimum of acetone and refrigerated until crystals separated. This cold acetone mixture was centrifuged and the supernatant liquid removed by pipette. To the remaining crystals, a few drops of ice-cold ether-acetone, three to one mixture, were added, shaken, recentrifuged and the supernatant wash liquid removed by pipette. The ether-acetone wash was repeated. The resulting crystals were dried under vacuum yielding 3.3 mg of pure compound F, 17- hydroxycorticosterone.

Clinical Use

Hydrocortisone is endogenous, and it has both glucocorticoid and mineralocorticoid activity. It is the fundamental structure by which the glucocorticoid and mineralocorticoid activities of all other corticosteroids are judged. Functional groups that are essential for both mineralocorticoid and glucocorticoid activity include the pregnane skeleton with an all-trans backbone, the ring A-en-one system (?4 -3-one ring A) and the 17β-ketol side chain (C-20-keto-C-21-hydroxy). The glucocorticoid activity is enhanced by the C-11 and C-17 hydroxyl groups. Hydrocortisone can be used to treat severe asthmatic attacks that do not respond to conventional treatment. It is available as various ester forms.
InChI:InChI=1/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+/m1/s1

50-23-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (H0533)  Hydrocortisone  >98.0%(HPLC) 50-23-7 1g 100.00CNY Detail
TCI America (H0533)  Hydrocortisone  >98.0%(HPLC) 50-23-7 25g 800.00CNY Detail
Alfa Aesar (A16292)  Hydrocortisone, 98%    50-23-7 1g 206.0CNY Detail
Alfa Aesar (A16292)  Hydrocortisone, 98%    50-23-7 5g 861.0CNY Detail
Alfa Aesar (A16292)  Hydrocortisone, 98%    50-23-7 25g 2316.0CNY Detail

50-23-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name cortisol

1.2 Other means of identification

Product number -
Other names Alacort

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50-23-7 SDS

50-23-7Synthetic route

hydrocortisone acetate
50-03-3

hydrocortisone acetate

HYDROCORTISONE
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

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

HYDROCORTISONE
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%
Cortexolone
152-58-9

Cortexolone

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

Cortisone
53-06-5

Cortisone

C

Androstenedione
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%
Cortexolone
152-58-9

Cortexolone

HYDROCORTISONE
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;
21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-disemicarbazone
104117-71-7

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

HYDROCORTISONE
50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With potassium borohydride anschliessend mit HNO2;
3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17,21-triol
76338-54-0

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

HYDROCORTISONE
50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With sulfuric acid
Progesterone
57-83-0

Progesterone

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

17-hydroxyprogesterone
68-96-2

17-hydroxyprogesterone

C

21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

D

Corticosterone
50-22-6

Corticosterone

E

Cortexolone
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
Progesterone
57-83-0

Progesterone

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

C

Corticosterone
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.
Progesterone
57-83-0

Progesterone

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

Corticosterone
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.
17-hydroxyprogesterone
68-96-2

17-hydroxyprogesterone

HYDROCORTISONE
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;
17-hydroxyprogesterone
68-96-2

17-hydroxyprogesterone

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

testosterone
58-22-0

testosterone

C

Androstenedione
63-05-8

Androstenedione

D

Cortexolone
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.
Cortexolone
152-58-9

Cortexolone

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

Cortisone
53-06-5

Cortisone

C

Epicortisol
566-35-8

Epicortisol

D

14,17,21-trihydroxy-pregn-4-ene-3,20-dione
595-18-6

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

E

(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
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.
Epicortisol
566-35-8

Epicortisol

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

Cortisone
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.
hydrocortisone hemisuccinate
2203-97-6

hydrocortisone hemisuccinate

HYDROCORTISONE
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

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

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

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

hydrocortisone sodium succinate

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

Cortisone
53-06-5

Cortisone

C

(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
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

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

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

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

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

(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

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

L-lysine
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

(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

Hydrocortisone pivalate

HYDROCORTISONE
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

HYDROCORTISONE
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

HYDROCORTISONE
50-23-7

HYDROCORTISONE

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

Pregnenolone

A

HYDROCORTISONE
50-23-7

HYDROCORTISONE

B

testosterone
58-22-0

testosterone

C

Androstenedione
63-05-8

Androstenedione

D

21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

E

Corticosterone
50-22-6

Corticosterone

F

Cortexolone
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
Cortisone acetate
50-04-4

Cortisone acetate

HYDROCORTISONE
50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: KBH4 / anschliessend mit HNO2
View Scheme
22-acetoxy-11β-hydroxy-3-oxo-23,24-dinor-5β-chol-17(20)ξ-ene-21-nitrile
102213-14-9

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

HYDROCORTISONE
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
RU 18760
64313-94-6

RU 18760

HYDROCORTISONE
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
Epicortisol
566-35-8

Epicortisol

HYDROCORTISONE
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
3,3;20,20-bis-ethanediyldioxy-17,21-dihydroxy-pregn-5-en-11-one
101524-47-4

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

HYDROCORTISONE
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
3,20-bis(ethylenedioxy)-11α,17α,21-trihydroxypregn-5-ene
102030-55-7

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

HYDROCORTISONE
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
HYDROCORTISONE
50-23-7

HYDROCORTISONE

(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
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

acetic anhydride
108-24-7

acetic anhydride

hydrocortisone acetate
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

diethyl dicarbonate
1609-47-8

diethyl dicarbonate

Hydrocortisone-21-ethyl carbonate

Hydrocortisone-21-ethyl carbonate

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

HYDROCORTISONE

5β-pregnane-11β,17α,21-triol-3,20-dione
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

C23H32O4

C23H32O4

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

succinic acid anhydride

HYDROCORTISONE
50-23-7

HYDROCORTISONE

hydrocortisone hemisuccinate
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

prednisolon
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;
succinic acid anhydride
108-30-5

succinic acid anhydride

HYDROCORTISONE
50-23-7

HYDROCORTISONE

hydrocortisone-succinate-hydrocortisone

hydrocortisone-succinate-hydrocortisone

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

HYDROCORTISONE

21-dehydrohydrocortisone dimer

21-dehydrohydrocortisone dimer

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

succinic acid anhydride

HYDROCORTISONE
50-23-7

HYDROCORTISONE

hydrocortisone sodium succinate

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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

cortienic acid
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%
formaldehyd
50-00-0

formaldehyd

HYDROCORTISONE
50-23-7

HYDROCORTISONE

6-methine 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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

21-tert-butyldimethylsilyloxy-11β,17-dihydroxypregn-4-ene-3,20-dione
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%
succinic acid anhydride
108-30-5

succinic acid anhydride

HYDROCORTISONE
50-23-7

HYDROCORTISONE

21-(3-Carboxy-1-oxopropoxy)-17α-hydroxy-11α-hydroxypregna-4-ene-3,20-dione
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(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
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

11β,7α-dihydroxy-21-<(methylsulfonyl)oxy>pregn-4-ene-3,20-dione
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

Corticosterone
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

hexanoic acid
142-62-1

hexanoic acid

21-hexanoyloxy-11β,17α-dihydroxypregn-4-en-3,20-dione
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

acetic acid methyl ester
79-20-9

acetic acid methyl ester

hydrocortisone acetate
50-03-3

hydrocortisone acetate

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

HYDROCORTISONE

Octanoic acid
124-07-2

Octanoic acid

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

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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

adrenosterone
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
HYDROCORTISONE
50-23-7

HYDROCORTISONE

C14H19NO4
1070955-54-2

C14H19NO4

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
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

methyl hexanoate
106-70-7

methyl hexanoate

21-hexanoyloxy-11β,17α-dihydroxypregn-4-en-3,20-dione
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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

methyl octanate
111-11-5

methyl octanate

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

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

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

HYDROCORTISONE

1-allyl-1-isopropoxysiletane

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

(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%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

methacrylic anhydride

methacrylic anhydride

cortisol 21-monomethacrylate

cortisol 21-monomethacrylate

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

HYDROCORTISONE

4-bromocortisol

4-bromocortisol

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

HYDROCORTISONE

acetic anhydride
108-24-7

acetic anhydride

A

3,11β,17α,21-tetraacetoxy-3,5-pregnadiene-20-one
991-08-2

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

B

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