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(4R)-4-[(8R,9S,10R,12S,13R,14S,17R)-12-hydroxy-10,13-dimethyl-3-oxo-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid, commonly known as hydrocortisone or cortisol, is a steroid hormone and a glucocorticoid. It is synthesized by the adrenal glands in response to stress and plays a crucial role in regulating metabolism, immune function, and the body's response to inflammation. Hydrocortisone exhibits anti-inflammatory and immunosuppressive properties, making it a valuable compound for treating various medical conditions.

13535-96-1

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13535-96-1 Usage

Uses

Used in Medical Treatments:
Hydrocortisone is utilized as a medication for various conditions, including allergies, asthma, and autoimmune disorders, due to its anti-inflammatory and immunosuppressive properties. It helps alleviate symptoms and manage the severity of these conditions by modulating the immune system's response.
Used in Topical Treatments for Skin Conditions:
Hydrocortisone is commonly used topically in the form of creams or ointments to treat skin conditions such as eczema and dermatitis. It reduces swelling, itching, and redness associated with these conditions by suppressing the inflammatory response in the affected areas.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, hydrocortisone is used as an active ingredient in various formulations, such as tablets, injections, and topical applications, to treat a wide range of medical conditions. Its versatile properties make it a valuable compound for developing new drugs and therapies.
Used in Research and Development:
Hydrocortisone is also used in research and development for studying the effects of glucocorticoids on various biological processes, including inflammation, immune response, and metabolism. Understanding its mechanisms of action can lead to the discovery of new therapeutic targets and the development of more effective treatments for various diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 13535-96-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,5,3 and 5 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 13535-96:
(7*1)+(6*3)+(5*5)+(4*3)+(3*5)+(2*9)+(1*6)=101
101 % 10 = 1
So 13535-96-1 is a valid CAS Registry Number.
InChI:InChI=1/C24H34O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h10-12,14,17-21,26H,4-9,13H2,1-3H3,(H,27,28)/t14-,17+,18-,19+,20+,21+,23+,24-/m1/s1

13535-96-1SDS

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 3-oxo-12α-hydroxy-4,6-choladien-24-oic acid

1.2 Other means of identification

Product number -
Other names 12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

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:13535-96-1 SDS

13535-96-1Synthetic route

12α-formyloxy-3-oxochola-4,6-dien-24-oic acid
88674-57-1

12α-formyloxy-3-oxochola-4,6-dien-24-oic acid

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
With sodium hydroxide Heating;78%
cholic acid
81-25-4

cholic acid

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
With streptomyces-artene
With aspergillus cinnamomeus
12α-acetoxy-3-oxo-choladien-(4,6)-oic acid-(24)
2506-16-3

12α-acetoxy-3-oxo-choladien-(4,6)-oic acid-(24)

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
With potassium hydroxide
3-oxo-7α,12α-diformoxy-5β-cholan-24-oic acid
88674-52-6

3-oxo-7α,12α-diformoxy-5β-cholan-24-oic acid

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / Br2 / acetic acid / Ambient temperature
2: 58 percent / Li2CO3, LiBr / dimethylformamide / 6 h / 120 °C
3: 78 percent / 0.2 N NaOH / Heating
View Scheme
cholic acid triformate
2097-89-4

cholic acid triformate

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 0.2 N NaOH / acetone / Ambient temperature
2: 92 percent / CrO3, H2SO4 / acetone / 0 °C
3: 93 percent / Br2 / acetic acid / Ambient temperature
4: 58 percent / Li2CO3, LiBr / dimethylformamide / 6 h / 120 °C
5: 78 percent / 0.2 N NaOH / Heating
View Scheme
3-oxo-4β-bromo-7α,12α-diformyloxy-5β-cholan-24-oic acid
88674-54-8

3-oxo-4β-bromo-7α,12α-diformyloxy-5β-cholan-24-oic acid

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 58 percent / Li2CO3, LiBr / dimethylformamide / 6 h / 120 °C
2: 78 percent / 0.2 N NaOH / Heating
View Scheme
3α-hydroxy-7α,12α-diformyloxy-5β-cholan-24-oic acid
64986-86-3

3α-hydroxy-7α,12α-diformyloxy-5β-cholan-24-oic acid

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / CrO3, H2SO4 / acetone / 0 °C
2: 93 percent / Br2 / acetic acid / Ambient temperature
3: 58 percent / Li2CO3, LiBr / dimethylformamide / 6 h / 120 °C
4: 78 percent / 0.2 N NaOH / Heating
View Scheme
3-oxo-7α,12α-diacetoxy-5β-cholan-24-oic acid
300386-87-2

3-oxo-7α,12α-diacetoxy-5β-cholan-24-oic acid

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen bromide; acetic acid; bromine
2: pyridine
3: aqueous KOH-solution
View Scheme
4β-bromo-7α.12α-diacetoxy-3-oxo-5β-cholanoic acid-(24)
111825-05-9

4β-bromo-7α.12α-diacetoxy-3-oxo-5β-cholanoic acid-(24)

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aqueous KOH-solution
View Scheme
7-ketodeoxycholic acid
911-40-0

7-ketodeoxycholic acid

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cultures of aspergillus cinnamomeus
2: aspergillus cinnamomeus
View Scheme
12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

12α-hydroxy-3-oxo-chola-4,6-dien-24-oic acid methyl ester
20314-96-9

12α-hydroxy-3-oxo-chola-4,6-dien-24-oic acid methyl ester

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

3,12-dioxo-chola-4,6-dien-24-oic acid
88378-76-1

3,12-dioxo-chola-4,6-dien-24-oic acid

Conditions
ConditionsYield
With chromium(VI) oxide
12α-hydroxy-3-oxochola-4,6-dien-24-oic acid
13535-96-1

12α-hydroxy-3-oxochola-4,6-dien-24-oic acid

3,12-dioxo-chola-4,6-dien-24-oic acid methyl ester
102399-65-5

3,12-dioxo-chola-4,6-dien-24-oic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: CrO3
View Scheme

13535-96-1Downstream Products

13535-96-1Relevant academic research and scientific papers

IMPROVED SYNTHESIS OF 3-KETO, 4-ENE-3-KETO, AND 4,6-DIENE-3-KETO BILE ACIDS

Leppik, Raymond A.

, p. 475 - 484 (1983)

Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80percent yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups.The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60percent yield, via bromination, dehydrobromination, and deformylation.By extending the dehydrobromination reaction, the 7α-formoxyl group of the intermediate 4-ene-3-keto-7α,12α-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.

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