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2152-44-5

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2152-44-5 Usage

Chemical Properties

White Solid

Originator

Valisone,Schering,US,1967

Uses

Different sources of media describe the Uses of 2152-44-5 differently. You can refer to the following data:
1. Betamethasone 17-Valerate is a corticosteroid with anti-inflammatory properties. Topical application of Betamethasone 17-Valerate has been shown to inhibit heat-induced vasodilatation in man.
2. Antiepileptic non-selective phosphodiesterase inhibitor
3. Betamethasone 17-valerate is a glucocorticoid with anti-inflammatory and immunosuppressive activity.
4. A potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties

Definition

ChEBI: A steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester.

Indications

Betamethasone valerate (Psorion, Beta-Val, Luxiq) is a synthetic fluorinated corticosteroid.

Manufacturing Process

The valerate is made from betamethasone as a starting material as follows: A suspension of 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene- 3,20-dione(betamethasone) (2 grams) in sodium dried benzene (500 ml) was distilled vigorously for a few minutes, toluene-p-sulfonic acid monohydrate (30 mg) and methyl orthovalerate (5 ml) were added and distillation was continued for 10 minutes. The mixture was then boiled under reflux for 1.5 hours after which time unreacted betamethasone alcohol (400 mg) was removed by filtration. The benzene solution was treated with solid sodium .bicarbonate and a few drops of pyridine, filtered and evaporated to dryness at about 50°C. The residue, in ether, was filtered through grade III basic alumina (20grams) to remove traces of unreacted betamethasone alcohol, the ether removed in vacuo and the residue of crude betamethasone 17,21- methyl orthovalerate was treated with acetic acid (20ml) and a few drops of water and left overnight at room temperature. The acetic acid solution was poured into water (100 ml) and extracted with chloroform. The chloroform extracts were washed in turn with water, saturated sodium bicarbonate solution and water, dried and evaporated in vacuo. The residual gum was triturated with ether and a white crystalline solid (1.16 grams) isolated by filtration. Recrystallization from ether (containing a small amount of acetone)-petroleum ether gave 9α-fluoro-11β,21-dihydroxy-16β- methyl-17α-valeryloxypregna-1,4-diene-3,20-dione (871 mg) as fine needles.

Brand name

Betatrex (Savage); Luxiq (Connetics); Valisone (Schering).

Therapeutic Function

Corticosteroid

Biochem/physiol Actions

Betamethasone 17-valerate is a synthetic glucocorticoid. It exhibitstherapeutic effects against various allergic and inflammatory skin diseases. Betamethasone 17-valerate also possesses anti-inflammatory properties.

Check Digit Verification of cas no

The CAS Registry Mumber 2152-44-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,5 and 2 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2152-44:
(6*2)+(5*1)+(4*5)+(3*2)+(2*4)+(1*4)=55
55 % 10 = 5
So 2152-44-5 is a valid CAS Registry Number.
InChI:InChI=1/C27H37FO6/c1-5-6-7-23(33)34-27(22(32)15-29)16(2)12-20-19-9-8-17-13-18(30)10-11-24(17,3)26(19,28)21(31)14-25(20,27)4/h10-11,13,16,19-21,29,31H,5-9,12,14-15H2,1-4H3/t16-,19?,20?,21?,24-,25-,26-,27-/m0/s1

2152-44-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Sigma-Aldrich

  • (B1054000)  Betamethasone17-valerate  European Pharmacopoeia (EP) Reference Standard

  • 2152-44-5

  • B1054000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001027)  Betamethasone valerate for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 2152-44-5

  • Y0001027

  • 1,880.19CNY

  • Detail
  • USP

  • (1069007)  Betamethasone valerate  United States Pharmacopeia (USP) Reference Standard

  • 2152-44-5

  • 1069007-200MG

  • 4,662.45CNY

  • Detail

2152-44-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name betamethasone valerate

1.2 Other means of identification

Product number -
Other names Betamethasone 17-valerate

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:2152-44-5 SDS

2152-44-5Synthetic route

aqueous perchloric acid

aqueous perchloric acid

9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-valerate 21-acetate

9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-valerate 21-acetate

betamethasone-valerate
2152-44-5

betamethasone-valerate

Conditions
ConditionsYield
In methanol
trimethyl orthovalerate
13820-09-2

trimethyl orthovalerate

betamethasone
378-44-9

betamethasone

betamethasone-valerate
2152-44-5

betamethasone-valerate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature;
aqueous perchloric acid

aqueous perchloric acid

9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-valerate 21-acetate
5919-89-1

9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17-valerate 21-acetate

betamethasone-valerate
2152-44-5

betamethasone-valerate

Conditions
ConditionsYield
In methanol
betamethasone-valerate
2152-44-5

betamethasone-valerate

N-(all-trans-Retinoyl)-imidazole
61319-45-7

N-(all-trans-Retinoyl)-imidazole

C47H63FO7

C47H63FO7

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 4h; Heating;83%
betamethasone-valerate
2152-44-5

betamethasone-valerate

1-(13-cis-Retinoyl)imidazole
85610-79-3

1-(13-cis-Retinoyl)imidazole

C47H63FO7

C47H63FO7

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 4h; Heating;72%
succinic acid
110-15-6

succinic acid

betamethasone-valerate
2152-44-5

betamethasone-valerate

C58H76F2O14
1351762-42-9

C58H76F2O14

Conditions
ConditionsYield
Stage #1: succinic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: betamethasone-valerate In dichloromethane at 20℃; Inert atmosphere;
53%
betamethasone-valerate
2152-44-5

betamethasone-valerate

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Pentanoic acid (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-17-(2-methanesulfonyloxy-acetyl)-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester
15423-82-2

Pentanoic acid (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-17-(2-methanesulfonyloxy-acetyl)-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
In pyridine at 0 - 5℃; for 1.5h;
betamethasone-valerate
2152-44-5

betamethasone-valerate

(17R)-5'-butyl-4'-ethylthio-9α-fluoro-11β-hydroxy-16β-methyl-spiro-3,3'-dione
128292-26-2

(17R)-5'-butyl-4'-ethylthio-9α-fluoro-11β-hydroxy-16β-methyl-spiro-3,3'-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 78 percent / acetone / 7 h / Ambient temperature
View Scheme
betamethasone-valerate
2152-44-5

betamethasone-valerate

9α-fluoro-11β-hydroxy-16β-methyl-21-methylthio-17α-valeryloxy-1,4-pregnadiene-3,20-dione
128292-10-4

9α-fluoro-11β-hydroxy-16β-methyl-21-methylthio-17α-valeryloxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 91 percent / acetone / 1 h / Ambient temperature
View Scheme
betamethasone-valerate
2152-44-5

betamethasone-valerate

21-ethylthio-9α-fluoro-11β-hydroxy-16β-methyl-17α-valeryloxy-1,4-pregnadiene-3,20-dione
128292-11-5

21-ethylthio-9α-fluoro-11β-hydroxy-16β-methyl-17α-valeryloxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 53 percent / NaOMe / acetone / 0.83 h / Ambient temperature
View Scheme
betamethasone-valerate
2152-44-5

betamethasone-valerate

(17R)-5'-butyl-9α-fluoro-11β-hydroxy-16β-methyl-4'-propylthio-spiro-3,3'-dione
128292-27-3

(17R)-5'-butyl-9α-fluoro-11β-hydroxy-16β-methyl-4'-propylthio-spiro-3,3'-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 74 percent / acetone / 7 h / Ambient temperature
View Scheme
betamethasone-valerate
2152-44-5

betamethasone-valerate

9α-fluoro-11β-hydroxy-16β-methyl-21-propylthio-17α-valeryloxy-1,4-pregnadiene-3,20-dione
128292-12-6

9α-fluoro-11β-hydroxy-16β-methyl-21-propylthio-17α-valeryloxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 80 percent / NaOMe / acetone / 0.83 h / Ambient temperature
View Scheme
betamethasone-valerate
2152-44-5

betamethasone-valerate

(17R)-5'-butyl-4'-butylthio-9α-fluoro-11β-hydroxy-16β-methyl-spiro-3,3'-dione
128292-28-4

(17R)-5'-butyl-4'-butylthio-9α-fluoro-11β-hydroxy-16β-methyl-spiro-3,3'-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 78 percent / acetone / 7 h / Ambient temperature
View Scheme
betamethasone-valerate
2152-44-5

betamethasone-valerate

21-butylthio-9α-fluoro-11β-hydroxy-16β-methyl-17α-valeryloxy-1,4-pregnadiene-3,20-dione
128292-13-7

21-butylthio-9α-fluoro-11β-hydroxy-16β-methyl-17α-valeryloxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 66 percent / NaOMe / acetone / 0.83 h / Ambient temperature
View Scheme
betamethasone-valerate
2152-44-5

betamethasone-valerate

9α-fluoro-11β-hydroxy-16β-methyl-21-phenylthio-17α-valeryloxy-1,4-pregnadiene-3,20-dione
128292-14-8

9α-fluoro-11β-hydroxy-16β-methyl-21-phenylthio-17α-valeryloxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.5 h / 0 - 5 °C
2: 45 percent / NaOMe / acetone / 0.83 h / Ambient temperature
View Scheme
boc-valine (Boc-Val-OH)

boc-valine (Boc-Val-OH)

dicyclohexylcarbodiimidazole

dicyclohexylcarbodiimidazole

betamethasone-valerate
2152-44-5

betamethasone-valerate

A

(2S)-2-((1,1-Dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-3,20-dioxo-9-fluoro-16β-methyl-17-valeroyloxy -pregna-1,4-dien-21-yl] ester (Boc-Val-O-BMV)

(2S)-2-((1,1-Dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-3,20-dioxo-9-fluoro-16β-methyl-17-valeroyloxy -pregna-1,4-dien-21-yl] ester (Boc-Val-O-BMV)

B

(2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-3,20-dioxo-9-fluoro-16β-methyl-17-valeroyloxy-pregna-1,4-dien-21-yl] ester

(2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-3,20-dioxo-9-fluoro-16β-methyl-17-valeroyloxy-pregna-1,4-dien-21-yl] ester

Conditions
ConditionsYield
With dmap In 1,4-dioxane; hexane; dichloromethaneA 10.1 g (73%)
B n/a
succinic acid
110-15-6

succinic acid

(S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid
104091-09-0, 136083-74-4, 121343-82-6

(S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid

betamethasone-valerate
2152-44-5

betamethasone-valerate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine

Fmoc-L-Gln(Trt)-OH
132327-80-1

Fmoc-L-Gln(Trt)-OH

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

betamethasone valerate-succinoyl-EEMQRR-NH2

betamethasone valerate-succinoyl-EEMQRR-NH2

Conditions
ConditionsYield
Stage #1: Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 25 - 32℃; for 5h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h;
Stage #3: succinic acid; (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid; betamethasone-valerate; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Fmoc-L-Gln(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

2152-44-5Relevant articles and documents

Cosmetic use of microorganism(s) for the treatment of scalp disorders

-

, (2010/03/02)

The present invention relates to a use of an effective amount of at least one probiotic microorganism and/or a fraction thereof and/or a metabolite thereof for preventing and/or treating dandruff disorders of the scalp, as well as a cosmetic process for preventing and/or treating a dandruff condition including the administration a first cosmetic active agent and of at least a second cosmetic active agent, topically, the said first and second cosmetic active agents being formulated in separate compositions, the first cosmetic active agent being chosen from probiotic microorganisms, and mixtures thereof, and the second cosmetic active agent being chosen from antidandruff active agents.

Amide derivatives and intermediates for the synthesis thereof

-

, (2008/06/13)

Novel compounds which are amide derivatives represented by general formula (I) and medicinal preparations containing the same having an eosinophilic infiltration inhibitory effect based on a potent interferon (α,γ)-inducing activity and an exellent percutaneous absorbability and being efficacious in treating allergic inflammatory diseases such as atopic dermatitis, various tumors and viral diseases. In said formula, each symbol has the following meaning: R1 and R2 : each lower alkyl, etc.; X and Y: independently representing each oxygen, NR4, CR5 etc. (wherein R4 and R5 independently represent each hydrogen, an aromatic group, etc.); Z: an aromatic ring or heterocycle; R3 : hydrogen, lower alkoxy, etc.; g, i and k: independently representing each an integer of from 0 to 6; h, i and l: independently representing each an integer of 0 or 1; m: an integer of from 0 to 5; and n: an integer of from 2 to 12.

Process of selective solvolysis

-

, (2008/06/13)

The 17α-monoesters and 17α,21-diesters of corticosteriods are well known and represent nowadays the most efficient group of anti-inflammatory compounds for topical application, having minimal systemic action.

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