Product Name

  • Name

    Betamethasone 17-valerate

  • EINECS 218-439-3
  • CAS No. 2152-44-5
  • Article Data13
  • CAS DataBase
  • Density 1.24 g/cm3
  • Solubility 9.29 mg/L at 25 °C in water
  • Melting Point 183-184oC
  • Formula C27H37FO6
  • Boiling Point 598.9 °C at 760 mmHg
  • Molecular Weight 476.586
  • Flash Point 316 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance White powder
  • Safety 22-24/25
  • Risk Codes 48
  • Molecular Structure Molecular Structure of 2152-44-5 (Betamethasone 17-valerate)
  • Hazard Symbols HarmfulXn
  • Synonyms Pregna-1,4-diene-3,20-dione,9-fluoro-11b,17,21-trihydroxy-16b-methyl-, 17-valerate (7CI,8CI);9a-Fluoro-16b-methylprednisolone 17-valerate;Beta-Val;Betamethasone valerate;Betnesol V;Betnovate;Betoid;Bextasol;Celestan V;Celestoderm;Celeston valerate;Dermovaleas;Fuciderm;Rinderon V;Tokuderm;b-Methasone 17-valerate;
  • PSA 100.90000
  • LogP 3.63680

Synthetic 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
...Expand
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;
...Expand

Betamethasone 17-valerate Chemical Properties


IUPAC Name: [(8S,9R,10S,11S,13S,14S,16S,17R)-9-Fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] pentanoate
Molecular Weight: 476.577483 [g/mol]
Molecular Formula: C27H37FO6
XLogP3: 3.6
H-Bond Donor: 2
H-Bond Acceptor: 7 
EINECS: 218-439-3
storage temp.: 2-8 °C 
Index of Refraction: 1.56
Molar Refractivity: 123.71 cm3
Molar Volume: 382.3 cm3
Surface Tension: 50.8 dyne/cm
Density: 1.24 g/cm3
Flash Point: 316 °C
Enthalpy of Vaporization: 102.31 kJ/mol
Boiling Point: 598.9 °C at 760 mmHg
Vapour Pressure: 7.72E-17 mmHg at 25 °C
Water Solubility: 9.29 mg/L at 25 °C
Melting Point: 183-184 °C
Classification Code of Betamethasone 17-valerate (CAS NO.2152-44-5): Adrenal Cortex Hormones; Anti-Inflammatory Agents; Drug / Therapeutic Agent; Glucocorticoid; Glucocorticoids; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Reproductive Effect 

Betamethasone 17-valerate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 632mg/kg (632mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
mouse LD50 oral 4067mg/kg (4067mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
mouse LD50 subcutaneous 496mg/kg (496mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
rabbit LD50 subcutaneous 61200ug/kg (61.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat LD50 intraperitoneal > 4500mg/kg (4500mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat LD50 oral > 3gm/kg (3000mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat LDLo subcutaneous 2gm/kg (2000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 2102, 1977.

Betamethasone 17-valerate Safety Profile

Poison by subcutaneous route. Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of F−.
Hazard Codes: HarmfulXn
Risk Statements: 48 
R48:Danger of serious damage to health by prolonged exposure.
Safety Statements: 22-24/25 
S24/25:Avoid contact with skin and eyes. 
S22:Do not breathe dust.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 2
RTECS: TU3835000

Betamethasone 17-valerate Specification

  Betamethasone 17-valerate (CAS NO.2152-44-5), its Synonyms are Betamethasone valerate ; 9-Fluoro-11-beta,17,21-trihydroxy-16-beta-methylpregna-1,4-diene-3,20-dione-17-valerate ; 9-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-valerate ; Betaderm ; Betamethason-17-valerate ; Betatrex ; Betnovate ; Betnovateat ; Celestoderm ; Dermabet ; Luxiq ; Pregna-1,4-diene-3,20-dione, 9-fluoro-11,21-dihydroxy-16-methyl-17-((1-oxopentyl)oxy)-, (11beta,16beta)- ; Valisone ; Valnac ; beta-Methasone 17-valerate ; beta-Val .

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View