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1255-49-8

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  • Testosterone phenylpropionate/ CAS:1255-49-8 /Testosterone phenylpropionate raw material/ high-quality

    Cas No: 1255-49-8

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1255-49-8 Usage

Description

Testosterone phenylpropionate (BAN; TPP) (brand name Testolent), or testosterone phenpropionate, also known as testosterone hydrocinnamate, is a synthetic anabolic-androgenic steroid (AAS) and an androgen ester – specifically, the C17β phenylpropionate ester of testosterone – which was formerly marketed in Romania. It was first synthesized in 1951 and was first described in the literature by 1953. The medication was an ingredient of several isolated AAS commercial products, but was never widely used. Testosterone phenylpropionate was also notably a component of Sustanon and Omnadren, as well as of Estandron Prolongatum, Lynandron Prolongatum, and Mixogen. TPP was previously available in Great Britain.

Biological Functions

Testosterone phenylpropionate is a synthetic anabolic-androgenic steroid (AAS) and an androgen ester. It was first reported in the scientific literature in 1955 and was an ingredient of several isolated AAS commercial products, but was never widely used. Testosterone phenylpropionate was also notably a component of Sustanon and Omnadren.

Synthesis

In a 100 ml reaction flask, 0.397 g (3 mmol) of cinnamaldehyde was added.0.411g (1.5mmol) Nandrolone, 0.06g (0.3mmol) [Bmim][OAc] catalyst, 10ml 1,4-dioxane, heated to 120 ° C and then reacted for 2h, after the reaction was completed, cooled to room temperature, added 30 ml of water and 20 ml of ethyl acetate were extracted, and the phases were allowed to stand. The organic phase was concentrated and crystallized to obtain the target product. The yield was 64%.

Check Digit Verification of cas no

The CAS Registry Mumber 1255-49-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,5 and 5 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1255-49:
(6*1)+(5*2)+(4*5)+(3*5)+(2*4)+(1*9)=68
68 % 10 = 8
So 1255-49-8 is a valid CAS Registry Number.
InChI:InChI=1/C28H36O3/c1-27-16-14-21(29)18-20(27)9-10-22-23-11-12-25(28(23,2)17-15-24(22)27)31-26(30)13-8-19-6-4-3-5-7-19/h3-7,18,22-25H,8-17H2,1-2H3/t22-,23-,24-,25-,27-,28-/m0/s1

1255-49-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Testosterone phenylpropionate

1.2 Other means of identification

Product number -
Other names TESTOSTERONE 17-PHENYLPROPIONATE

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:1255-49-8 SDS

1255-49-8Synthetic route

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

testosterone
58-22-0

testosterone

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
With Zn4(OCOCF3)6O In di-isopropyl ether for 40h; Heating;96%
testosterone
58-22-0

testosterone

3-phenyl-propenal
104-55-2

3-phenyl-propenal

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
With 3-butyl-1-methylimidazolium acetate In 1,4-dioxane at 120℃; for 2h;64%
testosterone triphenylphosphoranylideneacetate
131447-69-3

testosterone triphenylphosphoranylideneacetate

benzyl alcohol
100-51-6

benzyl alcohol

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
With potassium tert-butylate; C16H35BrMnN3O2P2 In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;62.8%
testosterone
58-22-0

testosterone

3-phenylpropionic anhydride
15781-96-1

3-phenylpropionic anhydride

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
With pyridine at 20℃;
at 100℃;
With pyridine at 20℃;
at 100℃;
testosterone
58-22-0

testosterone

hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
With pyridine
With pyridine; benzene
With pyridine
With pyridine; benzene
testosterone
58-22-0

testosterone

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
With carbon dioxide at 220℃;
3-Phenyl-propionic acid (3S,8R,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
52129-14-3

3-Phenyl-propionic acid (3S,8R,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide In toluene
3-Phenyl-propionic acid (3S,8R,9S,10R,13S,14S,17S)-3-acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
52129-09-6

3-Phenyl-propionic acid (3S,8R,9S,10R,13S,14S,17S)-3-acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOH / methanol; CH2Cl2
2: Al(OiPr)3, cyclohexanone / toluene
View Scheme
androstenediol-3-acetate
1639-43-6

androstenediol-3-acetate

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) PhSO2Cl, Py, (ii) /BRN= 2510253/
2: KOH / methanol; CH2Cl2
3: Al(OiPr)3, cyclohexanone / toluene
View Scheme
3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

cell culture of Dioscoreophyllum cumminsii

cell culture of Dioscoreophyllum cumminsii

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) PhSO2Cl, Py, (ii) /BRN= 2510253/
2: KOH / methanol; CH2Cl2
3: Al(OiPr)3, cyclohexanone / toluene
View Scheme
testosterone
58-22-0

testosterone

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N,N-dimethyl-aniline / 1,4-dioxane / 3 h / 0 °C
2: benzene / 24 h
3: sodium hydroxide / water; methanol / 3 h
4: potassium tert-butylate; C16H35BrMnN3O2P2 / 1,4-dioxane / 24 h / 130 °C / Inert atmosphere
View Scheme
17β-bromoacetoxy-4-androsten-3-one
4588-81-2

17β-bromoacetoxy-4-androsten-3-one

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzene / 24 h
2: sodium hydroxide / water; methanol / 3 h
3: potassium tert-butylate; C16H35BrMnN3O2P2 / 1,4-dioxane / 24 h / 130 °C / Inert atmosphere
View Scheme
((8R,9S,10R,13S,14S,17S)-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-yloxycarbonylmethyl)-triphenyl-phosphonium; bromide

((8R,9S,10R,13S,14S,17S)-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-yloxycarbonylmethyl)-triphenyl-phosphonium; bromide

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; methanol / 3 h
2: potassium tert-butylate; C16H35BrMnN3O2P2 / 1,4-dioxane / 24 h / 130 °C / Inert atmosphere
View Scheme
i-Amyl alcohol
123-51-3

i-Amyl alcohol

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

3-isopentyloxy-17β-(3-phenyl-propionyloxy)-androsta-3,5-diene
120024-15-9

3-isopentyloxy-17β-(3-phenyl-propionyloxy)-androsta-3,5-diene

Conditions
ConditionsYield
With 2,2,4-trimethylpentane; toluene-4-sulfonic acid
testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

phenylmethanethiol
100-53-8

phenylmethanethiol

3-benzylsulfanyl-17β-(3-phenyl-propionyloxy)-androsta-3,5-diene
120614-49-5

3-benzylsulfanyl-17β-(3-phenyl-propionyloxy)-androsta-3,5-diene

Conditions
ConditionsYield
With 2,2,4-trimethylpentane; toluene-4-sulfonic acid
testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

3-Chlor-17β-<3-phenyl-propionyloxy>-androsta-3,5-dien
1255-48-7

3-Chlor-17β-<3-phenyl-propionyloxy>-androsta-3,5-dien

Conditions
ConditionsYield
With acetyl chloride; trichlorophosphate
2,2,3,3,3-pentafluoropropanoic anhydride
356-42-3

2,2,3,3,3-pentafluoropropanoic anhydride

testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

2,2,3,3,3-Pentafluoro-propionic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3-phenyl-propionyloxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

2,2,3,3,3-Pentafluoro-propionic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3-phenyl-propionyloxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions
ConditionsYield
at 70℃; for 0.25h;
testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
24589-78-4

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

3-Phenyl-propionic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

3-Phenyl-propionic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With ammonium iodide; 1,4-dithio-erythritol at 60℃; for 0.25h;
testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

3-Phenyl-propionic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-(2,2,2-trifluoro-acetoxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

3-Phenyl-propionic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-(2,2,2-trifluoro-acetoxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
at 70℃; for 0.25h;
testosterone 17β-phenylpropionate
1255-49-8

testosterone 17β-phenylpropionate

heptafluorobutyric anhydride
336-59-4

heptafluorobutyric anhydride

2,2,3,3,4,4,4-Heptafluoro-butyric acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3-phenyl-propionyloxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

2,2,3,3,4,4,4-Heptafluoro-butyric acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3-phenyl-propionyloxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions
ConditionsYield
at 70℃; for 0.25h;

1255-49-8Relevant articles and documents

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Liu, Xin,Werner, Thomas

, p. 1096 - 1104 (2020/12/31)

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

Transesterification of various methyl esters under mild conditions catalyzed by tetranuclear zinc cluster

Iwasaki, Takanori,Maegawa, Yusuke,Hayashi, Yukiko,Ohshima, Takashi,Mashima, Kazushi

, p. 5147 - 5150 (2008/09/21)

(Chemical Equation Presented) A new catalytic transesterification promoted by a tetranuclear zinc cluster was developed. The mild reaction conditions enabled the reactions of various functionalized substrates to proceed in good to high yield. A large-scale reaction under solvent-free conditions proceeded with a low E-factor value (0.66), indicating the high environmental and economical advantage of the present catalysis.

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