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6157-87-5

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6157-87-5 Usage

Description

Trestolone Acetate is a synthetic and injectable anabolic and androgenic steroid (AAS) that has been derived from the famous steroid nandrolone (19-nortestosterone) that doesn’t have any medical uses but is very helpful for physique and performance enhancement purposes.This steroid has firstly been described in 1963 and although there are many people searching and using Trestolone Acetate, is not as famous as many other steroids.Trestolone Acetate is also known as MENT acetate or Ment Trestolone and this is a steroid considered really beneficial for purpose of bodybuilding and strength training. Known as a steroid that is more powerful than testosterone, Trestolone is believed to offer fast and effective results.Ment Trestolone is believed to be the only steroid that can maintain a normal male physiology in a complete absence of testosterone, even including sexual life.

Uses

Trestolone is a synthetic anabolic-androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group. In Vivo: Trestolone is used as trestolone acetate, which is administered via intramuscular injection and acts as a long-lasting prodrug of trestolone.

Definition

Trestolone acetate is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was never marketed. It is an androgen ester – specifically, the C17 acetate ester of [DB05830].

Side effects

Trestolone Acetate is quite obvious to offer negative side effects when is considered to be about 10 times more potent than testosterone. Side effects are only possible and they can be well reduced or completely avoided if you know how to use the compound properly.For example, if you would use a PCT plan at the end of the cycle all along with various meds (like Aromatase Inhibitors) and different cycle supporting supplements, without exceeding cycle length and dosage then you would be fine in most cases (unless you have low tolerance or pre existent health issues).Side effects include those of estrogen related (since it aromatizes) and the obvious androgen related ones. All in all, side effects include:AcneHair lossWater retentionHypertensionGynecomastiaAggressionSuppressionNegative effects on lipidsAffects cardiovascular health and othersRemember to use Ment Trest properly if you want to avoid the side effects, because an improper use is almost guaranteeing getting negative side effects.

Check Digit Verification of cas no

The CAS Registry Mumber 6157-87-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,5 and 7 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6157-87:
(6*6)+(5*1)+(4*5)+(3*7)+(2*8)+(1*7)=105
105 % 10 = 5
So 6157-87-5 is a valid CAS Registry Number.
InChI:InChI=1/C21H30O3/c1-12-10-14-11-15(23)4-5-16(14)17-8-9-21(3)18(20(12)17)6-7-19(21)24-13(2)22/h11-12,16-20H,4-10H2,1-3H3

6157-87-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 17.β.-Hydroxy-7.α.-methylestr-4-en-3-one acetate

1.2 Other means of identification

Product number -
Other names MENT 17-acetate

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:6157-87-5 SDS

6157-87-5Synthetic route

6-dehydro-19-nortestosterone acetate
2590-41-2

6-dehydro-19-nortestosterone acetate

methylmagnesium chloride
676-58-4

methylmagnesium chloride

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper diacetate In tetrahydrofuran at -45 - -35℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 10℃; for 0.5h;
78%
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper(l) chloride In tetrahydrofuran at -30℃; for 3 - 4h;
Stage #2: With sulfuric acid; water In tetrahydrofuran for 1.33333h;
7alpha-Methyl-19-nortestosterone acetate

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: zirconocene methyl chloride With silver trifluoromethanesulfonate; copper(l) chloride; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine In diethyl ether; dichloromethane at 20℃; for 0.166667h; Darkness; Inert atmosphere;
Stage #2: 6-dehydro-19-nortestosterone acetate With chloro-trimethyl-silane In diethyl ether; dichloromethane at 20℃; for 15h; Inert atmosphere; Darkness; stereoselective reaction;
61%
6-dehydro-19-nortestosterone acetate
2590-41-2

6-dehydro-19-nortestosterone acetate

methylmagnesium chloride
676-58-4

methylmagnesium chloride

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper diacetate In tetrahydrofuran at -45 - -35℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 10℃; for 0.5h;
78%
Stage #1: 6-dehydro-19-nortestosterone acetate; methylmagnesium chloride; copper(l) chloride In tetrahydrofuran at -30℃; for 3 - 4h;
Stage #2: With sulfuric acid; water In tetrahydrofuran for 1.33333h;
zirconocene methyl chloride

zirconocene methyl chloride

6-dehydro-19-nortestosterone acetate
2590-41-2

6-dehydro-19-nortestosterone acetate

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Stage #1: zirconocene methyl chloride With silver trifluoromethanesulfonate; copper(l) chloride; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine In diethyl ether; dichloromethane at 20℃; for 0.166667h; Darkness; Inert atmosphere;
Stage #2: 6-dehydro-19-nortestosterone acetate With chloro-trimethyl-silane In diethyl ether; dichloromethane at 20℃; for 15h; Inert atmosphere; Darkness; stereoselective reaction;
61%
17β-hydroxy-7α-methyl-estr-5-en-3-one acetate
54793-00-9

17β-hydroxy-7α-methyl-estr-5-en-3-one acetate

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene
7α-methyl-19-nortestosterone
3764-87-2

7α-methyl-19-nortestosterone

acetyl chloride
75-36-5

acetyl chloride

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
With pyridine at 20℃;
19-nortestosterone
434-22-0

19-nortestosterone

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: AcCl
2: (i) NBS, Py, aq. NaOAc, AcOH, acetone, (ii) LiBr, Li2CO3, DMF
3: (i) CuI, Et2O, (ii) /BRN= 3121674/, THF
4: TsOH / benzene
View Scheme
3,17β-diacetoxy-estra-3,5-diene
4999-76-2

3,17β-diacetoxy-estra-3,5-diene

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) NBS, Py, aq. NaOAc, AcOH, acetone, (ii) LiBr, Li2CO3, DMF
2: (i) CuI, Et2O, (ii) /BRN= 3121674/, THF
3: TsOH / benzene
View Scheme
6-dehydro-19-nortestosterone acetate
2590-41-2

6-dehydro-19-nortestosterone acetate

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) CuI, Et2O, (ii) /BRN= 3121674/, THF
2: TsOH / benzene
View Scheme
C24H38O3Si

C24H38O3Si

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

Conditions
ConditionsYield
With water In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

17β-acetoxy-4-chloro-7α-methylestr-4-en-3-one
2061-47-4

17β-acetoxy-4-chloro-7α-methylestr-4-en-3-one

Conditions
ConditionsYield
With pyridine; sulfuryl dichloride for 1h; Ambient temperature;80%
methanol
67-56-1

methanol

7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

3-methoxy-7α-methylestra-1,3,5(10)-trien-17β-ol
15506-01-1

3-methoxy-7α-methylestra-1,3,5(10)-trien-17β-ol

Conditions
ConditionsYield
Stage #1: methanol; 7alpha-Methyl-19-nortestosterone acetate With copper(ll) bromide In toluene at 17 - 23℃; Industry scale;
Stage #2: With potassium hydroxide In water Heating / reflux; Industry scale;
80%
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

3-hydroxy-7α-methylestra-1,3,5(10)-trien-17β-yl acetate
14507-68-7

3-hydroxy-7α-methylestra-1,3,5(10)-trien-17β-yl acetate

Conditions
ConditionsYield
With lithium bromide; copper(ll) bromide In acetonitrile for 2.5h; Ambient temperature;77%
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

methyllithium
917-54-4

methyllithium

Acetic acid (7S,8R,9S,10R,13S,14S,17S)-3,7,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Acetic acid (7S,8R,9S,10R,13S,14S,17S)-3,7,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
(i) THF, Et2O, (ii) aq. HCl, acetone; Multistep reaction;
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

17β-Acetoxy-3-brom-androsta-3,5-dien
800-09-9

17β-Acetoxy-3-brom-androsta-3,5-dien

Conditions
ConditionsYield
With phosphorus(V) oxybromide In acetic acid
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

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

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

Conditions
ConditionsYield
(i) LiAlH4, THF, (ii) aq. HCl, acetone; Multistep reaction;
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

4-chloro-7α-methyl-17β-estradiol
137576-19-3

4-chloro-7α-methyl-17β-estradiol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 85 percent / SeO2 / 2-methyl-propan-2-ol / 15 h / Heating
3: 85 percent / 5percent KOH / methanol / 1 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 80 percent / pyridine / acetic anhydride / 3 h / Heating
3: 60 percent / N-bromosuccinimide, water / dimethylformamide / 0.5 h / 0 °C
4: 1) HCl, 2) 5percent KOH / 1) acetone, reflux 2.5 h, 2) MeOH, reflux, 1 h
View Scheme
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

4-chloro-7α-methylestrone
137576-22-8

4-chloro-7α-methylestrone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 85 percent / SeO2 / 2-methyl-propan-2-ol / 15 h / Heating
3: 85 percent / 5percent KOH / methanol / 1 h / Heating
4: 80 percent / Jones' reagent / acetone / 0.33 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 80 percent / pyridine / acetic anhydride / 3 h / Heating
3: 60 percent / N-bromosuccinimide, water / dimethylformamide / 0.5 h / 0 °C
4: 1) HCl, 2) 5percent KOH / 1) acetone, reflux 2.5 h, 2) MeOH, reflux, 1 h
5: 80 percent / Jones' reagent / acetone / 0.33 h / Ambient temperature
View Scheme
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

4-chloro-17α-ethynyl-7α-methyl-17β-estradiol
137576-23-9

4-chloro-17α-ethynyl-7α-methyl-17β-estradiol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 85 percent / SeO2 / 2-methyl-propan-2-ol / 15 h / Heating
3: 85 percent / 5percent KOH / methanol / 1 h / Heating
4: 80 percent / Jones' reagent / acetone / 0.33 h / Ambient temperature
5: 75 percent / dimethylsulfoxide / 72 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 80 percent / pyridine / acetic anhydride / 3 h / Heating
3: 60 percent / N-bromosuccinimide, water / dimethylformamide / 0.5 h / 0 °C
4: 1) HCl, 2) 5percent KOH / 1) acetone, reflux 2.5 h, 2) MeOH, reflux, 1 h
5: 80 percent / Jones' reagent / acetone / 0.33 h / Ambient temperature
6: 75 percent / dimethylsulfoxide / 72 h / Ambient temperature
View Scheme
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

17β-acetoxy-4-chloro-7α-methyl-17β-estradiol
137576-18-2

17β-acetoxy-4-chloro-7α-methyl-17β-estradiol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 85 percent / SeO2 / 2-methyl-propan-2-ol / 15 h / Heating
View Scheme
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

17β-acetoxy-6β-bromo-4-chloro-7α-methylestr-4-en-3-one
137576-21-7

17β-acetoxy-6β-bromo-4-chloro-7α-methylestr-4-en-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 80 percent / pyridine / acetic anhydride / 3 h / Heating
3: 60 percent / N-bromosuccinimide, water / dimethylformamide / 0.5 h / 0 °C
View Scheme
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

4-chloro-7α-methylestra-3,5(6)-diene-3,17β-diyl diacetate
137576-20-6

4-chloro-7α-methylestra-3,5(6)-diene-3,17β-diyl diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / pyridine, SO2Cl2 / 1 h / Ambient temperature
2: 80 percent / pyridine / acetic anhydride / 3 h / Heating
View Scheme
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

3-bromo-androsta-3,5-dien-17β-ol
60397-54-8

3-bromo-androsta-3,5-dien-17β-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POBr3 / acetic acid
2: aq. NaOH / methanol
View Scheme
7alpha-Methyl-19-nortestosterone acetate
6157-87-5

7alpha-Methyl-19-nortestosterone acetate

7α-methyl-19-nortestosterone
3764-87-2

7α-methyl-19-nortestosterone

Conditions
ConditionsYield
Stage #1: 7alpha-Methyl-19-nortestosterone acetate With methanol; potassium hydroxide for 3 - 4h;
Stage #2: With citric acid pH=6;

6157-87-5Relevant articles and documents

Structure-activity relationship study of human liver microsomes-catalyzed hydrolysis rate of ester prodrugs of MENT by comparative molecular field analysis (CoMFA)

Bursi, Roberta,Grootenhuis, Arijan,Van Der Louw, Jaap,Verhagen, Jos,De Gooyer, Marcel,Jacobs, Peter,Leysen, Dirk

, p. 213 - 220 (2003)

A series of MENT esters (3-71) was designed, prepared and tested to study the structure-activity relationship (SAR) of the hydrolysis rate with human liver microsomes of these prodrugs. Compounds were obtained covering a wide range of metabolic stability. The results are useful for the proper selection of prodrugs for different pharmaceutical formulations to deliver the potent and prostate-sparing androgen MENT. The MENT esters can especially be administered for male hormone replacement therapy and male contraception. Comparative molecular field analysis (CoMFA) was applied to a dataset of 28 esters, for which ED50 values could be obtained. The CoMFA model where the electrostatic and H-bond molecular fields were combined turned out to be most predictive. Despite the limited size of the dataset, CoMFA can help to rationalize the SAR of the ester hydrolysis rate of ester prodrugs of MENT.

Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

Li, Chun,Qiu, Wenwei,Yang, Zhengfeng,Luo, Jian,Yang, Fan,Liu, Mingyao,Xie, Juan,Tang, Jie

experimental part, p. 859 - 869 (2010/10/18)

A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803.

Process for the production of 7alpha-methyl steroids

-

Page 4, (2008/06/13)

This invention relates to a process for the production of 7α-methyl steroids of general formula I, starting from compounds of general formula II, which are reacted in an aprotic solvent in the presence of 1-30 mol % of a copper compound CuYnLm with 1-3 molar equivalents of CH3MgX, then with a strong acid. The process according to the invention is distinguished in that 7α-methyl steroids are obtained in good yields as well as high chemical purity and high diastereomer purities. The process is distinguished in that less waste accumulates with considerably higher throughput. The process according to the invention can therefore be suitable for the production of 7α-methyl steroids on the industrial scale.

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