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(5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol

    Cas No: 3275-64-7

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  • 3275-64-7 Structure
  • Basic information

    1. Product Name: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
    2. Synonyms: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;Nsc63329;Madol;(5alpha,17beta)-17-Methylandrost-2-en-17-ol;17a-methyl-etioallocholan-2-ene;Androst-2-en-17-ol,17-methyl-, (5a,17b)-;(5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenthren-17-ol;17-Methyl-5-alpha-androst-2-en-17-beta-ol
    3. CAS NO:3275-64-7
    4. Molecular Formula: C20H32O
    5. Molecular Weight: 288.46748
    6. EINECS: N/A
    7. Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
    8. Mol File: 3275-64-7.mol
  • Chemical Properties

    1. Melting Point: 144-146?C
    2. Boiling Point: 370.69°C (rough estimate)
    3. Flash Point: 160.866 °C
    4. Appearance: /
    5. Density: 0.9789 (rough estimate)
    6. Vapor Pressure: 2.72E-07mmHg at 25°C
    7. Refractive Index: 1.4500 (estimate)
    8. Storage Temp.: Refrigerator
    9. Solubility: N/A
    10. PKA: 15.16±0.60(Predicted)
    11. CAS DataBase Reference: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol(CAS DataBase Reference)
    12. NIST Chemistry Reference: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol(3275-64-7)
    13. EPA Substance Registry System: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol(3275-64-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 3275-64-7(Hazardous Substances Data)

3275-64-7 Usage

Chemical Properties

White Solid

Uses

It is an anabolic er as compared to dihydrotestosterone (DHT).

Check Digit Verification of cas no

The CAS Registry Mumber 3275-64-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,7 and 5 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3275-64:
(6*3)+(5*2)+(4*7)+(3*5)+(2*6)+(1*4)=87
87 % 10 = 7
So 3275-64-7 is a valid CAS Registry Number.
InChI:InChI=1/C20H32O/c1-18-11-5-4-6-14(18)7-8-15-16(18)9-12-19(2)17(15)10-13-20(19,3)21/h4-5,14-17,21H,6-13H2,1-3H3/t14-,15-,16+,17+,18+,19+,20+/m1/s1

3275-64-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol

1.2 Other means of identification

Product number -
Other names Madol

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:3275-64-7 SDS

3275-64-7Synthetic route

methylmagnesium bromide
75-16-1

methylmagnesium bromide

17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;39%
In diethyl ether; benzene
2α-bromo-17β-hydroxy-5α-androstan-3-one
29041-91-6

2α-bromo-17β-hydroxy-5α-androstan-3-one

17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) NaBH4, EtOH, (ii) Zn, AcOH, (iii) NaOH, MeOH
2: CrO3, H2SO4 / acetone
3: diethyl ether; benzene
View Scheme
(5α,17β)-androst-2-en-17-ol
2639-53-4

(5α,17β)-androst-2-en-17-ol

17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CrO3, H2SO4 / acetone
2: diethyl ether; benzene
View Scheme
Epiandrosterone
481-29-8

Epiandrosterone

A

17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

B

17β-hydroxy-17α-methyl-5α-androstan-3-ene
62797-46-0, 94901-78-7, 1229-05-6

17β-hydroxy-17α-methyl-5α-androstan-3-ene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane
2: 2,6-dimethylpyridine / Heating
View Scheme
3β-tosyloxy-5α-androstan-17-one
10429-07-9

3β-tosyloxy-5α-androstan-17-one

methylmagnesium bromide
75-16-1

methylmagnesium bromide

A

17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

B

17β-hydroxy-17α-methyl-5α-androstan-3-ene
62797-46-0, 94901-78-7, 1229-05-6

17β-hydroxy-17α-methyl-5α-androstan-3-ene

Conditions
ConditionsYield
Stage #1: 3β-tosyloxy-5α-androstan-17-one With 2,6-dimethylpyridine Heating;
Stage #2: methylmagnesium bromide In tetrahydrofuran
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

2,3-epoxy-17-methyl-androstan-17-ol
968-54-7

2,3-epoxy-17-methyl-androstan-17-ol

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 5h; Ambient temperature;95%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h; Inert atmosphere;91%
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

17-methyl-5α-androstane-3α,17β-diol
641-82-7

17-methyl-5α-androstane-3α,17β-diol

Conditions
ConditionsYield
(i) B2H6, THF, (ii) aq. H2O2, NaOH; Multistep reaction;
(i) B2H6, (ii) aq. H2O2, OH-; Multistep reaction;
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

2α,17β-Dihydroxy-17α-methyl-androstan
98243-02-8

2α,17β-Dihydroxy-17α-methyl-androstan

Conditions
ConditionsYield
(i) B2H6, THF, (ii) aq. H2O2, NaOH; Multistep reaction;
(i) B2H6, (ii) aq. H2O2, OH-; Multistep reaction;
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

(2R,3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Dihydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-2-carbonitrile
141691-37-4

(2R,3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Dihydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-2-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / m-chloroperoxybenzoic acid / CHCl3 / 5 h / Ambient temperature
2: 98 percent / toluene / 4 h / Ambient temperature
View Scheme
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

C21H33(2)HO4
141691-39-6

C21H33(2)HO4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / m-chloroperoxybenzoic acid / CHCl3 / 5 h / Ambient temperature
2: 98 percent / toluene / 4 h / Ambient temperature
3: 10.6 percent / D2O, CH3OD, Ba(OH)2 / 48 h / 80 °C
View Scheme
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

(2R,3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Dihydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid
141691-38-5

(2R,3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Dihydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / m-chloroperoxybenzoic acid / CHCl3 / 5 h / Ambient temperature
2: 98 percent / toluene / 4 h / Ambient temperature
3: 13 percent / aq. Ba(OH)2 / acetone / 48 h / 80 °C
View Scheme
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

mestanolone
521-11-9

mestanolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) B2H6, THF, (ii) aq. H2O2, NaOH
2: CrO3, aq. H2SO4 / acetone
View Scheme
Multi-step reaction with 2 steps
1: (i) B2H6, (ii) aq. H2O2, OH-
2: aq. CrO3
View Scheme
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

17α-Methyl-2-methylen-androstanol-(17β)

17α-Methyl-2-methylen-androstanol-(17β)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) B2H6, THF, (ii) aq. H2O2, NaOH
2: CrO3, aq. H2SO4 / acetone; dioxane
3: (i) nBuLi, Et2O, (ii) /BRN= 7193671/, THF
View Scheme
Multi-step reaction with 3 steps
1: (i) B2H6, (ii) aq. H2O2, OH-
2: aq. CrO3
View Scheme
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

17α-Methyl-5α-androstan-17β-ol-2-on
10455-12-6

17α-Methyl-5α-androstan-17β-ol-2-on

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) B2H6, THF, (ii) aq. H2O2, NaOH
2: CrO3, aq. H2SO4 / acetone; dioxane
View Scheme
Multi-step reaction with 2 steps
1: (i) B2H6, (ii) aq. H2O2, OH-
2: aq. CrO3
View Scheme
17β-hydroxy-17α-methyl-5α-androst-2-ene
3275-64-7

17β-hydroxy-17α-methyl-5α-androst-2-ene

17β-benzyloxy-17α-methyl-5α-androst-2-ene

17β-benzyloxy-17α-methyl-5α-androst-2-ene

3275-64-7Downstream Products

3275-64-7Relevant articles and documents

Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen-Deuterium Exchange Reactions

Li, Jiaming,Li, Jian,Ji, Xiaoliang,He, Runfa,Liu, Yang,Chen, Zebin,Huang, Yubing,Liu, Qiang,Li, Yibiao

supporting information, p. 7412 - 7417 (2021/10/01)

Herein we have developed a reversible hydrogen-deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of compatibility of functional groups was achieved.

In vitro metabolism studies of desoxy-methyltestosterone (DMT) and its five analogues, and in vivo metabolism of desoxy-vinyltestosterone (DVT) in horses

Kwok, Wai Him,Kwok, Karen Y.,Leung, David K. K.,Leung, Gary N. W.,Wong, Colton H. F.,Wong, Jenny K. Y.,Wan, Terence S. M.

, p. 994 - 1005 (2015/11/10)

The positive findings of norbolethone in 2002 and tetrahydrogestrinone in 2003 in human athlete samples confirmed that designer steroids were indeed being abused in human sports. In 2005, an addition to the family of designer steroids called 'Madol' [also known as desoxy-methyltestosterone (DMT)] was seized by government officials at the US-Canadian border. Two years later, a positive finding of DMT was reported in a mixed martial arts athlete's sample. It is not uncommon that doping agents used in human sports would likewise be abused in equine sports. Designer steroids would, therefore, pose a similar threat to the horseracing and equestrian communities. This paper describes the in vitro metabolism studies of DMT and five of its structural analogues with different substituents at the 17α position (R£H, ethyl, vinyl, ethynyl and 2H3-methyl). In addition, the in vivo metabolism of desoxy-vinyltestosterone (DVT) in horses will be presented. The in vitro studies revealed that the metabolic pathways of DMT and its analogues occurred predominantly in the A-ring by way of a combination of enone formation, hydroxylation and reduction. Additional biotransformation involving hydroxylation of the 17α-alkyl group was also observed for DMT and some of its analogues. The oral administration experiment revealed that DVT was extensively metabolised and the parent drug was not detected in urine. Two in vivo metabolites, derived respectively from (1) hydroxylation of the A-ring and (2) di-hydroxylation together with A-ring double-bond reduction, could be detected in urine up to a maximum of 46 h after administration. Another in vivo metabolite, derived from hydroxylation of the A-ring with additional double-bond reduction and di-hydroxylation of the 17α-vinyl group, could be detected in urine up to a maximum of 70 h post-administration. All in vivo metabolites were excreted mainly as glucuronides and were also detected in the in vitro studies.

2-(N-SUBSTITUTED PIPERAZINYL) STEROID DERIVATIVES

-

Page/Page column 54; 93, (2010/06/17)

Novel chemical agents of Formula I are described herein. More specifically, 2-(N-substituted piperazinyl) pregnane and 2-(N-substituted piperazinyl) androstane derivatives exhibiting cytotoxicity on a variety of cancer cell lines are disclosed herein. (I)

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