(8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-17-(tetrahydro-furan-2-yloxy)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
17-methyltestosterone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With <(C4Ph4COHOCC4Ph4)(μ-H)><(CO)4Ru2>; acetone at 56℃; for 18h; | 93% |
With chromium(VI) oxide; bromine; acetic acid Behandeln des Reaktionsprodukts mit CrCl2 in wss.Methanol unter Kohlendioxyd; | |
With aluminum tri-tert-butoxide; acetone; benzene |
17-methyltestosterone
Conditions | Yield |
---|---|
With hydrogenchloride In water; toluene at 60 - 65℃; Solvent; Reagent/catalyst; | 81.6% |
A
17-methyltestosterone
B
5α-17β-hydroxy-17α-methyl-Δ1-androsten-3-one
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 65℃; for 24h; | A 10% B 74% |
With 1-n-butyl-3-methylimidazolim bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione at 65℃; for 22h; | A 10% B 74% |
Conditions | Yield |
---|---|
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature; | 34% |
pyridine
methylandrostenediol
trityl chloride
17-methyltestosterone
Conditions | Yield |
---|---|
Erhitzen des Reaktionsprodukts mit Kupfer-Spaenen unter vermindertem Druck auf 250-300grad; |
3-ethoxyandrosta-3,5-dien-17-one
methylmagnesium bromide
17-methyltestosterone
Conditions | Yield |
---|---|
With diethyl ether; toluene anschliessend Behandeln mit wss.NH4Cl und Behandeln des Reaktionsprodukts mit wss.Saeure; |
Conditions | Yield |
---|---|
With aluminum isopropoxide; toluene |
methylandrostenediol
cyclohexanone
aluminum isopropoxide
toluene
17-methyltestosterone
Conditions | Yield |
---|---|
With pyridine Erhitzen des Reaktionsprodukts mit Kupfer-Spaenen unter vermindertem Druck auf 250-300grad; | |
With pyridine Erhitzen des Reaktionsprodukts mit Kupfer-Spaenen unter vermindertem Druck auf 250-300grad; |
methylandrostenediol
aluminum isopropoxide
acetone
benzene
17-methyltestosterone
methylandrostenediol
aluminum tri-tert-butoxide
acetone
benzene
17-methyltestosterone
Conditions | Yield |
---|---|
With diethyl ether; toluene anschliessend mit wss.NH4Cl und Behandeln des Reaktionsprodukts mit wss.Saeure; |
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit wss.-methanol. CrCl2-Loesung unter Kohlendioxyd; | |
Behandeln des Reaktionsprodukts in Aethanol und Benzol oder in Eisessig mit Zink-Pulver; | |
Behandeln des Reaktionsprodukts in Aethanol und Benzol oder in Eisessig mit Zink-Pulver; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: bromine; acetic acid; CrO3 / Behandeln von Loesungen des Reaktionsprodukts in Aethanol und Benzol oder in Essigsaeure mit Zink-Pulver View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether 2: bromine; acetic acid; CrO3 / Behandeln des Reaktionsprodukts mit CrCl2 in wss.Methanol unter Kohlendioxyd View Scheme |
Progesterone
A
16-dehydroprogesterone
B
17-methyltestosterone
C
Pregnenolone
D
21-Hydroxyprogesterone
E
pregna-4,7-diene-3,20-dione
F
pregnane-3,6,20-trione
G
pregnane-3,20-dione
Conditions | Yield |
---|---|
With Hortaea werneckii B-763 at all growth phases In YNB growth medium; N,N-dimethyl-formamide at 28℃; for 24h; Enzymatic reaction; |
Conditions | Yield |
---|---|
Stage #1: Chlorodifluoromethane With iodine; triethylamine In tetrahydrofuran at 40 - 45℃; for 1h; Stage #2: C22H36O3 In tetrahydrofuran; toluene at 1 - 45℃; for 24h; | 33.9 g |
17-methyltestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine; trichlorophosphate / N,N-dimethyl-formamide 2: sodium hydroxide; sodium tetrahydroborate 3: manganese(IV) oxide View Scheme |
Conditions | Yield |
---|---|
With manganese(IV) oxide |
3-acetyloxypregna-5,16-diene-20-one
17-methyltestosterone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride 2: pyridine; trichlorophosphate / N,N-dimethyl-formamide 3: sodium hydroxide; sodium tetrahydroborate 4: manganese(IV) oxide View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride / ethanol / 20 - 25 °C 2.1: magnesium / tetrahydrofuran / 45 - 50 °C 2.2: 50 - 55 °C 3.1: hydrogenchloride / toluene; water / 60 - 65 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrogenchloride / ethanol / 20 - 25 °C 2.1: magnesium / diethyl ether / 35 - 40 °C 2.2: 50 - 55 °C 3.1: hydrogenchloride / toluene; water / 60 - 65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 45 - 50 °C 1.2: 50 - 55 °C 2.1: hydrogenchloride / toluene; water / 60 - 65 °C View Scheme |
tetrahydrofuran
17-methyltestosterone
(8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-17-(tetrahydro-furan-2-yloxy)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
With tetrachloromethane; manganese at 65℃; for 8h; | 91% |
With ceric triethylammonium nitrate In toluene at 100℃; for 8h; | 40% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium tert-butylate; oxygen In toluene at -25℃; for 4h; | 91% |
17-methyltestosterone
17β-hydroxy-17α-methyl-3,5-seco-4-nor-5-oxo-androstan-3-oic acid
Conditions | Yield |
---|---|
With ozone at -31 - -29℃; for 1.5h; Inert atmosphere; | 87% |
With acetic acid Ozonolyse; | |
With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; water; acetone for 0.5h; | 10.96 g |
17-methyltestosterone
A
(1R,8S,9S,10R,13S,14S,17S)-1,17-Dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-2-oxa-cyclopenta[a]phenanthren-3-one
B
(1S,8S,9S,10R,13S,14S,17S)-1,17-Dihydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-2-oxa-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
With crown ether; potassium tert-butylate; oxygen In toluene 1.) -25 deg C, 1.5-4 h, 2.) room temperature, 3 d; Title compound not separated from byproducts; | A n/a B 85% |
17-methyltestosterone
ethylene glycol
3,3-(ethylenedioxy)-17α-methyl-5-androsten-17β-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 4.5h; Heating; | 82% |
With toluene-4-sulfonic acid; benzene | |
With boron trifluoride diethyl etherate; orthoformic acid triethyl ester In chloroform at 30 - 35℃; for 9h; Solvent; | 22.3 g |
Conditions | Yield |
---|---|
With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 0 - 20℃; for 48h; | 78% |
With selenium(IV) oxide | |
mit Hilfe von Didymella lycopersici; |
17-methyltestosterone
6-Ketomethyltestosterone
Conditions | Yield |
---|---|
With potassium hydroxide; tetrazolium blue In ethanol Heating; | 73% |
Multi-step reaction with 2 steps 1: mit Hilfe von Rhizopus nigricans 2: CrO3; acetic acid View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride at 60℃; for 0.5h; | 65% |
With N-(2-chloro-1,1,2-trifluoroethyl)diethylamine In acetonitrile | |
With hydrogenchloride In methanol Heating; | |
With hydrogenchloride | |
With hydrogenchloride; acetic acid |
17-methyltestosterone
Conditions | Yield |
---|---|
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 312h; Enzymatic reaction; | A 65% B 31% |
17-methyltestosterone
Conditions | Yield |
---|---|
Stage #1: 17-methyltestosterone With C19H26ClIrN3O(1+)*Cl(1-) In water; acetonitrile at 80℃; for 0.166667h; Green chemistry; Stage #2: With formic acid In water; acetonitrile at 80℃; for 2h; Green chemistry; | 63% |
(i) LiAlH4, THF, (ii) aq. HCl, acetone; Multistep reaction; |
formaldehyde diethyl acetal
17-methyltestosterone
17β-hydroxy-17α-methyl-6-methyleneandrost-4-en-3-one
Conditions | Yield |
---|---|
With sodium acetate; trichlorophosphate In chloroform for 1h; Heating; | 51% |
With sodium acetate; trichlorophosphate In chloroform |
Conditions | Yield |
---|---|
With copper(II) nitrate In ethanol for 12h; Heating; | A 47% B 6% |
17-methyltestosterone
B
11α,17β-Dihydroxy-17α-methylandrost-4-en-3-one
C
7α,17β-dihydroxy-17-methyl-4-androsten-3-one
Conditions | Yield |
---|---|
With D-glucose In water; acetone at 25℃; Reagent/catalyst; Microbiological reaction; | A 19% B 17% C 45% |
17-methyltestosterone
C
11α,17β-Dihydroxy-17α-methylandrost-4-en-3-one
D
6β,17β-dihydroxy-17α-methylandrost-4-en-3-one
F
7α,17β-dihydroxy-17-methyl-4-androsten-3-one
Conditions | Yield |
---|---|
With D-glucose In water; acetone at 25℃; Reagent/catalyst; Microbiological reaction; | A 9% B 29% C 5% D 34% E 4% F 6% |
17-methyltestosterone
B
11α,17β-Dihydroxy-17α-methylandrost-4-en-3-one
C
6β,17β-dihydroxy-17α-methylandrost-4-en-3-one
G
7α,17β-dihydroxy-17-methyl-4-androsten-3-one
Conditions | Yield |
---|---|
With D-glucose In water; acetone at 25℃; Reagent/catalyst; Microbiological reaction; | A 31% B 20% C 7% D 7% E 4% F 5% G 16% |
17-methyltestosterone
A
17-methyl-estra-1,3,5(10)-triene-3,17α-diol
D
6β,17β-dihydroxy-17α-methylandrost-4-en-3-one
E
6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one
Conditions | Yield |
---|---|
With Acremonium strictum PTCC 5282 strain at 25℃; for 144h; pH=6.5; Enzymatic reaction; | A 7.6% B 24.3% C 16.7% D 28.4% E 9.5% |
17-methyltestosterone
A
6β,17β-dihydroxy-17α-methylandrost-4-en-3-one
Conditions | Yield |
---|---|
With fungus Cephalosporium aphidicola In ethanol for 120h; hydroxylation; | A 17% B 4% |
Conditions | Yield |
---|---|
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4; | A 14% B n/a C n/a |
17-methyltestosterone
Conditions | Yield |
---|---|
With silica gel for 46h; Irradiation; | 7.9% |
Conditions | Yield |
---|---|
for 4h; Irradiation; | A 1% B 5% |
pyrrolidine
17-methyltestosterone
17α-methyl-3-pyrrolidino-androsta-3,5-dien-17β-ol
Conditions | Yield |
---|---|
With benzene |
Conditions | Yield |
---|---|
With tetrahydrofuran; ammonia; lithium |
Conditions | Yield |
---|---|
With copper(II) sulfate at 135 - 150℃; under 0.01 Torr; |
IUPAC Name: (8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Molecular Structure:
Molecular Formula : C20H30O2
Molecular Weight : 302.45
CAS NO: 58-18-4
EINECS : 200-366-3
Index of Refraction: 1.556
Surface Tension: 43.7 dyne/cm
Density: 1.1 g/cm3
Flash Point: 185.3 °C
Enthalpy of Vaporization: 79.71 kJ/mol
Boiling Point: 434.4 °C at 760 mmHg
Vapour Pressure: 2.28E-09 mmHg at 25 °C
Melting point 162-168 &dec;C
Alpha : 79 º (c=1, alcohol)
Storage temp: 2-8 °C
Solubility H2O: ≤0.5 mg/mL
Appearance: Methyltestosterone (CAS NO. 58-18-4) is white to slightly yellowish-white crystalline .
Classification Code of Methyltestosterone (CAS NO. 58-18-4): Anabolic Agents; Androgen; Antineoplastic Agents; Antineoplastic agents, hormonal; Drug / Therapeutic Agent; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Mutation data; Reproductive Effect; Tumor data
1.Methyltestosterone (CAS NO. 58-18-4) is used for androgen medicines, used for supplement treatment with testosterone deficiency .
2.Methyltestosterone (CAS NO. 58-18-4) can also be used for functional bleeding of uterine, aplastic anemia and other diseases treatment.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | oral | 39mg/kg/33W-I (39mg/kg) | LIVER: "JAUNDICE, CHOLESTATIC" | American Journal of Gastroenterology. Vol. 82, Pg. 461, 1987. |
mouse | LD50 | intraperitoneal | 400mg/kg (400mg/kg) | Drugs in Japan Vol. 6, Pg. 830, 1982. | |
mouse | LD50 | oral | 1860mg/kg (1860mg/kg) | Drugs in Japan Vol. 6, Pg. 830, 1982. | |
mouse | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 830, 1982. | |
rat | LD50 | intraperitoneal | 1050mg/kg (1050mg/kg) | Drugs in Japan Vol. 6, Pg. 830, 1982. | |
rat | LD50 | oral | 2500mg/kg (2500mg/kg) | Drugs in Japan Vol. 6, Pg. 830, 1982. | |
rat | LD50 | subcutaneous | 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 830, 1982. |
Hazard Codes: T,Xn,Xi ,F
Risk Statements: 45-63-22-20-19-11-61-60-36/37/38
R45:May cause cancer.
R63:Possible risk of harm to the unborn child.
R22:Harmful if swallowed.
R20:Harmful by inhalation.
R19:May form explosive peroxides.
R11:Highly flammable.
R60:May impair fertility.
R61:May cause harm to the unborn child.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 53-36/37-45-24/25-22
S53:Avoid exposure - obtain special instructions before use.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24/25:Avoid contact with skin and eyes.
S22:Do not breathe dust.
RIDADR: 3249
WGK Germany: 3
RTECS: BV8400000
HazardClass: 6.1(b)
PackingGroup: III
Methyltestosterone (CAS NO. 58-18-4), its Synonyms are (17-beta)-17-Hydroxy-17-methylandrost-4-en-3-one ; 17(alpha)-Methyl-delta4-androsten-17(beta)-ol-3-one ; 17-Hydroxy-17-methyl-3-keto-androstene-4 ; 17-beta-Hydroxy-17-methylandrost-4-en-3-one ; 17alpha-Methyl-3-oxo-4-androsten-17beta-ol ; 17alpha-Methyl-delta-androsten-17beta-ol-3-one ; M.T.Mucorettes ; Malestrone ; Androst-4-en-3-one, 17-beta-hydroxy-17-methyl- ; Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17beta)- ; Androst-4-en-3-one, 17beta-hydroxy-17-methyl- .
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