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High Quality Dehydroepiandrosterone/DHEA 53-43-0 Factory Supply
Cas No: 53-43-0
No Data 10 Gram 500 Kilogram/Week WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD Contact Supplier
High quality of Dehydroepiandrosterone
Cas No: 53-43-0
USD $ 1.0-1.0 / Metric Ton 1 Metric Ton 1000 Kilogram/Month Career Henan Chemical Co Contact Supplier
Dehydroepiandrosterone
Cas No: 53-43-0
No Data No Data No Data Luyunjia Chemistry Xiamen Limited Contact Supplier
High purity Dehydroepiandrosterone CAS No.:53-43-0
Cas No: 53-43-0
USD $ 2.0-2.0 / Kilogram 1 Kilogram 1 Metric Ton/Month Hangzhou Think Chemical Co. Ltd Contact Supplier
BLOOM TECH Advanced API/Technology support DHEA/Dehydroepiandrosterone CAS 53-43-0
Cas No: 53-43-0
USD $ 5.0-5.0 / Gram 1 Gram 300 Kilogram/Month Shaanxi BLOOM TECH Co.,Ltd Contact Supplier
DHEA hormones 7-keto Dehydroepiandrosterone CAS: 53-43-0 in stock
Cas No: 53-43-0
No Data No Data 10 Metric Ton/Month HANWAYS CHEMPHARM CO.,LIMITED Contact Supplier
Dehydroepiandrosterone CAS NO.53-43-0 DHEA
Cas No: 53-43-0
No Data 10 Gram 100000 Kilogram/Month Shanghai PengMo Biotechnology Co.,Ltd Contact Supplier
Dehydroepiandrosterone/DHEA
Cas No: 53-43-0
No Data 10 Gram 10000 Kilogram/Week Hubei Mawer Biological Technology Co., Ltd. Contact Supplier
High purity dehydroepiandrosterone with high quality cas:53-43-0
Cas No: 53-43-0
USD $ 190.0-290.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
DHEA Dehydroisoandrosterone 53-43-0
Cas No: 53-43-0
USD $ 220.0-230.0 / Kilogram 1 Kilogram 200 Metric Ton/Month Kono Chem Co.,Ltd Contact Supplier

53-43-0 Usage

Brand name

17-chetovis 17-hormoforin;Cetavister;Climatost;Dastonil;Dha-s (prasterone);Gynodian;Longevital 5000;Maxepa;Mentalormon;Mylis;Neurocotex;Psicosterone;Ro 66827;Sh 833;Ultrapla.

Originator

Aslera ,Genelabs Technologies, Inc.

World Health Organization (WHO)

The World Health Organization has no information further to the above regarding preparations containing prasterone or to indicate that such preparations remain available.

Indications and Usage

Dehydroepiandrosterone (DHEA,) chemical name 3β-hydroxy-5alpha-androstane-17-ketone, is an esterifying 3–β–hydroxy steroid retaining 5,6 cholesterol. A white crystalline powder, soluable in ethanol, ether, and benzene, and slightly soluable in chroloform and petroleum ether. Precipitates in digitalis. DHEA is an estrogen precursor secreted by the reticular layer of the human adrenal cortex. Prevents obesity, resists diabetes, fights cancer, fights cortical disease, and delays senility treats immune deficiencies, promotes the growth and differentiation of bone cells, and promotes the synthesis of protein. It also resists viral infections, improves memory, and relieves nervous tension. DHEA is the main ingredient in steroid hormone intermediates (such as norethindrone and bisacetylene, etc.) and in birth control, and is involved in the secretion of many adrenal hormones. It has undergone extensive clinical research on treating menopausal syndrom, chorionitis, coronary heart disease, gout, psoriasis, AIDS and so on.

Mechanisms of Action

DHEA has a thyroid stimulating effect inhibiting food and fat intake and reducing fat accumulation, etc. It improves glucose tolerance, increases insulin level and fights diabetes. It can enhance endocrine system actiity, reduce cortisol levels, and resist a variety of pathological processes. It can help the body obtain cortical antibodies. DHEA has a strong protective and synergistic effect when used to treat tumors, becuase it inhibits ribose 5-phosphate. Inhibits cancer by inhibiting excessive mitochondria (NADPH) and ribose 5-phosphate esters. Regulates the growth of pancreatic cancer cells by regulating the concentration of estrogen in blood plasma. A decline in GnRH gene expression leads to aging, and DHEA can restore GnRH neuronal activity, stopping or improving certain diseases associated with declines in DHEA by stimulating GnRH biosynthesis. Restores impaired immune response, improves T- and B-cell function, and plays an important role in enhancing the physiological activity of insulin-like growth factor (IGF-1,) and is a potentially useful drug for immunodeficiency. DHEA alone cannot directly affect the growth and differential of osteoblasts, but it can do so by influencing 1,25-dihydroxyvitamin D3. The effects of DHEA on bone mass depend on the presence and form of sex hormones in bone cells and their endrocine effects on osteoblasts. DHEA is an anabolic protein hormone which promotes protein synthesis. According to the findings of Marrero and others, feeding DHEA (0.45%) to mice increased liver weight, increasing liver mitochondria by guiding liver protein restoring RNA and protein synthesis.

Safety Profile

An experimental teratogen.Experimental reproductive effects. Questionablecarcinogen with experimental neoplastigenic data. Whenheated to decomposition it emits acrid smoke andirritating fumes.

Chemical Properties

white fine crystalline powder

description

Dehydroepiandrosterone (DHEA) is a steroid hormone that is a popular nonprescription oral “dietary supplement” used by men to enhance cognitive function, mood, libido, and athletic performance. Before 1994, DHEA was a prescription medicine. After the passage of the Dietary Supplement Health and Education Act of 1994, DHEA was reclassified as a nutritional supplement. Although sold over the counter in 25- and 50-mg strengths, DHEA is widely touted to maximize results at doses of 200 mg or higher. DHEA is banned by the International Olympic Committee and the National Collegiate Athletic Association as an anabolic agent. Limited information is available regarding potential harmful effects resulting from its supplemental use.

Therapeutic Function

Glucocorticoid

Uses

Major secretory steroidal product of the adrenal gland; secretion progresively declines with aging. May have estrogen-or androgen-like effects depending on the hormonal milieu. Intracellularly converted to androstenedione. It is used in treatment of menopausal syndrome.

Manufacturing Process

To a solution of 1 gram of 16-dehydropregnenolon-3β-acetate in 10 ml pyridine is added 0.22 gram of hydroxylamine hydrochloride, and the mixture is allowed to stand at room temperature for four days. One gram of 16dehydropregnenolon-3β-acetate oxime is dissolved in 30 ml of hot dioxane, and then the solution is cooled in an ice bath until about one-half of the dioxane has solidified. Then 1 gram of phosphorus pentachloride is added and the mixture is shaken until all the dioxane has melted. The mixture is maintained at 35°C, for seventy-five minutes, then an excess of ice is added and the solution is again allowed to stand at 35°C. After about thirty minutes, a solution of 5 ml of concentrated hydrochloric acid in 10 ml of water is added, and the mixture is diluted with water, extracted with ether and the ethereal extract washed with dilute sodium hydroxide solution. The ether is removed on a steam bath and the residue is worked up to yield dehydroisoandrosterone.

Uses

adrenocortical hormone, antidepressant

Occurrence

DHEA is naturally occurring in yam (see Wild Yam, p. 596-597).
InChI:InChI=1/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15?,16?,18-,19-/m0/s1

53-43-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name dehydroepiandrosterone

1.2 Other means of identification

Product number -
Other names PRASTERONE

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:53-43-0 SDS

53-43-0Synthetic route

prasterone acetate
853-23-6

prasterone acetate

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With sodium hydroxide In methanol98.54%
With methanol; sodium hydroxide at 40℃; for 4h; Inert atmosphere;94.8%
With potassium hydroxide In ethanol
(1aR,3aR,3bS,5aS,8aS,8bR,10aR)-10-Hydroxy-3a,5a-dimethyl-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-one
1028084-93-6

(1aR,3aR,3bS,5aS,8aS,8bR,10aR)-10-Hydroxy-3a,5a-dimethyl-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-one

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With Me3SiN=CMe(1+)*BF4(1-); water In acetonitrile96%
Acetic acid (1aR,3aR,3bS,5aS,8aS,8bR,10aR)-3a,5a-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10-yl ester
24357-31-1, 58691-91-1

Acetic acid (1aR,3aR,3bS,5aS,8aS,8bR,10aR)-3a,5a-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10-yl ester

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With Me3SiN=CMe(1+)*BF4(1-); water In acetonitrile96%
(17Ξ)-spiro[androst-5-en-17,2'-[1,3]oxathiolan]-3β-ol
327622-68-4

(17Ξ)-spiro[androst-5-en-17,2'-[1,3]oxathiolan]-3β-ol

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetone at 20℃; for 8h; Hydrolysis;88%
3β-[2-(triphenylsilyl)ethoxycarbonyloxy]androst-5-en-17-one
1310361-06-8

3β-[2-(triphenylsilyl)ethoxycarbonyloxy]androst-5-en-17-one

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; cesium fluoride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;88%
5-androsten-3β,17α-diol-17-carboxylic acid
81481-38-1

5-androsten-3β,17α-diol-17-carboxylic acid

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite In diethyl ether 1.) 0 deg C -> room temperature, 2.) room temperature, 3 h;85%
Androstenedione
63-05-8

Androstenedione

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
Stage #1: Androstenedione With titanium(IV) oxide; platinum In toluene at 100℃; for 3h;
Stage #2: With hydrogen In toluene under 15001.5 Torr; for 8h; Temperature; Reagent/catalyst; Pressure;
85%
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / tert-butyl alcohol / 1.5 h / 35 - 40 °C / Inert atmosphere
1.2: 20 - 25 °C
2.1: NADP; magnesium(II) chloride hexahydrate; alpha-D-glucopyranose; NAD+ / 2-methyltetrahydrofuran; aq. phosphate buffer / 20 - 32 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: potassium tert-butylate / tert-butyl alcohol / 1 h / 30 - 35 °C / Inert atmosphere
2: D-glucose; NAD; glucose dehydrogenase (CDX-901)_; ketoreductase from Sphingomonas wittichii; potassium carbonate / ethyl acetate; aq. phosphate buffer / 21 h / 32.5 °C / pH 6.3 - 6.5 / Inert atmosphere; Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1: aluminum (III) chloride; 5-sulfosalicylic Acid / 5 h / 20 - 30 °C / Inert atmosphere; Large scale
2: orthoformic acid triethyl ester; boron trifluoride diethyl etherate / dichloromethane / 5 h / 20 - 30 °C / Inert atmosphere
3: calcium borohydride / dichloromethane / 15 h / -20 - -15 °C
4: toluene-4-sulfonic acid / acetone; water / 1 h / 45 - 50 °C / Inert atmosphere
View Scheme
17-oxo-androst-5-en-3β-yl Se-phenyl selenocarbonate
76920-40-6

17-oxo-androst-5-en-3β-yl Se-phenyl selenocarbonate

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

3β-formyl-oxy-5-androsten-17-one
29163-23-3

3β-formyl-oxy-5-androsten-17-one

C

5-androsten-17-one
25824-80-0

5-androsten-17-one

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃;A 9%
B 76%
C 5%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In 1,3,5-trimethyl-benzene at 164℃;A 10%
B 28%
C 62%
3-tetrahydropyran-2-yloxy-androst-5-en-17-one
19637-35-5

3-tetrahydropyran-2-yloxy-androst-5-en-17-one

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In dichloromethane for 24h; Heating;70%
3β-acetoxy-20-hydroxyiminopregna-5,16-diene
23549-24-8, 23549-26-0, 2174-13-2

3β-acetoxy-20-hydroxyiminopregna-5,16-diene

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
Stage #1: 3β-acetoxy-20-hydroxyiminopregna-5,16-diene With pyridine; trichlorophosphate at 0 - 20℃; for 3h; Inert atmosphere;
Stage #2: With methanol; sodium hydroxide for 12h; Reflux;
64%
Stage #1: 3β-acetoxy-20-hydroxyiminopregna-5,16-diene With pyridine; trichlorophosphate In toluene at 10 - 20℃; for 4h; Bechmanns' reaction;
Stage #2: With potassium hydroxide In methanol Heating;
51.8%
With pyridine; trichlorophosphate at -5℃; Beckmann rearrangement;
Multi-step reaction with 2 steps
1: phosphorus (III) oxychloride
2: potassium hydroxide / methanol
View Scheme
16α-iodo-3β-hydroxy-5-androsten-17-one
17134-39-3

16α-iodo-3β-hydroxy-5-androsten-17-one

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

16α-hydroxy dehydroepiandrosterone
1232-73-1

16α-hydroxy dehydroepiandrosterone

Conditions
ConditionsYield
With sodium hydroxide In pyridine; water for 1h;A 20%
B 60%
With sodium hydroxide In pyridine; water for 1h;A 20%
B 60%
With sodium hydroxide In pyridine; water for 1h; Mechanism; var. of NaOH conc. and time;A 20%
B 60%
Trifluoro-methanesulfonic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

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

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

bis(3β-androst-5-en-17-one) ether
66147-28-2

bis(3β-androst-5-en-17-one) ether

Conditions
ConditionsYield
With 1,2,2,6,6-pentamethylpiperidine In water Heating;A 60%
B 40%
3β-O-(tetrahydropyranyl)-17-cycloethylenedioxy-androst-5-ene

3β-O-(tetrahydropyranyl)-17-cycloethylenedioxy-androst-5-ene

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

3β-hydroxy-17,17-ethylenedioxo-5-androstene
7745-40-6, 14456-21-4

3β-hydroxy-17,17-ethylenedioxo-5-androstene

C

3-tetrahydropyran-2-yloxy-androst-5-en-17-one
19637-35-5

3-tetrahydropyran-2-yloxy-androst-5-en-17-one

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In benzene at 25℃; for 40h;A 17%
B 59%
C 2%
With silica gel; copper(II) sulfate In chloroform at 25℃; for 40h;A 51%
B 6%
C 30%
C28H47NO2

C28H47NO2

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.166667h;46%
Phenylselenyl bromide
34837-55-3

Phenylselenyl bromide

androstenone hydrazone
63015-10-1, 77059-27-9

androstenone hydrazone

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

17-bromo-3β-hydroxy-17-selenophenylandrost-5-ene
114474-49-6

17-bromo-3β-hydroxy-17-selenophenylandrost-5-ene

C

3β-hydroxy-17-phenylselenoandrosta-5,16-diene
91414-16-3

3β-hydroxy-17-phenylselenoandrosta-5,16-diene

Conditions
ConditionsYield
With pyridine In tetrahydrofuranA 45%
B 8%
C 20%
5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate
1259-22-9

5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

androst-5-ene-3β,17α-diol
1963-03-7

androst-5-ene-3β,17α-diol

C

17β-methyl-18-norandrosta-5,13-diene-3β-ol
82309-44-2

17β-methyl-18-norandrosta-5,13-diene-3β-ol

17-methyl-18-norandrosta-5,13(17)-diene-3β-ol
23930-65-6

17-methyl-18-norandrosta-5,13(17)-diene-3β-ol

Conditions
ConditionsYield
With potassium acetate In dimethyl sulfoxide at 100℃; for 6h;A 25%
B 41%
C n/a
D n/a
17-(N-2-pyridylmethyl)imino-3β-hydroxy-androst-5-ene

17-(N-2-pyridylmethyl)imino-3β-hydroxy-androst-5-ene

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

(-)-3β,12β-dihydroxyandrost-5-ene-17-one
828938-19-8

(-)-3β,12β-dihydroxyandrost-5-ene-17-one

Conditions
ConditionsYield
Multistep reaction;A 22%
B 35%
cholesterol
57-88-5

cholesterol

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

Androstenedione
63-05-8

Androstenedione

Conditions
ConditionsYield
With [2,2]bipyridinyl; Cephalosporium longisporum; Micrococcus sp; Pseudomonas stutzeri at 29℃; for 72h;A 27%
B 6%
17-(N-2-pyridylmethyl)imino-3β-hydroxy-androst-5-ene

17-(N-2-pyridylmethyl)imino-3β-hydroxy-androst-5-ene

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

12β-chloro-3β-hydroxy-androst-5-en-17-one

12β-chloro-3β-hydroxy-androst-5-en-17-one

C

(-)-3β,12β-dihydroxyandrost-5-ene-17-one
828938-19-8

(-)-3β,12β-dihydroxyandrost-5-ene-17-one

Conditions
ConditionsYield
Multistep reaction;A 21%
B 19%
C 25%
Pregnenolone
145-13-1

Pregnenolone

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

17α-Hydroperoxy-5-pregnen-3β-ol-20-on
34069-59-5

17α-Hydroperoxy-5-pregnen-3β-ol-20-on

Conditions
ConditionsYield
With 18-crown-6 ether In tetrahydrofuran; benzene at 18℃; under 760 Torr; for 24h;A 23%
B 9%
Conditions
ConditionsYield
With Gelasinospora retispora GRK002 In methanol; water at 34℃; for 336h; pH=5; Microbiological reaction;A 23%
B 18%
C 11%
Pregnenolone
145-13-1

Pregnenolone

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

17-Hydroxypregnenolone
387-79-1

17-Hydroxypregnenolone

Conditions
ConditionsYield
With potassium phosphate buffer; α-D-glucose 6-phosphate; NADP; phosphatidylcholine Mechanism; pig 17α-hydroxylase-17,20-lyase, NADPH-cytochrome-P-450-reductase, glucose-6-phosphate dehydrogenase, pH 7.2; also in the presence of cytochrome b5 or bovine tests microsomes; also 3β-hydroxyandrost-5-ene-17β-carbaldehyde;A 16%
B 21%
cholesterol
57-88-5

cholesterol

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

β-sitosterol
83-46-5

β-sitosterol

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

dehydroepiandrosterone sulfate
651-48-9

dehydroepiandrosterone sulfate

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

6β-hydroxy-3α,5-cycloandrostan-17-one
663-39-8, 24357-32-2, 57236-38-1, 118013-84-6

6β-hydroxy-3α,5-cycloandrostan-17-one

Conditions
ConditionsYield
Ausbeute in gepufferten wss. Loesungen (pH 1.2-6.8);
5-androstenedione
571-36-8

5-androstenedione

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
With ethanol; nickel Hydrogenation;
3β-benzoyloxy-androst-5-en-17-one
83205-52-1, 2080-86-6

3β-benzoyloxy-androst-5-en-17-one

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide
17β-Aminoandrost-5-en-3β-ol
4350-66-7

17β-Aminoandrost-5-en-3β-ol

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With diethyl ether; hypochloric acid; sodium sulfate at 0℃; Erwaermen des Reaktionsprodukts mit Natriumaethylat und Aethanol und Behandeln des Reaktionsloesung mit wss.H2SO4;
3β,17-dihydroxy-androst-5-ene-17α-carbonitrile
35060-03-8

3β,17-dihydroxy-androst-5-ene-17α-carbonitrile

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
unter vermindertem Druck;
at 110 - 120℃;
3β-acetoxy-20-methyl-pregnadiene-(5,17(20))
60446-55-1

3β-acetoxy-20-methyl-pregnadiene-(5,17(20))

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Conditions
ConditionsYield
With chloroform; bromine anschliessendes Behandeln mit Ozon; Erhitzen des erhaltenen Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Hydrolysieren des isolierten 3β-Acetoxy-androsten-(5)-ons-(17);
With potassium permanganate; acetic acid at 50℃; Erhitzen des erhaltenen Reaktionsprodukts mit Zink-Pulver und Essigsaeure und Hydrolysieren des isolierten 3β-Acetoxy-androsten-(5)-ons-(17);
formic acid
64-18-6

formic acid

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

3β-formyl-oxy-5-androsten-17-one
29163-23-3

3β-formyl-oxy-5-androsten-17-one

Conditions
ConditionsYield
In water for 19h;100%
at 20 - 25℃; for 4h;100%
for 5h; Reflux;89.3%
for 5h; Reflux;
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

Epiandrosterone
481-29-8

Epiandrosterone

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol at 20℃; under 2068.65 Torr; Inert atmosphere;100%
With palladium on activated charcoal; hydrogen In ethanol under 2068.65 Torr;100%
With palladium 10% on activated carbon; hydrogen In ethanol at 40℃; under 2068.65 Torr; for 12h;99%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

acetic anhydride
108-24-7

acetic anhydride

prasterone acetate
853-23-6

prasterone acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.0111667h; microwave irradiation;100%
With dmap; triethylamine In dichloromethane at 20℃; for 5h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 5h;100%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

ethylene glycol
107-21-1

ethylene glycol

3β-hydroxy-17,17-ethylenedioxo-5-androstene
7745-40-6, 14456-21-4

3β-hydroxy-17,17-ethylenedioxo-5-androstene

Conditions
ConditionsYield
With camphor-10-sulfonic acid In toluene at 111℃;100%
With toluene-4-sulfonic acid In benzene for 4.5h; Heating;99%
With camphor-10-sulfonic acid In cyclohexane for 20h; Reflux;99%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one
42151-23-5

(3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one

Conditions
ConditionsYield
With dmap In dichloromethane 1.) 0 deg C, 1 h, 2.) room temperature, 16 h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 15h;100%
With 1H-imidazole In dichloromethane at 25℃; for 12h;99%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

diethyl dicarbonate
1609-47-8

diethyl dicarbonate

3β-ethoxycarbonyloxyandrost-5-en-17-one
86270-42-0

3β-ethoxycarbonyloxyandrost-5-en-17-one

Conditions
ConditionsYield
for 0.5h; Heating;100%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one
191677-71-1

(3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 120h; Ambient temperature;100%
With impramine99%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 5h;98%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

PdCl2(PPh3)2
3747-91-9

PdCl2(PPh3)2

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 20℃;97%
Stage #1: dehydroepiandrosterone With 1H-imidazole In dichloromethane at 20 - 30℃; for 0.0833333h;
Stage #2: chloro-trimethyl-silane In dichloromethane at 20 - 30℃; for 2h; Reagent/catalyst;
81.6%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

(3S,8R,9S,10R,13S,14S)-5',5',10,13-tetramethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxan]-3-ol

(3S,8R,9S,10R,13S,14S)-5',5',10,13-tetramethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxan]-3-ol

Conditions
ConditionsYield
With camphor-10-sulfonic acid In cyclohexane at 85℃; for 16h; Dean-Stark;99.8%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

dehydroepiandrosterone-17-hydrazone
63015-10-1

dehydroepiandrosterone-17-hydrazone

Conditions
ConditionsYield
With barium sulfate; hydrazine hydrate In ethanol; water at 20 - 30℃; for 12h; Large scale;99.2%
With sulfuric acid; hydrazine hydrate In ethanol at 20℃; for 40h;98.7%
Stage #1: dehydroepiandrosterone With hydrazine hydrate In ethanol at 35℃;
Stage #2: With hydrazinium sulfate In ethanol at 35℃; for 20h;
98.5%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

(3β)-3-(methoxymethoxy)-androst-5-en-17-one
18000-76-5

(3β)-3-(methoxymethoxy)-androst-5-en-17-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3.5h;99%
With N,N-dimethyl-aniline In dichloromethane; benzene for 12h; Ambient temperature;75%
cycloheptanoic acid
1460-16-8

cycloheptanoic acid

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

17-oxaandrost-5-ene-3β-yl cycloheptanoate
1470067-56-1

17-oxaandrost-5-ene-3β-yl cycloheptanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;99%
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;88%
With dmap; dicyclohexyl-carbodiimide In chloroform Steglich Esterification;
With dmap; dicyclohexyl-carbodiimide
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

androst-5-en-3β-ol-17-one mesylate
25810-70-2

androst-5-en-3β-ol-17-one mesylate

Conditions
ConditionsYield
With pyridine at 20 - 25℃; for 20h; Inert atmosphere;98.4%
With pyridine at 20℃; for 24h;76%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

pivaloyl chloride
3282-30-2

pivaloyl chloride

(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ylpivalate
158300-47-1

(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ylpivalate

Conditions
ConditionsYield
With pyridine at 10 - 28℃; for 16.5h;98.1%
With pyridine at 85℃; for 14h;91%
With pyridine; dmap at 0℃; for 4h;5.83 g
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

androst-5-en-3β-ol
1476-64-8

androst-5-en-3β-ol

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate In diethylene glycol a) 120 deg C, 1 h, b) 230 deg C, 3.5 h;98%
Stage #1: dehydroepiandrosterone With hydrazine hydrate In diethylene glycol at 130℃; for 2h; Wolff-Kishner Reduction;
Stage #2: With potassium hydroxide In diethylene glycol at 210℃; for 4h;
Stage #3: With sulfuric acid In water; diethylene glycol
95.8%
With chloro-trimethyl-silane; zinc In methanol; dichloromethane at 0 - 20℃; for 18h; Clemmensen Reduction;75%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

benzaldehyde
100-52-7

benzaldehyde

16-benzylidene-17-oxo-5-androsten-3β-ol
17243-87-7, 74708-33-1

16-benzylidene-17-oxo-5-androsten-3β-ol

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 1h;98%
With methanol; potassium hydrogencarbonate
With Aliquat 336; sodium carbonate In water at 80℃; for 2.5h; Aldol Condensation;
With potassium fluoride on basic alumina In ethanol for 1h; Claisen-Schmidt Condensation; Reflux;
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

benzoyl chloride
98-88-4

benzoyl chloride

3β-benzoyloxy-androst-5-en-17-one
83205-52-1, 2080-86-6

3β-benzoyloxy-androst-5-en-17-one

Conditions
ConditionsYield
With pyridine at 10 - 25℃; Reagent/catalyst; Temperature;98%
With tetramethylurea at 70 - 75℃; for 3h;78%
With pyridine at 20℃; for 12h;76%
With pyridine
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

iopanoic acid
96-83-3

iopanoic acid

dehydroepiandrosterone iopanoate
83172-20-7

dehydroepiandrosterone iopanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;98%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

3β-hydroxy-16α-bromoandrost-5-ene-17-one
1093-91-0

3β-hydroxy-16α-bromoandrost-5-ene-17-one

Conditions
ConditionsYield
With copper(ll) bromide In methanol for 12h; Heating;98%
With copper(ll) bromide In methanol at 70℃; for 12h;97%
With copper(I) bromide In methanol; benzene for 4h; Heating / reflux;62.77%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

1-amino-2-propene
107-11-9

1-amino-2-propene

17β-allylamino-3β-hydroxyandrost-5-ene
1322574-37-7

17β-allylamino-3β-hydroxyandrost-5-ene

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; 1,2-dichloro-ethane at 20℃;98%
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; 1,2-dichloro-ethane for 48h;
Cyclobutanecarboxylic acid
3721-95-7

Cyclobutanecarboxylic acid

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

3β-cyclobutylcarbonyloxy-5-androsten-17-one
1345406-89-4

3β-cyclobutylcarbonyloxy-5-androsten-17-one

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;90.4%
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 2h;84%
With dmap; dicyclohexyl-carbodiimide In chloroform Steglich Esterification;
With dmap; dicyclohexyl-carbodiimide
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

(E)-16-(4-fluorophenyl)methylidene-trans-dehydroandrosterone
1428382-54-0

(E)-16-(4-fluorophenyl)methylidene-trans-dehydroandrosterone

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 1h;98%
With potassium fluoride on basic alumina In ethanol for 1h; Claisen-Schmidt Condensation; Reflux;
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

(E)-16-(2-methylphenyl)methylidene-trans-dehydroandrosterone
1428382-57-3

(E)-16-(2-methylphenyl)methylidene-trans-dehydroandrosterone

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 1h;98%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

dehydroepiandrosterone-17-p-toluenesulfonyl hydrazone
34988-34-6

dehydroepiandrosterone-17-p-toluenesulfonyl hydrazone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran Inert atmosphere; Reflux;98%
With toluene-4-sulfonic acid In tetrahydrofuran Reflux; Inert atmosphere;98%
With toluene-4-sulfonic acid In tetrahydrofuran for 3h; Inert atmosphere;98%
With sulfuric acid In methanol for 5h; Reflux;91.6%
With sulfuric acid In methanol at 15℃; for 2h; Concentration; Reflux;81.4%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

1-(3,4-dichlorophenyl)-1H-1,2,3-triazole-4-carbaldehyde
1325724-92-2

1-(3,4-dichlorophenyl)-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

(E)-16-((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

1-(2-bromophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

1-(2-bromophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(2-bromophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

(E)-16-((1-(2-bromophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

C9H6BrN3O

C9H6BrN3O

(E)-16-((1-(3-bromophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

(E)-16-((1-(3-bromophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

1-(2-fluorophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

1-(2-fluorophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

(E)-16-((1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

1-(3-fluorophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

1-(3-fluorophenyl)-4,5-dihydro-1H-1,2,3-triazole-4-carbaldehyde

(E)-16-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

(E)-16-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-3-hydroxy-10,13-dimethyl-1,3,4,7,8,9,10,11,12,13,15,16-dodecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Reflux;98%

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