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100% Natural Cyanotis Arachnoidea Extract 98% Ecdysterone
Cas No: 5289-74-7
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Ecdysterone CAS NO.5289-74-7
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High Quality beta ecdysterone powder
Cas No: 5289-74-7
USD $ 5.0-9.0 / Gram 10 Gram 100 Metric Ton/Month Salus Nutra Inc Contact Supplier
Beta-Ecdysone Hydroxyecdysone 5289-74-7
Cas No: 5289-74-7
USD $ 600.0-600.0 / Kilogram 1 Kilogram 5000 Metric Ton/Day Kono Chem Co.,Ltd Contact Supplier
Pure Bulk 95% Beta Ecdysterone or 20-Hydroxyecdysone or 20-Hydroxy Ecdysterone Powder with Best Price 5289-74-7
Cas No: 5289-74-7
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Cyanotis Arachnoisea Extract Powder 50%-98% Ecdysterone
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USD $ 2160.0-2160.0 / Kilogram 5 Kilogram 2000 Kilogram/Week ShangHai Soyoung Biotechnology Inc Contact Supplier
beta ecdysterone powder uv90 95 cas 5289-74-7
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Beta-Ecdysterone
Cas No: 5289-74-7
No Data 20 Milligram 5 Gram/Day Chengdu Alfa Biotechnology Co.,Ltd. Contact Supplier
Cyanotis Arachnoisea Extract 95% beta Ecdysterone
Cas No: 5289-74-7
USD $ 15.0-15.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Greenutra Resource Inc Contact Supplier
factory supply 98% Hydroxyecdysone Ecdysone Extract β-ecdysone
Cas No: 5289-74-7
USD $ 175.0-550.0 / Kilogram 1 Kilogram 20 Metric Ton/Month Sinoway Industrial Co., Ltd. Contact Supplier

5289-74-7 Usage

Purification Methods

Crystallise -ecdyson from water, tetrahydrofuran/pet ether, MeOH and EtOAc after chromatographic purification. It has max (EtOH) at 240nm ( 12,670 M-1cm-1). [Also IR & NMR: Hüppi & Siddall J Am Chem Soc 89 6799 1967, Kametani et al. Tetrahedron Lett 21 4855 1980, Beilstein 8 IV 343.]

Chemical Properties

White or off-white powder

Definition

ChEBI: An ecdysteroid that is ecdysone substituted by a hydroxy group at position 20.

Uses

insect molting hormone
InChI:InChI=1/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15?,17?,19-,20+,21?,22-,24-,25-,26-,27-/m1/s1

5289-74-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (H1480)  20-Hydroxyecdysone  >97.0%(HPLC) 5289-74-7 25mg 790.00CNY Detail
TCI America (H1480)  20-Hydroxyecdysone  >97.0%(HPLC) 5289-74-7 100mg 2,350.00CNY Detail

5289-74-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 20-hydroxyecdysone

1.2 Other means of identification

Product number -
Other names (2β,3β,5β,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one

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:5289-74-7 SDS

5289-74-7Synthetic route

(8R,20R,22R)-2β,3β,20,22,25-pentahydroxy-8,13-cyclo-13,14-seco-5β-cholestane-6,14-dione

(8R,20R,22R)-2β,3β,20,22,25-pentahydroxy-8,13-cyclo-13,14-seco-5β-cholestane-6,14-dione

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2.5h; Heating;89%
14alpha-Hydroperoxy-20-hydroxyecdysone
115040-67-0

14alpha-Hydroperoxy-20-hydroxyecdysone

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

(8R,20R,22R)-2β,3β,20,22,25-pentahydroxy-8,13-cyclo-13,14-seco-5β-cholestane-6,14-dione

(8R,20R,22R)-2β,3β,20,22,25-pentahydroxy-8,13-cyclo-13,14-seco-5β-cholestane-6,14-dione

Conditions
ConditionsYield
With iron(II) sulfate In tetrahydrofuran; water Ambient temperature; pH=3;A 5%
B 85%
(2S,3R,5R,9R,10R,13R,14S,17S)-14-Hydroxy-17-((1R,2R)-5-hydroxy-1,2-diisopropoxy-1,5-dimethyl-hexyl)-2,3-diisopropoxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one

(2S,3R,5R,9R,10R,13R,14S,17S)-14-Hydroxy-17-((1R,2R)-5-hydroxy-1,2-diisopropoxy-1,5-dimethyl-hexyl)-2,3-diisopropoxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With lithium In tetrahydrofuran; ammonia for 1h;82%
(20R,22R)-22-hydroxy-2β,3β,14,20,25-pentakis-(trimethyl-silanyloxy)-5β-cholest-7-en-6-one
135024-06-5

(20R,22R)-22-hydroxy-2β,3β,14,20,25-pentakis-(trimethyl-silanyloxy)-5β-cholest-7-en-6-one

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

(20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one
123238-67-5

(20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;A 80%
B n/a
22-Dehydro-20-hydroxyecdysone
19974-12-0

22-Dehydro-20-hydroxyecdysone

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

(20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one
123238-67-5

(20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one

Conditions
ConditionsYield
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran 1) -78 deg C, 3h, 2) 20 deg C, 1h;A 6%
B 68%
Yield given. Yields of byproduct given;
With lithium tri-t-butoxyaluminum hydride Yield given. Multistep reaction. Yields of byproduct given;
Turkesterone
41451-87-0

Turkesterone

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With sodium nitrite; palladium on activated charcoal In ethanol; water under 760 Torr; for 1h;67%
(20R,22R)-2β,3β,14α,25-tetrahydroxy-20,22-(butan-2-yl)boranediyldioxy-5β-cholest-7-en-6-one
1450761-60-0

(20R,22R)-2β,3β,14α,25-tetrahydroxy-20,22-(butan-2-yl)boranediyldioxy-5β-cholest-7-en-6-one

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With dihydrogen peroxide In tetrahydrofuran; water for 0.166667h;58%
(20R,22R)-6-ethoxy-5β-cholesta-6,8(14)-diene-2β,3β,20,22,25-pentol

(20R,22R)-6-ethoxy-5β-cholesta-6,8(14)-diene-2β,3β,20,22,25-pentol

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

14alpha-Hydroperoxy-20-hydroxyecdysone
115040-67-0

14alpha-Hydroperoxy-20-hydroxyecdysone

Conditions
ConditionsYield
With oxalic acid In methanol for 6h; Ambient temperature; darkness;A 9%
B 57%
2,3-didehydro-2,3-dideoxy-20-hydroxyecdysone
1373335-50-2

2,3-didehydro-2,3-dideoxy-20-hydroxyecdysone

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

2,3-di-epi-20-hydroxyαecdysone

2,3-di-epi-20-hydroxyαecdysone

Conditions
ConditionsYield
With pyridine; osmium(VIII) oxideA 54%
B 32%
20-hydroxyecdysone-2,3,22-triacetate
19404-87-6, 84507-62-0

20-hydroxyecdysone-2,3,22-triacetate

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With potassium hydroxide In methanol Heating;
(20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one
54289-60-0

(20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
Yield given. Multistep reaction;
2,22-dideoxyecdysone
41408-38-2

2,22-dideoxyecdysone

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

ecdysone
3604-87-3

ecdysone

C

22-Deoxyecdysone
34209-85-3

22-Deoxyecdysone

Conditions
ConditionsYield
With Locusta migratoria at 33℃; for 6h; Product distribution; tissue distr. of C22 hydroxylase;
ecdysterone 20-O-benzoate
114317-60-1

ecdysterone 20-O-benzoate

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With potassium hydrogencarbonate In methanol; water at 20 - 38℃; for 204h;7 mg
Sileneoside B
84699-93-4

Sileneoside B

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

ecdysterone 22-O-α-D-galactopyranoside
81655-86-9

ecdysterone 22-O-α-D-galactopyranoside

Conditions
ConditionsYield
In water at 27℃; for 528h; galactosidase;A 10 mg
B 7 mg
14alpha-Hydroperoxy-20-hydroxyecdysone
115040-67-0

14alpha-Hydroperoxy-20-hydroxyecdysone

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With dimethylsulfide In dichloromethane Ambient temperature; Yield given;
Acetic acid (2S,3R,5R,9R,10R,13R,14S,17S)-3-acetoxy-17-((S)-1,5-dihydroxy-1,5-dimethyl-hexyl)-14-hydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester

Acetic acid (2S,3R,5R,9R,10R,13R,14S,17S)-3-acetoxy-17-((S)-1,5-dihydroxy-1,5-dimethyl-hexyl)-14-hydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

Taxisterone

Taxisterone

Conditions
ConditionsYield
With potassium carbonate In methanol for 0.5h; Ambient temperature;A n/a
B 11 mg
(2S,3R,5R,9R,10R,13R,14S,17S)-10,13-Dimethyl-17-((1R,2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl)-1,2,3,4,5,6,9,10,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-2,3,6,14-tetraol
69841-30-1

(2S,3R,5R,9R,10R,13R,14S,17S)-10,13-Dimethyl-17-((1R,2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl)-1,2,3,4,5,6,9,10,11,12,13,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-2,3,6,14-tetraol

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane
Multi-step reaction with 2 steps
1: O2 / Pt / H2O
2: NaBH4 / ethanol; tetrahydrofuran
View Scheme
Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; ethanol
ecdysone
3604-87-3

ecdysone

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With ecdysone 20-monooxygenase; oxygen; NADPH hydroxylation catalyzed by ecdysone 20-monooxygenase; other reagents;
20-hydroxyecdysone 3-O-α-D-galactoside
93552-68-2

20-hydroxyecdysone 3-O-α-D-galactoside

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With almond enzymes; water at 36℃; for 720h; Hydrolysis; Enzymatic reaction;
ecdysone
3604-87-3

ecdysone

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

3-epi-26-hydroxyecdysone
75319-59-4

3-epi-26-hydroxyecdysone

C

26-hydroxyecdysone
52717-49-4

26-hydroxyecdysone

E

3-epi-20,26-dihydroxyecdysone
71939-17-8

3-epi-20,26-dihydroxyecdysone

F

20,26-dihydroxyecdysone
19458-46-9

20,26-dihydroxyecdysone

G

4 polar acidic metabolites

4 polar acidic metabolites

Conditions
ConditionsYield
metabolism after injection into Pieris brassicae (Lepidoptera) pharate pupae, 3H labeled study;

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

inokosterone
88980-54-5

inokosterone

C

25-deoxy-20-hydroxyecdyson-26-oic acid
59971-16-3

25-deoxy-20-hydroxyecdyson-26-oic acid

D

20-hydroxyecdyson-26-oic acid
86583-58-6

20-hydroxyecdyson-26-oic acid

E

20,26-dihydroxyecdysone
19458-46-9

20,26-dihydroxyecdysone

F

very polar products (VVP), conjugates (C)

very polar products (VVP), conjugates (C)

Conditions
ConditionsYield
With air; D-glucose; epidermis of premolt crab Carcinus maenas L; penicillin G; 2-amino-2-hydroxymethyl-1,3-propanediol; monophenylthiourea In water at 20℃; for 48h; Mechanism; different metabolism after incubation of various tissues or injection in intermolt and premolt crabs (Carcinus maenas L.), 3H labeled studies;
26-hydroxyecdysone
52717-49-4

26-hydroxyecdysone

A

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

B

ecdysone
3604-87-3

ecdysone

C

3-epi-26-hydroxyecdysone
75319-59-4

3-epi-26-hydroxyecdysone

E

3-epi-20,26-dihydroxyecdysone
71939-17-8

3-epi-20,26-dihydroxyecdysone

F

20,26-dihydroxyecdysone
19458-46-9

20,26-dihydroxyecdysone

G

4 polar acidic metabolites

4 polar acidic metabolites

Conditions
ConditionsYield
metabolism after injection into Pieris brassicae (Lepidoptera) pharate pupae, 3H labeled study;
[2β-2H]cholesterol
54594-70-6

[2β-2H]cholesterol

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With Tween 80; hairy roots of Ajuga reptans var. atropurpurea In methanol; chloroform; acetone hydroxylation; Irradiation;6.0 mg
20-Hydroxyecdysone-3-beta-D-glucopyranoside
128365-93-5

20-Hydroxyecdysone-3-beta-D-glucopyranoside

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With hydrogenchloride In methanol for 4h; Heating;
6β-hydroxy-5α-cholest-2-ene
27948-74-9

6β-hydroxy-5α-cholest-2-ene

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 83 percent / p-TsOH*H2O / CH2Cl2 / 0.5 h / 20 °C
2: 80 percent / m-chloroperbenzoic acid; Na2CO3 / CH2Cl2 / 0.5 h / 20 °C
3: 93 percent / LiAlD4 / tetrahydrofuran / 0.5 h / 60 °C
4: pyridinium chlorochromate; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 0.17 h / 20 °C
5: LiAlH4 / tetrahydrofuran / 0.33 h / 20 °C
6: pyridine / 20 °C
7: 2 N aq. HCl / methanol; tetrahydrofuran / 6 h / 20 °C
8: POCl3; pyridine / 3 h / 20 °C
9: KOH / methanol; tetrahydrofuran / 20 °C
10: 6.0 mg / hairy roots of Ajuga reptans var. atropurpurea; Tween 80 / acetone; CHCl3; methanol / Irradiation
View Scheme
C29H47(2)HO2
264925-89-5

C29H47(2)HO2

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOH / methanol; tetrahydrofuran / 20 °C
2: 6.0 mg / hairy roots of Ajuga reptans var. atropurpurea; Tween 80 / acetone; CHCl3; methanol / Irradiation
View Scheme
2-[(5S,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yloxy]-tetrahydro-pyran
264925-82-8

2-[(5S,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yloxy]-tetrahydro-pyran

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 80 percent / m-chloroperbenzoic acid; Na2CO3 / CH2Cl2 / 0.5 h / 20 °C
2: 93 percent / LiAlD4 / tetrahydrofuran / 0.5 h / 60 °C
3: pyridinium chlorochromate; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 0.17 h / 20 °C
4: LiAlH4 / tetrahydrofuran / 0.33 h / 20 °C
5: pyridine / 20 °C
6: 2 N aq. HCl / methanol; tetrahydrofuran / 6 h / 20 °C
7: POCl3; pyridine / 3 h / 20 °C
8: KOH / methanol; tetrahydrofuran / 20 °C
9: 6.0 mg / hairy roots of Ajuga reptans var. atropurpurea; Tween 80 / acetone; CHCl3; methanol / Irradiation
View Scheme
[2β-2H]-5α-cholestane-3β,6β-diol 3-acetate
264925-88-4

[2β-2H]-5α-cholestane-3β,6β-diol 3-acetate

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3; pyridine / 3 h / 20 °C
2: KOH / methanol; tetrahydrofuran / 20 °C
3: 6.0 mg / hairy roots of Ajuga reptans var. atropurpurea; Tween 80 / acetone; CHCl3; methanol / Irradiation
View Scheme
(2R,3S,5S,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexadecahydro-20-oxa-cyclopropa[2,3]cyclopenta[a]phenanthrene
264925-83-9

(2R,3S,5S,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexadecahydro-20-oxa-cyclopropa[2,3]cyclopenta[a]phenanthrene

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 93 percent / LiAlD4 / tetrahydrofuran / 0.5 h / 60 °C
2: pyridinium chlorochromate; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 0.17 h / 20 °C
3: LiAlH4 / tetrahydrofuran / 0.33 h / 20 °C
4: pyridine / 20 °C
5: 2 N aq. HCl / methanol; tetrahydrofuran / 6 h / 20 °C
6: POCl3; pyridine / 3 h / 20 °C
7: KOH / methanol; tetrahydrofuran / 20 °C
8: 6.0 mg / hairy roots of Ajuga reptans var. atropurpurea; Tween 80 / acetone; CHCl3; methanol / Irradiation
View Scheme
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

acetone
67-64-1

acetone

20-hydroxyecdysone 2,3:20,22-diacetonide
84507-66-4, 22798-98-7

20-hydroxyecdysone 2,3:20,22-diacetonide

Conditions
ConditionsYield
With (1S)-10-camphorsulfonic acid at 25℃; Inert atmosphere;97%
With toluene-4-sulfonic acid Cyclization;85%
With phosphomolybdic acid at 25℃; for 0.583333h;82%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

acetone
67-64-1

acetone

20-hydroxyecdysone 20,22-acetonide
84507-68-6, 22798-96-5

20-hydroxyecdysone 20,22-acetonide

Conditions
ConditionsYield
With tetrafluoroboric acid at 25℃; for 0.166667h;97%
With toluene-4-sulfonic acid93%
With toluene-4-sulfonic acid In methanol89%
With phosphomolybdic acid In methanol at 20℃; for 0.166667h;45.43%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

(20R,22R)-2β,3β,14α,20,22,25-hexahydroxy-7,8α-dihydro-5β-cholestan-6-one

(20R,22R)-2β,3β,14α,20,22,25-hexahydroxy-7,8α-dihydro-5β-cholestan-6-one

Conditions
ConditionsYield
With sodium nitrite; palladium on activated charcoal In ethanol; water under 760 Torr; for 3h;96%
With palladium 10% on activated carbon; hydrogen; sodium In methanol at 20℃; for 3h;91%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 0.5h;21%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

14alpha-Hydroperoxy-20-hydroxyecdysone
115040-67-0

14alpha-Hydroperoxy-20-hydroxyecdysone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 6h; Ambient temperature;95%
Multi-step reaction with 2 steps
1: ammonia; lithium / tetrahydrofuran / 0.5 h / -33 °C
2: oxygen
View Scheme
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

(20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one
54289-60-0

(20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.05h;95%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

propargyl bromide
106-96-7

propargyl bromide

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

Conditions
ConditionsYield
Stage #1: 20-Hydroxyecdysone With ammonia; lithium In tetrahydrofuran at -33℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
94%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

acetone
67-64-1

acetone

A

20-hydroxyecdysone 20,22-acetonide
84507-68-6, 22798-96-5

20-hydroxyecdysone 20,22-acetonide

B

20-hydroxyecdysone 2,3:20,22-diacetonide
84507-66-4, 22798-98-7

20-hydroxyecdysone 2,3:20,22-diacetonide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 1h;A 93%
B 2%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

cyclohexanone
108-94-1

cyclohexanone

20-hydroxyecdysone 2,3;20,22-di(cyclohexylacetal)

20-hydroxyecdysone 2,3;20,22-di(cyclohexylacetal)

Conditions
ConditionsYield
With (1S)-10-camphorsulfonic acid at 25℃; Inert atmosphere;93%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

propargyl bromide
106-96-7

propargyl bromide

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7α-(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7α-(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

Conditions
ConditionsYield
Stage #1: 20-Hydroxyecdysone With lithium In tetrahydrofuran at -33℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
92%
vinyl acetate
108-05-4

vinyl acetate

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

20-Hydroxyecdysone-2-acetate
19536-25-5

20-Hydroxyecdysone-2-acetate

Conditions
ConditionsYield
In pyridine; tert-Amyl alcohol at 45℃; for 168h; Candida antarctica lipase B supported on acrylic resin (Novozym 435);90%
With pyridine; lipase In tert-Amyl alcohol at 45℃; Product distribution / selectivity;
With pyridine; lipase In acetonitrile at 45℃; Product distribution / selectivity;
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

acetaldehyde
75-07-0

acetaldehyde

20,22-O-[(1RS)-ethylidene]-20-hydroxyecdysone

20,22-O-[(1RS)-ethylidene]-20-hydroxyecdysone

Conditions
ConditionsYield
With phosphomolybdic acid at 25℃; for 0.5h;90%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

acetaldehyde
75-07-0

acetaldehyde

2,3:20,22-bis-O-[(1R)-ethylidene]-20-hydroxyecdysone

2,3:20,22-bis-O-[(1R)-ethylidene]-20-hydroxyecdysone

Conditions
ConditionsYield
Stage #1: 20-Hydroxyecdysone; acetaldehyde at 2℃; for 72h;
Stage #2: With phosphomolybdic acid at 25℃; for 0.166667h;
88%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

benzoyl chloride
98-88-4

benzoyl chloride

20-hydroxyecdysone 2,3,22-tribenzoate

20-hydroxyecdysone 2,3,22-tribenzoate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;87%
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

(20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one
54289-60-0

(20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one

Conditions
ConditionsYield
With 2,6-dimethylpyridine In tetrahydrofuran at 20℃;86%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

14,15-anhydro-20-hydroxyecdysone (6Z)-oxime

14,15-anhydro-20-hydroxyecdysone (6Z)-oxime

Conditions
ConditionsYield
Stage #1: 20-Hydroxyecdysone With hydroxylamine hydrochloride In pyridine at 70℃; for 72h;
Stage #2: With potassium hydroxide In ethanol
Stage #3: With phosphomolybdic acid In methanol for 1h;
86%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

20,22-O-(1-hydroxy-2,2,2-trifluoromethylethylidene)-20-hydroxyecdysone

20,22-O-(1-hydroxy-2,2,2-trifluoromethylethylidene)-20-hydroxyecdysone

Conditions
ConditionsYield
In chloroform at 25℃; for 24h;85%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

20-hydroxyecdysone 2,22-dicinnamate

20-hydroxyecdysone 2,22-dicinnamate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;85%
indole-3-acetic acid
87-51-4

indole-3-acetic acid

20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

20-hydroxyecdysone 2,3,22-tri(2-(1H-indol-3-yl)acetate)

20-hydroxyecdysone 2,3,22-tri(2-(1H-indol-3-yl)acetate)

Conditions
ConditionsYield
Stage #1: indole-3-acetic acid With dicyclohexyl-carbodiimide In 1,4-dioxane for 1h; Inert atmosphere;
Stage #2: 20-Hydroxyecdysone With dmap In 1,4-dioxane at 40℃; for 22h; Inert atmosphere;
83%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

methyl iodide
74-88-4

methyl iodide

A

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7α-methyl-5β-cholest-8(14)-en-6-one

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7α-methyl-5β-cholest-8(14)-en-6-one

B

(20R,22R)-7α-methyl-2β-methoxy-3β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

(20R,22R)-7α-methyl-2β-methoxy-3β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

C

(20R,22R)-7α-methyl-3β-methoxy-2β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

(20R,22R)-7α-methyl-3β-methoxy-2β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

Conditions
ConditionsYield
Stage #1: 20-Hydroxyecdysone With ammonia; lithium In tetrahydrofuran at -33℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 24h; stereospecific reaction;
A 82%
B 8%
C 8%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In methanol at 20℃; for 0.75h;81.41%
With bis-[(trifluoroacetoxy)iodo]benzene In methanol at 20℃; for 1h;57.8%
With bis-[(trifluoroacetoxy)iodo]benzene57.8%
With chromium(VI) oxide; sulfuric acid In acetone
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

acetic anhydride
108-24-7

acetic anhydride

20-hydroxyecdysone-2,3,22-triacetate
19404-87-6, 84507-62-0

20-hydroxyecdysone-2,3,22-triacetate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;80%
With pyridine at 20℃;34 mg
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

butanone
78-93-3

butanone

A

29α-ethyl-29β-methyl-20,22-O-methylidene-20-hydroxyecdysone

29α-ethyl-29β-methyl-20,22-O-methylidene-20-hydroxyecdysone

B

2,3-O-[(2RS)-butan-2-ylidene]-20,22-O-[(2R)-butan-2-ylidene]-20-hydroxyecdysone

2,3-O-[(2RS)-butan-2-ylidene]-20,22-O-[(2R)-butan-2-ylidene]-20-hydroxyecdysone

Conditions
ConditionsYield
With phosphomolybdic acid at 25℃; for 0.0833333h;A 20%
B 78%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

Hexanoyl chloride
142-61-0

Hexanoyl chloride

20-hydroxyecdysone 2,22-dihexanoate

20-hydroxyecdysone 2,22-dihexanoate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;77%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

propargyl bromide
106-96-7

propargyl bromide

A

(20R,22R)-3β,20,22,25-tetrahydroxy-2β-(2-propyn-1-yl)oxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

(20R,22R)-3β,20,22,25-tetrahydroxy-2β-(2-propyn-1-yl)oxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

B

(20R,22R)-2β,20,22,25-tetrahydroxy-3β-(2-propyn-1-yl)oxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

(20R,22R)-2β,20,22,25-tetrahydroxy-3β-(2-propyn-1-yl)oxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

C

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

(20R,22R)-2β,3β,20,22,25-pentahydroxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

Conditions
ConditionsYield
Stage #1: 20-Hydroxyecdysone With ammonia; lithium In tetrahydrofuran at -33℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
A 12%
B 10%
C 75%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

allyl bromide
106-95-6

allyl bromide

A

(20R,22R)-7α-allyl-2β,3β,20,22,25-pentahydroxy-5β-cholest-8(14)-en-6-one

(20R,22R)-7α-allyl-2β,3β,20,22,25-pentahydroxy-5β-cholest-8(14)-en-6-one

B

(20R,22R)-7α-allyl-2β-allyloxy-2β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

(20R,22R)-7α-allyl-2β-allyloxy-2β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

C

(20R,22R)-7α-allyl-3β-allyloxy-2β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

(20R,22R)-7α-allyl-3β-allyloxy-2β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

D

(20R,22R)-7α-allyl-22-allyloxy-2β,3β,20,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

(20R,22R)-7α-allyl-22-allyloxy-2β,3β,20,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

Conditions
ConditionsYield
Stage #1: 20-Hydroxyecdysone With ammonia; lithium In tetrahydrofuran at -33℃; for 0.5h;
Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 24h; stereospecific reaction;
A 72%
B 10%
C 8%
D 7%
20-Hydroxyecdysone
5289-74-7

20-Hydroxyecdysone

2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

2,3,22-O-tri-(o-methoxybenzoyl)-20-hydroxyecdysone

2,3,22-O-tri-(o-methoxybenzoyl)-20-hydroxyecdysone

Conditions
ConditionsYield
With pyridine71.2%
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