Beta-Ecdysone supplier | CasNO.5289-74-7

Name
Hydroxyecdysone
EINECS 811-097-1
CAS No. 5289-74-7
Article Data22
CAS DataBase
Density 1.28 g/cm³
Solubility alcohol: soluble
Melting Point 242-244 °C
Formula C₂₇H₄₄O₇
Boiling Point 702.1 °C at 760 mmHg
Molecular Weight 480.642
Flash Point 392.4 °C
Transport Information
Appearance white powder
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5b-Cholest-7-en-6-one, 2b,3b,14,20,22,25-hexahydroxy-, (22R)- (8CI);5b-Cholest-7-en-6-one, 2b,3b,14,20,22b,25-hexahydroxy- (7CI);(+)-Ecdysterone;20-Hydroxy-a-ecdysone;20R-Hydroxyecdysone;2b,3b,14a,20b,22a,25-Hexahydroxycholest-7-en-6-one;2b,3b,14a,20b,22a,25b-Hexahydroxycholest-7-en-6-one;Commisterone;Ecdysten;Ecdysteron;Ekdisten;Isoinokosterone;Polypodin A;Polypodine C;THE 7;b-Ecdysone;b-Ecdysterone;β-ecdysone;
PSA 138.45000
LogP 1.85400

Synthetic route

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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 2.5h; Heating;	89%

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

A: 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

Conditions

Conditions	Yield
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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With lithium In tetrahydrofuran; ammonia for 1h;	82%

: 135024-06-5
(20R,22R)-22-hydroxy-2β,3β,14,20,25-pentakis-(trimethyl-silanyloxy)-5β-cholest-7-en-6-one

A: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	A 80% B n/a

: 19974-12-0
22-Dehydro-20-hydroxyecdysone

A: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
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;

: 41451-87-0
Turkesterone

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With sodium nitrite; palladium on activated charcoal In ethanol; water under 760 Torr; for 1h;	67%

: 1450761-60-0
(20R,22R)-2β,3β,14α,25-tetrahydroxy-20,22-(butan-2-yl)boranediyldioxy-5β-cholest-7-en-6-one

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

A: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
With oxalic acid In methanol for 6h; Ambient temperature; darkness;	A 9% B 57%

: 1373335-50-2
2,3-didehydro-2,3-dideoxy-20-hydroxyecdysone

A: 5289-74-7
20-Hydroxyecdysone

B: 2,3-di-epi-20-hydroxyαecdysone

Conditions

Conditions	Yield
With pyridine; osmium(VIII) oxide	A 54% B 32%

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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With potassium hydroxide In methanol Heating;

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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 41408-38-2
2,22-dideoxyecdysone

A: 5289-74-7
20-Hydroxyecdysone

B: 3604-87-3
ecdysone

C: 34209-85-3
22-Deoxyecdysone

D: 72630-20-7, 77732-73-1, 31575-91-4
2-deoxyecdysone

Conditions

Conditions	Yield
With Locusta migratoria at 33℃; for 6h; Product distribution; tissue distr. of C22 hydroxylase;

...Expand

: 114317-60-1
ecdysterone 20-O-benzoate

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With potassium hydrogencarbonate In methanol; water at 20 - 38℃; for 204h;	7 mg

: 84699-93-4
Sileneoside B

A: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
In water at 27℃; for 528h; galactosidase;	A 10 mg B 7 mg

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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

A: 5289-74-7
20-Hydroxyecdysone

B: Taxisterone

Conditions

Conditions	Yield
With potassium carbonate In methanol for 0.5h; Ambient temperature;	A n/a B 11 mg

: 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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

: 52094-73-2
3-Dehydro-2O-hydroxyecdyson

A: 5289-74-7
20-Hydroxyecdysone

B: 5289-74-7, 7703-93-7, 22678-71-3, 22678-72-4, 35241-82-8, 84580-28-9, 123238-67-5, 54053-93-9
Coronatasterone

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; ethanol

: 3604-87-3
ecdysone

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With ecdysone 20-monooxygenase; oxygen; NADPH hydroxylation catalyzed by ecdysone 20-monooxygenase; other reagents;

: 93552-68-2
20-hydroxyecdysone 3-O-α-D-galactoside

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With almond enzymes; water at 36℃; for 720h; Hydrolysis; Enzymatic reaction;

: 3604-87-3
ecdysone

A: 5289-74-7
20-Hydroxyecdysone

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

C: 52717-49-4
26-hydroxyecdysone

D: 5289-74-7, 7703-93-7, 22678-71-3, 22678-72-4, 35241-82-8, 84580-28-9, 123238-67-5, 54053-93-9
Coronatasterone

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

F: 19458-46-9
20,26-dihydroxyecdysone

G 4 polar acidic metabolites: 4 polar acidic metabolites

Conditions

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

...Expand

: 13408-48-5, 19338-77-3, 78148-78-4, 13408-56-5
ponasterone A

A: 5289-74-7
20-Hydroxyecdysone

B: 88980-54-5
inokosterone

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

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

E: 19458-46-9
20,26-dihydroxyecdysone

F very polar products (VVP), conjugates (C): very polar products (VVP), conjugates (C)

Conditions

Conditions	Yield
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;

...Expand

: 52717-49-4
26-hydroxyecdysone

A: 5289-74-7
20-Hydroxyecdysone

B: 3604-87-3
ecdysone

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

D: 5289-74-7, 7703-93-7, 22678-71-3, 22678-72-4, 35241-82-8, 84580-28-9, 123238-67-5, 54053-93-9
Coronatasterone

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

F: 19458-46-9
20,26-dihydroxyecdysone

G 4 polar acidic metabolites: 4 polar acidic metabolites

Conditions

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

...Expand

: 54594-70-6
[2β-2H]cholesterol

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With Tween 80; hairy roots of Ajuga reptans var. atropurpurea In methanol; chloroform; acetone hydroxylation; Irradiation;	6.0 mg

: 128365-93-5
20-Hydroxyecdysone-3-beta-D-glucopyranoside

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 4h; Heating;

: 27948-74-9
6β-hydroxy-5α-cholest-2-ene

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

Yield

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

: 264925-89-5
C29H47(2)HO2

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

: 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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

Yield

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

: 264925-88-4
[2β-2H]-5α-cholestane-3β,6β-diol 3-acetate

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

: 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

: 5289-74-7
20-Hydroxyecdysone

Conditions

Conditions	Yield
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

Yield

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

: 5289-74-7
20-Hydroxyecdysone

: 67-64-1
acetone

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

Conditions

Conditions	Yield
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%

: 5289-74-7
20-Hydroxyecdysone

: 67-64-1
acetone

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

Conditions

Conditions	Yield
With tetrafluoroboric acid at 25℃; for 0.166667h;	97%
With toluene-4-sulfonic acid	93%
With toluene-4-sulfonic acid In methanol	89%
With phosphomolybdic acid In methanol at 20℃; for 0.166667h;	45.43%

: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
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%

: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
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

: 5289-74-7
20-Hydroxyecdysone

: 81290-20-2
(trifluoromethyl)trimethylsilane

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

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.05h;	95%

: 5289-74-7
20-Hydroxyecdysone

: 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

Conditions

Conditions	Yield
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%

: 5289-74-7
20-Hydroxyecdysone

: 67-64-1
acetone

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

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

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 1h;	A 93% B 2%

...Expand

: 5289-74-7
20-Hydroxyecdysone

: 108-94-1
cyclohexanone

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

Conditions

Conditions	Yield
With (1S)-10-camphorsulfonic acid at 25℃; Inert atmosphere;	93%

: 5289-74-7
20-Hydroxyecdysone

: 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

Conditions

Conditions	Yield
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%

: 108-05-4
vinyl acetate

: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
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;

: 5289-74-7
20-Hydroxyecdysone

: 75-07-0
acetaldehyde

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

Conditions

Conditions	Yield
With phosphomolybdic acid at 25℃; for 0.5h;	90%

: 5289-74-7
20-Hydroxyecdysone

: 75-07-0
acetaldehyde

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

Conditions

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

: 5289-74-7
20-Hydroxyecdysone

: 98-88-4
benzoyl chloride

: 20-hydroxyecdysone 2,3,22-tribenzoate

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; Inert atmosphere;	87%

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In tetrahydrofuran at 20℃;	86%

: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
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%

: 5289-74-7
20-Hydroxyecdysone

: 407-25-0
trifluoroacetic anhydride

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

Conditions

Conditions	Yield
In chloroform at 25℃; for 24h;	85%

: 5289-74-7
20-Hydroxyecdysone

: 102-92-1
Cinnamoyl chloride

: 20-hydroxyecdysone 2,22-dicinnamate

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; Inert atmosphere;	85%

: 87-51-4
indole-3-acetic acid

: 5289-74-7
20-Hydroxyecdysone

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

Conditions

Conditions	Yield
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%

: 5289-74-7
20-Hydroxyecdysone

: 74-88-4
methyl iodide

A: (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

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

Conditions

Conditions	Yield
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%

...Expand

: 5289-74-7
20-Hydroxyecdysone

: 144405-75-4, 10162-99-9
Poststerone

Conditions

Conditions	Yield
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]benzene	57.8%
With chromium(VI) oxide; sulfuric acid In acetone

: 5289-74-7
20-Hydroxyecdysone

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; Inert atmosphere;	80%
With pyridine at 20℃;	34 mg

: 5289-74-7
20-Hydroxyecdysone

: 78-93-3
butanone

A: 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

Conditions

Conditions	Yield
With phosphomolybdic acid at 25℃; for 0.0833333h;	A 20% B 78%

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: 5289-74-7
20-Hydroxyecdysone

: 142-61-0
Hexanoyl chloride

: 20-hydroxyecdysone 2,22-dihexanoate

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; Inert atmosphere;	77%

: 5289-74-7
20-Hydroxyecdysone

: 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

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

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

Conditions

Conditions	Yield
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%

...Expand

: 5289-74-7
20-Hydroxyecdysone

: 106-95-6
allyl bromide

A: (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

C: (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

Conditions

Conditions	Yield
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%

...Expand

: 5289-74-7
20-Hydroxyecdysone

: 21615-34-9
2-Methoxybenzoyl chloride

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

Conditions

Conditions	Yield
With pyridine	71.2%

Beta-Ecdysone Specification

The IUPAC name of Beta-Ecdysone is (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one. With the CAS registry number 5289-74-7, it is also named as Ecdysterone. The product's categories are Miscellaneous Natural Products; Steroids; Natural Plant Extract. Besides, it is white powder, which should be sealed in dark, cool dry place at 2-8 °C. In addition, its molecular formula is C₂₇H₄₄O₇ and molecular weight is 480.64.

The other characteristics of Beta-Ecdysone can be summarized as: (1)ACD/LogP: -0.53; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.53; (4)ACD/LogD (pH 7.4): -0.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.25; (8)ACD/KOC (pH 7.4): 12.25; (9)#H bond acceptors: 7; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 72.45 Å²; (13)Index of Refraction: 1.596; (14)Molar Refractivity: 127.81 cm³; (15)Molar Volume: 375.2 cm³; (16)Polarizability: 50.66×10^-24cm³; (17)Surface Tension: 62.2 dyne/cm; (18)Density: 1.28 g/cm³; (19)Flash Point: 392.3 °C; (20)Melting Point: 242-244 °C; (21)Enthalpy of Vaporization: 117.45 kJ/mol; (22)Boiling Point: 702.1 °C at 760 mmHg; (23)Vapour Pressure: 8.7E-23 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. Please do not breathe dust. And in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Moreover, you should wear suitable protective clothing to avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C
(2)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+/m0/s1
(3)InChIKey: NKDFYOWSKOHCCO-YPVLXUMRBN

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	6400mg/kg (6400mg/kg)		Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 66, Pg. 551, 1970.
mouse	LD50	oral	> 9gm/kg (9000mg/kg)		Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 66, Pg. 551, 1970.

Product Name

Hydroxyecdysone

Synthetic route

Beta-Ecdysone Specification

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