5289-74-7

Basic information

• Product Name: Hydroxyecdysone
• Synonyms: 7,(5B)-CHOLESTEN-2BETA, 3BETA, 14ALPHA, 20BETA, 22R, 25-HEXOL-6-ONE;2B,3B,14A,20,22[R],25-HEXAHYDROXY-7-CHOLESTEN-6-ONE;2b,3b,14a,20b,22,25-hexahydroxycholest-7-en-6-one;2BETA,3BETA,14ALPHA,20BETA,22,25-HEXAHYDROXY-7-CHOLESTEN-6-ONE;(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-TRIHYDROXY-10,13-DIMETHYL-17-((1R,2R)-1,2,5-TRIHYDROXY-1,5-DIMETHYL-HEXYL)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-6-ONE;20-HYDROXYECDYSON;20-HYDROXYECDYSONE;20-Hydroxyecdysone, froM Arachnoides C. B. Clarke
• CAS NO: 5289-74-7
• Molecular Formula: C27H44O7
• Molecular Weight: 480.63
• EINECS: 208-288-1
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Miscellaneous Natural Products;Steroids;Natural Plant Extract;sy;Herb extract
• Mol File: 5289-74-7.mol
• Article Data: 22

Chemical Properties

• Melting Point: 242-244 °C
• Boiling Point: 498.63°C (rough estimate)
• Flash Point: 392.4 °C
• Appearance: white/powder
• Density: 1.0760 (rough estimate)
• Vapor Pressure: 8.7E-23mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: 2-8°C
• Solubility: alcohol: soluble
• PKA: 14.13±0.70(Predicted)
• Merck: 13,3525
• BRN: 1917578
• CAS DataBase Reference: Hydroxyecdysone(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxyecdysone(5289-74-7)
• EPA Substance Registry System: Hydroxyecdysone(5289-74-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 2
• RTECS: FZ8060000
• F: 10
• Hazardous Substances Data: 5289-74-7(Hazardous Substances Data)

Usage

Chemical Properties

White or off-white powder

Uses

Different sources of media describe the Uses of 5289-74-7 differently. You can refer to the following data:
1. insect molting hormone
2. 20-Hydroxyecdysone has been used:in Leibovitz′s dissecting medium for culturing sorting zone and neuropil-associated glia and antennal lobes of Manduca sextain Schneider′s medium to reproduce ex-vivo imaginal disc eversionas a supplement in Mcl8 medium for culturing Drosophila wing imaginal discs

Definition

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

Biochem/physiol Actions

20-Hydroxyecdysone is an ecdysteroid hormone that plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression involved in molting and metamorphosis. It acts through a heterodimeric receptor comprising the ecdysone receptor and the ultraspiracle proteins (USP).

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.]

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

Synthetic route

(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)

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

14alpha-Hydroperoxy-20-hydroxyecdysone (115040-67-0) → 20-Hydroxyecdysone (5289-74-7) + (8R,20R,22R)-2β,3β,20,22,25-pentahydroxy-8,13-cyclo-13,14-seco-5β-cholestane-6,14-dione

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 → 20-Hydroxyecdysone (5289-74-7)

Conditions	Yield
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) → 20-Hydroxyecdysone (5289-74-7) + (20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one (123238-67-5)

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

22-Dehydro-20-hydroxyecdysone (19974-12-0) → 20-Hydroxyecdysone (5289-74-7) + (20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one (123238-67-5)

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;

Turkesterone (41451-87-0) → 20-Hydroxyecdysone (5289-74-7)

Conditions	Yield
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) → 20-Hydroxyecdysone (5289-74-7)

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 → 20-Hydroxyecdysone (5289-74-7) + 14alpha-Hydroperoxy-20-hydroxyecdysone (115040-67-0)

Conditions	Yield
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) → 20-Hydroxyecdysone (5289-74-7) + 2,3-di-epi-20-hydroxyαecdysone

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

20-hydroxyecdysone-2,3,22-triacetate (19404-87-6, 84507-62-0) → 20-Hydroxyecdysone (5289-74-7)

Conditions	Yield
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) → 20-Hydroxyecdysone (5289-74-7)

Conditions	Yield
Yield given. Multistep reaction;

2,22-dideoxyecdysone (41408-38-2) → 20-Hydroxyecdysone (5289-74-7) + ecdysone (3604-87-3) + 22-Deoxyecdysone (34209-85-3) + 2-deoxyecdysone (72630-20-7, 77732-73-1, 31575-91-4)

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

ecdysterone 20-O-benzoate (114317-60-1) → 20-Hydroxyecdysone (5289-74-7)

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

Sileneoside B (84699-93-4) → 20-Hydroxyecdysone (5289-74-7) + ecdysterone 22-O-α-D-galactopyranoside (81655-86-9)

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

14alpha-Hydroperoxy-20-hydroxyecdysone (115040-67-0) → 20-Hydroxyecdysone (5289-74-7)

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 → 20-Hydroxyecdysone (5289-74-7) + Taxisterone

Conditions	Yield
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) → 20-Hydroxyecdysone (5289-74-7)

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

3-Dehydro-2O-hydroxyecdyson (52094-73-2) → 20-Hydroxyecdysone (5289-74-7) + Coronatasterone (5289-74-7, 7703-93-7, 22678-71-3, 22678-72-4, 35241-82-8, 84580-28-9, 123238-67-5, 54053-93-9)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; ethanol

ecdysone (3604-87-3) → 20-Hydroxyecdysone (5289-74-7)

Conditions	Yield
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 (5289-74-7)

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

ecdysone (3604-87-3) → 20-Hydroxyecdysone (5289-74-7) + 3-epi-26-hydroxyecdysone (75319-59-4) + 26-hydroxyecdysone (52717-49-4) + Coronatasterone (5289-74-7, 7703-93-7, 22678-71-3, 22678-72-4, 35241-82-8, 84580-28-9, 123238-67-5, 54053-93-9) + 3-epi-20,26-dihydroxyecdysone (71939-17-8) + 20,26-dihydroxyecdysone (19458-46-9) + 4 polar acidic metabolites

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

ponasterone A (13408-48-5, 19338-77-3, 78148-78-4, 13408-56-5) → 20-Hydroxyecdysone (5289-74-7) + inokosterone (88980-54-5) + 25-deoxy-20-hydroxyecdyson-26-oic acid (59971-16-3) + 20-hydroxyecdyson-26-oic acid (86583-58-6) + 20,26-dihydroxyecdysone (19458-46-9) + very polar products (VVP), conjugates (C)

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;

26-hydroxyecdysone (52717-49-4) → 20-Hydroxyecdysone (5289-74-7) + ecdysone (3604-87-3) + 3-epi-26-hydroxyecdysone (75319-59-4) + Coronatasterone (5289-74-7, 7703-93-7, 22678-71-3, 22678-72-4, 35241-82-8, 84580-28-9, 123238-67-5, 54053-93-9) + 3-epi-20,26-dihydroxyecdysone (71939-17-8) + 20,26-dihydroxyecdysone (19458-46-9) + 4 polar acidic metabolites

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

[2β-2H]cholesterol (54594-70-6) → 20-Hydroxyecdysone (5289-74-7)

Conditions	Yield
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 (5289-74-7)

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

6β-hydroxy-5α-cholest-2-ene (27948-74-9) → 20-Hydroxyecdysone (5289-74-7)

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

C29H47(2)HO2 (264925-89-5) → 20-Hydroxyecdysone (5289-74-7)

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

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) → 20-Hydroxyecdysone (5289-74-7)

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

[2β-2H]-5α-cholestane-3β,6β-diol 3-acetate (264925-88-4) → 20-Hydroxyecdysone (5289-74-7)

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

(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) → 20-Hydroxyecdysone (5289-74-7)

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

20-Hydroxyecdysone (5289-74-7) + acetone (67-64-1) → 20-hydroxyecdysone 2,3:20,22-diacetonide (84507-66-4, 22798-98-7)

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%

20-Hydroxyecdysone (5289-74-7) + acetone (67-64-1) → 20-hydroxyecdysone 20,22-acetonide (84507-68-6, 22798-96-5)

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%

20-Hydroxyecdysone (5289-74-7) → (20R,22R)-2β,3β,14α,20,22,25-hexahydroxy-7,8α-dihydro-5β-cholestan-6-one

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%

20-Hydroxyecdysone (5289-74-7) → 14alpha-Hydroperoxy-20-hydroxyecdysone (115040-67-0)

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

20-Hydroxyecdysone (5289-74-7) + (trifluoromethyl)trimethylsilane (81290-20-2) → (20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one (54289-60-0)

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

20-Hydroxyecdysone (5289-74-7) + propargyl bromide (106-96-7) → (20R,22R)-2β,3β,20,22,25-pentahydroxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

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%

20-Hydroxyecdysone (5289-74-7) + acetone (67-64-1) → 20-hydroxyecdysone 20,22-acetonide (84507-68-6, 22798-96-5) + 20-hydroxyecdysone 2,3:20,22-diacetonide (84507-66-4, 22798-98-7)

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

20-Hydroxyecdysone (5289-74-7) + cyclohexanone (108-94-1) → 20-hydroxyecdysone 2,3;20,22-di(cyclohexylacetal)

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

20-Hydroxyecdysone (5289-74-7) + propargyl bromide (106-96-7) → (20R,22R)-2β,3β,20,22,25-pentahydroxy-7α-(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

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%

vinyl acetate (108-05-4) + 20-Hydroxyecdysone (5289-74-7) → 20-Hydroxyecdysone-2-acetate (19536-25-5)

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;

20-Hydroxyecdysone (5289-74-7) + acetaldehyde (75-07-0) → 20,22-O-[(1RS)-ethylidene]-20-hydroxyecdysone

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

20-Hydroxyecdysone (5289-74-7) + acetaldehyde (75-07-0) → 2,3:20,22-bis-O-[(1R)-ethylidene]-20-hydroxyecdysone

Conditions	Yield
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) + benzoyl chloride (98-88-4) → 20-hydroxyecdysone 2,3,22-tribenzoate

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

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 20-Hydroxyecdysone (5289-74-7) → (20R,22R)-2β,3β,14,20,22,25-hexakis-(trimethylsilanyloxy)-5β-cholest-7-en-6-one (54289-60-0)

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

20-Hydroxyecdysone (5289-74-7) → 14,15-anhydro-20-hydroxyecdysone (6Z)-oxime

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%

20-Hydroxyecdysone (5289-74-7) + trifluoroacetic anhydride (407-25-0) → 20,22-O-(1-hydroxy-2,2,2-trifluoromethylethylidene)-20-hydroxyecdysone

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

20-Hydroxyecdysone (5289-74-7) + Cinnamoyl chloride (102-92-1) → 20-hydroxyecdysone 2,22-dicinnamate

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

indole-3-acetic acid (87-51-4) + 20-Hydroxyecdysone (5289-74-7) → 20-hydroxyecdysone 2,3,22-tri(2-(1H-indol-3-yl)acetate)

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%

20-Hydroxyecdysone (5289-74-7) + methyl iodide (74-88-4) → (20R,22R)-2β,3β,20,22,25-pentahydroxy-7α-methyl-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 + (20R,22R)-7α-methyl-3β-methoxy-2β,20,22,25-tetrahydroxy-5β-cholest-8(14)-en-6-one

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%

20-Hydroxyecdysone (5289-74-7) → Poststerone (144405-75-4, 10162-99-9)

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

20-Hydroxyecdysone (5289-74-7) + acetic anhydride (108-24-7) → 20-hydroxyecdysone-2,3,22-triacetate (19404-87-6, 84507-62-0)

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

20-Hydroxyecdysone (5289-74-7) + butanone (78-93-3) → 29α-ethyl-29β-methyl-20,22-O-methylidene-20-hydroxyecdysone + 2,3-O-[(2RS)-butan-2-ylidene]-20,22-O-[(2R)-butan-2-ylidene]-20-hydroxyecdysone

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

20-Hydroxyecdysone (5289-74-7) + Hexanoyl chloride (142-61-0) → 20-hydroxyecdysone 2,22-dihexanoate

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

20-Hydroxyecdysone (5289-74-7) + propargyl bromide (106-96-7) → (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)-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,3β,20,22,25-pentahydroxy-7,7-bis(2-propyn-1-yl)-5β-cholest-8(14)-en-6-one

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%

20-Hydroxyecdysone (5289-74-7) + allyl bromide (106-95-6) → (20R,22R)-7α-allyl-2β,3β,20,22,25-pentahydroxy-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 + (20R,22R)-7α-allyl-3β-allyloxy-2β,20,22,25-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	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%

20-Hydroxyecdysone (5289-74-7) + 2-Methoxybenzoyl chloride (21615-34-9) → 2,3,22-O-tri-(o-methoxybenzoyl)-20-hydroxyecdysone

Conditions	Yield
With pyridine	71.2%

Upstream product

• 19404-87-6 20-hydroxyecdysone-2,3,22-triacetate 
• 19974-12-0 22-Dehydro-20-hydroxyecdysone 
• 135024-06-5 (20R,22R)-22-hydroxy-2β,3β,14,20,25-pentakis-(trimethyl-silanyloxy)-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 
• 41408-38-2 2,22-dideoxyecdysone 
• 114317-60-1 ecdysterone 20-O-benzoate 
• 84699-93-4 Sileneoside B 
• 93552-68-2 20-hydroxyecdysone 3-O-α-D-galactoside 
• 3604-87-3 ecdysone 
• 13408-48-5 ponasterone A 
• 128365-93-5 20-Hydroxyecdysone-3-beta-D-glucopyranoside 
• 27948-74-9 6β-hydroxy-5α-cholest-2-ene 
• 22798-96-5 Crustecdyson-monoacetonid 
• 131643-66-8 ecdysterone 22,25-di-O-benzoate 

Downstream Products

• 144405-75-4 Poststerone 
• 51787-31-6 calonysterone 
• 19536-25-5 20-Hydroxyecdysone-2-acetate 
• 22799-02-6 20-Hydroxyecdysone-22-acetate 
• 22799-03-7 20-hydroxyecdysone 2,3-diacetate 
• 22961-68-8 20-Hydroxyecdysone-3-acetate 
• 84507-68-6 20-hydroxyecdysone 20,22-acetonide 

Relevant articles and documents

A furostanol saponin and phytoecdysteroid from roots of Helleborus orientalis

A furostanol saponin mixture and a known phytoecdysteroid were isolated from the roots of Helleborus orientalis Lam. Their structures were established as 26-[(β-D-glucopyranosyl)oxy]-22α-hidroxyfurosta-5,25(27)-dien- 1β,3β,11α-triol (1a), 26-[(β-D-glucopyranosyl)oxy]- 22α-methoxyfurosta-5,25(27)-dien-1β,3β,11α-triol (1b), and 20-hydroxy-β-ecdyson-3-O-β-D-glycoside (2). Acid hydrolysis of 1a,b gave (1β,3β,11α,22α)-22,26-dimethoxyfurosta-5,25(27)-dien- 1,3,11-triol (aglycone 1) and of 2 gave 20-hydroxy-β-ecdyson (aglycone 2). Their structures were elucidated by spectral analysis. Springer Science+Business Media, Inc. 2007.

Ecdysone 20-monooxygenase, a cytochrome P450 enzyme from spinach, Spinacia oleracea

A microsomal preparation isolated from first leaves of 25-day-old spinach catalysed the hydroxylation of ecdysone to produce the insect moulting hormone, 20-hydroxyecdysone. Hydroxylation was dependent on NADPH and molecular oxygen, and was inhibited by carbon monoxide. Carbon monoxide inhibition was partially reversible by white light. Polyclonal antibodies to the Jerusalem artichoke NADPH-cytochrome P450 reductase inhibited the hydroxylation reaction as well as the spinach microsomal NADPH cytochrome c reductase. These results taken together establish ecdysone hydroxylation as a cytochrome P450 dependent reaction in spinach, which is known to synthesize large amounts of phytoecdysteroids.

A PHYTOECDYSTEROID, TAXISTERONE, FROM TAXUS CUSPIDATA

A new phytoecdysteroid, taxisterone, was isolated from Taxus cuspidata and the structure was deduced to be 22-deoxyecdysterone by spectral data. - Key Word Index: Taxus cuspidata; Taxaceae; phytoecdysteroid; taxisterone; 22-deoxyecdysterone.

ECDYSTEROID ANALOGUES HAVING PLANT GROWTH PROMOTING ACTIVITY

The present disclosure relates to ecdysteroid analogues which have similar, identical, or enhanced biological activities as compared to brassinosteroids, for instance similar, identical, or enhanced plant growth promoting activity. The ecdysteroid analogues can have similar structures to particular brassinosteroids. Mixtures of ecdysteroid analogues, the mixture having similar, identical, or enhanced biological activities as compared to brassinosteroids, for instance similar, identical, or enhanced plant growth promoting activity, are also provided by the present disclosure.