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5289-74-7

Basic Information
CAS No.: 5289-74-7
Name: 20-Hydroxyecdysone
Article Data: 22
Cas Database
Molecular Structure:
Molecular Structure of 5289-74-7 (20-Hydroxyecdysone)
Formula: C27H44O7
Molecular Weight: 480.642
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;
EINECS: 811-097-1
Density: 1.28 g/cm3
Melting Point: 242-244 °C
Boiling Point: 702.1 °C at 760 mmHg
Flash Point: 392.4 °C
Solubility: alcohol: soluble
Appearance: white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
Transport Information: N/A
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
ConditionsYield
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
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

5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
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
ConditionsYield
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
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;
41451-87-0

Turkesterone

5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
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
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

A

5289-74-7

20-Hydroxyecdysone

B

115040-67-0

14alpha-Hydroperoxy-20-hydroxyecdysone

Conditions
ConditionsYield
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
ConditionsYield
With pyridine; osmium(VIII) oxideA 54%
B 32%
19404-87-6, 84507-62-0

20-hydroxyecdysone-2,3,22-triacetate

5289-74-7

20-Hydroxyecdysone

Conditions
ConditionsYield
With potassium hydroxide In methanol Heating;
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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.