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CAS No.: | 5289-74-7 |
---|---|
Name: | Hydroxyecdysone |
Article Data: | 22 |
Molecular Structure: | |
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: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 22-24/25-36-26 |
PSA: | 138.45000 |
LogP: | 1.85400 |
20-Hydroxyecdysone
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 2.5h; Heating; | 89% |
14alpha-Hydroperoxy-20-hydroxyecdysone
A
20-Hydroxyecdysone
Conditions | Yield |
---|---|
With iron(II) sulfate In tetrahydrofuran; water Ambient temperature; pH=3; | A 5% B 85% |
20-Hydroxyecdysone
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
A
20-Hydroxyecdysone
B
(20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | A 80% B n/a |
22-Dehydro-20-hydroxyecdysone
A
20-Hydroxyecdysone
B
(20R,22S)-2β,3β,14,20,22,25-hexahydro-5β-cholest-7-en-6-one
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
20-Hydroxyecdysone
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
20-Hydroxyecdysone
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran; water for 0.166667h; | 58% |
A
20-Hydroxyecdysone
B
14alpha-Hydroperoxy-20-hydroxyecdysone
Conditions | Yield |
---|---|
With oxalic acid In methanol for 6h; Ambient temperature; darkness; | A 9% B 57% |
2,3-didehydro-2,3-dideoxy-20-hydroxyecdysone
A
20-Hydroxyecdysone
Conditions | Yield |
---|---|
With pyridine; osmium(VIII) oxide | A 54% B 32% |
20-hydroxyecdysone-2,3,22-triacetate
20-Hydroxyecdysone
Conditions | Yield |
---|---|
With potassium hydroxide In methanol Heating; |
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. |