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CAS No.: | 467-55-0 |
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Name: | Hecogenin |
Article Data: | 24 |
Molecular Structure: | |
Formula: | C27H42O4 |
Molecular Weight: | 430.628 |
Synonyms: | 5a,25D-Spirostan-12-one, 3b-hydroxy- (7CI);5a-Spirostan-12-one, 3b-hydroxy-, (25R)- (8CI);(+)-Hecogenin;(25R)-3b-Hydroxy-5a-spirostan-12-one;(3b,5a,25R)-3-Hydroxyspirostan-12-one;12-Oxotigogenin;Gekogenin;Hocogenin;NSC 115921; |
EINECS: | 207-392-4 |
Density: | 1.16 g/cm3 |
Melting Point: | 268 °C |
Boiling Point: | 548.9 °C at 760 mmHg |
Flash Point: | 177.8 °C |
Appearance: | White solid. |
Hazard Symbols: | Xi |
Risk Codes: | R36/37/38 |
PSA: | 55.76000 |
LogP: | 4.97280 |
Conditions | Yield |
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With methanol; potassium hydroxide In dichloromethane at 20℃; for 18h; | 99% |
With methanol; potassium carbonate In tetrahydrofuran for 24h; | 97% |
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 12h; Inert atmosphere; | 95% |
hecogenin
Conditions | Yield |
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With sodium perborate tetrahydrate In tetrahydrofuran; water for 3h; | 79% |
hecogenin
Conditions | Yield |
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With sulfuric acid | 44.8% |
12-methylenetigogenin
hecogenin
Conditions | Yield |
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With sodium periodate; potassium carbonate; tert-butyl alcohol Reagens 4: Kaliumpermanganat; |
Conditions | Yield |
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With pyridine; sodium borate | |
With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether Behandeln des erhaltenen Reaktionsprodukts in Pyridin mit Bernsteinsaeure-anhydrid und mit Chrom(VI)-oxid und wss. Essigsaeure, danach mit methanol. Kalilauge; | |
Aspergillus niger; |
Conditions | Yield |
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With hydrogenchloride; ethanol |
(25R)-12α-(Aminomethyl)-5α-spirostan-3β,12β-diol
A
(25R)-3β-Hydroxy-C-homo-5α-spirostan-12-on
B
(25R)-3β-Hydroxy-C-homo-5α-spirostan-12-on
D
hecogenin
Conditions | Yield |
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With sodium azide; sodium nitrite Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
hecogenin
Conditions | Yield |
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With hydrogenchloride In ethanol at 100℃; for 3.5h; |
C
hecogenin
Conditions | Yield |
---|---|
With hydrogenchloride In butan-1-ol at 70℃; for 2.5h; | A 13.5 mg B 16.5 mg C 15 mg |
hecogenin
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 100℃; for 3.5h; | |
Multi-step reaction with 2 steps 1: 20 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C 2: 2M HCl / ethanol / 3.5 h / 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: 20 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C 2: 15 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C View Scheme |
The Hecogenin, with the CAS registry number 467-55-0, is also known as (25R)-3b-Hydroxy-5a-spirostan-12-one. It belongs to the product categories of Steroids; Biochemistry; Steroids (Others). Its EINECS registry number is 207-392-4. This chemical's molecular formula is C27H42O4 and molecular weight is 430.62. What's more, its systematic name is called (3β,5α,25R)-3-Hydroxyspirostan-12-one.
Physical properties about Hecogenin are: (1)ACD/LogP: 4.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.22; (4)ACD/LogD (pH 7.4): 4.22; (5)ACD/BCF (pH 5.5): 947.44; (6)ACD/BCF (pH 7.4): 947.44; (7)ACD/KOC (pH 5.5): 4701.29; (8)ACD/KOC (pH 7.4): 4701.29; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.558; (14)Molar Refractivity: 119.77 cm3; (15)Molar Volume: 371.1 cm3; (16)Surface Tension: 46.3 dyne/cm; (17)Density: 1.16 g/cm3; (18)Flash Point: 177.8 °C; (19)Enthalpy of Vaporization: 95.25 kJ/mol; (20)Boiling Point: 548.9 °C at 760 mmHg; (21)Vapour Pressure: 2.45E-14 mmHg at 25 °C.
Preparation of Hecogenin: this chemical can be prepared by a-D-Glucopyranosyl(1->4)a-D-glucopyranosyl(1->4)a-D-glucopyranosyl(1->3)hecogenin. This reaction needs reagent (NH2)2SO4. The yield is 44.8 %.
Uses of Hecogenin: (1) it is used in the preparation of steroidal hormones; (2) it is used to produce other chemicals. For example, it can produce 3b-Hydroxy-11b-bromo-12-oxo-(25R)-5a-spirostane. The reaction occurs with reagents Br2, HCl and solvents methanol, CH2Cl2. The yield is 59 %.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C2C[C@@H]1[C@@]6(C)CC[C@H](O)C[C@@H]6CC[C@H]1[C@H]5[C@]2([C@@H]4[C@@H](O[C@@]3(OC[C@@H](CC3)C)[C@H]4C)C5)C
(2) InChI: InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-22,24,28H,5-14H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1
(3) InChIKey: QOLRLLFJMZLYQJ-LOBDNJQFSA-N