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Ruscogenin

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Name

Ruscogenin

EINECS 207-447-2
CAS No. 472-11-7 Density 1.18 g/cm3
PSA 58.92000 LogP 4.68470
Solubility N/A Melting Point 198-202oC
Formula C27H42O4 Boiling Point 563.1 °C at 760 mmHg
Molecular Weight 430.628 Flash Point 294.3 °C
Transport Information N/A Appearance N/A
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 472-11-7 (Ruscogenin) Hazard Symbols N/A
Synonyms

Ruscogenin(6CI,7CI);Spirost-5-ene-1b,3b-diol, (25R)- (8CI);Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-[2H]pyran], spirost-5-ene-1,3-diolderiv.;25D-Spirost-5-ene-1β,3β-diol;

Article Data 14

Ruscogenin Synthetic route

1307292-22-3

(25R)-26-O-β-D-glucopyranosyl-furosta-5,20(22)-diene-1β,3β,26-triol 1-O-[α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside]

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With β-glucosidase In phosphoric acid at 37℃; for 24h; Enzymatic reaction;

β-D-xylopyranoside

A

58-86-6

D-xylose

B

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;A n/a
B 3.8 mg

(25R)-3β-hydroxyspitost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-xylopyranoside

A

58-86-6

D-xylose

B

3615-41-6

L-Rhamnose

C

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;A n/a
B n/a
C 2.8 mg

(25R)-3β-hydroxyspitost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside

A

3615-41-6

L-Rhamnose

B

50-99-7

D-glucose

C

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 95℃; for 1h; Inert atmosphere;A n/a
B n/a
C 1.5 mg
201858-23-3

3β-O-tert-butyldimethylsilyl-(25R)-ruscogenin

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In acetone for 1h; Ambient temperature;96%
With hydrogenchloride at 20℃; for 1h;96%
90802-64-5

3β-acetoxyspirost-5-ene-1-one

A

79037-17-5

(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene

B

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran cooling 1 h, r.t., 1 h;A 66%
B 34%
With LTBH In tetrahydrofuran cooling 1 h, r.t., 1 h;A 66%
B 34%

(25R)-3β-hydroxyspirost-5-en-1β-yl 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 95℃; for 1h;11.2 mg
With hydrogenchloride In methanol at 80℃; for 10h; Sealed tube;0.6 mg
14414-62-1

spirost-5-ene-1-oxo-3β-ol

A

79037-17-5

(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene

B

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 2h; Ambient temperature;A 70%
B 30%
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran cooling 1 h, r.t., 1 h;A 60%
B 40%

ruscogenin 1-O-α-L-arabinopyranosyl-(1-2)-β-D-glucopyranoside

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In methanol for 3h; Heating;
17676-33-4

spirosta-5(6),25(27)-diene-1β,3β-diol

472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
palladium on activated charcoal In ethanol; cyclohexene for 16h; Heating; Yield given;

Ruscogenin Specification

The CAS register number of Spirost-5-ene-1,3-diol,(1β,3β,25R)- is 472-11-7. It also can be called as 25D-Spirost-5-ene-1β,3β-diol and the systematic name about this chemical is (1β,3β,25R)-spirost-5-en-1,3-diol. The molecular formula about this chemical is C27H42O4 and the molecular weight is 430.62. It belongs to the following product category which includes Miscellaneous Natural Products.

Physical properties about Spirost-5-ene-1,3-diol,(1β,3β,25R)- are: (1)ACD/LogP: 4.29; (2)#H bond acceptors: 4; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 2; (5)Polar Surface Area: 36.92 Å2; (6)Index of Refraction: 1.576; (7)Molar Refractivity: 120.87 cm3; (8)Molar Volume: 364.7 cm3; (9)Polarizability: 47.91x10-24cm3; (10)Surface Tension: 48.7 dyne/cm; (11)Density: 1.18 g/cm3; (12)Flash Point: 294.3 °C; (13)Enthalpy of Vaporization: 97.24 kJ/mol; (14)Boiling Point: 563.1 °C at 760 mmHg; (15)Vapour Pressure: 5.03E-15 mmHg at 25 °C.

Preparation: this chemical can be prepared by (25R)-Ruscogenin. This reaction will need reagent of chromium (VI)-oxide, aqueous acetic acid.

Uses of Spirost-5-ene-1,3-diol,(1β,3β,25R)-: it can be used to produce epiruscogenin and (25R)-Ruscogenin. This reaction will need reagent of lithium aluminum tri-t-butoxyhydride and solvent of tetrahydrofuran. The reaction needs 1 hour of cooling and 1 hour of r.t.. The yield is about 40%.

You can still convert the following datas into molecular structure:
(1)SMILES: O1[C@@H]4[C@H]([C@@H]([C@]12OC[C@@H](CC2)C)C)[C@@]5(C)CC[C@@H]3[C@@]6(C(=C/C[C@H]3[C@@H]5C4)\C[C@@H](O)C[C@H]6O)C
(2)InChI: InChI=1/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
(3)InChIKey: QMQIQBOGXYYATH-IDABPMKMBV
(4)Std. InChI: InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
(5)Std. InChIKey: QMQIQBOGXYYATH-IDABPMKMSA-N

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