Product Name

  • Name

    Ruscogenin

  • EINECS 207-447-2
  • CAS No. 472-11-7
  • Article Data14
  • CAS DataBase
  • Density 1.18 g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 472-11-7 (Ruscogenin)
  • Hazard Symbols
  • 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;
  • PSA 58.92000
  • LogP 4.68470

Synthetic route

(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]
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]

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

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

β-D-xylopyranoside

A

D-xylose
58-86-6

D-xylose

B

(25R)-ruscogenin
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

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

A

D-xylose
58-86-6

D-xylose

B

L-Rhamnose
3615-41-6

L-Rhamnose

C

(25R)-ruscogenin
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

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

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-glucose
50-99-7

D-glucose

C

(25R)-ruscogenin
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
3β-O-tert-butyldimethylsilyl-(25R)-ruscogenin
201858-23-3

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

(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%
3β-acetoxyspirost-5-ene-1-one
90802-64-5

3β-acetoxyspirost-5-ene-1-one

A

(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
79037-17-5

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

B

(25R)-ruscogenin
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

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

(25R)-ruscogenin
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
spirost-5-ene-1-oxo-3β-ol
14414-62-1

spirost-5-ene-1-oxo-3β-ol

A

(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
79037-17-5

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

B

(25R)-ruscogenin
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

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

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In methanol for 3h; Heating;
spirosta-5(6),25(27)-diene-1β,3β-diol
17676-33-4

spirosta-5(6),25(27)-diene-1β,3β-diol

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
palladium on activated charcoal In ethanol; cyclohexene for 16h; Heating; Yield given;
26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1<*>2)-4-O-sulfo-α-L-arabinopyran...

26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1<*>2)-4-O-sulfo-α-L-arabinopyran...

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;
ruscogenin 1-O-α-L-rhamnopyranosyl(1<*>2)-4-O-sulfo-α-L-arabinopyranoside

ruscogenin 1-O-α-L-rhamnopyranosyl(1<*>2)-4-O-sulfo-α-L-arabinopyranoside

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;
(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[(1S,2S,4S,5′R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2′-oxane]-14-yl]oxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
125150-67-6

(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[(1S,2S,4S,5′R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2′-oxane]-14-yl]oxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;
ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside
94898-61-0

ruscogenin 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine; dioxane / 7 h / 80 °C
2: 2 N HCl / dioxane; H2O / 2 h / Heating
View Scheme
26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside
94901-57-2

26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl(1->2)-4-O-sulfo-β-D-fucopyranoside

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2O / 24 h / 37 °C / almond emulsin
2: pyridine; dioxane / 7 h / 80 °C
3: 2 N HCl / dioxane; H2O / 2 h / Heating
View Scheme
hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

(25S)-ruscogenin
35882-30-5

(25S)-ruscogenin

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

25(R,S)-spirost-5-en-1β,3β,7β-triol

25(R,S)-spirost-5-en-1β,3β,7β-triol

Conditions
ConditionsYield
With hydrogenchloride; dipotassium hydrogenphosphate; 2,3,4,5,6-pentahydroxy-hexanal; sodium chloride In water; dimethyl sulfoxide at 120℃; pH=7; Autoclave; Microbiological reaction;
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

25(R,S)-spirost-5-en-1β,3β,7β,12β-tetraol

25(R,S)-spirost-5-en-1β,3β,7β,12β-tetraol

Conditions
ConditionsYield
With hydrogenchloride; dipotassium hydrogenphosphate; 2,3,4,5,6-pentahydroxy-hexanal; sodium chloride In water; dimethyl sulfoxide at 120℃; pH=7; Autoclave; Microbiological reaction;
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

spirost-5-ene-1-oxo-3β-ol
14414-62-1

spirost-5-ene-1-oxo-3β-ol

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 2.5h; Ambient temperature;95%
With chromium(VI) oxide; acetic acid
UDP-glucose
133-89-1

UDP-glucose

(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

C33H52O9

C33H52O9

Conditions
ConditionsYield
With UGT74AN1; magnesium chloride In aq. buffer at 37℃; for 12h; pH=8; Enzymatic reaction;
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Cholest-5-ene-1β,3β,16β,26-tetrol
79037-11-9, 79037-16-4

Cholest-5-ene-1β,3β,16β,26-tetrol

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc In ethanol for 2.5h; Heating;33%
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

3β-acetoxyspirost-5-ene-1-one
90802-64-5

3β-acetoxyspirost-5-ene-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
View Scheme
Multi-step reaction with 2 steps
1: chromium (VI)-oxide; aqueous acetic acid
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

(20S,22R,25R)-1α,3β-diacetoxyspirost-5-ene
861674-94-4

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 72 percent / acetylation
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 72 percent / acetylation
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

C41H58O8S2

C41H58O8S2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
4: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C,
View Scheme
Multi-step reaction with 5 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
5: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C,
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

cholest-5-ene-1α,16β-diol
79037-09-5

cholest-5-ene-1α,16β-diol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
View Scheme
Multi-step reaction with 5 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

cholest-5-ene-1α,3β,16β-triol
79037-10-8

cholest-5-ene-1α,3β,16β-triol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
View Scheme
Multi-step reaction with 5 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

cholest-5-ene-1α,3β,16β,26-tetrol
79037-11-9, 79037-16-4

cholest-5-ene-1α,3β,16β,26-tetrol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
79037-17-5

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

1α,16β-diacetoxycholest-5-ene
79037-01-7

1α,16β-diacetoxycholest-5-ene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
5: 80 percent
View Scheme
Multi-step reaction with 6 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
6: 80 percent
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

Toluene-4-sulfonic acid (2R,6R)-2-methyl-6-((1S,3R,8S,9S,10R,13S,14S,16S,17R)-1,3,16-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-heptyl ester

Toluene-4-sulfonic acid (2R,6R)-2-methyl-6-((1S,3R,8S,9S,10R,13S,14S,16S,17R)-1,3,16-trihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-heptyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
4: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C,
View Scheme
Multi-step reaction with 5 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
5: pyridine / Ambient temperature; 1.) 1 h, -6 - -10 deg C, 2.) 23 deg C,
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

1α,3β,16β-triacetoxycholest-5-ene
79037-02-8

1α,3β,16β-triacetoxycholest-5-ene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
4: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
View Scheme
Multi-step reaction with 6 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
5: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

1α,3β,16β,26-tetraacetoxycholest-5-ene
79037-03-9, 79037-08-4

1α,3β,16β,26-tetraacetoxycholest-5-ene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 70 percent / sodium borohydride / methanol / 2 h / Ambient temperature
3: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
4: 87 percent
View Scheme
Multi-step reaction with 5 steps
1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature
2: 87.5 percent / acetylation
3: 66 percent / LTBH / tetrahydrofuran / cooling 1 h, r.t., 1 h
4: 30 percent / amalgamated Zn, HCl / aq. ethanol / Heating
5: 87 percent
View Scheme
(25R)-ruscogenin
472-11-7

(25R)-ruscogenin

cholest-5-ene-1β,3β-diol
63908-96-3

cholest-5-ene-1β,3β-diol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 33 percent / amalgamated Zn, HCl / aq. ethanol / 2.5 h / Heating
2: 1.) p-toluenesulfonyl chloride, 2.) LAH / 1.) pyridine, 1 h, -6 - -10 deg C, 23 deg C, 2.) reflux, 16 h, ether
3: 0.158 g / pyridine
4: 0.544 g / pyridine / 0 °C
5: 0.346 g / LAH / diethyl ether / Heating
View Scheme

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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