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Lupeol

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Name

Lupeol

EINECS 208-889-9
CAS No. 545-47-1 Density 0.978 g/cm3
PSA 20.23000 LogP 8.02480
Solubility N/A Melting Point 215-216oC
Formula C30H50O Boiling Point 488.1 °C at 760 mmHg
Molecular Weight 426.726 Flash Point 216.9 °C
Transport Information N/A Appearance white powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 545-47-1 (Lupeol) Hazard Symbols N/A
Synonyms

Lup-20(29)-en-3b-ol (8CI);Monogynol B (6CI);(+)-Lupeol;3b-Hydroxylup-20(29)-ene;Clerodol;Fagarasterol;Fagarsterol;Lupenol;NSC 90487;b-Viscol;

Article Data 30

Lupeol Synthetic route

Conditions
ConditionsYield
With potassium hydroxide In methanol for 0.0166667h; microwave irradiation;90%
With potassium hydroxide In ethanol for 5h; Heating;85%
With potassium hydroxide In ethanol for 5h; Reflux;85%
1190597-45-5

tert-butyl((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-9-yloxy)dimethylsilane

545-47-1

lupenol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 24h; Inert atmosphere;90%
27570-21-4

3-O-acetylbetulinal

545-47-1

lupenol

Conditions
ConditionsYield
Stage #1: 3-O-acetylbetulinal With hydrazine hydrate In diethylene glycol dimethyl ether at 80℃; for 3h;
Stage #2: With potassium hydroxide In diethylene glycol dimethyl ether for 5h; Reagent/catalyst; Temperature; Reflux;
68%
With hydrazine hydrate; potassium hydroxide In diethylene glycol for 6h; Reflux;65%
Multi-step reaction with 2 steps
1.1: p-toluenesulfonylhydrazine; Na2SO4 / ethanol / 3.5 h / 100 °C
1.2: 14 percent / NaBH3CN; p-toluenesulfonic acid monohydrate / dimethylformamide; tetrahydrothiophene 1,1-dioxide / 1 h / 100 °C
2.1: 70 percent / K2CO3 / methanol / 13 h / 50 °C
View Scheme
199665-79-7

lupeol-3-(3'R-hydroxy)-hexadecanoate

545-47-1

lupenol

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 38h; Reflux;64%
13159-28-9, 92594-07-5

betulinic aldehyde

545-47-1

lupenol

Conditions
ConditionsYield
Stage #1: betulinic aldehyde With hydrazine hydrate In dimethyl sulfoxide at 80℃; for 3h;
Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 160℃; for 5h;
61%

C32H52N2O2

545-47-1

lupenol

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 160℃; for 5h; Reagent/catalyst; Temperature; Solvent;55%
Conditions
ConditionsYield
With potassium hydroxide In diethylene glycol for 2h; Heating;A 50%
B 15%
With aluminum isopropoxide; isopropyl alcohol
1617-70-5

lupenone

545-47-1

lupenol

Conditions
ConditionsYield
With potassium hydroxide In diethylene glycol at 160℃; Heating; reflux 2 h, cooled, dil. HCl, ether extr., washed: water, dried, solvent distillation, chromatographed, petrol and benzene:petrol (2:3) elution; Further byproducts given. Yields of byproduct given;50%
Conditions
ConditionsYield
With potassium hydroxide In diethylene glycol for 2h; Heating;A 40%
B 8%
C 15%
1617-70-5

lupenone

555-31-7

aluminum isopropoxide

67-63-0

isopropyl alcohol

71-43-2

benzene

545-47-1

lupenol

Lupeol Chemical Properties

Molecular structure of Lup-20(29)-en-3-ol, (3b)- (CAS NO.545-47-1) is:

Product Name: Lup-20(29)-en-3-ol, (3b)-
CAS Registry Number: 545-47-1
IUPAC Name: (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Molecular Weight: 426.7174 [g/mol]  
Molecular Formula: C30H50O  
XLogP3-AA: 9.9  
H-Bond Donor: 1  
H-Bond Acceptor: 1
Storage temp.: 2-8 °C
Surface Tension: 34.2 dyne/cm 
Density: 0.977 g/cm3 
Flash Point: 216.9 °C 
Enthalpy of Vaporization: 86.89 kJ/mol 
Boiling Point: 488.1 °C at 760 mmHg 
Vapour Pressure: 1.41E-11 mmHg at 25 °C
EINECS: 208-889-9
Product Categories: Tri-Terpenoids

Lupeol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 2gm/kg (2000mg/kg)   Fitoterapia. Vol. 68, Pg. 9, 1997.
rat LD50 oral > 2gm/kg (2000mg/kg)   Fitoterapia. Vol. 68, Pg. 9, 1997.

Lupeol Safety Profile

WGK Germany: 2
RTECS: OK5763000

Lupeol Specification

 Lup-20(29)-en-3-ol, (3b)- , its cas register number is 545-47-1. It also can be called Lupeol ; (3beta)-Lup-20(29)-en-3-ol ; Fagarasterol .

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