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472-15-1

Basic Information
CAS No.: 472-15-1
Name: Betulinic acid
Article Data: 59
Molecular Structure:
Molecular Structure of 472-15-1 (Betulinic acid)
Formula: C30H48O3
Molecular Weight: 456.709
Synonyms: 3-Hydroxylup-20(29)-en-28-oic acid;Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-;Lup-20(29)-en-28-oic acid,3-hydroxy-,(3a)-;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid;Lup-20 (29)-en-28-oic acid, 3.beta.-hydroxy-;Mairin;Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-;Prestwick_95;Lup-20 (29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-;Lup-20(29)-en-28-oic acid, 3beta-hydroxy- (8CI);Betulic acid;RL9-080;Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3β)-;
EINECS: 207-448-8
Density: 1.065 g/cm3
Melting Point: 295-298 °C (dec.)(lit.)
Boiling Point: 550 °C at 760 mmHg
Flash Point: 300.5 °C
Appearance: powder
Hazard Symbols: IrritantXi
Safety: 24/25
PSA: 57.53000
LogP: 7.08950
Synthetic route
4481-62-3

betulonic acid

472-15-1

Betulinic acid

Conditions
ConditionsYield
Stage #1: betulonic acid With aluminum isopropoxide; benzyl alcohol In tetrahydrofuran at 65℃; for 2h;
Stage #2: With sodium hydroxide In water; xylene at 130℃; for 1h;
Stage #3: With acetic acid In water Conversion of starting material;
96.3%
Stage #1: betulonic acid With aluminum isopropoxide; benzyl alcohol In tetrahydrofuran at 65℃; for 2h; Heating / reflux;
Stage #2: With sodium hydroxide; water In xylenes at 130℃; for 1h;
Stage #3: With acetic acid In water
96.3%
With sodium tetrahydroborate; isopropyl alcohol; sodium hydroxide In water for 3h;94%
7020-34-0

betulone

472-15-1

Betulinic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran Acidic conditions;94%
10376-50-8, 38736-81-1

3-O-acetylbetulinic acid

472-15-1

Betulinic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 3h; Heating;89%
With potassium carbonate In methanol for 24h;88%
With potassium hydroxide
With potassium hydroxide In methanol
473-98-3

betulin

472-15-1

Betulinic acid

Conditions
ConditionsYield
Stage #1: betulin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In acetic acid butyl ester; water; tert-butyl alcohol at 20℃; for 6h;
Stage #2: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In acetic acid butyl ester; water; tert-butyl alcohol Solvent; Concentration; Reagent/catalyst;
89%
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium chlorite; tetrabutylammomium bromide; sodium hypochlorite In phosphate buffer at 50℃;86%
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; tetrabutylammomium bromide; sodium hypochlorite In phosphate buffer at 50℃; pH=7.6;72%
13159-28-9, 92594-07-5

betulinic aldehyde

472-15-1

Betulinic acid

Conditions
ConditionsYield
With sodium dihydrogenphosphate; sodium permanganate In dichloromethane; water; tert-butyl alcohol at 25℃; for 3h;85%
With sodium chlorite; sodium dihydrogenphosphate; 2-Methyl-1-butene; tert-butyl alcohol In toluene at 21℃; for 22h; Reagent/catalyst; Solvent; Temperature; Time;76%
With potassium permanganate In acetone at 0 - 20℃;
With sodium chlorite; sodium dihydrogenphosphate In dichloromethane; tert-butyl alcohol
4481-62-3

betulonic acid

A

472-15-1

Betulinic acid

B

38736-77-5

3-epibetulinic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran Yields of byproduct given;A 75%
B n/a
Stage #1: betulonic acid With L-Selectride In tetrahydrofuran at -80℃; for 5h;
Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran for 1h;
A 19%
B 38%
With sodium tetrahydroborate In tetrahydrofuran Yield given. Yields of byproduct given. Title compound not separated from byproducts;
473-98-3

betulin

A

4439-98-9

betulonic aldehyde

B

472-15-1

Betulinic acid

C

7020-34-0

betulone

Conditions
ConditionsYield
With synthetic air In 1,3,5-trimethyl-benzene at 140℃; under 760.051 Torr; for 6h; Catalytic behavior;A 20%
B 9%
C 27%
With CeO2/TiO2; air In 1,3,5-trimethyl-benzene at 140℃; for 6h; Overall yield = 8 %;
473-98-3

betulin

A

4439-98-9

betulonic aldehyde

B

13159-28-9, 92594-07-5

betulinic aldehyde

C

472-15-1

Betulinic acid

D

4481-62-3

betulonic acid

Conditions
ConditionsYield
With dipyridinium dichromate In water; N,N-dimethyl-formamideA 20%
B 7%
C 8%
D 13%
473-98-3

betulin

A

472-15-1

Betulinic acid

B

7020-34-0

betulone

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene at 140℃; for 4h;A n/a
B 5.3%
135757-66-3

lup-20(29)-en-28-oic-3-O-β-D-glucopyranosyl (2->1)-O-β-D-glucopyranoside

472-15-1

Betulinic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol at 100℃; for 4h;
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Chemistry

The Molecular formula of Betulinic acid (CAS NO.472-15-1): C30H48O3
The Molecular Weight: 456.7
Molecular Structure :
EINECS: 207-448-8
Synonyms of Betulinic acid (CAS NO.472-15-1): CCRIS 6748 ; Mairin ; NSC 113090 ; NSC 677578 ; 3-Hydroxylup-20(29)-en-28-oic acid ; Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)- ; Lup-20(29)-en-28-oic acid, 3beta-hydroxy- (8CI) Index of Refraction: 1.533 
Molar Refractivity: 133.17 cm
Molar Volume: 428.7 cm3 
Polarizability: 52.79 10-24 cm
Surface Tension: 39.9 dyne/cm 
Density: 1.065 g/cm
Flash Point: 300.5 °C 
Enthalpy of Vaporization: 95.41 kJ/mol 
Boiling Point: 550 °C at 760 mmHg 
Vapour Pressure: 2.17E-14 mmHg at 25°C 
refractive index: 7.8 ° (C=0.9, Pyridine)
Merck: 1190
IUPAC Name: 9-hydroxy-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-2,3,4,5,5a,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
Synonyms: 3BETA-HYDROXY-20(29)-LUPENE-28-OIC ACID;3-B-HYDROXY-LUPA-20(30)-ENE 28-OIC ACID;3BETA-HYDROXY-20(29)-LUPAENE-28-OIC ACID;3B-HYDROXY-20(29)-LUPENE-28-OIC ACID;BETULINIC ACID;BETULIC ACID;MAIRIN;LUP-20(29)-EN-28-OIC ACID, 3-HYDROXY-, (3B)-;

History

1.In 1995, Betulinic acid (CAS NO.472-15-1) was reported as a selective inhibitor of human melanoma.

Uses

 Betulinic acid (CAS NO.472-15-1) is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase.

Safety Profile

The Hazard Codes of Betulinic acid (CAS NO.472-15-1):  Xi
WGK Germany: 3