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| CAS No.: | 472-15-1 |
|---|---|
| Name: | Betulinic acid |
| Article Data: | 59 |
| Molecular Structure: | |
|
|
|
| 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: |
 Xi
|
| Safety: | 24/25 |
| PSA: | 57.53000 |
| LogP: | 7.08950 |
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| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In tetrahydrofuran Acidic conditions; | 94% |
- 10376-50-8, 38736-81-1
3-O-acetylbetulinic acid
- 472-15-1
Betulinic acid
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With dipyridinium dichromate In water; N,N-dimethyl-formamide | A 20% B 7% C 8% D 13% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 cm3
Molar Volume: 428.7 cm3
Polarizability: 52.79 10-24 cm3
Surface Tension: 39.9 dyne/cm
Density: 1.065 g/cm3
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