Betulinic acid supplier | CasNO.472-15-1

Name
Betulinic acid
EINECS 207-448-8
CAS No. 472-15-1
Article Data59
CAS DataBase
Density 1.065 g/cm³
Solubility
Melting Point 295-298 °C (dec.)(lit.)
Formula C₃₀H₄₈O₃
Boiling Point 550 °C at 760 mmHg
Molecular Weight 456.709
Flash Point 300.5 °C
Transport Information
Appearance powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols Xi
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)-;
PSA 57.53000
LogP 7.08950

Synthetic route

: 4481-62-3
betulonic acid

: 472-15-1
Betulinic acid

Conditions

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%

: 7020-34-0
betulone

: 472-15-1
Betulinic acid

Conditions

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

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

: 473-98-3
betulin

: 472-15-1
Betulinic acid

Conditions

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

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

: 4481-62-3
betulonic acid

A: 472-15-1
Betulinic acid

B: 38736-77-5
3-epibetulinic acid

Conditions

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;

: 473-98-3
betulin

A: 4439-98-9
betulonic aldehyde

B: 472-15-1
Betulinic acid

C: 7020-34-0
betulone

Conditions

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 %;

...Expand

: 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

Conditions	Yield
With dipyridinium dichromate In water; N,N-dimethyl-formamide	A 20% B 7% C 8% D 13%

...Expand

: 473-98-3
betulin

A: 472-15-1
Betulinic acid

B: 7020-34-0
betulone

Conditions

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

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

: 80832-44-6
3β-trans-(3,4-dihydroxycinnamoyloxy)-20(29)-lupen-28-oic acid

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 16h; Ambient temperature;	220 mg

: 75365-42-3
α-L-rhamnopyranosyl-3β-hydroxy-lup-20(29)-en-28-oic acid

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With sulfuric acid for 5h; Heating;

: lup-20(29)-en-28-oic-3-O-α-L-rhamnopyranosyl-(2->1)-O-β-D-glucopyranoside

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With sulfuric acid In ethanol for 5h; Heating;

: pavophylline

A: 2280-44-6
D-Glucose

B: 73-34-7
L-rhamnose

C: 532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7
L-arabinose

D: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With sulfuric acid In water for 6h; Product distribution; Heating;

...Expand

: pavophylline

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With sulfuric acid In water for 6h; Heating;

: 22333-85-3
28-O-β-D-glucopyranosyl 3β-hydroxy-lup-20(29)-en-28-oate

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With enzyme β-glucosidase In N,N-dimethyl-formamide at 37℃; for 72h; phosphate buffer (pH 5);

: 1617-70-5
lupenone

A: 472-15-1
Betulinic acid

B: 38736-77-5
3-epibetulinic acid

Conditions

Conditions	Yield
Quantum yield; Product distribution; Further Variations:; Temperatures; Solvents;

: (2'E,3S,5R,8R,9R,10R,13R,14R,17S,18R,19R)-3-O-trans-feruloyllup-20(29)-en-28-oic acid

A: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 3h; Heating;	A 1.8 mg B 3.1 mg

: 18-hydroxyoctadec-9-enoic acid, sodium salt

: 9,10-epoxy-18-hydroxyoctadecanoic acid, sodium salt

: threo-9,10,18-trihydroxyoctadecanoic acid, sodium salt

: 22-hydroxydocosanoic acid, sodium salt

: sodium betulinate

A: 3329-38-2
18-hydroxyoctadec-9-enoic acid

B: 3233-92-9
9,10-epoxy-18-hydroxyoctadecanoic acid

C: threo-9,10,18-trihydroxyoctadecanoic acid

D: 506-45-6
22-hydroxydocosanoic acid

E: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With hydrogenchloride In water

...Expand

: 18-hydroxyoctadec-9-enoic acid, potassium salt

: 9,10-epoxy-18-hydroxyoctadecanoic acid, potassium salt

: threo-9,10,18-trihydroxyoctadecanoic acid, potassium salt

: 22-hydroxydocosanoic acid, potassium salt

: potassium betulinate

A: 3329-38-2
18-hydroxyoctadec-9-enoic acid

B: 3233-92-9
9,10-epoxy-18-hydroxyoctadecanoic acid

C: threo-9,10,18-trihydroxyoctadecanoic acid

D: 506-45-6
22-hydroxydocosanoic acid

E: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With hydrogenchloride In water

...Expand

: 27570-20-3
betulin monoacetate

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tert-butyl chromate 2: KOH / methanol View Scheme
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; water containing acetic acid 2: ethanolic KOH-solution View Scheme
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; water containing acetic acid 2: ethanolic KOH-solution View Scheme

: 27570-20-3
betulin monoacetate

CrO3: CrO3

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / CrO3, H2SO4 / acetone / 1.5 h / 0 °C 2: 88 percent / aq. K2CO3 / methanol / 24 h View Scheme

: 189571-52-6
3-hydroxy-28-[(tetrahydro-2H-pyran-2-yl)oxy]lup-20(29)-ene

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / pyridine / 36 h / Ambient temperature 2: 95 percent / pyridinium p-toluene sulfonic acid salt / methanol / 36 h / Ambient temperature 3: 80 percent / CrO3, H2SO4 / acetone / 1.5 h / 0 °C 4: 88 percent / aq. K2CO3 / methanol / 24 h View Scheme

: 189571-53-7
3-O-acetyl-28-O-tetrahydropyranylbetulin

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / pyridinium p-toluene sulfonic acid salt / methanol / 36 h / Ambient temperature 2: 80 percent / CrO3, H2SO4 / acetone / 1.5 h / 0 °C 3: 88 percent / aq. K2CO3 / methanol / 24 h View Scheme

: 1721-69-3
betulin diacetate

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzene; KOH; ethanol 2: chromium (VI)-oxide; water containing acetic acid 3: ethanolic KOH-solution View Scheme
Multi-step reaction with 3 steps 1: benzene; KOH; ethanol 2: chromium (VI)-oxide; water containing acetic acid 3: ethanolic KOH-solution View Scheme

: 1125546-06-6
28-O-β-glucuronide betulinic acid

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With Escherichia coli β-D-glucuronidase at 37℃; for 1h;

: 473-98-3
betulin

A: 13159-28-9, 92594-07-5
betulinic aldehyde

B: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 70h;	A n/a B 235 mg

: 4439-98-9
betulonic aldehyde

: 13159-28-9, 92594-07-5
betulinic aldehyde

A: 472-15-1
Betulinic acid

B: 4481-62-3
betulonic acid

Conditions

Conditions	Yield
Stage #1: betulonic aldehyde; betulinic aldehyde With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 18.5h; Inert atmosphere; Stage #2: With sodium hydroxide In water; tert-butyl alcohol at 20℃; for 1.5h; Stage #3: With hydrogenchloride In water for 2.5h; Overall yield = 17.8 g;

...Expand

: 4439-98-9
betulonic aldehyde

: 472-15-1
Betulinic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 15.5 h / 20 °C / Inert atmosphere 1.2: 1.5 h / 20 °C 1.3: 2.5 h 2.1: sodium hydroxide; sodium tetrahydroborate / water; isopropyl alcohol / 3 h / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / tert-butyl alcohol; water / 0.25 h 1.2: 1 h / Reflux 2.1: sodium tetrahydroborate / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: sodium chlorite; dihydrogen peroxide; sodium dihydrogenphosphate / tert-butyl alcohol; water / 0.25 h / 0 - 10 °C 2: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C View Scheme

: 472-15-1
Betulinic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 2259-06-5, 25493-95-2
methyl betulinate

Conditions

Conditions	Yield
In methanol; benzene	100%
In methanol; toluene at 20℃; for 3h; Inert atmosphere;	97%
In methanol at 20℃; for 2h;	96%

: 472-15-1
Betulinic acid

: 106-95-6
allyl bromide

: 475562-57-3
allyl betulinate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 3h; Heating / reflux;	100%
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 7h;	85%
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 7h;	84%
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 7h;	84%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;

: 61798-18-3
4-methoxycarbonyl-3,3-dimethylbutyryl chloride

: 472-15-1
Betulinic acid

: 3-O-(5'-methoxy-3',3'-dimethylglutaryl)betulinic acid

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	100%

: 472-15-1
Betulinic acid

: (3β)-3-hydroxylup-20(29)-en-28-amide

Conditions

Conditions	Yield
Stage #1: Betulinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With ammonia In water; N,N-dimethyl-formamide at 20℃; for 16h;	100%
Multi-step reaction with 3 steps 1.1: triethylamine; dmap; pyridine / 12 h / 25 °C 2.1: oxalyl dichloride / dichloromethane / 2 h / 25 °C / Cooling with ice 2.2: 1 h / 25 °C 3.1: potassium hydroxide / methanol; tetrahydrofuran / 24 h / 25 °C View Scheme

: 472-15-1
Betulinic acid

: 100-39-0
benzyl bromide

: 192211-42-0
benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3.5h; Inert atmosphere;	99%
With potassium carbonate In acetone at 20℃; for 24h;	99%
With potassium carbonate; caesium carbonate In acetone for 10h; Heating;	98%

: 472-15-1
Betulinic acid

: 212773-15-4
3-aminolup-20(29)-en-28-oic acid

Conditions

Conditions	Yield
With ammonium acetate; sodium cyanoborohydride In methanol for 40h;	99%
Stage #1: Betulinic acid With ammonium acetate; sodium cyanoborohydride In methanol for 40h; Stage #2: With hydrogenchloride In methanol; water pH=2; Stage #3: With potassium hydroxide In water pH=10;	99%
Multi-step reaction with 2 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 6 h / 20 °C 2: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; tetrahydrofuran / 6 h / 20 °C 2: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: Jones reagent / acetone / 25 °C 2: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 25 °C View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 472-15-1
Betulinic acid

: 2259-06-5, 25493-95-2
methyl betulinate

Conditions

Conditions	Yield
Stage #1: diazomethane; Betulinic acid In diethyl ether at 0 - 5℃; Stage #2: With acetic acid	98%
In diethyl ether at 0 - 5℃; for 24h;	90%
In diethyl ether; chloroform	87%

: 472-15-1
Betulinic acid

: 2845-62-7
benzenesulphonyl isocyanate

: 1187569-36-3
3-O-[N-(phenylsulfonyl)carbamoyl-17β-N-(phenylsulfonyl)amide]-betulinic acid

Conditions

Conditions	Yield
With triethylamine In toluene for 1h; Reflux;	98%

: 472-15-1
Betulinic acid

: 106-96-7
propargyl bromide

: 1400262-27-2
prop-2'-ynyl 3β-hydroxylup-20(29)-en-28-oate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 14h; Reflux;	98%
With potassium carbonate In acetone at 50℃;	96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	95%

: 25542-62-5
6-bromo-hexanoic acid ethyl ester

: 472-15-1
Betulinic acid

: 1400262-32-9
C38H62O5

Conditions

Conditions	Yield
Stage #1: Betulinic acid With caesium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 6-bromo-hexanoic acid ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;	98%

: 472-15-1
Betulinic acid

: 5437-45-6
Benzyl bromoacetate

: benzyloxycarbonylmethyl 3β-hydroxylup-20(29)-en-28-oate

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 50℃;	98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; acetonitrile at 20℃; for 72h;	72%
With potassium carbonate In N,N-dimethyl-formamide at 21℃; for 14h;

: 472-15-1
Betulinic acid

: 108-24-7
acetic anhydride

: 10376-50-8, 38736-81-1
3-O-acetylbetulinic acid

Conditions

Conditions	Yield
Stage #1: Betulinic acid; acetic anhydride With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 65℃; for 2h; Stage #2: With hydrogenchloride; water at 100℃; for 0.5h;	97%
Stage #1: Betulinic acid; acetic anhydride With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 65℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride; water at 100℃; for 0.5h;	97%
With pyridine at 20℃; for 72h;	96.2%

: 472-15-1
Betulinic acid

: 102-92-1
Cinnamoyl chloride

: 267219-69-2
(1R,3aS,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-(cinnamoyloxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid

Conditions

Conditions	Yield
With dmap In benzene at 60℃;	97%

: 472-15-1
Betulinic acid

: 100-44-7
benzyl chloride

: 192211-42-0
benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	97%
With potassium carbonate In acetone at 20℃; for 20h;	93%
With potassium carbonate In acetone at 20℃; for 20h;	93%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In acetone

: 34446-64-5, 42996-84-9
(E)-3-(4-methoxyphenyl)propenoyl chloride

: 472-15-1
Betulinic acid

: 3-O-(E)-p-methoxycinnamoylbetulinic acid

Conditions

Conditions	Yield
With dmap In benzene at 60℃;	96%

: 472-15-1
Betulinic acid

: 79-04-9
chloroacetyl chloride

: 689279-93-4
(3S)-3-(2-chloroacetyloxy)-lup-20(29)-en-28-oic acid

Conditions

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	96%
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h; Inert atmosphere;	86%
With N-ethyl-N,N-diisopropylamine; dmap In tetrahydrofuran Inert atmosphere;	86%
In N,N-dimethyl acetamide at 20℃; for 24h;

: 637-59-2
1-Bromo-3-phenylpropane

: 472-15-1
Betulinic acid

: 1400262-29-4
C39H58O3

Conditions

Conditions	Yield
Stage #1: Betulinic acid With caesium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-Bromo-3-phenylpropane In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;	96%

: 472-15-1
Betulinic acid

: C30H48O6S*2H3N

Conditions

Conditions	Yield
With aminosulfonic acid; urea In 1,4-dioxane; N,N-dimethyl-formamide at 65 - 75℃;	96%

: 472-15-1
Betulinic acid

: 32213-95-9
dimethyl L-aspartate hydrochloride

: 228419-37-2
(S)-2-[((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-succinic acid dimethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 19h;	95%

: 67-56-1
methanol

: 472-15-1
Betulinic acid

: 2259-06-5, 25493-95-2
methyl betulinate

Conditions

Conditions	Yield
With diazomethyl-trimethyl-silane In hexane; toluene at 20℃;	95%
With Penicillium citreonigrum In chloroform; dimethyl sulfoxide Sonication;	31.6 mg

: 110-89-4
piperidine

: 472-15-1
Betulinic acid

: 96042-30-7
4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

: methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bS)-1-(1-acetoxy-2-hydroxypropan-2-yl)-3a-amino-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Conditions

Conditions	Yield
In chloroform	95%

...Expand

: 472-15-1
Betulinic acid

: 2450-71-7
Propargylamine

: 1596376-96-3
N-propargyl-3β-hydroxy-lup-20(29)-en-28-amide

Conditions

Conditions	Yield
Stage #1: Betulinic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Stage #2: Propargylamine With potassium carbonate In N,N-dimethyl-formamide at 20℃;	95%
Stage #1: Betulinic acid With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: Propargylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	76%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 0 - 20℃; for 25h; Inert atmosphere;	51%

: 472-15-1
Betulinic acid

: 123624-90-8
2-(chloromethyl)-3,5,6-trimethylpyrazine

: 3β-hydroxylup-20(29)-ene-28-oic acid 3,5,6-trimethylpyrazin-2-methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;	95%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h;	54.1%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h;

: 472-15-1
Betulinic acid

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 22333-86-4
2,3,4,6-tetra-O-acetyl β-D-glucopyranosyl-3β-hydroxylup-20(29)-en-28-oate

Conditions

Conditions	Yield
With pyridine; silver(l) oxide for 3h;	94%

: 472-15-1
Betulinic acid

: 765-30-0
Cyclopropylamine

: N-cyclopropyl-3-hydroxylup-20(29)-en-28-amide

Conditions

Conditions	Yield
Stage #1: Betulinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: Cyclopropylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	94%

: 629-27-6
1-Iodooctane

: 472-15-1
Betulinic acid

: 1400262-34-1
C38H64O3

Conditions

Conditions	Yield
Stage #1: Betulinic acid With caesium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-Iodooctane In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;	94%

: 472-15-1
Betulinic acid

: 92-95-5
4-biphenyl isocyanate

: 1187569-38-5
3-O-[N-(biphenyl)-p-carbamoyl]betulinic acid

Conditions

Conditions	Yield
With triethylamine In toluene for 1h; Reflux;	93.5%

: 472-15-1
Betulinic acid

: 4481-62-3
betulonic acid

Conditions

Conditions	Yield
With pyridinium chlorochromate In chloroform for 2h; Ambient temperature;	93%
With Jones reagent In dichloromethane; acetone at 20℃; for 0.25h; Cooling;	93%
With Jones reagent In dichloromethane; acetone at 20℃; Cooling;	93%

Betulinic acid Chemical Properties

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)-;

Betulinic acid History

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

Betulinic acid 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.

Betulinic acid Safety Profile

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

Product Name

Betulinic acid

Synthetic route

Betulinic acid Chemical Properties

Betulinic acid History

Betulinic acid Uses

Betulinic acid Safety Profile

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