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472-15-1

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472-15-1 Usage

Chemical Description

Betulinic acid is a compound isolated from Malaysian Callistemon speciosus.

Description

Betulinic acid (472-15-1) is a natural Lupane triterpenoid from white birch tree (Betula pubescens). Induces apoptosis in a variety of cell lines.1 Induces mitochondrial permeability transition pore opening.2 ?Acts as a chemosensitizer for anticancer drug treatment in chemoresistant colon cancer cell lines.3 Cell permeable.

Uses

Different sources of media describe the Uses of 472-15-1 differently. You can refer to the following data:
1. antineoplastic
2. Betulinic Acid is a natural pentacyclic triterpenoid. Betulinic Acid displays anti-inflammatory and anti-HIV activity. Betulinic Acid selectively induces apoptosis in tumor cells by directly activati ng the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic Acid also exhibits TGR5 agonist activity
3. Betulinic acid (BetA) has been used:to test its effects as an antiviral agent against Dengue virus (DENV)as a sterol regulatory element-binding protein (SREBP) inhibitor to repress the lipid metabolism and proliferation of clear cell renal cell carcinoma (ccRCC) cellsas a treatment to test its anti-tumor properties for cell viability and apoptotic cell death assays in multiple myeloma models

Definition

ChEBI: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium cla iflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.

General Description

Betulinic acid is a lupane-type triterpene, which can be prepared from betulin via oxidation using chromium oxide (VI). Along with anti-HIV-1 and anti-tumor activity, it also shows other bioactivities such as anti-inflammatory, antibacterial, in vitro antimalarial, anthelmintic and antioxidant activities.

Biological Activity

Natural triterpenoid that displays anti-HIV and antitumor activity. Induces the production of reactive oxygen species (ROS) and activates NF- κ B. Exhibits TRG5 agonist activity (EC 50 = 1.04 μ M).

Biochem/physiol Actions

Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.

Anticancer Research

This compound is a pentacyclic triterpene obtained from Betula and Zizyphus species,which shows selective cytotoxicity against human melanoma cells (Shoeb2006). It generates reactive oxygen species, activates MAPK cascade, inhibitstopoisomerase I, inhibits angiogenesis, modulates pro-growth transcriptionalactivators, modulates the activity of aminopeptidase-N, and thereby inducesapoptosis in cancer cells (Desai et al. 2008; Fulda 2008).

References

1) Ehrhardt et al. (2004) Betulinic acid-induced apoptosis in leukemia cells; Leukemia, 18 1406 2) Mullauer et al. (2009) Betulinic acid induces cytochrome c release and apoptosis in Bax/Bak-independent, permeability transition pore dependent fashion.; Apoptosis, 14 191 3) Jung et al. (2007) Effect of betulinic acid on anticancer drug-resistant colon cancer cells; Basic Clin. Pharmacol. Toxicol., 101 277

Check Digit Verification of cas no

The CAS Registry Mumber 472-15-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 2 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 472-15:
(5*4)+(4*7)+(3*2)+(2*1)+(1*5)=61
61 % 10 = 1
So 472-15-1 is a valid CAS Registry Number.
InChI:InChI=1/C29H46O3/c1-17(2)18-9-15-29(25(31)32)16-10-20-19(24(18)29)7-8-22-27(20,5)13-11-21-26(3,4)23(30)12-14-28(21,22)6/h18-24,30H,1,7-16H2,2-6H3,(H,31,32)/t18-,19-,20?,21?,22?,23+,24?,27-,28-,29-/m0/s1

472-15-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B2836)  Betulinic Acid  >97.0%(GC)(T)

  • 472-15-1

  • 100mg

  • 750.00CNY

  • Detail
  • TCI America

  • (B2836)  Betulinic Acid  >97.0%(GC)(T)

  • 472-15-1

  • 1g

  • 3,750.00CNY

  • Detail
  • Sigma-Aldrich

  • (91466)  Betulinicacid  analytical standard

  • 472-15-1

  • 91466-10MG

  • 1,100.97CNY

  • Detail
  • Aldrich

  • (855057)  Betulinicacid  technical grade, 90%

  • 472-15-1

  • 855057-100MG

  • 687.96CNY

  • Detail
  • Aldrich

  • (855057)  Betulinicacid  technical grade, 90%

  • 472-15-1

  • 855057-500MG

  • 2,369.25CNY

  • Detail
  • Sigma

  • (B8936)  Betulinicacid  ≥98% (HPLC)

  • 472-15-1

  • B8936-5MG

  • 436.41CNY

  • Detail
  • Sigma

  • (B8936)  Betulinicacid  ≥98% (HPLC)

  • 472-15-1

  • B8936-25MG

  • 1,471.86CNY

  • Detail

472-15-1Synthetic route

betulonic acid
4481-62-3

betulonic acid

Betulinic 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%
betulone
7020-34-0

betulone

Betulinic acid
472-15-1

Betulinic acid

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

3-O-acetylbetulinic acid

Betulinic 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
betulin
473-98-3

betulin

Betulinic acid
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%
betulinic aldehyde
13159-28-9, 92594-07-5

betulinic aldehyde

Betulinic acid
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
betulonic acid
4481-62-3

betulonic acid

A

Betulinic acid
472-15-1

Betulinic acid

B

3-epibetulinic acid
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;
betulin
473-98-3

betulin

A

betulonic aldehyde
4439-98-9

betulonic aldehyde

B

Betulinic acid
472-15-1

Betulinic acid

C

betulone
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 %;
betulin
473-98-3

betulin

A

betulonic aldehyde
4439-98-9

betulonic aldehyde

B

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

betulinic aldehyde

C

Betulinic acid
472-15-1

Betulinic acid

D

betulonic acid
4481-62-3

betulonic acid

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

betulin

A

Betulinic acid
472-15-1

Betulinic acid

B

betulone
7020-34-0

betulone

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene at 140℃; for 4h;A n/a
B 5.3%
lup-20(29)-en-28-oic-3-O-β-D-glucopyranosyl (2->1)-O-β-D-glucopyranoside
135757-66-3

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

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol at 100℃; for 4h;
3β-trans-(3,4-dihydroxycinnamoyloxy)-20(29)-lupen-28-oic acid
80832-44-6

3β-trans-(3,4-dihydroxycinnamoyloxy)-20(29)-lupen-28-oic acid

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 16h; Ambient temperature;220 mg
α-L-rhamnopyranosyl-3β-hydroxy-lup-20(29)-en-28-oic acid
75365-42-3

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

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With sulfuric acid for 5h; Heating;
lup-20(29)-en-28-oic-3-O-α-L-rhamnopyranosyl-(2->1)-O-β-D-glucopyranoside

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

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With sulfuric acid In ethanol for 5h; Heating;
pavophylline

pavophylline

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With sulfuric acid In water for 6h; Heating;
28-O-β-D-glucopyranosyl 3β-hydroxy-lup-20(29)-en-28-oate
22333-85-3

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

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With enzyme β-glucosidase In N,N-dimethyl-formamide at 37℃; for 72h; phosphate buffer (pH 5);
lupenone
1617-70-5

lupenone

A

Betulinic acid
472-15-1

Betulinic acid

B

3-epibetulinic acid
38736-77-5

3-epibetulinic acid

Conditions
ConditionsYield
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

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

A

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

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 3h; Heating;A 1.8 mg
B 3.1 mg
18-hydroxyoctadec-9-enoic acid, sodium salt

18-hydroxyoctadec-9-enoic acid, sodium salt

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

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

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

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

22-hydroxydocosanoic acid, sodium salt

22-hydroxydocosanoic acid, sodium salt

sodium betulinate

sodium betulinate

A

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

18-hydroxyoctadec-9-enoic acid

B

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

9,10-epoxy-18-hydroxyoctadecanoic acid

C

threo-9,10,18-trihydroxyoctadecanoic acid

threo-9,10,18-trihydroxyoctadecanoic acid

D

22-hydroxydocosanoic acid
506-45-6

22-hydroxydocosanoic acid

E

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With hydrogenchloride In water
18-hydroxyoctadec-9-enoic acid, potassium salt

18-hydroxyoctadec-9-enoic acid, potassium salt

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

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

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

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

22-hydroxydocosanoic acid, potassium salt

22-hydroxydocosanoic acid, potassium salt

potassium betulinate

potassium betulinate

A

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

18-hydroxyoctadec-9-enoic acid

B

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

9,10-epoxy-18-hydroxyoctadecanoic acid

C

threo-9,10,18-trihydroxyoctadecanoic acid

threo-9,10,18-trihydroxyoctadecanoic acid

D

22-hydroxydocosanoic acid
506-45-6

22-hydroxydocosanoic acid

E

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With hydrogenchloride In water
betulin monoacetate
27570-20-3

betulin monoacetate

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
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
betulin monoacetate
27570-20-3

betulin monoacetate

CrO3

CrO3

Betulinic acid
472-15-1

Betulinic acid

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

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

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
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
3-O-acetyl-28-O-tetrahydropyranylbetulin
189571-53-7

3-O-acetyl-28-O-tetrahydropyranylbetulin

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
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
betulin diacetate
1721-69-3

betulin diacetate

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
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
28-O-β-glucuronide betulinic acid
1125546-06-6

28-O-β-glucuronide betulinic acid

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
With Escherichia coli β-D-glucuronidase at 37℃; for 1h;
betulin
473-98-3

betulin

A

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

betulinic aldehyde

B

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
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
betulonic aldehyde
4439-98-9

betulonic aldehyde

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

betulinic aldehyde

A

Betulinic acid
472-15-1

Betulinic acid

B

betulonic acid
4481-62-3

betulonic acid

Conditions
ConditionsYield
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;
betulonic aldehyde
4439-98-9

betulonic aldehyde

Betulinic acid
472-15-1

Betulinic acid

Conditions
ConditionsYield
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
Betulinic acid
472-15-1

Betulinic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

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

methyl betulinate

Conditions
ConditionsYield
In methanol; benzene100%
In methanol; toluene at 20℃; for 3h; Inert atmosphere;97%
In methanol at 20℃; for 2h;96%
Betulinic acid
472-15-1

Betulinic acid

allyl bromide
106-95-6

allyl bromide

allyl betulinate
475562-57-3

allyl betulinate

Conditions
ConditionsYield
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;
4-methoxycarbonyl-3,3-dimethylbutyryl chloride
61798-18-3

4-methoxycarbonyl-3,3-dimethylbutyryl chloride

Betulinic acid
472-15-1

Betulinic acid

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

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

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;100%
Betulinic acid
472-15-1

Betulinic acid

(3β)-3-hydroxylup-20(29)-en-28-amide

(3β)-3-hydroxylup-20(29)-en-28-amide

Conditions
ConditionsYield
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
Betulinic acid
472-15-1

Betulinic acid

benzyl bromide
100-39-0

benzyl bromide

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
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
ConditionsYield
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%
Betulinic acid
472-15-1

Betulinic acid

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

3-aminolup-20(29)-en-28-oic acid

Conditions
ConditionsYield
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
Betulinic acid
472-15-1

Betulinic acid

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

methyl betulinate

Conditions
ConditionsYield
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; chloroform87%
Betulinic acid
472-15-1

Betulinic acid

benzenesulphonyl isocyanate
2845-62-7

benzenesulphonyl isocyanate

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

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

Conditions
ConditionsYield
With triethylamine In toluene for 1h; Reflux;98%
Betulinic acid
472-15-1

Betulinic acid

propargyl bromide
106-96-7

propargyl bromide

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

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

Conditions
ConditionsYield
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%
6-bromo-hexanoic acid ethyl ester
25542-62-5

6-bromo-hexanoic acid ethyl ester

Betulinic acid
472-15-1

Betulinic acid

C38H62O5
1400262-32-9

C38H62O5

Conditions
ConditionsYield
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%
Betulinic acid
472-15-1

Betulinic acid

Benzyl bromoacetate
5437-45-6

Benzyl bromoacetate

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

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

Conditions
ConditionsYield
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;
Betulinic acid
472-15-1

Betulinic acid

acetic anhydride
108-24-7

acetic anhydride

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

3-O-acetylbetulinic acid

Conditions
ConditionsYield
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%
Betulinic acid
472-15-1

Betulinic acid

Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

(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
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
ConditionsYield
With dmap In benzene at 60℃;97%
Betulinic acid
472-15-1

Betulinic acid

benzyl chloride
100-44-7

benzyl chloride

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
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
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide97%
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
(E)-3-(4-methoxyphenyl)propenoyl chloride
34446-64-5, 42996-84-9

(E)-3-(4-methoxyphenyl)propenoyl chloride

Betulinic acid
472-15-1

Betulinic acid

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

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

Conditions
ConditionsYield
With dmap In benzene at 60℃;96%
Betulinic acid
472-15-1

Betulinic acid

chloroacetyl chloride
79-04-9

chloroacetyl chloride

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

(3S)-3-(2-chloroacetyloxy)-lup-20(29)-en-28-oic acid

Conditions
ConditionsYield
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;
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

Betulinic acid
472-15-1

Betulinic acid

C39H58O3
1400262-29-4

C39H58O3

Conditions
ConditionsYield
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%
Betulinic acid
472-15-1

Betulinic acid

C30H48O6S*2H3N

C30H48O6S*2H3N

Conditions
ConditionsYield
With aminosulfonic acid; urea In 1,4-dioxane; N,N-dimethyl-formamide at 65 - 75℃;96%
Betulinic acid
472-15-1

Betulinic acid

dimethyl L-aspartate hydrochloride
32213-95-9

dimethyl L-aspartate hydrochloride

(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
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
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 19h;95%
methanol
67-56-1

methanol

Betulinic acid
472-15-1

Betulinic acid

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

methyl betulinate

Conditions
ConditionsYield
With diazomethyl-trimethyl-silane In hexane; toluene at 20℃;95%
With Penicillium citreonigrum In chloroform; dimethyl sulfoxide Sonication;31.6 mg
piperidine
110-89-4

piperidine

Betulinic acid
472-15-1

Betulinic acid

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
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

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
ConditionsYield
In chloroform95%
Betulinic acid
472-15-1

Betulinic acid

Propargylamine
2450-71-7

Propargylamine

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

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

Conditions
ConditionsYield
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%
Betulinic acid
472-15-1

Betulinic acid

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

2-(chloromethyl)-3,5,6-trimethylpyrazine

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

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

Conditions
ConditionsYield
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;
Betulinic acid
472-15-1

Betulinic acid

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

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

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

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

Conditions
ConditionsYield
With pyridine; silver(l) oxide for 3h;94%
Betulinic acid
472-15-1

Betulinic acid

Cyclopropylamine
765-30-0

Cyclopropylamine

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

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

Conditions
ConditionsYield
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%
1-Iodooctane
629-27-6

1-Iodooctane

Betulinic acid
472-15-1

Betulinic acid

C38H64O3
1400262-34-1

C38H64O3

Conditions
ConditionsYield
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%
Betulinic acid
472-15-1

Betulinic acid

4-biphenyl isocyanate
92-95-5

4-biphenyl isocyanate

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

3-O-[N-(biphenyl)-p-carbamoyl]betulinic acid

Conditions
ConditionsYield
With triethylamine In toluene for 1h; Reflux;93.5%
Betulinic acid
472-15-1

Betulinic acid

betulonic acid
4481-62-3

betulonic acid

Conditions
ConditionsYield
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%

472-15-1Downstream Products

472-15-1Relevant articles and documents

A SAPONIN FROM ASPARAGUS GONOCLADUS

Mandloi, Dilip,Sant, P. G.

, p. 1687 - 1688 (1981)

The ethanolic extract of the aerial part of Asparagus gonocladus yielded a new saponin.It was identified as lup-20(29)-en-28-oic-3-O-α-L-rhamnopyranosyl-(2->1)-O-β-D-glucopyranoside. - Keywords: Asparagus gonocladus; Liliaceae; lup-20(29)-en-28-oic-3-O-α-L-rhamnopyranosyl-(2->1)-O-β-D-glucopyranoside.

α-L-RHAMNOPYRANOSYL-3β-HYDROXY-LUP-20(29)-EN-28-OIC ACID FROM THE STEM OF DILLENIA PENTAGYNA

Tiwari, Kamala P.,Srivastava, Savitri D.,Srivastava, Santosh K.

, p. 980 - 981 (1980)

Key Word Index: Dillenia pentagyna; Dilleniaceae; α-L-rhamnopyranosyl-3β-hydroxy-lup-20(29)-en-28-oic acid; a new saponin.

Design, synthesis and evaluation of antiproliferative activity of fluorinated betulinic acid

Li, Jizhen,Chang, Ling-Chu,Hsieh, Kan-Yen,Hsu, Pei-Ling,Capuzzi, Stephen J.,Zhang, Ying-Chao,Li, Kang-Po,Morris-Natschke, Susan L.,Goto, Masuo,Lee, Kuo-Hsiung

, p. 2871 - 2882 (2019)

Betulinic acid (BA), a pentacyclic triterpenoid, exhibits broad spectrum antiproliferative activity, but generally with only modest potency. To improve BA's pharmacological properties, fluorine was introduced as a single atom at C-2, creating two diastereomers, or in a trifluoromethyl group at C-3. We evaluated the impact of these groups on antiproliferative activity against five human tumor cell lines. A racemic 2-F-BA (compound 6) showed significantly improved antiproliferative activity, while each diastereomer exhibited similar effects. We also demonstrated that 2-F-BA is a topoisomerase (Topo) I and IIα dual inhibitor in cell-based and cell-free assays. A hypothetical mode of binding to the Topo I-DNA suggested a difference between the hydrogen bonding of BA and 2-F-BA to DNA, which may account for the difference in bioactivity against Topo I.

A BETULINIC ACID GLYCOSIDE FROM SCHEFFLERA VENULOSA

Purohit, M. C.,Pant, G.,Rawat, M. S. M.

, p. 2419 (1991)

A new betulinic acid glycoside, lup-20(29)-en-28-oic-3-O-β-D-glucopyranosyl (2->1)-O-β-D-glucopyranoside has been characterized from the leaves of Schefflera venulosa.

Genotoxic and mutagenic properties of synthetic betulinic acid and betulonic acid

Frolova,Kukina,Sinitsyna

, p. 409 - 413 (2015)

Abstract Betulinic acid was synthesized from birch bark extract (Betula pendula), with betulonic acid being an intermediate of the synthesis. Both compounds were isolated with a purity of 95%. Genotoxicity and mutagenicity of the prepared compounds was analyzed by the Ames test and SOS chromotest and it was found that the substances show no mutagenic and genotoxic activity.

The Effect of Experimental BCG Antigen–Betulin-Derived Conjugates on the Guinea Pig Immunological Response

Koshkin, I. N.,Kulakov, I. V.,Vlasenko, V. S.

, p. 837 - 844 (2021/08/25)

Abstract: The immunopotentiating properties of BCG vaccine strain antigen conjugated with betulin derivatives have been evaluated. The experiments were carried out on agouti guinea pigs (n = 20). The animals of the experimental groups (n = 5) were immunized with the following antituberculosis drugs: group 1, with antigens of the BCG vaccine strain conjugated with betulinic acid; group 2, with BCG antigens conjugated with betulonic acid; and group 3, with the BCG vaccine. The animals of the control group (n = 5) were injected with a saline solution. All the animals were infected with a virulent culture of Mycobacterium bovis (strain 8) on day 30 after the administration of antituberculosis drugs. The blood sampling for the assessment of the immune status was conducted on day 30 after the administration of drugs and day 30 after the infection with M. bovis. The designed conjugates were found to display immunopotentiating activity characterized by a 1.7–3.8-fold increase in the number of immunocompetent cells and an increase in the neutrophil functional activity observed to a greater degree in the guinea pig group 2. After infection with M. bovis some key parameters of the immune system, such as a T-lymphocyte count and the activity of enzymatic (myeloperoxidase) and nonenzymatic (cationic proteins) bactericidal systems of neutrophilic granulocytes significantly increased in groups 2 and 3, which implied the highest antituberculosis activity of the agents administered to these animals. The guinea pigs were euthanized 45 days after the infection with M. bovis. The next pathoanatomical experiments proved that the vaccine strain conjugates with betulonic acid and the BCG vaccine induced marked resistance against the pathogenic mycobacteria. The protection indexes for these agents were approximately the same and achieved 66 and 71%, respectively.

Synthesis of a Hexavalent Betulinic Acid Derivative as a Hemagglutinin-Targeted Influenza Virus Entry Inhibitor

Chen, Yingying,Si, Longlong,Wang, Xinchen,Xiao, Sulong,Zhang, Bo,Zhang, Lihe,Zhang, Yongmin,Zhou, Demin,Zhu, Yinbiao

, p. 2546 - 2554 (2020/08/14)

Naturally occurring pentacyclic triterpenes, such as betulinic acid (BA) and its derivatives, exhibit various pharmaceutical activities and have been the subject of great interest, in particular for their antiviral properties. Here, we found a new anti-influenza virus conjugate, hexakis 6-deoxy-6-[4-N-(3β-hydroxy-lup-20(29)-en-28-oate)aminomethyl-1H-1,2,3-triazol-1-yl]-2,3-di-O-acetyl-α-cyclodextrin (CYY1-11, 1), in a mini library of pentacyclic triterpene-cyclodextrin conjugates by performing a cell-based screening assay and then exploring the underlying mechanisms. Our results showed that conjugate 1 possessed a high-level activity against the influenza virus A/WSN/33 with an IC50 value of 5.20 μM (SI > 38.4). The study of the mechanism of action indicated that conjugate 1 inhibited viral replication by directly targeting the influenza hemagglutinin protein (KD = 1.50 μM), thus efficiently preventing the attachment of the virion to its receptors on host cells and subsequent infection. This study suggests that multivalent BA derivatives have possible use as a new class of influenza virus entry inhibitors.

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