• Name

  Ursolic acid

• EINECS 201-034-0
• CAS No. 77-52-1
• Article Data16
• CAS DataBase
• Density 1.09 g/cm³
• Solubility insoluble in water
• Melting Point 292 °C (dec.)(lit.)
• Formula C₃₀H₄₈O₃
• Boiling Point 556.9 °C at 760 mmHg
• Molecular Weight 456.709
• Flash Point 304.7 °C
• Transport Information
• Appearance white to light yellow crystal powder
• Safety 24/25-36-26
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• Synonyms Ursolic Acid;Ursolicacid;Ursoliic acid;3beta-Hydroxyurs-12-en-28-oic acid;Prunol;Urs-12-en-28-oic acid, 3.beta.-hydroxy-;(3beta)-3-Hydroxyurs-12-en-28-oic acid;(1S,2R,4aS,6aS,6bR,10S,12aS,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid;Urson;10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid;Prestwick_355;(1S,2R,4aS,6aS,6aS,6bR,8aS,10S,12aS,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid;Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)-;Bungeolic acid;Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-;Urs-12-en-28-oic acid, 3beta-hydroxy- (8CI);
• PSA 57.53000
• LogP 7.08950

Synthetic route

915-32-2, 26532-60-5, 32208-45-0, 74984-68-2, 94482-47-0, 121468-30-2

methyl (3β)-3-hydroxyurs-12-en-28-oate

77-52-1

ursolic acid

Conditions

Conditions	Yield
With lithium In ethylenediamine for 4h; Heating;	70%

104668-95-3

phenyl-3β-acetoxy-urs-12-en-28-oate

77-52-1

ursolic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethylene glycol for 15h; Heating;	1.33%

127-09-3

sodium acetate

A

77-52-1

ursolic acid

B

508-02-1

Oleanolic acid

Conditions

Conditions	Yield
With cultured cells of Rabdosia japonica Hara for 96h; Mechanism; labelling studies;

3-O-{[β-D-xylopyranosyl-(1->2)]-[β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranosyl}ursolic acid-28-O-[β-D-glucopyranosyl] ester

77-52-1

ursolic acid

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane for 4h; Heating;	23 mg

1198208-27-3

3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate

77-52-1

ursolic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In 1,4-dioxane at 20℃; for 18h;

28288-99-5

3-O-(β-D-glucopyranosyl)-ursolic acid 28-O-(β-D-glucopyranosyl) ester

A

50-99-7

D-glucose

B

77-52-1

ursolic acid

Conditions

Conditions	Yield
With hydrogenchloride; water In methanol for 2h; Reflux;

3β-hydroxyurs-12-en-28-oic acid 3-α-L-rhamnopyranoside

1038914-11-2

3β-hydroxyurs-12-en-28-oic acid 3-α-L-rhamnopyranoside

A

73-34-7

L-rhamnose

B

77-52-1

ursolic acid

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 2h;

C36H56O9

77-52-1

ursolic acid

Conditions

Conditions	Yield
With Helix pomatia β-glucuronidase; water In aq. acetate buffer at 37℃; for 4h; pH=5.27; Enzymatic reaction;

186581-53-3, 908094-01-9

diazomethane

77-52-1

ursolic acid

915-32-2, 26532-60-5, 32208-45-0, 74984-68-2, 94482-47-0, 121468-30-2

methyl (3β)-3-hydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0℃;	100%
In diethyl ether at 0℃; for 24h;	98%
With diethyl ether

77-52-1

ursolic acid

94482-51-6, 6246-46-4

ursonic acid

Conditions

Conditions	Yield
With Jones reagent; silica gel In acetone at 0℃; for 0.5h; Jones Oxidation;	100%
With Jones reagent In acetone Cooling with ice;	99%
With chromium(VI) oxide; sulfuric acid In acetone	98%

77-52-1

ursolic acid

108-24-7

acetic anhydride

915-79-7, 7372-30-7, 94482-46-9, 105452-47-9, 121470-75-5

(3β)-3-acetoxy-urs-12-en-28-carboxylic acid

Conditions

Conditions	Yield
With pyridine	100%
With pyridine at 20℃; for 24h;	100%
With pyridine; dmap at 20℃; for 2.5h;	97%

77-52-1

ursolic acid

572-09-8

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

16684-20-1

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water for 8h; Heating;	99%
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	90%

77-52-1

ursolic acid

74-88-4

methyl iodide

915-32-2, 26532-60-5, 32208-45-0, 74984-68-2, 94482-47-0, 121468-30-2

methyl (3β)-3-hydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;	99%
Stage #1: ursolic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 5h;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;	95%

57260-73-8

N-BOC-1,2-diaminoethane

77-52-1

ursolic acid

C37H62N2O4

Conditions

Conditions	Yield
Stage #1: ursolic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: N-BOC-1,2-diaminoethane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	99%
Stage #1: ursolic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: N-BOC-1,2-diaminoethane In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	95%

77-52-1

ursolic acid

870-63-3

prenyl bromide

1198208-27-3

3'-methyl-2'-butenyl 3β-hydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;	98%
With potassium carbonate In acetone at 20℃;	30%
With potassium carbonate In acetone at 20℃;

77-52-1

ursolic acid

106-95-6

allyl bromide

1220960-77-9

3-hydroxy-urs-12-en-28-oic acid allyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;	98%
Stage #1: ursolic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 8h;	91%
With potassium carbonate In N,N-dimethyl-formamide for 24h;	90.4%
Stage #1: ursolic acid With sodium hydroxide In acetone Stage #2: allyl bromide In acetone at 70℃; for 4h;	10.1%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;

77-52-1

ursolic acid

1-bromoacetone

1-bromoacetone

C33H52O4

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	98%

77-52-1

ursolic acid

18107-18-1

diazomethyl-trimethyl-silane

915-32-2, 26532-60-5, 32208-45-0, 74984-68-2, 94482-47-0, 121468-30-2

methyl (3β)-3-hydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
In methanol; benzene	97%
In methanol; hexane; toluene at 20℃;	95%
In methanol; benzene	84.7%
In methanol
With methanol In hexane; benzene at 50℃; for 1.5h;	66.3 mg

77-52-1

ursolic acid

100-39-0

benzyl bromide

benzyl ursolate

Conditions

Conditions	Yield
With potassium carbonate In acetone	97%

77-52-1

ursolic acid

100-39-0

benzyl bromide

192211-41-9

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	97%
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water at 0 - 20℃; for 18h;	93%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	92%

77-52-1

ursolic acid

192211-41-9

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 2h;	96%
With potassium carbonate In N,N-dimethyl-formamide for 5h; Heating;	95%
With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;	94%

77-52-1

ursolic acid

2450-71-7

Propargylamine

N-propargyl 3β-dihydroxyurs-12-en-28-amide

Conditions

Conditions	Yield
Stage #1: ursolic 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;	96%

77-52-1

ursolic acid

106-96-7

propargyl bromide

1243271-20-6

prop-2-yn-1-yl (1S,2R,4aS,6aS,6bR,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;	93%
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 12h;	93%

77-52-1

ursolic acid

96-32-2

bromoacetic acid methyl ester

1283594-24-0

2-methoxy-2-oxoethyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	86.1%

74-83-9

methyl bromide

77-52-1

ursolic acid

915-32-2, 26532-60-5, 32208-45-0, 74984-68-2, 94482-47-0, 121468-30-2

methyl (3β)-3-hydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h;	95%

77-52-1

ursolic acid

657-24-9

dimethylbiguanide

1541169-42-9

ursolic acid metformin salt

Conditions

Conditions	Yield
In acetonitrile for 16h;	94%

77-52-1

ursolic acid

13288-06-7

1-(2-bromoethoxy)-4-nitrobenzene

1446690-25-0

C38H55NO6

Conditions

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

77-52-1

ursolic acid

125700-67-6

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

1-benzotriazolyl 3β-dihydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	93%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	93%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4h;

77-52-1

ursolic acid

C10H24NO(1+)

C40H70NO3(1+)

Conditions

Conditions	Yield
With dmap In chloroform at 0℃; for 48h;	93%

77-52-1

ursolic acid

C13H30NO(1+)

C43H76NO3(1+)

Conditions

Conditions	Yield
With dmap In chloroform at -5℃; for 24h;	93%

77-52-1

ursolic acid

545-46-0

uvaol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Reflux;	92%
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Reflux; Inert atmosphere; Sealed tube;	90.9%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 8h; Inert atmosphere; Reflux;	15%

Ursolic acid Chemical Properties

Ursolic acid Uses

Ursolic acid Production