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77-52-1

Basic Information
CAS No.: 77-52-1
Name: Ursolic acid
Molecular Structure:
Molecular Structure of 77-52-1 (Ursolic acid)
Formula: C30H48O3
Molecular Weight: 456.71
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);
EINECS: 201-034-0
Density: 1.09 g/cm3
Melting Point: 292 °C (dec.)(lit.)
Boiling Point: 556.9 °C at 760 mmHg
Flash Point: 304.7 °C
Solubility: insoluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
Transport Information:
PSA: 57.53000
LogP: 7.08950
Synthetic route

77-52-1

ursolic acid

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

C36H56O9

77-52-1

ursolic acid

Conditions
ConditionsYield
With Helix pomatia β-glucuronidase; water In aq. acetate buffer at 37℃; for 4h; pH=5.27; Enzymatic reaction;
Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃;100%
In diethyl ether at 0℃; for 24h;98%
With diethyl ether
77-52-1

ursolic acid

Conditions
ConditionsYield
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 acetone98%
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
ConditionsYield
With pyridine100%
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
ConditionsYield
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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;98%
77-52-1

ursolic acid

18107-18-1

diazomethyl-trimethyl-silane

Conditions
ConditionsYield
In methanol; benzene97%
In methanol; hexane; toluene at 20℃;95%
In methanol; benzene84.7%
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
ConditionsYield
With potassium carbonate In acetone97%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

Conditions
ConditionsYield
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
ConditionsYield
In acetonitrile for 16h;94%
77-52-1

ursolic acid

13288-06-7

1-(2-bromoethoxy)-4-nitrobenzene

1446690-25-0

C38H55NO6

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With dmap In chloroform at 0℃; for 48h;93%
77-52-1

ursolic acid

C13H30NO(1+)

C43H76NO3(1+)

Conditions
ConditionsYield
With dmap In chloroform at -5℃; for 24h;93%
77-52-1

ursolic acid

Conditions
ConditionsYield
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%
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    Ursolic Acid CAS:77-52-1

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Chemistry

Ursolic acid is a pentacyclic triterpene acid,Ursolic acid's other name is known as Prunol, Malol, Urson, beta-Ursolic acid,
Molecular formula :C30H48O3
Molar mass 456.70 g/mol

Uses

Ursolic acid can be used in cosmetics, and capable of inhibiting various types of cancer cells by inhibiting the STAT3 activation pathway and human fibrosarcoma cells by reducing the expression of matrix metalloproteinase-9 by acting through the glucocorticoid receptor.As medicine it is well tolerated and can be used topically and orally.

Production

Ursolic acid is present in many plants, including apples,  bilberries, cranberries, elder flower,  rosemary, lavender, oregano, thyme, prunes. Apple peels contain high quantity of ursolic acid and related compounds which are responsible for the anti-cancer activity of apple. Ursolic acid can also serve as a starting material for synthesis of more potent bioactive derivatives, such as anti-tumor agents.
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