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77-52-1

Basic Information
CAS No.: 77-52-1
Name: Ursolic acid
Article Data: 16
Molecular Structure:
Molecular Structure of 77-52-1 (Ursolic acid)
Formula: C30H48O3
Molecular Weight: 456.709
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
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
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    : Ursolic acid Formula: C30H48O3 · 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,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.