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Basic Information
| CAS No.: | 77-52-1 |
|---|---|
| Name: | Ursolic acid |
| Molecular Structure: | |
|
|
|
| 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: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 24/25-36-26 |
| PSA: | 57.53000 |
| LogP: | 7.08950 |
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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% |
Conditions
| Conditions | Yield |
|---|---|
| With cultured cells of Rabdosia japonica Hara for 96h; Mechanism; labelling studies; |
- 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; |
- 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 |
Raw Materials
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Ursolic acid
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.