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508-02-1

Basic Information
CAS No.: 508-02-1
Name: Oleanic acid
Article Data: 103
Cas Database
Molecular Structure:
Molecular Structure of 508-02-1 (Oleanic acid)
Formula: C30H48O3
Molecular Weight: 456.709
Synonyms: 3-beta-Hydroxyolean-12-en-28-oic acid;Olean-12-en-28-oic acid, 3-beta-hydroxy- (8CI);(4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid;Giganteumgenin C;Olean-12-en-28-oic acid,3-hydroxy-,(3a)-;Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-;Virgaureagenin B;Caryophyllin;Astrantiagenin C;
EINECS: 208-081-6
Density: 1.1 g/cm3
Melting Point: >300 °C
Boiling Point: 553.5 °C at 760 mmHg
Flash Point: 302.6 °C
Solubility: N/A
Appearance: light yellow
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: N/A
PSA: 57.53000
LogP: 7.23360
Synthetic route
152487-68-8

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(tert-Butyl-dimethyl-silanyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid

508-02-1

Oleanolic acid

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 55℃; for 13h;96%

C54H72NO5Pol

508-02-1

Oleanolic acid

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 20℃; for 0.5h; solid phase reaction;94.6%

C61H76NO6PolS

A

1310058-25-3

3β-[(E)-3-(thiophen-2-yl)acryloxyl]-olean-12-en-28-oic acid

B

508-02-1

Oleanolic acid

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 20℃; for 0.5h; solid phase reaction;A 92%
B 0.5 mg
1310058-23-1

{2-[2-(triphenylmethyl)aminoethoxy]ethoxy}methyl olean-12-en-28-oate

508-02-1

Oleanolic acid

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 20℃; for 0.5h;89.6%
25493-69-0, 122798-61-2, 1721-57-9

(4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

508-02-1

Oleanolic acid

Conditions
ConditionsYield
With Me2AlTeMe In toluene at 50℃; for 10h;80%
1724-17-0, 73584-64-2

oleanolic acid methyl ester

508-02-1

Oleanolic acid

Conditions
ConditionsYield
With lithium In ethylenediamine for 4h; Heating;70%
With lithium In ethylenediamine for 4h; Heating; other hindered esters;70%
86532-12-9

3β-acetyl-12α-bromo-oleanan-28 <*> 13β-olide

A

508-02-1

Oleanolic acid

B

17990-43-1

3-dehydroxy-oleanolic acid

Conditions
ConditionsYield
With lithium; ethylenediamine for 2h; Heating;A 35%
B 30%
77-52-1

ursolic acid

Nocardia sp. NRRL 5646

Nocardia sp. NRRL 5646

A

508-02-1

Oleanolic acid

C

1724-17-0, 73584-64-2

oleanolic acid methyl ester

Conditions
ConditionsYield
at 28℃; for 120h; pH=7.0; Product distribution; Microbiological reaction;A 21%
B 9%
C 13%

3-hydroxy-23-semicarbazono-olean-12-en-28-oic acid

141-52-6

sodium ethanolate

508-02-1

Oleanolic acid

Conditions
ConditionsYield
at 180℃; im Rohr;

3-acetoxy-23-semicarbazono-olean-12-en-28-oic acid

141-52-6

sodium ethanolate

508-02-1

Oleanolic acid

Conditions
ConditionsYield
at 160 - 170℃; im Rohr;
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Chemistry

IUPAC Name: 10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid 
Synonyms of Oleanolic acid (CAS NO.508-02-1): 3Beta-Hydroxyolean-12-en-28-oic acid
Molecular Structure:
Molecular Formula: C30H48O3
Molecular Weight: 456.71
CAS NO: 508-02-1 
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 35.53 Å2
Index of Refraction: 1.557
Molar Refractivity: 133.57 cm3
Molar Volume: 414.9 cm3
EINECS : 208-081-6
Mol File: 508-02-1.mol
Melting point: >300°C
Storage temp: 2-8°C
Surface Tension: 45.4 dyne/cm
Density: 1.1 g/cm3
Flash Point: 302.6 °C
Enthalpy of Vaporization: 95.9 kJ/mol
Boiling Point: 553.5 °C at 760 mmHg
Vapour Pressure: 1.47E-14 mmHg at 25°C 
Color: light yellow.
Product Categories of Oleanolic acid (CAS NO.508-02-1): Pentacyclic triterpenes;Tri-Terpenoids;Biochemistry;Terpenes;Terpenes (Others);Natural Plant Extract;Anti-proliferative AgentsAsymmetric Synthesis;Complex MoleculesNutrition Research;Isoprenoid/terpenoidCancer Research;Phase I Enzyme Inhibitors;Phase I Enzyme InhibitorsCancer Research;Biochemicals Found in Plants;Cancer Research;Chemopreventive Agents;Chiral Building Blocks;Multidrug Resistance

Uses

 Oleanolic acid (CAS NO.508-02-1) is suitable for all types of hepatitis, with the promotion of liver regeneration to accelerate the repair of damaged liver cells, and has a strong effects on heart, diuretic and anti-inflammatory.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1500mg/kg (1500mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.
mouse LD50 oral > 2gm/kg (2000mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Drugs of the Future. Vol. 19, Pg. 450, 1994.
rat LD50 oral > 2gm/kg (2000mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Oleanolic acid (CAS NO. 508-02-1) is irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 2
RTECS: RK0177965

Specification

 Oleanolic acid (CAS NO.508-02-1) is a naturally occurring triterpenoid, which distributed in food and medicinal plants, related to betulinic acid. And it can be widely  found in Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc. It is quite non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties.

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