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Basic Information

Molecular Structure:
CAS No.:	508-02-1
Name:	Oleanic acid
Article Data:	103

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
Appearance:	light yellow
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
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

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

: C54H72NO5Pol

: 508-02-1
Oleanolic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

B: 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

C: 1724-17-0, 73584-64-2
oleanolic acid methyl ester

Conditions

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

...Expand

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

: 141-52-6
sodium ethanolate

: 508-02-1
Oleanolic acid

Conditions

Conditions	Yield
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

Conditions	Yield
at 160 - 170℃; im Rohr;

Raw Materials

77-52-1

127-09-3

Downstream Products

4373-41-5

17990-42-0

218600-50-1

471-67-0

545-48-2

486-34-0

122746-62-7

110700-49-7

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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)	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: Irritant Xi
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.