(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
Oleanolic acid
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 55℃; for 13h; | 96% |
Oleanolic acid
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 20℃; for 0.5h; solid phase reaction; | 94.6% |
A
3β-[(E)-3-(thiophen-2-yl)acryloxyl]-olean-12-en-28-oic acid
B
Oleanolic acid
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 20℃; for 0.5h; solid phase reaction; | A 92% B 0.5 mg |
{2-[2-(triphenylmethyl)aminoethoxy]ethoxy}methyl olean-12-en-28-oate
Oleanolic acid
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 20℃; for 0.5h; | 89.6% |
(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
Oleanolic acid
Conditions | Yield |
---|---|
With Me2AlTeMe In toluene at 50℃; for 10h; | 80% |
oleanolic acid methyl ester
Oleanolic acid
Conditions | Yield |
---|---|
With lithium In ethylenediamine for 4h; Heating; | 70% |
With lithium In ethylenediamine for 4h; Heating; other hindered esters; | 70% |
3β-acetyl-12α-bromo-oleanan-28 <*> 13β-olide
A
Oleanolic acid
B
3-dehydroxy-oleanolic acid
Conditions | Yield |
---|---|
With lithium; ethylenediamine for 2h; Heating; | A 35% B 30% |
ursolic acid
A
Oleanolic acid
B
methyl (3β)-3-hydroxyurs-12-en-28-oate
C
oleanolic acid methyl ester
Conditions | Yield |
---|---|
at 28℃; for 120h; pH=7.0; Product distribution; Microbiological reaction; | A 21% B 9% C 13% |
Conditions | Yield |
---|---|
at 180℃; im Rohr; |
Conditions | Yield |
---|---|
at 160 - 170℃; im Rohr; |
methanol
A
methyl α-L-xylopyranoside
B
Oleanolic acid
C
1-O-methyl-α-D-glucopyranuronic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride for 3h; Product distribution; Heating; | A n/a B 207 mg C n/a |
methanol
A
methyl α-L-xylopyranoside
B
Oleanolic acid
C
1-O-methyl-α-D-glucopyranuronic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride for 3h; Product distribution; Heating; | A n/a B 12 mg C n/a |
Conditions | Yield |
---|---|
With cultured cells of Rabdosia japonica Hara for 96h; Mechanism; labelling studies; |
mimonoside A
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 4h; | 2 mg |
mimonoside B
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 4h; |
oleanolic acid 3-O-
A
Oleanolic acid
B
β-hederin
C
fatsiaside A1
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 1.5h; Heating; | A 348 mg B 23 mg C 52 mg |
Digitoside B
Oleanolic acid
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 3h; Heating; | 32 mg |
Digitoside A
Oleanolic acid
Conditions | Yield |
---|---|
With sulfuric acid In methanol for 3h; Heating; | 29 mg |
Pseudo-ginsenoside-RI3
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 4h; Heating; |
kalopanax-saponin D (3-O-α-rhamnopyranosyl-(1->2)-<β-glucopyranosyl-(1->3)>-α-arabinopyranosyl oleanolic acid 28-O-α-rhamnopyranosyl-(1->4)-β-glucopyranosyl-(1->6)-β-glucopyranosyl ester
A
D-Glucose
B
L-rhamnose
C
L-(+)-arabinose
D
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Heating; |
hederacholichiside E
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 3h; |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Heating; |
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 3h; Heating; Yield given; |
A
2,3,4,6-tetra-O-methyl-D-glucopyranose
B
Oleanolic acid
C
erythrodiol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; sulfuric acid Multistep reaction; |
C46H72O17
A
D-Xylose
C
Oleanolic acid
Conditions | Yield |
---|---|
With sulfuric acid for 6h; on the water bath; |
3-O-{[β-D-glucopyranosyl (1->2)]-[α-L-arabinopyranosyl (1->3)]-β-D-glucuronopyranosyl}oleanolic acid
A
D-Glucose
C
L-(+)-arabinose
D
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Heating; |
3-O-<α-L-arabinopyranosyl (1->3)-β-D-glucuronopyranosyl>-oleanolic acid β-D-glucopyranosyl (1->28) ester
A
D-Glucose
C
L-(+)-arabinose
D
Oleanolic acid
Conditions | Yield |
---|---|
sulfuric acid In methanol; water for 6h; Product distribution; Heating; The structure of the compound was confirmed by chemical degradation; |
3-O-[β-D-xylopyranosyl-(1->4)-β-D-glucuronopyranosyl]-28-O-[β-D-glucopyranosyl]oleanolic acid
Oleanolic acid
Conditions | Yield |
---|---|
With sulfuric acid at 95℃; for 6h; | 22 mg |
C47H74O18
A
D-Xylose
B
D-Glucose
D
Oleanolic acid
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 4h; |
Oleanolic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Yield given; |
diazomethane
Oleanolic acid
oleanolic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 0℃; | 100% |
In diethyl ether at 0℃; for 24h; | 98% |
With diethyl ether | 94% |
Conditions | Yield |
---|---|
With pyridine for 10h; Reflux; | 100% |
With pyridine; dmap for 5h; | 99% |
With pyridine; dmap at 20℃; | 99% |
Oleanolic acid
diazomethyl-trimethyl-silane
oleanolic acid methyl ester
Conditions | Yield |
---|---|
In methanol; benzene | 100% |
In methanol; diethyl ether at 20℃; for 1h; | 99% |
In methanol; diethyl ether; toluene at 20℃; for 0.5h; | 94% |
In methanol; benzene | 80.1% |
In methanol |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran tritylationprotection; Heating; | 100% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran | 91% |
Conditions | Yield |
---|---|
at 20℃; for 0.166667h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere; | 99% |
Oleanolic acid
Oleanonsaeure
Conditions | Yield |
---|---|
With Dess-Martin periodane In dichloromethane at 20℃; for 1h; Inert atmosphere; | 99% |
With Jones reagent In dichloromethane; acetone at 0 - 5℃; for 0.75h; Jones Oxidation; | 99% |
With Jones reagent In acetone Cooling with ice; | 98% |
Conditions | Yield |
---|---|
With pyridine; dmap for 48h; Heating; | 99% |
With pyridine at 20℃; for 24h; | 62% |
With dmap In pyridine for 36h; Heating; | 57.1% |
With dmap In pyridine Heating; | |
With pyridine; dmap Heating; |
Conditions | Yield |
---|---|
With pyridine; dmap for 12h; Heating; | 99% |
Conditions | Yield |
---|---|
With pyridine at 80℃; for 1h; | 99% |
With pyridine at 0℃; |
Conditions | Yield |
---|---|
With triethylsilane; N-iodo-succinimide In 2,2,2-trifluoroethanol at 20℃; for 3.5h; | 98% |
With hydrogenchloride; chloroform |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 98% |
With sodium hydroxide In ethanol Reflux; | 96% |
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 20℃; | 98% |
With potassium carbonate In tetrahydrofuran; water at 20℃; | 98% |
With tetra-(n-butyl)ammonium iodide; potassium carbonate In tetrahydrofuran; water at 20℃; | 98% |
Oleanolic acid
allyl bromide
3-hydroxy-olean-12-en-28-oic acid allyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 97% |
Stage #1: Oleanolic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: allyl bromide In N,N-dimethyl-formamide for 8h; | 92% |
Oleanolic acid
propargyl bromide
prop-2-yn-1-yl (4aS,6aS,6bR,12aR)-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-octadecahydropicene-4a(2H)carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; | 97% |
With caesium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; acetone at 80℃; | 98% |
Conditions | Yield |
---|---|
Stage #1: Oleanolic acid With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 20℃; for 12h; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 45℃; | 92% |
With potassium carbonate In N,N-dimethyl-formamide at 45℃; Large scale; | 92% |
With potassium hydroxide |
1 ,6-dibromohexane
Oleanolic acid
3β-hydroxyoleanane-12-en-28-oic acid(6-bromohexyl) ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 12h; | 58% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 97% |
Oleanolic acid
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
Stage #1: Oleanolic acid With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; | 97% |
Conditions | Yield |
---|---|
Stage #1: Oleanolic 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; | 97% |
Oleanolic acid
erythrodiol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; | 96% |
With lithium aluminium tetrahydride In tetrahydrofuran for 3.5h; Heating; | 95% |
With lithium aluminium tetrahydride In tetrahydrofuran at -12 - 20℃; for 24h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature; | 96% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 92% |
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water for 6h; Heating; | 78% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 96% |
Oleanolic acid
methyl 3β-hydroxyolean-12-en-28-oate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 96% |
Oleanolic acid
Conditions | Yield |
---|---|
With N-chloro-succinimide In 1,2-dimethoxyethane at 20℃; for 96h; Reagent/catalyst; Solvent; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; | 95% |
Stage #1: Oleanolic acid With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.5h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 120℃; for 0.5h; | 95.1% |
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate
Oleanolic acid
oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester
Conditions | Yield |
---|---|
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction; | 95% |
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
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.
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. |
Hazard Codes: 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
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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