(3β)-3-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-olean-12-en
beta-amyrin
Conditions | Yield |
---|---|
With zinc In acetic acid at 20 - 40℃; for 4h; Reagent/catalyst; Solvent; | 97% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 55℃; for 12h; | 95% |
β-amyrin acetate
beta-amyrin
Conditions | Yield |
---|---|
With ethylenediamine In methanol for 0.0666667h; Microwave irradiation; | 94% |
With potassium hydroxide In methanol | |
With potassium hydroxide In ethanol for 1h; | |
With potassium hydroxide In methanol Reflux; |
β-amyrone
beta-amyrin
Conditions | Yield |
---|---|
With lithium; ethylenediamine for 2h; Heating; | 85% |
(3S,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-Hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde
beta-amyrin
Conditions | Yield |
---|---|
Stage #1: (3S,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-Hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde With hydrazine hydrate In ethanol; diethylene glycol for 1h; Heating; Huang-Minlon reduction; Stage #2: With potassium hydroxide for 2h; Heating; | 77% |
β-amyrone
A
beta-amyrin
B
3α-hydroxyolean-12-ene
Conditions | Yield |
---|---|
With potassium hydroxide In diethylene glycol for 2h; Heating; | A 50% B 15% |
Imidazole-1-carbothioic acid O-((4aS,6aS,6bR,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-picen-4a-ylmethyl) ester
beta-amyrin
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In xylene at 130℃; for 10h; | 40% |
Conditions | Yield |
---|---|
bei der Verseifung; β-amyrin palmitate (balanophorin); |
Conditions | Yield |
---|---|
With ethanol; sodium ethanolate; hydrazine hydrate at 200℃; |
sodium ethanolate
A
beta-amyrin
B
11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-ol
Conditions | Yield |
---|---|
at 200℃; |
A
beta-amyrin
B
11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-ol
Conditions | Yield |
---|---|
With ethanol; sodium at 200℃; |
Conditions | Yield |
---|---|
With ethanol at 200℃; | |
at 200℃; |
A
beta-amyrin
B
erythrodiol
Conditions | Yield |
---|---|
With ethanol; sodium at 200℃; |
squalene 2,3(S)-oxide
beta-amyrin
Conditions | Yield |
---|---|
With potassium phosphate; β-amyrin cyclase; Triton X-100 at 30℃; for 1h; changes of the activity of the cyclase from ea seedlings; |
beta-amyrin
Conditions | Yield |
---|---|
With acetic acid; platinum Hydrogenation; | |
With ethanol; sodium; xylene |
Conditions | Yield |
---|---|
With ethanol; nickel at 200℃; under 22065.2 - 47808 Torr; | |
With ethanol; nickel at 200℃; under 22065.2 - 47808 Torr; Hydrogenation; |
Conditions | Yield |
---|---|
Hydrogenation; |
tetrachloromethane
ethanol
β-amyrone
beta-amyrin
3β-hydroxy-olean-12-en-16-one
sodium methylate
hydrazine
beta-amyrin
Conditions | Yield |
---|---|
at 230℃; |
Conditions | Yield |
---|---|
Hydrogenation; |
sodium ethanolate
hydrazine hydrate
A
beta-amyrin
B
3α-hydroxyolean-12-ene
Conditions | Yield |
---|---|
at 200℃; |
squalene 2,3(S)-oxide
A
beta-amyrin
B
germanicol
C
lupenol
D
taraxasterol
Conditions | Yield |
---|---|
With Arabidopsis thaliana LUP1 Product distribution; Cyclization; Enzymatic reaction; | A 8 % Chromat. B 7 % Chromat. C 38 % Chromat. D 4 % Chromat. |
3β-benzoyloxy-24-oxoolean-12-ene
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 2.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 2.2: 77 percent / KOH / 2 h / Heating View Scheme |
Benzoic acid (3S,4S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4-hydroxymethyl-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 2.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 3.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 3.2: 77 percent / KOH / 2 h / Heating View Scheme |
24-trityloxyolean-12-en-3β-ol
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 2.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 3.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 4.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 5.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 5.2: 77 percent / KOH / 2 h / Heating View Scheme |
3β-benzoyloxy-24-trityloxyolean-12-ene
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 2.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 3.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 4.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 4.2: 77 percent / KOH / 2 h / Heating View Scheme |
3β,24-dihydroxyolean-12-ene
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: pyridine / 5 h / Heating 2.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 3.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 4.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 5.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 6.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 6.2: 77 percent / KOH / 2 h / Heating View Scheme |
C33H52O3
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 6 percent / sodium / 2-methyl-propan-2-ol; toluene / 22 h / Heating 2.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / 20 °C 3.1: 79 percent / lithium triethylborohydride / dimethylsulfoxide / 1 h / 65 °C 4.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 5.1: pyridine / 5 h / Heating 6.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 7.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 8.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 9.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 10.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 10.2: 77 percent / KOH / 2 h / Heating View Scheme |
22β-hydroxy-3β,24-isopropylidenedioxyolean-12-ene
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / 20 °C 2.1: 79 percent / lithium triethylborohydride / dimethylsulfoxide / 1 h / 65 °C 3.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 4.1: pyridine / 5 h / Heating 5.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 6.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 7.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 8.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 9.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 9.2: 77 percent / KOH / 2 h / Heating View Scheme |
C33H52O2
beta-amyrin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 2.1: pyridine / 5 h / Heating 3.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 4.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 5.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 6.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 7.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 7.2: 77 percent / KOH / 2 h / Heating View Scheme |
Conditions | Yield |
---|---|
With Candida rugosa lipase In hexane at 37℃; for 24h; Kinetics; | 99.9% |
Conditions | Yield |
---|---|
With dmap In dichloromethane for 3h; | 88% |
With pyridine | |
In pyridine | |
With pyridine for 5h; Heating; |
glutaric anhydride,
beta-amyrin
3-[(3-carboxypropyl)carbonyloxy]-β-amyrin
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; | 81% |
succinic acid anhydride
beta-amyrin
3-[(2-carboxyethyl)carbonyloxy]-β-amyrin
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; | 79% |
Conditions | Yield |
---|---|
With dmap In dichloromethane for 3h; | 75% |
beta-amyrin
β-amyrone
Conditions | Yield |
---|---|
With chromium trioxide pyridine In dichloromethane for 24h; Ambient temperature; | 72% |
With chromium(VI) oxide; sulfuric acid In acetone | |
With 4-methylisopropylbenzene; nickel Heating; |
beta-amyrin
A
β-amyrone
B
3,11-dioxo-β-amyrene
C
3β,11α-dihydroxy-olean-12-ene
D
3β-hydroxy-olean-9(11),12-diene
Conditions | Yield |
---|---|
With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; iodosylbenzene In dichloromethane at 20℃; for 5h; Oxidation; | A 4% B 9% C 35% D 5% |
beta-amyrin
methyl 3'-(cyanocarbonyl)-2,2'-binaphthalene-3-carboxylate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; | 9% |
pyridine
beta-amyrin
acetic anhydride
β-amyrin acetate
pyridine
beta-amyrin
p-toluenesulfonyl chloride
oleana-2,12-diene
Conditions | Yield |
---|---|
With selenium at 350℃; |
Conditions | Yield |
---|---|
With selenium at 350℃; |
Conditions | Yield |
---|---|
With pyridine; p-toluenesulfonyl chloride at 100℃; |
Conditions | Yield |
---|---|
With sulfur | |
With selenium |
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic acid at 70℃; |
beta-amyrin
3β-methoxyolean-12-ene
Conditions | Yield |
---|---|
With potassium; benzene anschliessendes Kochen mit Methyljodid; |
beta-amyrin
Conditions | Yield |
---|---|
ueber mehrere Stufen; |
beta-amyrin
A-neooleana-3(5),12-diene
Conditions | Yield |
---|---|
With phosphorus pentachloride; Petroleum ether |
beta-amyrin
5(4=>3)-abeo-oleanadiene-(3.12)
Conditions | Yield |
---|---|
With phosphorus pentachloride; Petroleum ether |
beta-amyrin
Conditions | Yield |
---|---|
With Perbenzoic acid; chloroform | |
With monoperoxyphthalic acid |
beta-amyrin
Conditions | Yield |
---|---|
With nitrogen; sulfur at 220℃; |
The beta-Amyrin, with the cas registry number 559-70-6, is also known as NSC 527971 and Olean-12-en-3beta-ol. It belongs to the product categories of Tri-Terpenoids. Its EINECS number is 209-204-6. This chemical's molecular formula is C30H50O and formula weight is 426.72. What's more, its systematic name is called (3β)-Olean-12-en-3-ol. This chemical is white crystalline powder.
Physical properties about this chemical are: (1)ACD/LogP: 10.48; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 10.481; (4)ACD/LogD (pH 7.4): 10.481; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.539; (14)Molar Refractivity: 131.922 cm3; (15)Molar Volume: 420.836 cm3; (16)Surface Tension: 39.479 dyne/cm; (17)Density: 1.014 g/cm3; (18)Flash Point: 217.667 °C; (19)Enthalpy of Vaporization: 87.236 kJ/mol; (20)Boiling Point: 490.669 °C at 760 mmHg; (21)Melting Point: 187-190 °C; (22)Vapour Pressure: 0 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. Besides, it is harmful if swallowed. You should not breathe its dust. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: C[C@@]12CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]1CC(CC2)(C)C)C
(2)InChI: InChI=1/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h9,21-24,31H,10-19H2,1-8H3/t21-,22-,23+,24-,27+,28-,29+,30+/m0/s1
(3)InChIKey: JFSHUTJDVKUMTJ-QHPUVITPBE
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