98%| A1457022|Formula:C30H48O3|Molecular Weight:456.700350000+ products instock " />
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CAS No. : | 472-15-1 | MDL No. : | MFCD00009619 |
Formula : | C30H48O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QGJZLNKBHJESQX-FZFNOLFKSA-N |
M.W : | 456.70 | Pubchem ID : | 64971 |
Synonyms : |
Lupatic acid;Betulic acid;Mairin;NSC 113090;ALS-357
|
Chemical Name : | (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; | Preparation of suberinic and betulinic free acidsProduct V was acidified with a 2% solution of HCl in water (35 L) and the solution was then filtered. The solid residue recovered from the filter was washed twice with water (10 L) and dried at 40-45 C in vacuum (200 mm Hg) for 8 hours to yield VI (3.38 kg). Product VI comprises the acidic organic compounds free acid form 204 of the preferred embodiment shown in Figure 1.Composition of VI 18-Hydroxyoctadec-9-enoic acid 11.66 %18-hydroxy-9, 10-epoxyoctadecanoic acid 44.6 %Threo-9, 10,18 -trihydroxyoctadecanoic acid 11.3 %22-Hydroxydocosanoic acid 11.66 %Betulinic acid 12.86 % Other ω-hydroxy fatty acids 7.8 %; Preparation of suberinic and betulinic free acids Pressed outer birch bark (1 kg, d=0.6 g/ml) was added portionally to a solution of NaOH (230 g, 5.75 mol) in H2O (90 ml) and EtOH (2.5 L) at 70 0C. The reaction mixture was refluxed with good stirring for 1 hr. Xylenes (6 L) was then added to the reaction mixture. A solution of EtOH and H2O in xylenes (3.6 L) was distilled from the reaction mixture. Distillation was continued until temperature of vapors reached 133 0C. An additional amount of H2O (15 ml) was distilled from the reaction mixture by using a Dean-Stark receiver. The reaction mixture was filtrated at 800C. Solid part was added to xylenes (3 L) and refluxed for 1 hr. H2O (15 ml) was distilled from the reaction mixture by using a Dean-Stark receiver and the reaction mixture was filtered at 80 0C. Washing of solid part with xylenes (3 L) was repeated. Solid part after extraction with xylenes were added to ethanol (8 liters) and refluxed for 1 hour. The reaction mixture was filtrated at 700C and solid part was added to ethanol (4 L) and refluxed for 1 hr. The reaction mixture was filtrated at 70 0C and solid part was extracted with ethanol (4 L) using the same procedure as is it was described above. Ethanol solutions were combined, evaporated from solvent and dried in vacuum at 80 0C to give the acids as their sodium salts (330 g), which, was acidified with a 2 % solution of HCl (2.3 L) and filtered. The solid residue was washed twice with water (10 L) and dried in vacuum (200 mm Hg) at 40-45 0C <n="42"/>for 8 hours to give XVII (250 g). Product XVII comprises the acidic organic compounds free acid form 204 of the preferred embodiment shown in Figure 2. Composition of XVII1 S-Hydroxyoctadec-9-enoic acid 11.4 % 18-Hydroxyl-9,10-epoxyoctadecanoic acid 43.8 % Threo-9, 10, 18-trihydroxyoctadecanoic acid 12.1 % 22-Hydroxydocosanoic acid 11.84 %Betulinic acid 12.78 %Other ω-hydroxy fatty acids 8.14 % |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; | Preparation of suberinic and betulinic free acidsProduct XI was acidified with a 2% solution of HCl in water (35 L) and the solution was then filtered. The solid residue recovered from the filter was washed twice with water (10 L) then dried at 40-45 0C under vacuum (200 mm Hg.) for 8 hours to yield XII (5.28 kg). Product XI comprises the acidic organic compounds free acid form 204 of the preferred embodiment shown in Figure 1. Composition of XII1 δ-Hydroxyoctadec-Q-enoic acid 11.23 %18-hydroxy-9, 10-epoxyoctadecanoic acid 34.3 % t/jreo-9,0,18-trihydroxyoctadecanoic acid 14.9 %22-Hydroxydocosanoic Acid 14.99 %Betulinic acid 5.8 %Other ω-Hydroxy fatty acids 18.2 %; Preparation of suberinic and bctulinic free acidsPressed outer birch bark (1 kg) was added in portions to a solution of KOH (300 g, 5.35 mol) in H2O (60 ml) and EtOH (2.0 L) at 70 0C. The reaction mixture was refluxed with good stirring for 1 hr. Xylenes (6 L) was then added to the reaction mixture. A solution of EtOH and H2O in xylenes (3.6 L) was distilled from the reaction mixture. Distillation was continued until temperature of vapors reached 133 0C. An additional amount of H2O (15 ml) was distilled from the reaction mixture using a Dean-Stark receiver. The reaction mixture was filtered at 80 0C. The solid residue was added to xylenes (3 L) and refluxed for 1 hr. Water (15 ml) was distilled from the reaction mixture using a Dean- Stark receiver and the reaction mixture was filtered at 80 0C. Washing of the solid residue with xylenes (3 L) was repeated. The solid residue after extraction with xylenes was added to ethanol (8 L) and refluxed for 1 hr. The mixture was filtered at 70 0C and the extraction with EtOH was repeated twice using 4 L of EtOH. After filtration at 70 0C, the combined ethanol solutions were evaporated and the residue cidified with a 2 % solution of HCl in water (2.5 L). The precipitate was separated by filtration, washed twice with water (1 L), and dried at 40-45 0C under vacuum (200 mm Hg) for 8 hours giving XXII (341 g) Composition of XXII 18-Hydroxyoctadec-9-enoic acid 10.14 %18-Hydroxy-9, 10-epoxyoctadecanoic acid 40.8 %Threo-9, 10,18-trihydroxyoctadecanoic acid 10.1 %22-Hydroxydocosanoic acid 12.6 %Betulinic acid 7.98 % Other ω-hydroxy fatty acids 18.38 % |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoromethanesulfonic acid anhydride; In tetrahydrofuran; chloroform; | Step 1. Preparation of methyl 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(1-morpholinopropan-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate. In a 1 dram vial with rubber septum and stirbar were combined methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-1-(1-hydroxypropan-2-yl)-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate Isomer 1 (0.025 g, 0.035 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.021 g, 0.104 mmol) in dry chloroform (1 mL). To the stirred solution was added dropwise trifluoromethanesulfonic anhydride (0.013 g, 0.045 mmol) at rt. The mixture was stirred at rt for 1 h, then to the mixture was added morpholine (0.030 mL, 0.346 mmol) and the resulting solution was stirred at rt for 30 min and was then heated to 60 degrees C. for 90 min. The reaction mixture was concentrated under nitrogen stream and redissolved in a minimum quantity of a mixture of THF and MeOH. Purification by reverse phase preparative HPLC (Prep HPLC Method 3) gave the desired product as a white powder (0.0199 g, 50.7percent yield) TFA salt. LCMS: m/z=792.7 (M+H)+, 1.97 min (method 5). |