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[ CAS No. 1120-25-8 ] {[proInfo.proName]}

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Chemical Structure| 1120-25-8
Chemical Structure| 1120-25-8
Structure of 1120-25-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1120-25-8 ]

CAS No. :1120-25-8 MDL No. :MFCD00042911
Formula : C17H32O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IZFGRAGOVZCUFB-HJWRWDBZSA-N
M.W : 268.43 Pubchem ID :643801
Synonyms :
(Z)-Methyl hexadec-9-enoate;Methyl cis-9-Hexadecenoate;C16:1 (cis-9) Methyl ester;Methyl hexadecenoate (cis-9)

Safety of [ 1120-25-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1120-25-8 ]

* 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.

  • Downstream synthetic route of [ 1120-25-8 ]

[ 1120-25-8 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 1120-25-8 ]
  • [ 29242-09-9 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; acetic acid at 20℃; der Methylester entsteht; lower-melting λ.ι-dioxy-palmitic acid;
  • 2
  • [ 1120-25-8 ]
  • [ 908329-09-9 ]
YieldReaction ConditionsOperation in experiment
83% With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 20℃; for 2h; 1 Preparation of Compound 1-A Methyl palmitoleate (10 g, 1 eq) containing a double bond, as a start material, a mixture solvent of tetrahydrofuran (THF) and water (a volume ratio of THF/H2O=3/1) (80 mL), OsO4 (Osmium tetraoxide, 4% in H2O) (24 mL, 0.1 eq), and NMP (4-Methylmorpholine N-Oxide) (5.65 g, 1.5 eq) were reacted at room temperature for 2 hours. When the reaction was completed, an aqueous NaHCO3 solution (100 mL) was added thereto, and then the organic layer was extracted with ethyl acetate (100 mL× three times), followed by column chromatography, thereby separating and purifying Compound 1-A (9.35 g, yield 83%).[0032]1H-NMR (400 MHz, CDCl3); δ 3.66 (s, 3H), 3.56 (bs, 2H), 3.16 (bs, 2H), 2.30 (t, 2H), 1.62 (t, 2H), 1.51-1.22 (m, 20H), 0.88 (t, 3H)[0033]13C-NMR (100 MHz, CDCl3); δ 174.5, 74.9, 74.8, 34.1, 32.0, 31.4, 31.3, 29.6, 29.6, 29.3, 29.2, 26.3, 26.2, 25.0, 22.8, 14.2
With dihydrogen peroxide; acetic acid at 20℃; methyl ester of/the/ lower-melting λ.ι-dioxy-palmitic acid;
  • 3
  • [ 1120-25-8 ]
  • [ 267003-95-2 ]
YieldReaction ConditionsOperation in experiment
With nickel kieselguhr; hydrogen at 170 - 180℃; Hydrogenation.entsteht der Methylester;
  • 4
  • [ 1120-25-8 ]
  • [ 62640-81-7 ]
YieldReaction ConditionsOperation in experiment
With nickel kieselguhr; hydrogen at 170 - 180℃; Hydrogenation.entsteht der Methylester;
  • 5
  • [ 1931-63-1 ]
  • [ 13423-48-8 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
91.52% Stage #1: triphenylheptylphosphonium bromide With sodium amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 1.5h; Stage #2: methyl ester of azelaic acid aldehyde In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -73 - 20℃;
(i) K, HMPT, (ii) /BRN= 1766823/; Multistep reaction;
With sodium amide 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT; Yield given. Multistep reaction;
1.7 g With potassium carbonate In toluene for 4h; Reflux;

  • 7
  • [ 1120-25-8 ]
  • [ 10378-01-5 ]
YieldReaction ConditionsOperation in experiment
96% With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; for 5h;
92% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h;
0.14 g With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Ambient temperature;
2.3 g With lithium aluminium tetrahydride In diethyl ether for 2h; Reflux;

  • 8
  • [ 10030-74-7 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
With 2-hydroxyethanethiol; dinitrogen monoxide; <i>tert</i>-butyl alcohol at 22℃; γ-Irradiation;
  • 9
  • [ 1120-25-8 ]
  • [ 10030-74-7 ]
YieldReaction ConditionsOperation in experiment
With 2-hydroxyethanethiol; dinitrogen monoxide; <i>tert</i>-butyl alcohol at 22℃; γ-Irradiation;
With methanesulfonyl chloride In ethanol; water at 22℃; γ-Irradiation;
  • 10
  • [ 75-11-6 ]
  • [ 1120-25-8 ]
  • (±)-methyl cis-9,10-methylenehexadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: (Z)-9-hexadecenoic acid methyl ester In hexane; dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
39% With diethylzinc In dichloromethane at 20℃; for 24h;
  • 11
  • [ 1120-25-8 ]
  • methyl (Z)-8-(2-hexylcyclopropan-1-yl)-8-oxooctanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 39 percent / Et2Zn / CH2Cl2 / 24 h / 20 °C 2: 14 mg / CrO3; AcOH; H2O / CCl4 / 96 h / 20 °C
  • 12
  • [ 1120-25-8 ]
  • methyl (Z)-8-(2-(1-oxo)-hexylcyclopropan-1-yl)octanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 39 percent / Et2Zn / CH2Cl2 / 24 h / 20 °C 2: 15 mg / CrO3; AcOH; H2O / CCl4 / 96 h / 20 °C
  • 13
  • methyl aleuritate [ No CAS ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 2.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 2.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
  • 14
  • [ 1120-25-8 ]
  • [ 56219-04-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 2: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C
Multi-step reaction with 2 steps 1: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature
With 1-methyl-piperazine; sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 20℃; for 2h; Sealed tube; Inert atmosphere; Cooling with ice; 3 Reduction of methyl hexadec-9-enoate with sodiumbis(2-methoxyethoxy) aluminumhydride In an oven-dried, nitrogen-flushed flask sealed with a rubber septum and containing a magnetic stir bar is added 0.47 g N-methylpiperazine (CAS 109-01-3) and 10 mL of dry, degassed toluene. The flask is submerged in an ice bath and, with magnetic stirring, 1.48 g of a 70% solution of sodium bis(2-methoxyethoxy)aluminumhydride (CAS 22722-98-1) in toluene is added dropwise. In a separate oven dried, nitrogen-flushed flask sealed with a rubber septum is added 1.00 g of methyl hexadec-9-enoate, prepared through the process detailed in Example 2, and 20 mL of dry, degassed toluene. The flask is then submerged in an ice bath and stirrer via an external magnetic stirrer. After stirring for one hour, the N-methylpiperazine/sodium bis(2-methoxyethoxy)aluminumhydride mixture is added dropwise via a cannula to the toluene solution of ester. The resulting mixture is stirred at ice-bath temperature for one hour and then brought to ambient temperature and stirred for an additional hour. The reaction is quenched by addition of 20 mL of deionized water and then extracted with 20 mL of EtOAc. The organic layer is washed with 20 mL of deionized water, dried over sodium sulfated and then concentrated in vacuo. The product is analyzed by GC-MS, indicating that (Z)-hexadec-9-enal is formed in high yield.
  • 15
  • (+)-threo-9,10,16-trihydroxyhexadecanoic acid [ No CAS ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 97.95 percent / aq. H2SO4 / 0.11 h / microwave irradiation 2.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 3.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 3.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
  • 16
  • [ 6308-96-9 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: KOH, PEG 400 / 0.5 h / 150 - 200 °C 2: p-TSA / 12 h / Ambient temperature 3: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 4: 84 percent / O3 / CH2Cl2 / -78 °C 5: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
  • 17
  • [ 112-38-9 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 97 percent / Br2 / CCl4 / 1.5 h 2: KOH, PEG 400 / 0.5 h / 150 - 200 °C 3: p-TSA / 12 h / Ambient temperature 4: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 5: 84 percent / O3 / CH2Cl2 / -78 °C 6: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
  • 18
  • [ 22202-65-9 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: p-TSA / 12 h / Ambient temperature 2: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 3: 84 percent / O3 / CH2Cl2 / -78 °C 4: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
  • 19
  • [ 18937-76-3 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
  • 20
  • [ 54299-07-9 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 84 percent / O3 / CH2Cl2 / -78 °C 2: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
  • 21
  • [ 1120-25-8 ]
  • (8R,11R)-8,11-Dihydroxy-hexadecanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SeO2, tert-butyl hydroperoxide (TBHP) / CH2Cl2 / 24 h / Ambient temperature 2: hydrazine hydrate, O2 / ethanol / 48 h / 60 °C
  • 22
  • [ 1120-25-8 ]
  • (8R,11S)-8,11-Dihydroxy-hexadecanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SeO2, tert-butyl hydroperoxide (TBHP) / CH2Cl2 / 24 h / Ambient temperature 2: hydrazine hydrate, O2 / ethanol / 48 h / 60 °C
  • 23
  • [ 57491-64-2 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 2: 0.19 g / conc. H2SO4 / 6 h / Heating
  • 24
  • [ 1120-25-8 ]
  • [ 34010-20-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature 2: 0.1 g / pyridine / 25 h / Ambient temperature
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 2 h / Reflux 2: pyridine / 24 h / 20 °C
  • 25
  • [ 533-87-9 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C 3: 0.30 g / NaI / acetone / 16 h / Heating 4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 5: 0.19 g / conc. H2SO4 / 6 h / Heating
  • 26
  • [ 1619-68-7 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 0.51 g / pyridine / 15 h / -5 °C 2: 0.30 g / NaI / acetone / 16 h / Heating 3: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 4: 0.19 g / conc. H2SO4 / 6 h / Heating
  • 27
  • [ 57491-62-0 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 0.30 g / NaI / acetone / 16 h / Heating 2: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 3: 0.19 g / conc. H2SO4 / 6 h / Heating
  • 28
  • [ 67-56-1 ]
  • fish oil [ No CAS ]
  • [ 124-41-4 ]
  • [ 108698-02-8 ]
  • [ 16326-32-2 ]
  • [ 2566-90-7 ]
  • [ 1120-25-8 ]
  • [ 112-62-9 ]
  • [ 112-63-0 ]
  • [ 2390-09-2 ]
  • [ 301-00-8 ]
  • [ 2733-88-2 ]
  • [ 111-82-0 ]
  • [ 124-10-7 ]
  • [ 112-39-0 ]
  • [ 1731-92-6 ]
  • [ 112-61-8 ]
  • [ 1120-28-1 ]
  • [ 2734-47-6 ]
  • [ 56219-06-8 ]
  • [ 61012-47-3 ]
  • [ 61012-46-2 ]
  • cis-10-heptadecenoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 55℃; for 1.5h;Product distribution / selectivity; Freeze-dried tissue samples were uniformly distributed by grinding for 10 -15 sec in a room-temperature coffee bean grinder. Samples of freeze-dried tissue (0.25g), or oils (20 mul) were placed into a 16 x 125 mm screw- cap Pyrex culture tube to which 1.0 ml methyl Cl 3:0 internal standard (0.5mg methyl C13:0/ml methanol) was added. Two ml of sodium methoxide (0.5 M) or 2 ml of boron trifluoride in methanol (14%, wt/vol) were added to the Pyrex tubes containing the samples. The tubes were incubated in a 55 0C water bath for 1.5 h with vigorous 5 sec hand-shaking every 20 min. Two ml of a saturated solution Of NaHCO3 and 3 ml hexane were then added and the tubes were vortex-mixed. After centrifugation, the hexane layer containing the FAME was placed into a GC vial. The vial was capped and placed at -20 C until GC analysis; A comparison was made between the base catylyst sodium methoxide, the acid catylyst boron trifluoride, and direct synthesis, on FAME production from fish oil commercially obtained as a human nutritional supplement. The results are shown in Table 2.Twenty fatty acids were identified in the fish oil sample. Direct FAME synthesis recovered more total amount of fatty acid than did either of the other two methods as would be expected if direct FAME synthesis generated methyl esters of all the fatty acids in the sample. In comparison, base catalysis with sodium methoxide methylated esterified fatty acids, but not free fatty acid anions (Kramer et al., 1997), whereas, acid catalysis by boron trifluoride should have methylated all fatty acids, including esterified, unesterified, and those in salt form (Carrapiso and Garcia, 2000).In analyzing the total fatty acids methylated, direct FAME synthesis converted 22% more fatty acids to FAME than did sodium methoxide and 14% more than did boron trifluoride indicating that there must be groups of fatty acids present that the latter two methods did not recognize. Such limitations with these two reagents have been previously noted (Kramer et al., 1997; Christie, 2003). The direct FAME synthesis method apparently methylates all of the fatty acids present, which explains why the direct FAME synthesis recoveries were higher than the other two methods. When the peak areas were expressed as % of total fatty acid (% FA) present by each method, the % FAs were similar for all three methods even though total recovery among the three methods was somewhat different. This indicates that the fatty acids not methylated by sodium methoxide or boron trifluoride were present in similar ratios for all of the fatty acids present. The results with sodium methoxide, which does not methylate free fatty acid anions, <n="22"/>indicates that because it methylated only 82% of the total fatty acids present the other 18% of the fatty acids present may have been free fatty acid anions.
  • 29
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 108698-02-8 ]
  • [ 1937-63-9 ]
  • [ 16326-32-2 ]
  • [ 2566-89-4 ]
  • [ 1120-25-8 ]
  • [ 112-62-9 ]
  • [ 112-63-0 ]
  • [ 2390-09-2 ]
  • [ 301-00-8 ]
  • [ 111-82-0 ]
  • [ 124-10-7 ]
  • [ 7132-64-1 ]
  • [ 112-39-0 ]
  • [ 1731-92-6 ]
  • [ 112-61-8 ]
  • [ 1120-28-1 ]
  • [ 929-77-1 ]
  • [ 21061-10-9 ]
  • [ 2734-47-6 ]
  • [ 13487-42-8 ]
  • [ 56219-06-8 ]
  • [ 35042-75-2 ]
YieldReaction ConditionsOperation in experiment
at 55℃; for 1.5h;Product distribution / selectivity; Freeze-dried tissue samples were uniformly distributed by grinding for 10 -15 sec in a room-temperature coffee bean grinder. Samples of freeze-dried tissue (0.25g), or oils (20 mul) were placed into a 16 x 125 mm screw- cap Pyrex culture tube to which 1.0 ml methyl Cl 3:0 internal standard (0.5mg methyl C13:0/ml methanol) was added. Two ml of sodium methoxide (0.5 M) or 2 ml of boron trifluoride in methanol (14%, wt/vol) were added to the Pyrex tubes containing the samples. The tubes were incubated in a 55 0C water bath for 1.5 h with vigorous 5 sec hand-shaking every 20 min. Two ml of a saturated solution Of NaHCO3 and 3 ml hexane were then added and the tubes were vortex-mixed. After centrifugation, the hexane layer containing the FAME was placed into a GC vial. The vial was capped and placed at -20 C until GC analysis; The analysis of freeze-dried beef longissimus muscle fatty acids using sodium methoxide, boron trifluoride and direct FAME synthesis is presented in Table 4. Once again, there were striking differences among the three methods. Direct FAME synthesis recovered more fatty acids than did sodium methoxide and much more than did boron trifluoride. Since most of the fatty acids were esterified in longissimus muscle, as opposed to unesterified in the CLA capsule (Table 3), it was not surprising that sodium methoxide performed much better <n="23"/>in FAME synthesis of this sample, although it methylated only 78% of the fatty acids present. This sample also shows that boron trifluoride performed much better with the free fatty acid anions in the CLA sample (Table 3) than with the esterified fatty acids in muscle tissue. This latter result was surprising since boron trifluoride can methylate all families of fatty acids (Carrapiso and Garcia, 2000). Although boron trifluoride did methylate all of the different fatty acids present, as all of the peaks were identical to direct FAME synthesis, it did not do so quantitatively. It is unclear at this time why boron trifluoride gave such poor results. It can be mentioned that Bolte et al. reports satisfactory FAME synthesis results using boron trifluoride on freeze-dried lamb muscle tissue fatty acids by using much higher temperature and more concentrated effort, i.e., by incubating at 8O0C and vortex-mixing two to three times/min. However, our results do not seem to be due to the fact that boron trifluoride cannot permeate the meat sample, because similar results were observed when using a chloroform :methanol extract according to the method of Folch et al.(1956), where extraction of fatty acids by boron trifluoride would no longer be an issue (data not shown). Apparently, and unexpectedly, there are fatty acid structures in beef longissimus muscle that can be easily methylated by direct synthesis but not by boron trifluoride.When expressed as % FA, sodium methoxide and direct FAME synthesis were quite similar in their results, but boron trifluoride was different, and in this latter case the %FA values were higher when the concentration of fatty acid was lower. This difference could be explained by the fact that boron trifluoride methylated only 46% of the fatty acids present in longissimus muscle, and did so preferentially. With boron trifluoride, long chain unsaturated fatty acids appeared to be methylated more efficiently than short chain or saturated fatty acids, whereas, direct FAME synthesis methylated fatty acids without bias to chain length or structure. As a result, direct FAME synthesis consistently methylated more fatty acid, averaging 1.3 times that of sodium methoxide and 2.2 times that of boron trifluoride.
  • 30
  • [ 67-56-1 ]
  • fish oil [ No CAS ]
  • [ 108698-02-8 ]
  • [ 16326-32-2 ]
  • [ 2566-90-7 ]
  • [ 1120-25-8 ]
  • [ 112-62-9 ]
  • [ 112-63-0 ]
  • [ 2390-09-2 ]
  • [ 301-00-8 ]
  • [ 2733-88-2 ]
  • [ 111-82-0 ]
  • [ 1731-88-0 ]
  • [ 124-10-7 ]
  • [ 112-39-0 ]
  • [ 1731-92-6 ]
  • [ 112-61-8 ]
  • [ 1120-28-1 ]
  • [ 2734-47-6 ]
  • [ 56219-06-8 ]
  • [ 61012-47-3 ]
  • [ 61012-46-2 ]
  • cis-10-heptadecenoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Samples were uniformly distributed by grinding for 10 -15 sec in a room-temperature coffee bean grinder. Samples could be processed in the state obtained, e.g., wet, dry, freeze- dried, or semi-frozen. Samples (0.5g wet, dry, or semi-frozen sample), (0.25g freeze-dried sample), or oils (20 mul) were placed into a 16 x 125 mm screw-cap Pyrex culture tube to which 1.0 ml Cl 3:0 internal standard (0.5mg C13:0/ml methanol), 0.7 ml 10 N KOH in water, and 5.3 ml methanol was added. The tube was incubated in a 55 C water bath for 1.5 h with vigorous 5 sec hand-shaking every 20 min to properly permeate, dissolve and hydrolyze the sample. After cooling below room temperature in a cold tap water bath, 0.58 ml of 24 N H2SO4 in water was added. (Care is taken in the preparation of the stock solutions IO N KOH and 24 N H2SO4, especially as the H2SO4 solution is extremely exothermic.) The tube was mixed by inversion, and with precipitated K2SO4 present, was incubated again in a 55 C water bath for 1.5 h with 5 sec hand-shaking every 20 min. After FAME synthesis, the tube was cooled in a cold tap water bath. Three ml of hexane was added and the tube was vortex-mixed for 5 min on a multi-tube vortex. The tube was centrifuged for 5 min in a tabletop centrifuge and the hexane layer, containing the FAME, was placed into a gas chromatography (GC) vial. The vial was capped and placed at -20 0C until GC analysis; It is of great interest to know what the limiting concentration of water might be for the direct FAME synthesis method. There has to be such a limit, for no other reason than the fact there has to be a certain concentration of methylating reagents. In Figure 1, we show the effect of water concentration on the direct FAME synthesis method. As the percentage of water was increased, the total amount of fatty acids methylated decreased (data not shown), but this was easily corrected for by the internal standard. Most importantly, the percentage of each fatty acid remained constant up to 33% water. Only above 33% water do the FAME production results become problematic. In comparison, our reagents, without any sample present, constitute only 13% water in a final reaction volume of 7.58 ml. Thus, from a practical standpoint, one can replace 1.5 ml of MeOH with a 1.5 ml aqueous sample for a <n="25"/>final concentration of 33% water. For example, using the protocol as given, 1.5 ml of milk can be analyzed directly by our method.
  • 31
  • [ 67-56-1 ]
  • fish oil [ No CAS ]
  • [ 108698-02-8 ]
  • [ 16326-32-2 ]
  • [ 2566-90-7 ]
  • [ 1120-25-8 ]
  • [ 112-62-9 ]
  • [ 112-63-0 ]
  • [ 2390-09-2 ]
  • [ 301-00-8 ]
  • [ 2733-88-2 ]
  • [ 111-82-0 ]
  • [ 124-10-7 ]
  • [ 112-39-0 ]
  • [ 1731-92-6 ]
  • [ 112-61-8 ]
  • [ 1120-28-1 ]
  • [ 2734-47-6 ]
  • [ 56219-06-8 ]
  • [ 61012-47-3 ]
  • [ 61012-46-2 ]
  • cis-10-heptadecenoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Samples were uniformly distributed by grinding for 10 -15 sec in a room-temperature coffee bean grinder. Samples could be processed in the state obtained, e.g., wet, dry, freeze- dried, or semi-frozen. Samples (0.5g wet, dry, or semi-frozen sample), (0.25g freeze-dried sample), or oils (20 mul) were placed into a 16 x 125 mm screw-cap Pyrex culture tube to which 1.0 ml Cl 3:0 internal standard (0.5mg C13:0/ml methanol), 0.7 ml 10 N KOH in water, and 5.3 ml methanol was added. The tube was incubated in a 55 C water bath for 1.5 h with vigorous 5 sec hand-shaking every 20 min to properly permeate, dissolve and hydrolyze the sample. After cooling below room temperature in a cold tap water bath, 0.58 ml of 24 N H2SO4 in water was added. (Care is taken in the preparation of the stock solutions IO N KOH and 24 N H2SO4, especially as the H2SO4 solution is extremely exothermic.) The tube was mixed by inversion, and with precipitated K2SO4 present, was incubated again in a 55 C water bath for 1.5 h with 5 sec hand-shaking every 20 min. After FAME synthesis, the tube was cooled in a cold tap water bath. Three ml of hexane was added and the tube was vortex-mixed for 5 min on a multi-tube vortex. The tube was centrifuged for 5 min in a tabletop centrifuge and the hexane layer, containing the FAME, was placed into a gas chromatography (GC) vial. The vial was capped and placed at -20 0C until GC analysis; A comparison was made between the base catylyst sodium methoxide, the acid catylyst boron trifluoride, and direct synthesis, on FAME production from fish oil commercially obtained as a human nutritional supplement. The results are shown in Table 2.Twenty fatty acids were identified in the fish oil sample. Direct FAME synthesis recovered more total amount of fatty acid than did either of the other two methods as would be expected if direct FAME synthesis generated methyl esters of all the fatty acids in the sample. In comparison, base catalysis with sodium methoxide methylated esterified fatty acids, but not free fatty acid anions (Kramer et al., 1997), whereas, acid catalysis by boron trifluoride should have methylated all fatty acids, including esterified, unesterified, and those in salt form (Carrapiso and Garcia, 2000).In analyzing the total fatty acids methylated, direct FAME synthesis converted 22% more fatty acids to FAME than did sodium methoxide and 14% more than did boron trifluoride indicating that there must be groups of fatty acids present that the latter two methods did not recognize. Such limitations with these two reagents have been previously noted (Kramer et al., 1997; Christie, 2003). The direct FAME synthesis method apparently methylates all of the fatty acids present, which explains why the direct FAME synthesis recoveries were higher than the other two methods. When the peak areas were expressed as % of total fatty acid (% FA) present by each method, the % FAs were similar for all three methods even though total recovery among the three methods was somewhat different. This indicates that the fatty acids not methylated by sodium methoxide or boron trifluoride were present in similar ratios for all of the fatty acids present. The results with sodium methoxide, which does not methylate free fatty acid anions, <n="22"/>indicates that because it methylated only 82% of the total fatty acids present the other 18% of the fatty acids present may have been free fatty acid anions.
Freeze-dried tissue samples were uniformly distributed by grinding for 10 -15 sec in a room-temperature coffee bean grinder. Samples of freeze-dried tissue (0.25g), or oils (20 mul) were placed into a 16 x 125 mm screw- cap Pyrex culture tube to which 1.0 ml methyl Cl 3:0 internal standard (0.5mg methyl C13:0/ml methanol) was added. Two ml of sodium methoxide (0.5 M) or 2 ml of boron trifluoride in methanol (14%, wt/vol) were added to the Pyrex tubes containing the samples. The tubes were incubated in a 55 0C water bath for 1.5 h with vigorous 5 sec hand-shaking every 20 min. Two ml of a saturated solution Of NaHCO3 and 3 ml hexane were then added and the tubes were vortex-mixed. After centrifugation, the hexane layer containing the FAME was placed into a GC vial. The vial was capped and placed at -20 C until GC analysis; A comparison was made between the base catylyst sodium methoxide, the acid catylyst boron trifluoride, and direct synthesis, on FAME production from fish oil commercially obtained as a human nutritional supplement. The results are shown in Table 2.Twenty fatty acids were identified in the fish oil sample. Direct FAME synthesis recovered more total amount of fatty acid than did either of the other two methods as would be expected if direct FAME synthesis generated methyl esters of all the fatty acids in the sample. In comparison, base catalysis with sodium methoxide methylated esterified fatty acids, but not free fatty acid anions (Kramer et al., 1997), whereas, acid catalysis by boron trifluoride should have methylated all fatty acids, including esterified, unesterified, and those in salt form (Carrapiso and Garcia, 2000).In analyzing the total fatty acids methylated, direct FAME synthesis converted 22% more fatty acids to FAME than did sodium methoxide and 14% more than did boron trifluoride indicating that there must be groups of fatty acids present that the latter two methods did not recognize. Such limitations with these two reagents have been previously noted (Kramer et al., 1997; Christie, 2003). The direct FAME synthesis method apparently methylates all of the fatty acids present, which explains why the direct FAME synthesis recoveries were higher than the other two methods. When the peak areas were expressed as % of total fatty acid (% FA) present by each method, the % FAs were similar for all three methods even though total recovery among the three methods was somewhat different. This indicates that the fatty acids not methylated by sodium methoxide or boron trifluoride were present in similar ratios for all of the fatty acids present. The results with sodium methoxide, which does not methylate free fatty acid anions, <n="22"/>indicates that because it methylated only 82% of the total fatty acids present the other 18% of the fatty acids present may have been free fatty acid anions.
  • 32
  • [ 67-56-1 ]
  • [ 108698-02-8 ]
  • [ 1937-63-9 ]
  • [ 16326-32-2 ]
  • [ 2566-89-4 ]
  • [ 1120-25-8 ]
  • [ 112-62-9 ]
  • [ 112-63-0 ]
  • [ 2390-09-2 ]
  • [ 301-00-8 ]
  • [ 111-82-0 ]
  • [ 124-10-7 ]
  • [ 7132-64-1 ]
  • [ 112-39-0 ]
  • [ 1731-92-6 ]
  • [ 112-61-8 ]
  • [ 1120-28-1 ]
  • [ 929-77-1 ]
  • [ 21061-10-9 ]
  • [ 2734-47-6 ]
  • [ 13487-42-8 ]
  • [ 56219-06-8 ]
  • [ 35042-75-2 ]
YieldReaction ConditionsOperation in experiment
Samples were uniformly distributed by grinding for 10 -15 sec in a room-temperature coffee bean grinder. Samples could be processed in the state obtained, e.g., wet, dry, freeze- dried, or semi-frozen. Samples (0.5g wet, dry, or semi-frozen sample), (0.25g freeze-dried sample), or oils (20 mul) were placed into a 16 x 125 mm screw-cap Pyrex culture tube to which 1.0 ml Cl 3:0 internal standard (0.5mg C13:0/ml methanol), 0.7 ml 10 N KOH in water, and 5.3 ml methanol was added. The tube was incubated in a 55 C water bath for 1.5 h with vigorous 5 sec hand-shaking every 20 min to properly permeate, dissolve and hydrolyze the sample. After cooling below room temperature in a cold tap water bath, 0.58 ml of 24 N H2SO4 in water was added. (Care is taken in the preparation of the stock solutions IO N KOH and 24 N H2SO4, especially as the H2SO4 solution is extremely exothermic.) The tube was mixed by inversion, and with precipitated K2SO4 present, was incubated again in a 55 C water bath for 1.5 h with 5 sec hand-shaking every 20 min. After FAME synthesis, the tube was cooled in a cold tap water bath. Three ml of hexane was added and the tube was vortex-mixed for 5 min on a multi-tube vortex. The tube was centrifuged for 5 min in a tabletop centrifuge and the hexane layer, containing the FAME, was placed into a gas chromatography (GC) vial. The vial was capped and placed at -20 0C until GC analysis; The analysis of freeze-dried beef longissimus muscle fatty acids using sodium methoxide, boron trifluoride and direct FAME synthesis is presented in Table 4. Once again, there were striking differences among the three methods. Direct FAME synthesis recovered more fatty acids than did sodium methoxide and much more than did boron trifluoride. Since most of the fatty acids were esterified in longissimus muscle, as opposed to unesterified in the CLA capsule (Table 3), it was not surprising that sodium methoxide performed much better <n="23"/>in FAME synthesis of this sample, although it methylated only 78% of the fatty acids present. This sample also shows that boron trifluoride performed much better with the free fatty acid anions in the CLA sample (Table 3) than with the esterified fatty acids in muscle tissue. This latter result was surprising since boron trifluoride can methylate all families of fatty acids (Carrapiso and Garcia, 2000). Although boron trifluoride did methylate all of the different fatty acids present, as all of the peaks were identical to direct FAME synthesis, it did not do so quantitatively. It is unclear at this time why boron trifluoride gave such poor results. It can be mentioned that Bolte et al. reports satisfactory FAME synthesis results using boron trifluoride on freeze-dried lamb muscle tissue fatty acids by using much higher temperature and more concentrated effort, i.e., by incubating at 8O0C and vortex-mixing two to three times/min. However, our results do not seem to be due to the fact that boron trifluoride cannot permeate the meat sample, because similar results were observed when using a chloroform :methanol extract according to the method of Folch et al.(1956), where extraction of fatty acids by boron trifluoride would no longer be an issue (data not shown). Apparently, and unexpectedly, there are fatty acid structures in beef longissimus muscle that can be easily methylated by direct synthesis but not by boron trifluoride.When expressed as % FA, sodium methoxide and direct FAME synthesis were quite similar in their results, but boron trifluoride was different, and in this latter case the %FA values were higher when the concentration of fatty acid was lower. This difference could be explained by the fact that boron trifluoride methylated only 46% of the fatty acids present in longissimus muscle, and did so preferentially. With boron trifluoride, long chain unsaturated fatty acids appeared to be methylated more efficiently than short chain or saturated fatty acids, whereas, direct FAME synthesis methylated fatty acids without bias to chain length or structure. As a result, direct FAME synthesis consistently methylated more fatty acid, averaging 1.3 times that of sodium methoxide and 2.2 times that of boron trifluoride.
Freeze-dried tissue samples were uniformly distributed by grinding for 10 -15 sec in a room-temperature coffee bean grinder. Samples of freeze-dried tissue (0.25g), or oils (20 mul) were placed into a 16 x 125 mm screw- cap Pyrex culture tube to which 1.0 ml methyl Cl 3:0 internal standard (0.5mg methyl C13:0/ml methanol) was added. Two ml of sodium methoxide (0.5 M) or 2 ml of boron trifluoride in methanol (14%, wt/vol) were added to the Pyrex tubes containing the samples. The tubes were incubated in a 55 0C water bath for 1.5 h with vigorous 5 sec hand-shaking every 20 min. Two ml of a saturated solution Of NaHCO3 and 3 ml hexane were then added and the tubes were vortex-mixed. After centrifugation, the hexane layer containing the FAME was placed into a GC vial. The vial was capped and placed at -20 C until GC analysis; The analysis of freeze-dried beef longissimus muscle fatty acids using sodium methoxide, boron trifluoride and direct FAME synthesis is presented in Table 4. Once again, there were striking differences among the three methods. Direct FAME synthesis recovered more fatty acids than did sodium methoxide and much more than did boron trifluoride. Since most of the fatty acids were esterified in longissimus muscle, as opposed to unesterified in the CLA capsule (Table 3), it was not surprising that sodium methoxide performed much better <n="23"/>in FAME synthesis of this sample, although it methylated only 78% of the fatty acids present. This sample also shows that boron trifluoride performed much better with the free fatty acid anions in the CLA sample (Table 3) than with the esterified fatty acids in muscle tissue. This latter result was surprising since boron trifluoride can methylate all families of fatty acids (Carrapiso and Garcia, 2000). Although boron trifluoride did methylate all of the different fatty acids present, as all of the peaks were identical to direct FAME synthesis, it did not do so quantitatively. It is unclear at this time why boron trifluoride gave such poor results. It can be mentioned that Bolte et al. reports satisfactory FAME synthesis results using boron trifluoride on freeze-dried lamb muscle tissue fatty acids by using much higher temperature and more concentrated effort, i.e., by incubating at 8O0C and vortex-mixing two to three times/min. However, our results do not seem to be due to the fact that boron trifluoride cannot permeate the meat sample, because similar results were observed when using a chloroform :methanol extract according to the method of Folch et al.(1956), where extraction of fatty acids by boron trifluoride would no longer be an issue (data not shown). Apparently, and unexpectedly, there are fatty acid structures in beef longissimus muscle that can be easily methylated by direct synthesis but not by boron trifluoride.When expressed as % FA, sodium methoxide and direct FAME synthesis were quite similar in their results, but boron trifluoride was different, and in this latter case the %FA values were higher when the concentration of fatty acid was lower. This difference could be explained by the fact that boron trifluoride methylated only 46% of the fatty acids present in longissimus muscle, and did so preferentially. With boron trifluoride, long chain unsaturated fatty acids appeared to be methylated more efficiently than short chain or saturated fatty acids, whereas, direct FAME synthesis methylated fatty acids without bias to chain length or structure. As a result, direct FAME synthesis consistently methylated more fatty acid, averaging 1.3 times that of sodium methoxide and 2.2 times that of boron trifluoride.
  • 33
  • [ 67-56-1 ]
  • [ 50-99-7 ]
  • [ 1120-25-8 ]
  • [ 112-62-9 ]
  • [ 112-63-0 ]
  • [ 112-39-0 ]
YieldReaction ConditionsOperation in experiment
1: 18.4 %Chromat. 2: 9.7 %Chromat. 3: 6.5 %Chromat. 4: 58.4 %Chromat. Stage #1: D-glucose In water at 28℃; for 168h; Microbiological reaction; Stage #2: methanol With hydrogenchloride
  • 35
  • [ 89199-88-2 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogen; ethylenediamine In ethanol; water stereoselective reaction;
  • 36
  • [ 50816-20-1 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 1.2: -20 - 20 °C 2.1: Jones reagent / acetone / 0 - 4 °C 3.1: sulfuric acid / 20 °C 4.1: hydrogen; ethylenediamine / ethanol; water
  • 37
  • [ 1120-25-8 ]
  • [ 56-81-5 ]
  • [ 37515-61-0 ]
YieldReaction ConditionsOperation in experiment
68% With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In dimethyl sulfoxide at 20℃; regioselective reaction;
  • 38
  • [ 89155-39-5 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / 20 °C 2: hydrogen; ethylenediamine / ethanol; water
  • 39
  • [ 50816-19-8 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 2.2: -20 - 20 °C 3.1: Jones reagent / acetone / 0 - 4 °C 4.1: sulfuric acid / 20 °C 5.1: hydrogen; ethylenediamine / ethanol; water
  • 40
  • [ 25258-24-6 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Jones reagent / acetone / 0 - 4 °C 2: sulfuric acid / 20 °C 3: hydrogen; ethylenediamine / ethanol; water
  • 41
  • [ 1120-25-8 ]
  • [ 78387-69-6 ]
YieldReaction ConditionsOperation in experiment
With Wilkinson's catalyst; deuterium In toluene at 30℃; for 48h; regioselective reaction;
  • 42
  • [ 373-49-9 ]
  • [ 18107-18-1 ]
  • [ 1120-25-8 ]
  • 43
  • 9,10,16-trihydroxyhexadecanoic acid [ No CAS ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium metaperiodate 2: boron trifluoride diethyl etherate 3: potassium carbonate / toluene / 4 h / Reflux
  • 44
  • [ 2553-17-5 ]
  • [ 1120-25-8 ]
  • 45
  • [ 1120-25-8 ]
  • [ 624-92-0 ]
  • 9,10-bis-methylsulfanyl-hexadecanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine In hexane at 50℃; for 20h; 2.7 Treatment of FAMEs by dimethyl disulfide (DMDS) To 2mg of dried FAMEs, dissolved into 100μL n-hexane, were added 100μL DMDS and 20μL iodine in solution in diethylether (60mg/mL) [26]. The solution was then heated to 50°C for 20h in Pyrex tube sealed with a Teflon cap. Then, the excess iodine was reduced by adding 500μL of an aqueous solution of sodium thiosulfate (50mg/mL). The reaction mixture was extracted twice by 2×400μL n-hexane. The organic layers were pooled and concentrated under a N2 stream prior to GC and GC/MS analysis.
  • 46
  • [ 373-49-9 ]
  • [ 79-20-9 ]
  • [ 1120-25-8 ]
  • 47
  • [ 1120-25-8 ]
  • [ 624-92-0 ]
  • C19H38O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine at 60℃; for 24h; Inert atmosphere; Synthesis of bis(alkylthio)alkanoates. General procedure: All fatty acid methyl esters (1 mol) were reacted with dialkyl disulfide (6 mol) elemental iodine (0.01 mol) for 24 h at 60 °C under N2. Then the reaction mixture was cooled to room temperature. Volatile dialkyl disulfides were removed by a stream of nitrogen from the reaction mixture. Equal amounts (3 mL) of hexane and 5% aqueous sodium thiosulfate solution were added, and the mixture was washed with further aliquots of the sodium thiosulfate solution until the iodine color disappeared. The product was then dried with a sodium sulfate column and hexane removed under a stream of nitrogen, which also removed any additional remaining dialkyl disulfide. Further removal of less volatile dialkyl disulfide and unreacted starting material was carried out by high-performance liquid chromatography on a silica column using a 20:1 hexane/ethyl acetate solvent system. After removal of the solvent system by rotary evaporation, the products were obtained as colorless liquids. Yields as determined by NMR prior to HPLC purification decrease with increasing size of the dialkyl disulfide employed, ranging from quantitative or near-quantitative with DMDS to 50-60% when using DiPDS or dibutyl disulfide (DBDS).
  • 48
  • [ 110-81-6 ]
  • [ 1120-25-8 ]
  • C21H42O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine at 60℃; for 24h; Inert atmosphere; Synthesis of bis(alkylthio)alkanoates. General procedure: All fatty acid methyl esters (1 mol) were reacted with dialkyl disulfide (6 mol) elemental iodine (0.01 mol) for 24 h at 60 °C under N2. Then the reaction mixture was cooled to room temperature. Volatile dialkyl disulfides were removed by a stream of nitrogen from the reaction mixture. Equal amounts (3 mL) of hexane and 5% aqueous sodium thiosulfate solution were added, and the mixture was washed with further aliquots of the sodium thiosulfate solution until the iodine color disappeared. The product was then dried with a sodium sulfate column and hexane removed under a stream of nitrogen, which also removed any additional remaining dialkyl disulfide. Further removal of less volatile dialkyl disulfide and unreacted starting material was carried out by high-performance liquid chromatography on a silica column using a 20:1 hexane/ethyl acetate solvent system. After removal of the solvent system by rotary evaporation, the products were obtained as colorless liquids. Yields as determined by NMR prior to HPLC purification decrease with increasing size of the dialkyl disulfide employed, ranging from quantitative or near-quantitative with DMDS to 50-60% when using DiPDS or dibutyl disulfide (DBDS).
  • 49
  • [ 1120-25-8 ]
  • [ 629-19-6 ]
  • C23H46O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine at 60℃; for 24h; Inert atmosphere; Synthesis of bis(alkylthio)alkanoates. General procedure: All fatty acid methyl esters (1 mol) were reacted with dialkyl disulfide (6 mol) elemental iodine (0.01 mol) for 24 h at 60 °C under N2. Then the reaction mixture was cooled to room temperature. Volatile dialkyl disulfides were removed by a stream of nitrogen from the reaction mixture. Equal amounts (3 mL) of hexane and 5% aqueous sodium thiosulfate solution were added, and the mixture was washed with further aliquots of the sodium thiosulfate solution until the iodine color disappeared. The product was then dried with a sodium sulfate column and hexane removed under a stream of nitrogen, which also removed any additional remaining dialkyl disulfide. Further removal of less volatile dialkyl disulfide and unreacted starting material was carried out by high-performance liquid chromatography on a silica column using a 20:1 hexane/ethyl acetate solvent system. After removal of the solvent system by rotary evaporation, the products were obtained as colorless liquids. Yields as determined by NMR prior to HPLC purification decrease with increasing size of the dialkyl disulfide employed, ranging from quantitative or near-quantitative with DMDS to 50-60% when using DiPDS or dibutyl disulfide (DBDS).
  • 50
  • [ 111-66-0 ]
  • [ 25601-41-6 ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
With tungsten (1R)-3,3’-dibromo-2’-[[(1,1-dimethylethyl)dimethylsilyl]oxyl-5,5’,6,6,7,7,8,8’-octahydro[1,1‘-binaphthalen]-2-olato-κO] [2,6-dichlorobenzenaminato(2-)-κN] 2,5-dimethyl-1H-pyrrol-1-yl[(2-methoxyphenyl)methylene] In toluene at 40℃; for 4h; Glovebox; Inert atmosphere; Sealed tube; 2 Cross-metathesis of methyl dec-9-enoate withoct-1-ene Prior to introduction of the metathesis catalyst, methyl dec-9-enoate (CAS 25601-41-6) and oct-1-ene (CAS 111-66-0) are treated to reduce moisture, peroxides and other potential catalyst poisons to a level suitable for conducting the metathesis reaction as described in U.S. Pat. No. 9,388,097. In a nitrogen-filled glovebox, a 20 mL scintillation vial is charged with a magnetic stir bar, 1.00 g of pretreated methyl dec-9-enoate and 1.83 g of pretreated oct-1-ene. The vial is closed with a perforated septum and placed in an aluminum heating block regulated at 40° C. atop a hotplate/magnetic stirrer where the stirring rate is fixed at 500 rpm. A solution of 1-({3,3′-dibromo-2′-[(tert-butyldimethylsilyl)oxy]-5H,5′H,6H,6′H,7H,7′H,8H,8′H-[1,1′-binaphthalene]-2-yl}oxy)-1-(2,5-dimethylpyrrol-1-yl)-1-(2-methyl-2-phenylpropylidene)-N-phenyltungstenimine (CAS 1628041-76-8) catalyst in dry and degassed toluene is prepared by weighing 10 mg of the catalyst into a 1 mL volumetric flask and diluting to the calibration mark with solvent. Using a gas tight microliter syringe, 71 μL of the catalyst solution (0.71 mg cat., 0.025 wt %, 0.0029 mol %) is withdrawn from the volumetric flask and added reaction mixture. After four hours the vial is removed from the glovebox and the reaction mixture is analyzed by GC-MS. The GC-MS data indicates that methyl (Z)-hexadec-9-enoate is formed in high yield.
  • 51
  • [ 67-56-1 ]
  • [ 1120-25-8 ]
  • [ 201230-82-2 ]
  • [ 19102-92-2 ]
YieldReaction ConditionsOperation in experiment
With 2CHF3O3S*C24H44P2 at 90℃; for 18h; Inert atmosphere; Glovebox; Schlenk technique; Autoclave;
  • 52
  • [ 67-56-1 ]
  • 3-O-(9'Z-hexadecenoyl)ingenol [ No CAS ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In water at 20℃; for 2h;
  • 53
  • [ 1120-25-8 ]
  • (±)-cis-9,10-methylenehexadecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diethylzinc; trifluoroacetic acid / hexane; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 1.2: 1 h / 0 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / methanol; tetrahydrofuran; water / 24 h / 20 °C
  • 54
  • boron trifluoride-methanol [ No CAS ]
  • (22E)-ergosta-5,22-dien-3-yl 9-cis-hexadecenoate [ No CAS ]
  • [ 1120-25-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (22E)-ergosta-5,22-dien-3-yl 9-cis-hexadecenoate With hydrogenchloride; water monomer at 80℃; for 4h; Stage #2: boron trifluoride-methanol 2.4. Acid hydrolysis of compounds and GC-MS analyses General procedure: Compounds 1-5 (1.5 mg) were refluxed with 10 mL 10% HCl at80 C. After 4 h, the reflux was stopped, and 10 mL of cold water wasadded. The liquid-liquid extraction was performed using chloroform.The chloroform phase was methylated with BF3-MeOH reactive [27],then analyzed with GC-MS directly to check for fatty acid parts ofcompounds 2 and 3. The aqueous phases were lyophilized for compounds4 and 5 (Christ, Germany) to obtain the sugars. After lyophilization,the residue was dissolved in 10 μL pyridine for silylation. Afterthat, 15 μL of bis(trimetisilil)trifloroasetamit was added, the mixturewas kept at 80 C for 2 h. Then, the mixture was cooled and diluted with100 μL chloroform; 0.4 μL of the mixture was injected into GC-MScoupled with the apolar dimethylsiloxane column (30 m × 0.25 mm (i.d.), film thickness 0.25 μm). The oven temperature was started at 100 Cand increased with 5 C/min increments up to 300 C, then held at300 C for 15 min [28]. The fatty acid methyl esters and silylated sugarswere elucidated according to Wiley library, and co-injection of standardsamples were prepared at the same condition as that of the samples.
Same Skeleton Products
Historical Records