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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Methyl Laurate is a 12-carbon saturated fatty acid, an esterification product of lauric acid, commonly used in fragrances and analytical applications.
Synonyms: Methyl dodecanoate; C12:0 Methyl ester
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 111-82-0 |
Formula : | C13H26O2 |
M.W : | 214.34 |
SMILES Code : | CCCCCCCCCCCC(OC)=O |
Synonyms : |
Methyl dodecanoate; C12:0 Methyl ester
|
MDL No. : | MFCD00008966 |
InChI Key : | UQDUPQYQJKYHQI-UHFFFAOYSA-N |
Pubchem ID : | 8139 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H319-H372-H410 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 |
Class: | 9 |
UN#: | 3082 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
85% | at 100℃; for 5 h; | The raw materials fatty acidmethyl ester and diethanolamine (moleratio: 1:1.1)were mixed and reacted at 100 °C for 5 h. NaOH was used asa catalyst with mass concentration of 0.5 wtpercent. After the reaction, the solution was concentrated in rotary evaporator. After drying, the fatty acid alkanolamide is obtained. The yield is 85percent. |
84.24% | at 110℃; for 5 h; | A mixture of 21.43 g of methyl laurate (CnH23C00CH3, 0.1 mol) and 11.04 g of diethanolamine (0.105 mol) were mixed in a three-necked flask equipped with a magnetic rotor, a condenser and a thermometer, and 0.20 g of sodium hydroxide The total mass of the total reactants was 0.62percent). The flask was heated to 110 ° C in an oil bath. After stirring for 5 h, the flask was steam dried and cooled to give 24.21 g of lauric acid alkanolamide in a yield of 84.24percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | at 80℃; for 54 h; Inert atmosphere | General procedure: Commercially available ionized liquid tetrabutylphosphonium glycinate (Gly-TBP, manufactured by Katayama Pharmaceutical Co., Ltd., colorless transparent liquid, moisture content: 0.11 mass percent) was used as the component (A).In a high purity argon atmosphere, Lau-OMe was added to 1 kg of the above Gly-TBP so that the amount of methyl laurate (Lau-OMe, Wako Pure Chemical Industries, Ltd.) was 500 mmol (Gly-TBP: Lau-OMe molar ratio = 6: 1). After thorough stirring of the obtained solution, it was confirmed that the whole solution became homogeneous, and then the reaction was started by heating to 60 ° C. while stirring in a water bath. Each time-lapse sample was analyzed by HPLC to confirm formation of N-acylamino acid (N-lauroylglycine). After 86 hours, the yield of N-acylamino acid (N-lauroylglycine) was about 82percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
401.7 g | With Novozym 435; In n-heptane; at 65℃; under 65 - 85 Torr;Dean-Stark; | To a 3-neck, 2-L round bottom flask fitted with an overhead stirrer and a Dean-Stark trap with cold-finger condenser was added methyl laurate (302 g, 1 .41 mol) and 3-hydroxymethyl-1 -methylpiperidine (200 g, 1 .56 mol). Novozym 435 (30 g) was added, followed by the addition of heptane (120 mL). The internal pressure was reduced to 85 mm Hg and controlled by a vacuum regulator. The mixture was heated to 65°C. After 1 .5 hrs, 23 ml_ of methanol had collected in the Dean-Stark trap. At that point, the reaction was cooled to ambient temperature. The mixture was allowed to stand overnight. The following morning, the pressure was once again reduced to 85 mm Hg, and the mixture was heated to 65°C. The reaction was checked by 1 H NMR after 5.5 hours. Additional 3-hydroxymethyl-1 -methylpiperidine (9.00 g) was added. After 7.5 hrs, the mixture was cooled to ambient temperature. Then additional 3-hydroxymethyl-4-methylpiperidine (17.9 g) was once again added. The pressure was reduced to 65 mm Hg, and the mixture was heated to 65°C. After 5 hrs, the reaction was stopped. The mixture was filtered, and the solids were washed with additional heptane. Heptane (500 ml_) was added to the organics, which were then washed with water (1 x 500 ml_). After the layers were separated, the organics were dried with Na2SO4. After filtration, most of the volatiles were removed at reduced pressure. The remaining material was heated to 50°C and sparged (subsurface) for ca. 24 hrs with nitrogen at 100 mL/min to drive off residual heptane affording the title compound as a pale yellow oil (401 .7 g) that was 98.4percent pure by 1 H NMR analysis. 1 H NMR (300 MHz, CDCI3) delta 3.95 (m, 2H), 2.08 (m, 2H), 2.30 (t, J = 9 Hz, 2H), 2.27 (s, 3H) 2.01 -1 .83 (m, 2H); 1 .77-1 .56 (m, 8H); 1 .37-1 .21 (m, 17H), 0.89 (t, 3H).HPLC (150 x 4.6 mm Zorbax SB-C8 column, 75:25 (v:v) (0191) methanol :water (containing 0.1 vol percent trifluoroacetic acid) for 10 min, gradient to 100percent methanol over 1 min, held at 100percent methanol for 9 min, ELSD detection): tR (laurate ester) 5.0 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.67% | With magnesium oxide; potassium oxide; at 20 - 40℃; for 3h;pH 10 - 13; | The molar ratio of raw material methyl laurate and sodium glutamate of 1.8: 0.7 was chosen to mix potassium oxide in a molar ratio of 2: 1And magnesium oxide is a metal oxide catalyst, and the catalyst is added in an amount of 0.05 wtpercent of the total amount of the reactants.The synthesis was prepared according to the one-step synthesis method in Example 1, in which the reaction temperature of the primary mixer was generally controlled at20 to 30 degrees, in particular, a mixer inlet temperature control at 25 degrees, a mixer outlet temperature control at25 degrees; pH maintained at 10. The reaction temperature of the secondary mixer is generally controlled between 30 and 40 degrees. Specifically, the secondary mixingThe feed inlet temperature control 35 degrees, two mixer outlet temperature control at 35 degrees; pH maintained at 13.After the reaction was completed, 0.069percent methanol was separated to obtain lauroyl glutamic acid having an active content of 88.67percentSodium, purity up to 98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | at 80℃; for 54h;Inert atmosphere; | General procedure: Commercially available ionized liquid tetrabutylphosphonium glycinate (Gly-TBP, manufactured by Katayama Pharmaceutical Co., Ltd., colorless transparent liquid, moisture content: 0.11 mass percent) was used as the component (A).In a high purity argon atmosphere, Lau-OMe was added to 1 kg of the above Gly-TBP so that the amount of methyl laurate (Lau-OMe, Wako Pure Chemical Industries, Ltd.) was 500 mmol (Gly-TBP: Lau-OMe molar ratio = 6: 1). After thorough stirring of the obtained solution, it was confirmed that the whole solution became homogeneous, and then the reaction was started by heating to 60 ° C. while stirring in a water bath. Each time-lapse sample was analyzed by HPLC to confirm formation of N-acylamino acid (N-lauroylglycine). After 86 hours, the yield of N-acylamino acid (N-lauroylglycine) was about 82percent |
Tags: 111-82-0 synthesis path| 111-82-0 SDS| 111-82-0 COA| 111-82-0 purity| 111-82-0 application| 111-82-0 NMR| 111-82-0 COA| 111-82-0 structure
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