Alternatived Products of [ 10361-12-3 ]
Product Details of [ 10361-12-3 ]
| CAS No. : | 10361-12-3 |
MDL No. : | MFCD00016429 |
| Formula : |
C25H42O5
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | BRNPAEUKZMBRLQ-UHFFFAOYSA-N |
| M.W : |
422.60
|
Pubchem ID : | 473591 |
| Synonyms : |
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Chemical Name : | Octadecyl 3,4,5-trihydroxybenzoate |
Application In Synthesis of [ 10361-12-3 ]
* 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 [ 10361-12-3 ]
- 1
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[ 112-92-5 ]
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[ 149-91-7 ]
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[ 10361-12-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 97.2% |
With cation exchange resin 731 In ethyl acetate at 80 - 85℃; Dean-Stark; |
Synthesis of stearyl gallate
Add 178.5g (1.05mol) gallic acid, 270.5g (1mol) stearyl alcohol, 2.7g cation exchange resin 731, ethyl acetate into the reaction flask, add a water separator, and heat to 8085 to separate water and reflux. React for 4 to 5 hours, lower to room temperature (15 to 30°C), filter with suction, rinse the filter cake with 130ml ethyl acetate, wash the filtrate twice with 300ml 10% sodium hydroxide aqueous solution, and then wash with 300ml water once, then Wash once with 300ml saturated sodium chloride aqueous solution, separate the organic layer, distill under reduced pressure at 50-60°C, concentrate to 30% volume, freeze and stir to crystallize. After suction filtration, the filter cake is rinsed with a small amount of ethyl acetate at 0-5°C to obtain 410.7 g of the product with a yield of 97.2%. The content detected by HPLC is 99.43%, and the spectrum is shown in Figure 1 |
| 73% |
With toluene-4-sulfonic acid In 1,4-dioxane at 160℃; |
|
| 61% |
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 10h; |
Synthesis.
General procedure: To a solution of gallic acid (2.00 mM) and the corresponding alcohol (2.00 mM) in THF (10 mL) cooledat 0°C was added a solution of DCC (4.2 mM) in THF (10 mL). After stirring for 10 h, the solvent of the resulted mixture was removed under reduced pressure. The residue was extracted with ethyl acetate five times and filtered. The filter was washed successively with 4 M HCl solution, saturated NaHCO3 solution, and water, and then dried over Na2SO4 and evaporated.The crude products were purified by column chromatography on silica gel with petroleum ether-ethyl acetate (4:1) as eluent.The structures of the synthesized esters 1-15 were established by spectroscopic methods. Among them, 6, 8, and 12 are new compounds, and the others are known compounds. |
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With naphthalene-2-sulfonate; methoxybenzene; nitrobenzene unter Entfernen des entstehenden Wassers; |
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With toluene-4-sulfonic acid In toluene at 125℃; for 4h; |
1.1-1.4; 2.1-2.4; 3.1-3.4 Example 1A method for synthesizing stearyl gallate, including the following steps:
(1) Material preparation: mix anhydrous gallic acid and n-octadecyl alcohol at a mass ratio of 4:1 and then add to toluene, then add p-toluenesulfonic acid to the dispersant toluene to prepare a mixed solution; toluene and anhydrous gallic The mass ratio of acid is 1:0.8, and the mass ratio of catalyst p-toluenesulfonic acid to anhydrous gallic acid is 1:2.5;(2) Synthesis: Heat the mixed solution to 125°C in a reflux water separator, reflux for 4 hours. After the reaction, pour the reaction solution into a container containing 50 times the mass of gallic acid to disperse and crystallize. When the temperature of the reaction liquid drops to 30°C, suction filtration is started to obtain crude stearyl gallate;(3) Decolorization: Dissolve the crude stearyl gallate in 5 times the crude volume of ethyl acetate, add 3% crude quality activated carbon, heat to 60 and keep for 0.5 hours, then filter to obtain stearyl gallate Decolorizing liquid(4) Crystallization: The octadecyl gallate decolorizing solution was distilled under reduced pressure to remove ethyl acetate, the distillation residue was added to toluene of 1 times the mass of the residue, heated to dissolve the distillation residue, and then cooled to crystallize After the temperature is lowered to room temperature, it is filtered by suction to obtain the refined stearyl gallate. |
Reference：
[1]Current Patent Assignee: CHANGZHOU RUIBO BIO TECH - CN112830876, 2021, A
Location in patent: Paragraph 0024-0025
[2]Savi, Luciane A.; Leal, Paulo C.; Vieira, Tiago O.; Rosso, Rober; Nunes, Ricardo J.; Yunes, Rosendo A.; Creczynski-Pasa, Tania B.; Barardi, Celia R. M.; Simoes, Claudia Maria Oliveira
[Arzneimittel-Forschung/Drug Research, 2005, vol. 55, # 1, p. 66 - 75]
[3]Zhao, Xiao-Long; Li, Chun-Qing; Song, Xiao-Mei; Yan, Shuang-Mei; Luo, Du-Qiang
[Chemistry of Natural Compounds, 2021, vol. 57, # 1, p. 38 - 43][Khim. Prir. Soedin., 2021, vol. 57, p. 6,6]
[4]Ault et al.
[Journal of the American Chemical Society, 1947, vol. 69, p. 2003]
[5]Current Patent Assignee: JIURUI BIOLOGY AND CHEMISTRY - CN111217702, 2020, A
Location in patent: Paragraph 0013-0015
- 2
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3,4,5-tris-benzyloxy-benzoic acid octadec-9<i>c</i>-enyl ester
[ No CAS ]
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[ 10361-12-3 ]
| Yield | Reaction Conditions | Operation in experiment |
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With ethanol; platinum Hydrogenation; |
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| Yield | Reaction Conditions | Operation in experiment |
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With palladium on activated charcoal; ethanol Hydrogenation; |
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| Yield | Reaction Conditions | Operation in experiment |
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Practical examples of particularly preferred phenol derivatives include phenol compounds such as p-phenyphenol, ... n-butyl-4,4-(4'-hydroxyphenyl)acetate, 4,4'-thiobis(2-t-butyl-5-methylphenol), benzyl-p-hydroxybenzoate, chlorobenzyl-p-hydroxybenzoate, dimethyl-4-hydroxyphthalate, benzyl gallate, stearyl gallate, salicylic anilide, 5-chlorosalicylic anilide, salicylic acid, ... |
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Specific examples of such electron accepting compounds are as follows: ... 4,4'-diphenolsulfoxide, isopropyl p-hydroxybenzoate, benzyl p-hydroxybenzoate, benzyl protocatechuate, stearyl gallate, lauryl gallate, octyl gallate, 1,3-bis(4-hydroxyphenylthio)-2-hydroxypropane, ... |
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Specific examples of the color developer for use in the present invention are as follows: ... benzyl p-hydroxybenzoate, benzyl protocatechuate, stearyl gallate, lauryl gallate, ... |
- 5
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[ 1063201-10-4 ]
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[ 10361-12-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 97% |
With hydrogen In ethyl acetate at 20℃; atmospheric pressure; |
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- 6
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[ 10361-12-3 ]
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[ 1329454-60-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2: boron trifluoride diethyl etherate / dichloromethane |
|
Reference：
[1]Maldonado, Olivia S.; Lucas, Ricardo; Comelles, Francesc; Jesús González, Ma; Parra, Jose Luis; Medina, Isabel; Morales, Juan Carlos
[Tetrahedron, 2011, vol. 67, # 38, p. 7268 - 7279]
- 7
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[ 10361-12-3 ]
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[ 1329454-72-9 ]
| Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 3 steps
1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2: boron trifluoride diethyl etherate / dichloromethane
3: trifluoroacetic acid / 24 h / 20 °C |
|
Reference：
[1]Maldonado, Olivia S.; Lucas, Ricardo; Comelles, Francesc; Jesús González, Ma; Parra, Jose Luis; Medina, Isabel; Morales, Juan Carlos
[Tetrahedron, 2011, vol. 67, # 38, p. 7268 - 7279]
- 8
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[ 10361-12-3 ]
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[ 1329454-84-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2.1: boron trifluoride diethyl etherate / dichloromethane
3.1: trifluoroacetic acid / 24 h / 20 °C
4.1: methanol; sodium carbonate / 1 h
4.2: pH 7 |
|
Reference：
[1]Maldonado, Olivia S.; Lucas, Ricardo; Comelles, Francesc; Jesús González, Ma; Parra, Jose Luis; Medina, Isabel; Morales, Juan Carlos
[Tetrahedron, 2011, vol. 67, # 38, p. 7268 - 7279]
- 9
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[ 10361-12-3 ]
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[ 77-76-9 ]
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[ 1329454-37-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With camphor-10-sulfonic acid In chloroform at 60℃; for 16h; |
4.2. General procedure for acetal formation
General procedure: All alkyl gallates were protected with isopropylydene acetal. The corresponding alkyl gallate and camphor sulfonic acid in catalytic amounts were dissolved in dry chloroform, 2,2-dimethoxypropane was then added and the reaction mixture was stirred for 16 h at 60 °C. NEt3 was then added in order to neutralize. Solvents were removed in vacuo and the crude was purified by flash chromatography with hexane/ethyl acetate by using different polarities depending on the alkyl group. Reactions yields rated from 40 to 60%. |
Reference：
[1]Location in patent: experimental part
Maldonado, Olivia S.; Lucas, Ricardo; Comelles, Francesc; Jesús González, Ma; Parra, Jose Luis; Medina, Isabel; Morales, Juan Carlos
[Tetrahedron, 2011, vol. 67, # 38, p. 7268 - 7279]
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