34487-30-4

Upstream product

• 112-62-9 Methyl oleate 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 56-81-5 glycerol 
• 122-32-7 trioleoylglycerol 
• 112-80-1 cis-Octadecenoic acid 
• 111-62-6 oleic acid ethyl ester 
• 33001-45-5 (+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (Z)-9-octadecenoate 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 506-24-1 Stearolic acid 
• 1120-32-7 stearolic acid methyl ester 
• 50816-19-8 8-bromooctanol 
• 168136-39-8 2-(octadec-9-yn-1-yloxy)tetrahydro-2H-pyran 
• 556-52-5 oxiranyl-methanol 
• 142-77-8 oleic acid butyl ester 

Downstream Products

• 20299-66-5 1,2-bis-lauroyloxy-3-oleoyloxy-propane 
• 18985-53-0 silicic acid tetrakis-(2-hydroxy-3-oleoyloxy-propylester) 
• 2465-32-9 1,3-diolein 
• 3443-84-3 2-Oleoylglycerol 
• 101200-99-1 1-oleoyl-3-acetyl-rac-glycerol 
• 55401-64-4 (Z)-9-octadecenoic acid 2,3-bis(acetyloxy)propyl ester 
• 124109-45-1 (+/-)-O¹-butyryl-O³-oleoyl-glycerol 
• 121235-57-2 (+/-)-1,2-bis-butyryloxy-3-oleoyloxy-propane 
• 1867-91-0 1,2-dipalmitoyl-3-oleoyl-rac-glycerol 
• 2190-29-6 (+-)-1-oleoyloxy-2,3-bis-stearoyloxy-propane 
• 20299-65-4 1,2-bis-decanyloxy-3-oleoyloxy-propane 
• 74160-01-3 1,2-bis-myristoyloxy-3-oleoyloxy-propane 
• 2190-29-6 1-oleoyloxy-2,3-bis-stearoyloxy-propane 
• 126451-63-6 (+/-)-1-linolenoyloxy-3-oleoyloxy-propan-2-ol 

Relevant academic research and scientific papers

Synthesis of Mono- and Diglycerides In Water-in-Oil Microemulsions

Enzyme-Catalyzed esterification was carried out in single-phase, oil-continuous microemulsions.The lipozyme was solubilized, along with glycerol and water, in the aqueous core of water / diethylhexyl sodium sulfosuccinate / hydrocarbon microemulsion system.Upon addition of fatty acid, mono- and diglycerides were formed, due to the esterification reaction taking place at the interface of the droplets in the microemulsion.The initial rate of conversion of oleic acid increases with oil chainlength of the continuous phase whereas final conversion is maximum for hexane.The conversion of stearic acid is 30percent whereas conversion of oleic acid is 70percent.The percent conversion of various fatty acids in the same continuous medium increases with fatty acid chainlength.The oleic acid / glycerol ratio is an important parameter for optimum conversion of oleic acid into glycerides.The yield can be increased by subsequent addition of glycerol after equilibrium is reached.High-performance liquid chromatography analysis of samples from microemulsions showes the presence of mono- and diglycerides.Possible mechanisms for the abovementioned effects are discussed. KEY WORDS: AOT, diglyceride, esterification, fatty acid, glycerol, hydrolysis, lipase, microemulsion, monoglyceride, reversed micelle.

Stereochemistry, lipid length and branching influences Mincle agonist activity of monoacylglycerides

Herein, we report on the synthesis of a series of enantiomerically pure linear, iso-branched, and α-branched monoacyl glycerides (MAGs) in 63-72% overall yield. The ability of the MAGs to signal through human macrophage inducible C-type lectin (hMincle) using NFAT-GFP reporter cells was explored, as was the ability of the compounds to activate human monocytes. From these studies, MAGs with an acyl chain length ≥C22 were required for Mincle activation and the production of interleukin-8 (IL-8) by human monocytes. Moreover, the iso-branched MAGs led to a more pronounced immune response compared to linear MAGs, while an α-branched MAG containing a C-32 acyl chain activated cells to a higher degree than trehalose dibehenate (TDB), the prototypical Mincle agonist. Across the compound classes, the activity of the sn-1 substituted isomers was greater than the sn-3 counterparts. None of the representative compounds were cytotoxic, thus mitigating cytotoxicity as a potential mediator of cellular activity. Taken together, 6h (sn-1, iC26+1), 8a (sn-1, C32) and 8b (sn-3, C32) exhibited the best immunostimulatory properties and thus, have potential as vaccine adjuvants.

High-selectivity synthesis method of long-chain fatty acid monoglyceride

The invention belongs to the field of fatty acid and synthetic fatty acid glycerides and relates to a high-selectivity synthesis method of long-chain fatty acid monoglyceride, in particular to a high-selectivity synthesis method of long-chain fatty acid and synthetic fatty acid glycerides. The method comprises the steps that tetraethyl silicate and glycerin are subjected to alcoholysis reaction, and part of glycerin is esterified to generate glyceryl silicate; then the glyceryl silicate is subjected to esterification reaction with fatty acid to generate fatty acid glyceride; finally the high activity (instability) of silicate ester is utilized to achieve hydrolysis under mild conditions to synthesize the synthetic fatty acid glyceride at high selectivity. A by-product is safe and harmlessSiO2. Accordingly, the product with high monoglyceride content is obtained by using a simple process under mild conditions.

Method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2

The invention belongs to the field of fatty acid glyceride synthesis and nano powder preparation, relates to a method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2,and particularly relates to a method for synthesizing fatty acid monoglyceride and co-producing the nano SiO2 by long-chain fatty acid and glycerinum. The method comprises the following steps of: using silicon tetrachloride to react with the glycerinum, so as to enable the glycerinum to be partially esterified to generate silicic acid glyceride; and performing an esterification reaction with fatty acid to generate fatty acid silicic acid glyceride; finally using high-activity (instability) of silicate ester, hydrolyzing in a mild condition, synthesizing the high-content fatty acid monoglyceride, and by-producing SiO2 powder in a nano state. So that a fatty acid monoglyceride product is high-selectively obtained and nano SiO2 powder is co-produced by a simple technology in the mild condition.

Method for synthesizing high content of fatty acid monoglyceride production of nano TiO2 The method of (by machine translation)

The invention belongs to the fatty acid glyceride synthesis and nano powder preparation field. In particular to fatty acid and glycerin synthesis of fatty acid monoglyceride, and cogeneration nano TiO2 Method. Method of this invention is: for the reaction of titanium tetrachloride and glycerin, glycerol partial esterification, generating titanate glycerides. Then with the fatty acid esterification reaction, to generate fatty acid glyceride titanate. Finally the use of a titanate high activity (instability), hydrolysis under mild conditions, synthesizing high-content fatty acid monoglyceride, the pressure of the by-product TiO2 Powder. Thus a simple process, under mild conditions, a high content of fatty acid monoglyceride product, production of nano TiO2 Powder. (by machine translation)

Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids

Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.

Non-ionic self-assembling amphiphilic polyester dendrimers as new drug delivery excipients

Solubility enhancement of poorly soluble antibiotics via self-assembling nano systems could be a promising approach to effectively treat bacterial infections in the current scenario of evolving resistant species. The study in this paper reports the synthesis of novel biocompatible G2 and G3 polyester amphiphilic dendrimers (ADs) (GMOA-G2-OH, GMOA-G3-OH, GMS-G2-OH and GMS-G3-OH) and their application as: (i) solubility enhancers for fusidic acid (FSD) as a model antibiotic with poor aqueous solubility and (ii) as stearic stabilizers in the preparation of solid lipid nanoparticles (SLNs). Two different series of ADs from glycerol monostearate (GMS) and glycerol monooleate (GMOA) were synthesized and their structures were confirmed employing FT-IR, NMR (1H and 13C) and HR-MS. The MTT assay confirmed their non-toxicity to mammalian cells. The critical aggregation concentration value order for ADs was GMS-G3-OH (5 × 10?6 mol l?1) ?6 mol l?1) ?5 mol l?1). All ADs formed micelles in the size range of 6.48 ± 0.04 nm to 12.38 ± 0.36 nm. At 1% w/w concentration FSD solubility enhancement in GMOA-G2-OH, GMOA-G3-OH, GMS-G2-OH and GMS-G3-OH was 43, 11, 9.1 and 6.8-fold respectively compared to water. As GMOA-G2-OH enabled the highest solubility of FSD, it was further evaluated for its antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA). The minimum inhibitory concentration values for FSD with and without GMOA-G2-OH against S. aureus were 0.23 μg ml?1 and 0.53 μg ml?1 respectively whereas the values were 0.23 μg ml?1 and 0.39 μg ml?1 against MRSA respectively. These results suggested that GM-OA-G2 not only enhanced the solubility but also enhanced antibacterial potency of FSD. Furthermore, these ADs showed their potential as promising pharmaceutical excipients as they acted as stearic stabilizers in the preparation of SLNs. Using these ADs stable SLNs with zeta potential value in the range of ?15.30 ± 1.44 to ?38.46 ± 3.04 were formed.

Fatty acid monomer, preparation method and thermoplastic macromolecule synthesized through application

The invention discloses a fatty acid monomer, a preparation method and a thermoplastic macromolecule synthesized through application. Tetramethyl guanidine and other catalysts are mainly utilized to catalyze a monomer containing halogen elements (Cl, Br and I) or halogen element and fatty acid, and the fatty acid monomer and thermoplastic macromolecule are obtained through efficient reaction. The application range can be thus widened by functionally improving the obtained fatty acid monomer and thermoplastic macromolecule. The reaction process is mild in condition, the catalytic efficiency of the catalysts is very high, few side reactions is produced, products are easy to separate and purify, and the fatty acid monomer and the thermoplastic macromolecule have a very high industrial application prospect.

Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids

The biocatalytic synthesis of monoacylglycerides (MAGs) was carried out by the direct esterification of fatty acids (i.e. capric, lauric, myristic, palmitic and oleic acids, respectively) with glycerol in different ionic liquids (ILs) based on cations with long alkyl side-chains (e.g. 1-hexadecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C16mim][NTf2], 1-dodecyl-3-methylimidazolium tetrafluoroborate [C12mim][BF4], etc.). Although all ILs have been shown as suitable reaction media for Novozym 435-catalyzed esterification of glycerol with free fatty acids, a high selectivity of MAGs was only observed in the [C12mim][BF4] case (e.g. up to 100% selectivity and 100% yield for monolaurin). Furthermore, as these ILs are temperature switchable ionic liquid/solid phases that behave as sponge-like systems, a straightforward protocol for IL-free MAG recovery, based on iterative centrifugations at controlled temperature, has been developed.

The chemical synthesis and preliminary biological studies of phosphodiester and phosphorothioate analogues of 2-methoxy-lysophosphatidylethanolamine

The chemical synthesis of phosphorothioate/phosphodiester analogues of 2-methoxy-lysophosphatidylethanolamine has been described. For the preparation of phosphorothioate derivatives oxathiaphospholane approach has been employed. The phosphodiester compounds were prepared by OXONE oxidation of corresponding phosphorothioates. Each lysophospholipid analogue was synthesized as a series of four compounds, bearing different fatty acid residues both saturated (14:0, 16:0, 18:0) and unsaturated (18:1). The methylation of glycerol 2-hydroxyl function was applied in order to increase the stability of prepared analogues by preventing 1→2 acyl migration. The cytotoxicity of newly synthesized 2-methoxy-lysophosphatidylethanolamine derivatives was evaluated with resazurin-based method in prostate cancer PC3 cell line. The highest reduction of cell viability was noted for LPE analogues containing myristoyl acyl chain.