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Dipalmitin Sale

(Synonyms: 二棕榈酸甘油酯) 目录号 : GC45697

A diacylglycerol

Dipalmitin Chemical Structure

Cas No.:26657-95-4

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产品描述

Dipalmitin is a diacylglycerol that contains the saturated 16-carbon fatty acid palmitic acid at two positions.

Chemical Properties

Cas No. 26657-95-4 SDF
别名 二棕榈酸甘油酯
Canonical SMILES OC(COC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O
分子式 C35H68O5 分子量 568.9
溶解度 DMF: 20 mg/ml,DMSO: 30 mg/ml,Ethanol: 0.25 mg/ml,PBS (pH 7.2): 0.7 mg/ml 储存条件 Store at -20°C
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1 mM 1.7578 mL 8.7889 mL 17.5778 mL
5 mM 0.3516 mL 1.7578 mL 3.5156 mL
10 mM 0.1758 mL 0.8789 mL 1.7578 mL
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Research Update

Surface properties of 1,2-dipalmitoyl-3-acyl-sn-glycerols

Biochemistry 1986 Jul 29;25(15):4468-72.PMID:3756148DOI:10.1021/bi00363a045.

Stereospecific 1,2-dipalmitoyl-sn-glycerol and a series of 1,2-dipalmitoyl-3-acyl-sn-glycerols (TGs) with 3-acyl chains of two through six and eight carbons in length were synthesized. Pressure-area isotherms at 27 degrees C, surface melting temperatures (Ts), and equilibrium spreading pressures (esp) measured at the bulk melting temperature (Tf) were obtained for each TG and for Dipalmitin. Whereas Dipalmitin and the 3-acetyl-TG condense directly to an expanded mesomorphous state (30-33 A2/palmitoyl chain at the vapor pressure, pi v), the 3-propionyl- through 3-octanoyl-TGs show an area per molecule (in the liquid at pi v) that increases linearly from 105 to 130 A2/molecule (slope = 5 A2/CH2 group). This slope suggests that the 3-acyl chains are lying flat on the water at the end of the gas-liquid transition. Before solidification at 42-47 A2/molecule, the 3-propionyl- through 3-hexanoyl-TGs show a transition corresponding to the immersion of the 3-acyl chain. The pressure at this transition, pi tr, vs. 3-acyl carbon number is linear and indicates a chain immersion energy of 497 cal mol-1 per CH2. In contrast, the 3-octanoyl chain is not forced into the water but rather is pushed into the monolayer to lie parallel to the palmitoyl chains. As the sn-3 chain is lengthened, Ts decreases from 68 to 25 degrees C, but the 3-octanoyl monolayer does not solidify even at 5 degrees C because the short upright octanoyl chains fluidize the palmitoyl chains. The esp (at Tf) drops from 31.7 mN m-1 for Dipalmitin to 20.6 mN m-1 for the 3-acetyl-TG.(ABSTRACT TRUNCATED AT 250 WORDS)

Chemical constituents of Typhonium giganteum Engl

J Asian Nat Prod Res 2001;3(4):277-83.PMID:11783581DOI:10.1080/10286020108040367.

A new cerebroside, named typhonoside (1), was isolated from the root tuber of Typhonium giganteum Engl. along with three known compounds Dipalmitin (2), alpha-monopalmitin (3) and 2,6-diamino-9-beta-D-ribofuranosylpurine (4). The structure of 1 was determined to be 1-O-beta-D-glucopyranosyl-(2S,3S,4R,8Z)-2-[(2'-hydroxyl-docosanoyl)amino]-8-otadecene-1,3,4-triol on the basis of spectral data.

Effects of Fe3+ and Antioxidants on Glycidyl Ester Formation in Plant Oil at High Temperature and Their Influencing Mechanisms

J Agric Food Chem 2017 May 24;65(20):4167-4176.PMID:28464610DOI:10.1021/acs.jafc.7b00858.

This research investigated the effects of Fe3+ and antioxidants on the formation of glycidyl esters (GEs) and the free radical mediated mechanisms involving the recognition of cyclic acyloxonium free radical intermediate (CAFRI) for GE formation in both the plant oil model (palm oil, camellia oil, soybean oil, and linseed oil) system and the chemical model (Dipalmitin and methyl linoleate) system heated at 200 °C. Results show that Fe3+ can promote the formation of GEs, which can be inhibited by antioxidants in plant oil during high-temperature exposure. Based on the monitoring of cyclic acyloxonium and ester carbonyl group by Fourier transform infrared spectroscopy, the promotion of Fe3+ and the inhibition of antioxidants (tert-butylhydroquinone and α-tocopherol) for GE formation occurred not only through lipid oxidation but also through directly affecting the formation of cyclic acyloxonium intermediate. Additionally, a quadrupole time-of-flight tandem mass spectrometry measurement was conducted to identify the presence of radical adduct captured by 5,5-dimethylpyrroline N-oxide, which provided strong evidence for the formation of CAFRI. Thus, one possible influencing mechanism can be that free radical generated in lipid oxidation may be transferred to Dipalmitin and promote CAFRI formation. Fe3+ can catalyze free radical generation while antioxidants can scavenge free radical, and therefore they also can directly affect CAFRI formation.

Correlation between bilayer destabilization and activity enhancement by diacylglycerols in reconstituted Ca-ATPase vesicles

Arch Biochem Biophys 1986 Jan;244(1):382-6.PMID:2936304DOI:10.1016/0003-9861(86)90127-x.

Using the reconstituted Ca-ATPase vesicles as a model system, we demonstrated that the presence of 1,2-dioleoyl-sn-glycerol (diolein) in the membrane introduces a pronounced enhancement in the Ca-transport function of Ca-ATPase, while the 1,2-dipalmitoyl-sn-glycerol (Dipalmitin) does not. We also found by both 31P NMR and freeze-fraction electron microscopy that diolein destabilized lipid bilayers to a greater extent than did Dipalmitin. We conclude that the tendency of diacylglycerols to destabilize the phospholipid bilayer is related to their capacity to enhance the activity of the membrane calcium pump.

Molecular Reaction Mechanism for the Formation of 3-Chloropropanediol Esters in Oils and Fats

J Agric Food Chem 2019 Mar 6;67(9):2700-2708.PMID:30722664DOI:10.1021/acs.jafc.8b06632.

3-Chloro-1,2-propanediol fatty acid esters (3-MCPD esters) are a group of process-induced contaminants that form during the refining and heating of fats and oils. In this study, a combined method of simulated deodorization and computational simulation was used to explore the precursor substance and the generation path of 3-MCPD esters. From the results, 3-MCPD esters reached a content level of 2.268 mg/kg when the diacylglyceride (DAG) content was 4% and temperature was 220 °C. A good correlation was observed between DAG and 3-MCPD ester contents ( y = 0.0612 x2 - 1.6376 x + 10.558 [ R2 = 0.958]). There were three pathways for the formation of 3-MCPD esters: (A) a direct nucleophilic substitution reaction, (B) an indirect nucleophilic substitution reaction, and (C) a mechanism of an intermediate (glycidyl ester) from the calculation of Gaussian software at the B3LYP/6-31+g** level. The data showed that the ester-based direct nucleophilic substitution reaction was the most likely reaction pathway. The energy barriers for the formation of the 3-MCPD esters Dipalmitin, diolein, and dilinolein were 74.261, 66.017, and 59.856 kJ/mol, respectively, indicating that the formation process of 3-MCPD esters is a high-temperature endothermic process. Therefore, by controlling the introduction of precursor (DAG) and reducing the temperature, 3-MCPD ester formation was prevented.