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2-hydroxy Myristic Acid

(Synonyms: 2-羟基十四烷酸) 目录号 : GC42166

A hydroxy fatty acid

2-hydroxy Myristic Acid Chemical Structure

Cas No.:2507-55-3

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产品描述

2-hydroxy Myristic acid is a hydroxy fatty acid that has been found in bovine, human, and horse milk, cow and buffalo cheeses, sea bass filet, seal oil, human vernix caseosa, and wool wax. It inhibits cleavage between the enterovirus capsid proteins VP4 and VP2, a process required for enterovirus infectivity, as well as Junin and Tacaribe viral replication (IC50s = 20.1 and 14.2 μM, respectively). 2-hydroxy Myristic acid was previously characterized as a weak inhibitor of peptide myristoylation (Ki = 200 μM) but has been shown to be inactive in ARL1 cells when used at 100 μM.

Chemical Properties

Cas No. 2507-55-3 SDF
别名 2-羟基十四烷酸
Canonical SMILES CCCCCCCCCCCCC(O)C(=O)O
分子式 C14H28O3 分子量 244.4
溶解度 DMF: 30 mg/ml,DMSO: 27 mg/ml,Ethanol: 37 mg/ml,Ethanol:PBS (1:2): 0.35 mg/ml 储存条件 Store at -20°C
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1 mM 4.0917 mL 20.4583 mL 40.9165 mL
5 mM 0.8183 mL 4.0917 mL 8.1833 mL
10 mM 0.4092 mL 2.0458 mL 4.0917 mL
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Research Update

Isolation of a novel sphingoglycolipid containing glucuronic acid and 2-hydroxy fatty acid from Flavobacterium devorans ATCC 10829

J Biochem 1978 Apr;83(4):1213-6.PMID:659393DOI:10.1093/oxfordjournals.jbchem.a132015.

A new acidic sphingoglycolipid has been isolated from a Gram-negative, glucose-non-fermentative (obligatory aerobic) bacterium, Flavobacterium devorans ATCC 10829, by thin-layer chromatography on silica gel after mild alkaline hydrolysis of the cellular lipids. Chemical degradation studies, thin-layer chromatographic behavior, IR and mass-spectrometric analysis of the original and reduced glycolipid with LiA1H4 revealed that the lipid contained glucuronic acid, long-chain bases, and fatty acids in a molar ratio of approximately 1:1:1. The major long-chain bases were identified by gas chromatography-mass spectrometry as dihydrosphingosine (d-18 :0) and longer homologues, while the N-acyl group was exclusively 2-hydroxy Myristic Acid. The most probable structure of this glycolipid appeared to be a ceramide glucuronic acid (N-acyl dihydrosphingosine 1-glucuronic acid).

Isolation of an unusual 'lipid A' type glycolipid from Pseudomonas paucimobilis

Biochim Biophys Acta 1982 Sep 14;712(3):571-5.PMID:7126625DOI:10.1016/0005-2760(82)90285-5.

A new glycolipid was isolated from defatted cells of Pseudomonas paucimobilis IAM 12576, and called 'bound lipid'. The 'bound lipid' could not be extracted by hot phenol extraction, but could be extracted with hot chloroform/methanol after hydrolysis with 5% trichloroacetic acid. The 'bound lipid' was purified by thin-layer chromatography on silica gel plates using the solvent mixture CHCl3/CH3OH/CH3COOOH/ H2O (25:15:4:2, v/v). It consisted of glucosamine, 2-hydroxy Myristic Acid, galactose, mannose and uronic acid with ratios of 1.0:0.75:0.77:0.44:1.5, respectively, and other fatty acids besides 2-hydroxy Myristic Acid were not detected in the 'bound lipid'. 2-hydroxy Myristic Acid was probably bound to glucosamine residues by amide linkage, because mild alkali treatment did not liberate the fatty acid. From these results, we discussed the possibility that the 'bound lipid' was some kind of lipid A of this bacteria.

Stimulation of phagocytosis and phagosome-lysosome fusion by glycosphingolipids from Sphingomonas paucimobilis

J Biochem 1995 Aug;118(2):271-7.PMID:8543558DOI:10.1093/oxfordjournals.jbchem.a124902.

Sphingomonas paucimobilis, a Gram-negative opportunistic pathogen, is actively phagocytosed by human peripheral polymorphonuclear leukocytes (PMN) in vitro. However, when live or killed cells were delipidated, the phagocytic rate was clearly decreased. Therefore, we have investigated the physiological role of membrane lipids in phagocytic processes. S. paucimobilis type strain 2395 produces four classes of acidic glycosphingolipids (GL-1, GL-2, GL-3, and GL-4) with the common components of glucuronic acid, 2-hydroxy Myristic Acid and d18:0 or d21:1 long-chain base. The effect of acidic glycosphingolipids on phagocytosis by PMN using killed Staphylococcus aureus cells coated with glucuronosyl ceramide (GL-1) or ceramide tetrahexoside (GL-4) was also examined. The rate of phagosome-lysosome fusion by PMN was determined by counting acridine orange-stained bacteria under a fluorescence microscope. Both phagocytosis and phagosome-lysosome fusion by PMN of glycosphingolipid-coated bacteria were stimulated markedly in a dose-dependent manner. It was noted that GL-1 or GL-4 stimulated phagosome-lysosome fusion dramatically, but synthetic lipid A did not. Superoxide anion release from PMN was enhanced significantly by the coating with synthetic lipid A at higher concentration, but only slightly with GL-1 or GL-4. Glucuronic acid was an inhibitor of phagocytosis of GL-1-coated S. aureus by PMN. The effect of acidic glycosphingolipids obtained from mammalian tissue on phagocytosis was also compared with that of bacterial glycosphingolipids. Ganglioside GM3 and sulfatide showed a marked stimulative activity for phagocytosis by PMN, while the neutral glycosphingolipids did not. Thus, bacterial acidic glycosphingolipid and mammalian acidic glycosphingolipid promote phagocytosis and phagosome-lysosome fusion by PMN.