1561-07-5Relevant academic research and scientific papers
Synthesis of [14C]-Labelled glycidyl and glycerol ethers of aliphatic and aromatic alcohols.
Van Elburg,Ormskerk,De Kloe,Boogaard
, p. 147 - 167 (2000)
The synthesis of [14C]-labelled glycidyl ethers and the corresponding glycerol ethers is described for the monofunctional compounds 1-dodecanol and ortho-cresol and the bifunctional compounds 4,4'-dihydroxy-3,3',5,5'-tetramethyl biphenyl and 1,6-hexanediol. The synthesis is based on reaction between the alcohol and [U-14C]-epichlorohydrin. The aromatic compounds have been converted to the corresponding glycidyl ethers by using sodium hydroxide and the aliphatic compounds by using tin(IV) chloride as a catalyst. Thus radio-labelled glycidyl ethers were obtained in yields between 50-80, with a chemical purity of > 92 and a radiochemical purity of > 95 by HPLC. The specific activities of the glycidyl ethers were approximately 0.2 mCi/mmol for the monofunctional compounds and approximately 0.4 mCi/mmol for the bifunctional compounds.
Dermal penetration and metabolism of five glycidyl ethers in human, rat and mouse skin
Boogaard,Denneman,Van Sittert
, p. 469 - 483 (2000)
1. Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests. 2. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine th apparent permeability constants, lag times and metabolic profiles. 3. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a 14C-label using [U-14C]-epichlorohydrin. 4. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 12GE 12GE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time. 7. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.
New acetylenic enol ethers of glycerol from the sponge petrosia sp
Seo, Youngwan,Cho, Ki Woong,Lee, Hyi-Seung,Rho, Jung-Rae,Shin, Jongheon
, p. 122 - 126 (1999)
Ten acetylenic enol ethers of glycerols, including six new compounds (1- 6) and a linear acetylenic alcohol (7), have been isolated from a sponge of the genus Petrosia. The structures of the novel compounds were elucidated by spectroscopic methods. The absolute stereochemistry of 1-7 was determined by chemical transformations and the Mosher method. Some of these compounds exhibited weak cytotoxicity against a human leukemia cell-line (K-562).
Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities
Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto
, p. 2544 - 2550 (2019/11/13)
Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.
Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids
Alam, Md. Maqusood,Hassan, Ahmed H.E.,Lee, Kun Won,Cho, Min Chang,Yang, Ji Seul,Song, Jiho,Min, Kyung Hoon,Hong, Jongki,Kim, Dong-Hyun,Lee, Yong Sup
, p. 51 - 62 (2018/11/27)
Two series of erlotinib-alkylphospholipid hybrids were prepared and evaluated for their antiproliferative activities against a panel of four cell lines representing lung, breast, liver and skin cancers using erlotinib and miltefosine as reference standards. Amide analogs elicited more enhanced cytotoxic activity than analogous esters. Amide derivatives 8d and 8e exhibited promising broad-spectrum antiproliferative activity and higher efficacy than reference erlotinib and miltefosine. Their cellular GI50 values was in the ranges of 24.7–46.9 μM and 26.8–43.1 μM for 8e and 8d respectively. Assay results of the inhibitory activity of the prepared compounds on EGFR kinase reaction and Akt phosphorylation in conjugation with statistical correlation analysis indicated that other mechanisms might contribute to their elicited cytotoxicities. In addition, statistical correlation analysis revealed that mechanisms of elicited cytotoxicities for amide series might be different from ester series. In addition, correlation analysis indicated variations in the mechanisms according to the types of cell line.
DETERGENT FOR SKIN OR HAIR
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, (2019/08/27)
PROBLEM TO BE SOLVED: To provide a skin detergent and a hair detergent having excellent foam quality, low skin irritation, and excellent stability at a low temperature. SOLUTION: A detergent for skin or hair contains a compound represented by general formula (1) (A), an anionic surfactant (B), and an ampholytic surfactant (C). R1OCH2CH-[O(AO)mH]-CH2O(AO)nH (1) [where R1 is a C4-18 monovalent hydrocarbon group; m+n AO independently represent an ethyleneoxy group or a propyleneoxy group; m and n independently represent an integer of 0 or greater; m+n is an integer of 1-50]. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
METHODS FOR PREPARING ALKYLGLYCERYL ETHERS
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Paragraph 0093; 0094, (2018/08/07)
The present invention relates to a method for manufacturing alkyl glyceryl ether by conducting reaction of alkyl glycidyl ether and water in the presence of a solvent and a catalyst to obtain alkyl glyceryl ether, wherein the solvent comprises glycol ethers, and the catalyst comprises an alkali metal salt of a carboxylic acid. The method of the present invention does not require use of chemicals other than the solvent and the catalyst, so that the production cost is low and cost-effective.COPYRIGHT KIPO 2018
STABILIZED NUCLEOTIDES FOR MEDICAL TREATMENT
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, (2016/02/12)
5′-Deuterated nucleosides and nucleotides and modifications thereof are provided for use in medical therapies, including as antiviral, anti-tumor and anti-neoplastic agents. In one embodiment, compounds, methods and uses are provided for the treatment of
METHOD FOR PREPARING GLYCEROL ETHER AND GLYCOL ETHER
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Paragraph 0074, (2015/03/28)
The present invention concerns a method for preparing glycerol ether or glycol ether comprising the reaction of a compound of formula (II) with a compound of formula (III) in the presence of a heterogeneous acid catalyst of formulas (II) and (III).
PROCESS FOR PREPARING A POLYOL ETHER
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Paragraph 0124, (2014/02/16)
The present invention relates to a process for preparing a polyol ether of formula (I), comprising a step of reductive alkylation involving a compound of general formula (II) and a compound of general formula (III): in which R1, R2, R3 and R4 are as defined in claim 1.
