Hydroxyethylacrylate appears as a clear colorless liquid. Less dense than water. Vapors heavier than air. Corrosive to tissue. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. Used to make plastics.
IDENTIFICATION AND USE: 2-Hydroxyethyl acrylate (HEA) is a liquid. HEA is used mainly either as a co-monomer in the manufacture of polymers or as a chemical reactant in the manufacture of chemical intermediates. In the manufacture of polymers, HEA can be co-polymerized with acrylic acid, acrylates, methacrylates, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, and the like. Co-reactants with HEA include aromatic and aliphatic isocyanates, anhydrides, and epoxides. The polymers and chemical intermediates made with HEA find applications in automotive top coatings, architectural coatings, photocure resins, and adhesives. Derivatives of HEA had been tested as experimental therapy. HUMAN STUDIES: Irritation of eyes and nose was observed at exposure concentrations of 3 ppm (nominal) and higher. The severity of irritation increased with concentration and could be tolerated for several minutes at 10 ppm. A summary of 15 years of experience of patch testing to (meth)acrylates presented the results in 440 patients with a history of exposures to (meth)acrylates. The most frequent positive test reactions were seen with 2-hydroxyethyl acrylate (9.6%). ANIMAL STUDIES: Undiluted HEA is severely irritating to the skin. Several studies have shown that undiluted HEA is severely irritating and can damage the eye. Inhalation data available for rats on HEA indicate that a 7 hour exposure of 264 ppm (1250 mg/cu m) had no lethal effect. Inhalation exposures to 333 to 394 ppm for 4 or 8 hours respectively caused irritation and were in the threshold area for lethality. At exposures at 500 ppm and above, close to 100% lethality was observed. The key study evaluating the acute dermal toxicity of HEA used rabbits and applied undiluted test material. Topical doses of 63, 130, 160, 200 or, 250 mg/kg bw were applied for 24 hours under a plastic occlusive bandage. Marked erythema and edema of the skin was seen in all treated animals and slight to moderate necrosis of the skin was observed in some animals. Clinical signs of toxicity were lethargy, decreased activity, loss of appetite and at 250 mg/kg bw only, rapid shallow breathing. The key study evaluating the acute oral toxicity of HEA administered as a 10% solution by gavage to groups of four rats at doses of 266.7, 400, 600, and 900 mg/kg bw. The animals were observed for 14 days post-dosing. The mortality was 0/4, 0/4, 3/4, and 4/4 at each dose level, respectively. Clinical signs included hypoactivity, rough fur, labored breathing, muscle weakness, GI tract hemorrhage in the animals that died. Neat material may burn the tissues of the mouth, throat and gastrointestinal tract. Positive responses have been reported in mice in the local lymph node assay indicating HEA dermal sensitization. There was no indication of significant chronic toxicity or a carcinogenic effect in either the 5 or 0.5 ppm treatment groups in rats in a chronic inhalation study (male and female were exposed to HEA 6 hours per day, 5 days/week for 18 months). HEA did not alter the histopathology of the testes or uterus in either dogs or rats (dogs up to 0.4% in the diet, rats up to 150 mg/kg bw/day). There were no treatment-related increases in the number of implants, embryo/fetal mortality, or fetal malformations observed in developmental study in rats. Neurotoxic potential of HEA appears to be minimal when tested in rats. HEA was not mutagenic in Salmonella typhimurium with or without metabolic activation. ECOTOXICITY STUDIES: Using the Warburg test, HEA was judged non-toxic to adapted sewage sludge.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
暴露途径
该物质可以通过吸入其蒸汽、通过皮肤接触以及摄入进入人体。
The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
2-hydroxyethyl acrylate (HEA) has been evaluated in a study that examined metabolism and excretion in male Fischer 344 rat using oral, intraperitoneal, dermal and inhalation routes of exposure ... For the oral and intraperitoneal routes of exposure the rats (four animals/dose level/route of exposure) received a single dose of (14)C-HEA at 2.5 or 50 mg/kg bw. For the inhalation exposure, six rats were exposed to a target concentration of 8 ppm (14)C-HEA for six hours in a head only inhalation chamber. For the dermal exposure, four rats were treated with (14)C-HEA at a dose of 50 mg/kg. No qualitative differences in urinary metabolites between routes were observed, indicating no marked route-dependent differences in the metabolic fate of HEA. The results of the study indicate that once the chemical becomes systemically available it is rapidly metabolized and eliminated from the body as either CO2 in the expired air or urinary metabolites with approximately equal percentage of administered/exposed dose eliminated by each route. The half-lives of elimination of radioactivity were approximately 14 hours for urine and 17 hours for CO2. The halflife of elimination of radioactivity from plasma was approximately 26 hours although the label was not associated with parent HEA. The available metabolic data on HEA is consistent with information on studies with other acrylates where hydrolysis of the ester functionality is the primary metabolic pathway. By analogy with ethyl acrylate and acrylic acid, it is expected that a minor metabolic pathway for HEA will be via conjugation with glutathione with the resulting mercapturic acid derivatives being excreted in the urine.
The metabolism and excretion of HEA has been examined in male Fischer 344 rat using oral, intraperitoneal, dermal and inhalation routes of exposure ... For the oral and intraperitoneal routes of exposure the rats (4 animals/dose level/route of exposure) received a single dose of 2.5 or 50 mg/kg bw (approx 15-20 uCi). For the inhalation exposure six rats were exposed to a target concentration of 8 ppm (14)C HEA for 6 hours in a head only inhalation chamber. For the dermal exposure 4 rats were treated with (14)C HEA at a dose of 12.5 mg/kg bw. No qualitative differences in urinary metabolites between routes were observed, indicating no marked route-dependent differences in the metabolic fate of HEA. The results of the study indicate that once the chemical becomes systemically available it is rapidly metabolized and eliminated from the body as either CO2 in the expired air or urinary metabolites. The available metabolic data on HEA is consistent with information on substances with other acrylates where hydrolysis of the ester functionality is the primary metabolic pathway. By analogy with ethyl acrylate and acrylic acid it is expected that a minor metabolic pathway for HEA will be via conjugation with glutathione with the resulting mercapturic acid derivatives being excreted in the urine. For the oral and intraperitoneal routes (2.5 mg/kg bw) 35-36% of the administered dose was expired as (14)CO2 and 43-47% of the dose excreted via the urine by 48 hours post-dosing. At 50 mg/kg bw 40-45% of the dose was expired as (14)CO2 and 33-36% of the dose was excreted in the urine. Following dermal administration 66% of the dose was absorbed within 48 hours of the application with remaining 33% being associated with the application site. Of the absorbed dose 27% was excreted in the urine as metabolites of HEA and 27% was excreted in the expired air as (14)CO2. For inhalation 39% of the absorbed dose was eliminated in the urine by 48 hr and 41% was expired as (14)CO2. For all routes, 9-16% was found in the tissues and carcass and less than 3% in the feces.
Following oral administration of (14)C-HEA to Fisher 344 male rats, between 91 and 95% of the administered radioactivity was recovered in the urine, CO2, feces, tissues and carcass, volatile organics and final cage wash. At the low dose of 2.5 mg (14)C-HEA/kg body weight, for the oral route of administration, approximately 43-47 % of the dose was eliminated in the urine, the primary elimination route, whereas 35-36% of the dose was expired as (14)CO2, and the tissues and carcass accounted for between 9-13 % of the dose. Less than 1.5% of the administered dose of radioactivity was recovered in the feces and less than 1% was found in the final cage wash. Less than 0.2% of the dose was recovered as volatile organics in the expired air. At the higher dose of 50 mg/kg (14)C-HEA/kg body weight, for the oral route of administration, 33-36% of the dose was eliminated in the urine, whereas 40-45% of the dose was expired as (14)CO2. At this higher dose there was a shift from the urinary pathway as the primary route of elimination to the exhalation of (14)CO2 as the primary route of elimination. As with the 2.5 mg/kg dose, the tissues and carcass accounted for 10-13% of the dose and less than 0.6% of the recovered radioactivity was in the final cage wash, less than 0.1% was recovered as volatile organics in the expired air and less than 2.5% of the dose was recovered in the feces. Following the oral route of administration, 0.3-1.5% of the dose was expired as (14)CO2 as early as 15 minutes post-dosing. The peak of CO2 excretion occurred during or before the 4-8 hr collection interval. By 12 hr post-dosing with 2.5 mg/kg for the oral route of administration, 31-32 of the dose was expired as (14)CO2. For this same collection interval following 50 mg/kg oral administration, 41 of the dose was expired as (14)CO2. The exhalation of (14)CO2 derived from (14)C-HEA appeared to follow first-order kinetics as a biphasic process, except following dermal administration. Following oral administration, greater than 92% of the total radioactivity excreted via the urine was excreted during the first 12 hr collection interval.
1.周国泰,化学危险品安全技术全书,化学工业出版社,1997 2.国家环保局有毒化学品管理办公室、北京化工研究院合编,化学品毒性法规环境数据手册,中国环境科学出版社.1992 3.Canadian Centre for Occupational Health and Safety,CHEMINFO Database.1998 4.Canadian Centre for Occupational Health and Safety, RTECS Database, 1989
Synthesis of Well-Defined Y-Shaped Zwitterionic Block Copolymers via Atom-Transfer Radical Polymerization
摘要:
A series of well-defined Y-shaped (AB(2)-type) zwitterionic block copolymers were synthesized by atom-transfer radical polymerization (ATRP). First, a bishydroxy-functional ATRP initiator was synthesized by esterification of 2-hydroxyethyl acrylate with 2-bromoisobutyryl bromide, followed by Michael addition using excess diethanolamine. 2-(Diethylamino)ethyl methacrylate (DEA) was polymerized via ATRP using this bishydroxy-functional initiator. The bromine end groups of PDEA were then quantitatively removed by radical chain transfer using excess N,N,N',N",N"-pentamethyldiethylenetri-amine (PMDETA). Esterification of the omega-bishydroxyl end groups using excess 2-bromoisobutyryl bromide afforded a PDEA-based omega-bifunctional macroinitiator [PDEA-(Br)(2)]. A series of Y-shaped zwitterionic PDEA-(PSEMA)(2) [PSEMA poly(succinyloxyethyl methacrylate)] block copolymers were synthesized via ATRP of 2-hydroxyethyl methacrylate (HEMA) using this PDEA-(Br)(2) macroinitiator, followed by reacting the HEMA hydroxyl groups with succinic anhydride. The 'schizophrenic' micellization character of these Y-shaped zwitterionic block copolymers in aqueous solution was confirmed by H-1 NMR spectroscopy, aqueous electrophoresis, and dynamic light-scattering studies.
Adamantyl Antiestrogens with Novel Side Chains Reveal a Spectrum of Activities in Suppressing Estrogen Receptor Mediated Activities in Breast Cancer Cells
作者:Jian Min、Valeria Sanabria Guillen、Abhishek Sharma、Yuechao Zhao、Yvonne Ziegler、Ping Gong、Christopher G. Mayne、Sathish Srinivasan、Sung Hoon Kim、Kathryn E. Carlson、Kendall W. Nettles、Benita S. Katzenellenbogen、John A. Katzenellenbogen
DOI:10.1021/acs.jmedchem.7b00585
日期:2017.7.27
To search for new antiestrogens more effective in treating breast cancers, we explored alternatives to the acrylic acid side chain used in many antiestrogens. To facilitate our search, we used a simple adamantyl ligand core that by avoiding stereochemical issues enabled rapid synthesis of acrylate ketone, ester, and amide analogs. All compounds were high affinity estrogen receptorα (ERα) ligands but
ASYMMETRIC BIFUNCTIONAL SILYL MONOMERS AND PARTICLES THEREOF AS PRODRUGS AND DELIVERY VEHICLES FOR PHARMACEUTICAL, CHEMICAL AND BIOLOGICAL AGENTS
申请人:The University of North Carolina at Chapel Hill
公开号:US20170021030A1
公开(公告)日:2017-01-26
Asymmetric bifunctional silyl (ABS) monomers comprising covalently linked pharmaceutical, chemical and biological agents are described. These agents can also be covalently bound via the silyl group to delivery vehicles for delivering the agents to desired targets or areas. Also described are delivery vehicles which contain ABS monomers comprising covalently linked agents and to vehicles that are covalently linked to the ABS monomers. The silyl modifications described herein can modify properties of the agents and vehicles, thereby providing desired solubility, stability, hydrophobicity and targeting.
ArNMeCH(SiMe<sub>3</sub>)<sub>2</sub>: a useful precursor of formal α-aminoalkyl diradicals in visible-light-mediated homo- and hetero-diaddition with alkenes
作者:Shunfa Liu、Yufan Yang、Lu Gao、Zhenlei Song
DOI:10.1039/d0cc02277b
日期:——
ArNMeCH(SiMe3)2 has been developed as a useful precursor of a formal α-aminoalkyl diradical in Ru(bpy)3Cl2-catalzyed addition with alkenes under visible-light-mediated photoredox conditions. This approach leads to homo-diaddition with two identical alkenes in one-pot, or hetero-diaddition with two different alkenes via a sequential operation.