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(E,E,E)-glyceryl trioleate

中文名称
——
中文别名
——
英文名称
(E,E,E)-glyceryl trioleate
英文别名
Glycerine trioleate;[2-[(Z)-octadec-9-enoyl]oxy-3-[(E)-octadec-9-enoyl]oxypropyl] (E)-octadec-9-enoate
(E,E,E)-glyceryl trioleate化学式
CAS
——
化学式
C57H104O6
mdl
——
分子量
885.449
InChiKey
PHYFQTYBJUILEZ-BSCDBXJPSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    22.4
  • 重原子数:
    63
  • 可旋转键数:
    53
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.84
  • 拓扑面积:
    78.9
  • 氢给体数:
    0
  • 氢受体数:
    6

ADMET

代谢
/Triolein/ 通过 ICR 小鼠血浆中的肝三酰甘油脂肪酶的水解作用已在体外得到证实。
Hydrolysis of /Triolein/ by hepatic triacylglycerol lipase in plasma from ICR mice has been demonstrated in vitro.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在大鼠肝脏和大鼠后肢的离体灌注下,研究了三油酸甘油酯的体外代谢。这允许研究两者之间的脂质转移。在没有添加三油酸甘油酯的情况下,当测量组织床之间的游离脂肪酸梯度时,两种组织床都显示出游离脂肪酸的净移除。在系统中任一储液器中加入100毫克三油酸甘油酯(作为[(3)H]-甘油-[(14)C]三油酸甘油酯)后,30分钟内后肢梯度中游离脂肪酸的净产生量显著。这种后肢游离脂肪酸的外流量占三油酸甘油酯分解代谢的三分之一以上。
The metabolism of triolein in vitro was evaluated using isolated perfusion of a rat liver in tandem with an isolated rat hind-end. This permitted the study of lipid transfer between the two. In the absence of added triolein, a net removal of free fatty acids was demonstrated in both tissue beds when fatty acid gradients across tissue beds were measured. Following the addition of 100 mg of triolein (as [(3)H]-glycerol-[(14)C]triolein) to either reservoir in the system, an appreciable net production of free fatty acid was noted for the hind-end gradient at 30 minutes. This hind-end free fatty acid efflux amounted to more than one third of the catabolism of triolein.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在实验研究中,通过向大脑半球注入三油酸甘油酯乳剂进行栓塞,揭示了在亚急性阶段可逆的磁共振成像(MRI)发现。本研究旨在通过质子磁共振波谱(MRS)调查三油酸甘油酯乳剂诱导的大脑脂肪栓塞中主要代谢物的变化。19只猫的颈内动脉被注入三油酸甘油酯乳剂,并在30分钟后、1天后和7天后进行多体素MRS。对照组中,6只猫被注入生理盐水。MR光谱被评估以确定N-乙酰天门冬氨酸(NAA)、肌酸(Cr)和胆碱(Cho),以及脂质和乳酸的存在。NAA/Cr、Cho/Cr、NAA/Cho和脂质/Cr比值的半定量分析比较了栓塞组同侧代谢物比值的中位数与对侧和对照组在每个时间点的比值。栓塞组30分钟后、1天后和7天同侧大脑半球的NAA/Cr、Cho/Cr和NAA/Cho比值与栓塞组和对照组对侧大脑半球相比,没有显著差异(P>0.05)。栓塞组同侧大脑半球的脂质/Cr比值与对照组相比显著升高(30分钟时P=0.012,第1天时P=0.001,第7天时P=0.018)。由三油酸甘油酯乳剂诱导的大脑脂肪栓塞在急性阶段没有引起主要代谢物的显著变化,除了升高的脂质/Cr比值,这表明使用脂肪乳剂栓塞的损伤中没有显著的缺氧-缺血变化。
In experimental studies, embolization of the cerebral hemisphere with triolein emulsion has revealed reversible magnetic resonance imaging (MRI) findings in the subacute stage. /The aim of this study was/ to investigate the changes in the major metabolites, by proton magnetic resonance spectroscopy (MRS), in a cerebral fat embolism induced by a triolein emulsion.The internal carotid arteries of 19 cats were injected with a triolein emulsion, and multivoxel MRS was performed 30 min, 1 day, and 7 days later. In the control group, six cats were injected with normal saline. The MR spectra were evaluated for N-acetyl aspartate (NAA), creatine (Cr), and choline (Cho), along with the presence of lipid and lactate. Semiquantitative analyses of NAA/Cr, Cho/Cr, NAA/Cho, and lipid/Cr ratios compared the median values of the ipsilateral metabolite ratios with those of the contralateral side and in the control group for each point in time.The NAA/Cr, Cho/Cr, and NAA/Cho ratios in the ipsilateral cerebral hemisphere of the embolized group after 30 min, 1 day, and 7days were not significantly different from the contralateral hemisphere of the embolized and control groups (P>0.05). The lipid/Cr ratio in the ipsilateral cerebral hemisphere of the embolized group was significantly higher when compared with the control group (P=0.012 at 30 min, P=0.001 on day 1, and P=0.018 on day 7). Cerebral fat embolism induced by a triolein emulsion resulted in no significant change in the major metabolites of the brain in the acute stage, except for an elevated lipid/Cr ratio, which suggests the absence of any significant hypoxic-ischemic changes in the lesions embolized using a fat emulsion.
来源:Hazardous Substances Data Bank (HSDB)
代谢
人参叶中分离的原人参二醇(PDG)和原人参三醇(PTG)类型的人参皂苷对猪胰腺脂肪酶活性的影响在体外进行了测定。PDG以剂量依赖性方式抑制胰腺脂肪酶活性,浓度范围为0.25-1 mg/mL。在大约1 mg/mL的PDG浓度下,它抑制了大约83.2%的甘油三酯的水解。然而,PTG没有显示出抑制活性。因此,在喂食高脂肪饮食的小鼠中评估了PDG的抗肥胖活性。结果表明,PDG在预防和高脂肪饮食小鼠的肥胖、脂肪肝和高甘油三酯血症的治疗中是有效的。
Effects of protopanaxdiol (PDG) and protopanaxatriol (PTG) types of ginsenosides isolated from the leaves of American ginseng on porcine pancreatic lipase activity were determined in vitro. PDG inhibited the pancreatic lipase activity in a dose-dependent manner at the concentrations of 0.25-1 mg/mL. It inhibited hydrolysis of about 83.2% of triolein at about 1 mg/mL of PDG. However, PTG showed no inhibitory activity. Therefore, anti-obesity activity of PDG was evaluated in mice fed a high-fat diet. The results demonstrated that PDG was effective in preventing and healing obesity, fatty liver and hypertriglyceridemia in mice fed with a high-fat diet.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
盐酸四环素250毫克/千克通过静脉注射给予大鼠,显著降低了经胃内给药的甘油三油酸酯的肠道吸收。
IM administration of tetracycline hydrochloride 250 mg/kg /to rats/ significantly decreased the intestinal absorption of intragastrically administration triolein.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
口服每千克2克新霉素,每日两次,在大鼠体内减少了(14)C标记的三油酸的肠道吸收。
The oral administration of 2 g neomycin/kg, twice daily, reduced in rats the in vivo intestinal absorption of (14)C-labeled triolein.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
本研究旨在评估地塞米松对三油酸甘油酯乳剂引起的受损血眼屏障的影响,使用对比增强MR成像。将0.1毫升三油酸甘油酯与20毫升盐水混合的乳剂注入32只猫的颈动脉,其中12只猫被分配到治疗组,18只猫被分配到对照组。注入三油酸甘油酯乳剂后30分钟,获取一组眼眶前后对比的T1加权MR图像(T1WIs)。将10毫克/千克的地塞米松注入治疗组每只猫的同侧颈动脉,对照组的每只猫注入20毫升盐水。在注入三油酸甘油酯乳剂后三小时,获取第二组眼眶前后对比的T1WIs。对前房(AC)、后房(PC)和同侧及对侧眼玻璃体进行定性分析。在第一组和第二组T1WIs上的三个眼室内,定量评估同侧眼与对侧眼的信号强度比,并进行统计学比较。定性分析显示,AC、PC或玻璃体在第一组和第二组对比后T1WIs上没有立即显示出对比增强。然而,AC和PC在第二组对比前T1WIs上显示出延迟对比增强,两组猫均如此。玻璃体几乎没有增强或仅有最小程度的延迟增强。定量分析显示,治疗组猫的PC信号强度比在第二组T1WIs上显著低于对照组猫(p = 0.037)。AC和玻璃体在治疗组和对照组之间没有显示出统计学上的显著差异(p > 0.05)。对比增强MR图像揭示了在注入三油酸甘油酯乳剂后眼PC中血管通透性的增加。地塞米松似乎减少了PC中血房水的屏障破坏。
The purpose of this study is to evaluate the effect of dexamethasone on the damaged blood-ocular barrier caused by triolein emulsion, using contrast-enhanced MR imaging. An emulsion of 0.1-mL triolein in 20 mL of saline was infused into the carotid arteries of 32 cats, 12 cats were placed in the treatment group and 18 cats were placed in the Control group. Thirty minutes after the infusion of triolein emulsion, a set of orbital pre- and post-contrast T1-weighted MR images (T1WIs) were obtained. Infusion of 10 mg/kg dexamethasone into the ipsilateral carotid artery of each of the cats in the treatment group cats and 20 mL saline in each of the cats in the control group was given. A second set of pre- and post-contrast orbital T1WIs were obtained three hours following triolein emulsion infusion. Qualitative analysis was performed for the the anterior chamber (AC), the posterior chamber (PC), and in the vitreous humor of the ipsilateral and contralateral eyes. The signal intensity ratios of the ipsilateral eye over the contralateral eye were quantitatively evaluated in the three ocular chambers on the first and second set of T1WIs, and were then statistically compared. Qualitatively, the AC, the PC or the vitreous did not show immediate contrast enhancement on the first and the second set of post-contrast T1WIs. However, the AC and the PC showed delayed contrast enhancement for both groups of cats on the second pre-contrast T1WIs. No enhancement or minimally delayed enhancement was seen for the vitreous humor. Quantitatively, the signal intensity ratios in the PC of the treatment group of cats were statistically lower than the ratios of the control group of cats for the second set of T1WIs (p = 0.037). The AC and vitreous showed no statistically significant difference between the feline treatment group and control group (p > 0.05). Contrast-enhanced MR images revealed increased vascular permeability in the PC of the eye after infusion of triolein emulsion. Dexamethasone seems to decrease the breakdown of the blood-aqueous barrier in the PC.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
脂肪栓塞(FE)是骨骼创伤和一些骨科手术中经常被忽视且理解不足的并发症。脂肪栓塞可能导致与脂肪栓塞综合症(FES)相关的主要肺损伤。本研究使用未麻醉大鼠的脂肪栓塞模型,通过静脉注射中性脂肪三油酸甘油酯,来研究改变内源性血管紧张素(Ang)II的产生或对其反应对肺组织病理学潜在治疗效应。在通过三油酸甘油酯注射引起脂肪栓塞后1小时,分别注射了卡托普利(一种Ang I转化酶抑制剂)或洛萨坦(一种Ang II型1受体阻滞剂)。在48小时后安乐死,通过组织病理学评估比较了接受药物处理的动物与对照组动物(仅接受三油酸甘油酯的动物)。仅接受三油酸甘油酯的大鼠肺组织的组织学显示严重的弥漫性病理变化。肺泡间隔出现严重的弥漫性炎症。支气管腔内显示严重的粘膜上皮细胞丢失。肺小动脉和微动脉的血管中层增厚,管腔通畅性减少了60%到70%。三色染色确认了血管中层和血管外膜中胶原的丰富存在,以及胶原渗透到支气管肌肉中。卡托普利和洛萨坦治疗均减少了48小时时存在的炎症、血管收缩和促纤维化效应(p<0.001)。治疗后,血管腔保持通畅,脂肪滴的大小和数量减少。白细胞、巨噬细胞、肌成纤维细胞和嗜酸性粒细胞的浸润数量减少,出血和胶原沉积也显著减少(p<0.001)。支气管上皮的病理变化也减轻了。结果表明,使用作用于肾素-Ang系统的药物可能为脂肪栓塞综合症提供一种有效且针对性的治疗。
Fat embolization (FE) is an often overlooked and poorly understood complication of skeletal trauma and some orthopedic procedures. Fat embolism can lead to major pulmonary damage associated with fat embolism syndrome (FES). A model of FE in unanesthetized rats, using intravenous injection of the neutral fat triolein, was used to study the potential therapeutic effect on lung histopathology of altering the production of, or response to, endogenous angiotensin (Ang) II. Either captopril, an Ang I converting enzyme inhibitor, or losartan, an Ang II type 1 receptor blocker, was injected 1 hour after FE by triolein injection. After euthanasia at 48 hours, histopathologic evaluation was used to compare the drug-treated animals with control animals that received only triolein. Histology of the lungs of rats treated only with triolein revealed severe, diffuse pathology. Alveolar septa showed severe, diffuse inflammation. Bronchial lumina showed severe mucosal epithelial loss. The media of the pulmonary small arteries and arterioles was thicker, and the lumen patency was reduced 60% to 70%. Trichrome staining confirmed the abundant presence of collagen in the media and adventitia, as well as collagen infiltrating the bronchial musculature. Both captopril and losartan treatments reduced the inflammatory, vasoconstrictor, and profibrotic effects present at 48 hr (p<0.001). With treatment, the vascular lumen remained patent, and the fat droplets were reduced in size and number. There was a reduction in the number of infiltrating leukocytes, macrophages, myofibroblasts, and eosinophils, along with a significant decrease in hemorrhage and collagen deposition (p<0.001). Pathologic changes in bronchial epithelium were also diminished. The results suggest that the use of drugs that act on the renin-Ang system might provide an effective and targeted therapy for fat embolism syndrome.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 立即急救:确保已经进行了充分的中和。如果患者停止呼吸,请开始人工呼吸,最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩,按训练操作。如有必要,执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐,让患者向前倾或将其置于左侧(如果可能的话,头部向下),以保持呼吸道畅通,防止吸入。保持患者安静,维持正常体温。寻求医疗帮助。 /毒物A和B/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在小肠中,大多数甘油三酯被分解成单甘油、游离脂肪酸和甘油,它们被肠粘膜吸收。在上皮细胞内,重新合成的甘油三酯与胆固醇和磷脂一起聚集成小球,并被包裹在蛋白质外衣中形成乳糜微粒。乳糜微粒通过淋巴管运输到胸导管,最终进入静脉系统。乳糜微粒在通过脂肪组织的毛细血管时从血液中被移除。脂肪储存在脂肪细胞中,直到被运输到其他组织作为游离脂肪酸,用于细胞能量或并入细胞膜中。
In the small intestine, most triglycerides are split into monoglycerides, free fatty acids, and glycerol, which are absorbed by the intestinal mucosa. Within the epithelial cells, resynthesized triglycerides collect into globules along with cholesterol and phospholipids and are encased in a protein coat as chylomicrons. Chylomicrons are transported in the lymph to the thoracic duct and eventually to the venous system. The chylomicrons are removed from the blood as they pass through the capillaries of adipose tissue. Fat is stored in adipose cells until it is transported to other tissues as free fatty acids which are used for cellular energy or incorporated into cell membranes.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
当给予静脉注射14C标记的长链甘油三酯时,30到60分钟内约25%至30%的放射性标记可以在肝脏中找到,24小时后剩余的不到5%。脾脏和肺部可发现较少量的放射性标记。24小时后,近50%的放射性标记以二氧化碳的形式排出,1%的碳标记仍然存在于棕色脂肪中。精索脂肪中的放射性浓度不到棕色脂肪的一半。
When (14)C-labeled long-chain triglycerides are administered intravenously, 25% to 30% of the radiolabel is found in the liver within 30 to 60 minutes, with less than 5% remaining after 24 hours. Lesser amounts of radiolabel are found in the spleen and lungs. After 24 hours, nearly 50% of the radiolabel has been expired in carbon dioxide, with 1% of the carbon label remaining in the brown fat. The concentration of radioactivity in the epididymal fat is less than half that of the brown fat.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
大鼠通过胃管喂食了一种由95份三油酸甘油酯(甘油三油酸酯)和5份甘油1-(14)C-三油酸酯组成的乳液饮食。24小时内,在淋巴中检测到的甘油1-(14)C-三油酸酯的百分比是88%。在之前的一项研究中,四只体重为250克的雄性大鼠口服了[1-(14)C]三油酸酯。24小时内吸收的放射性活性百分比从57%到92%不等(平均=78.2%)。在胸导管淋巴脂肪中回收的吸收活性的百分比从51%到83%不等(平均=65.5%)。
Rats were fed an emulsion diet (via stomach tube) consisting of 95 parts triolein (Glycerol Trioleate) and 5 parts glycerol 1- (14)C-trioleate. The percentage of administered glycerol 1- (14)C-trioleate that was identified in the lymph in 24 hours was 88%. In an earlier study four male rats (weights 250 g) were dosed orally with [1-(14)C]triolein. The percentage of radioactivity that was absorbed in 24 hours ranged from 57% to 92% (mean =78.2%). The percentage of absorbed activity that was recovered in the lymph fat from the thoracic duct ranged from 51% to 83% (mean =65.5%).
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在禁食大鼠中,通过静脉注射单剂量的[1- (14)C]三油酸甘油酯后,在第一小时内,以下器官中观察到高吸收率:肝脏、心肌、胃粘膜和膈肌。然而,24小时后,这些组织中的放射性活性显著降低。在小鼠中也观察到了类似的分布模式;但是,即使在24小时后,棕色脂肪、白色脂肪组织和脾脏中也发现了大量的放射性活性。
After a single dose of [1- (14)C]triolein was administered intravenously into fasted rats, a high rate of uptake was noted within the first hour in the following organs: liver, myocardium, gastric mucosa, and diaphragm. However, after 24 hours, radioactivity in these tissues had decreased markedly. A similar pattern of distribution was noted in mice; however, large amounts of radioactivity were also noted in the brown fat, white adipose tissue, and spleen, even after 24 hours.
来源:Hazardous Substances Data Bank (HSDB)

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    参考文献:
    名称:
    EOE和EEO,含有松香油酸和脂肪酸油的三酰基甘油的合成和物理性质
    摘要:
    AbstractSymmetrical and non‐symmetrical triacylglycerols (TAG) containing oleic (O; 9c‐18:1) and elaidic (E; 9t‐18:1) acids were required as part of a study relating the physical characteristics and functionality of trans‐containing TAG with the mouth feel, taste characteristics and related characteristics desired by consumers in frying oils and pastries. To replace the trans isomers in frying oils—a significant part of frying oils prepared by partial hydrogenation of vegetable oils—without loss of the sensory properties desired by consumers, required the initiation of a study relating the structure of trans‐containing TAG with such characteristics as melting range, drop points, and other crystalline properties. Elaidic acid was esterified to trielaidin (EEE), and the EEE partially converted (glycerol/p‐toluenesulfonic acid) to a mixture containing ca. 40% DAG (the 1,3‐ and 1,2‐isomers). The DAG fraction was separated by silica gel chromatography, the 1,3‐dielaidylglycerol (1,3EE‐DAG) isomer isolated (structural purity >99%) by crystallization from acetone and esterified with oleic acid (O) to yield EOE. The 1(3)O‐MAG was purchased commercially and esterified with E acid to prepare OEE. Both syntheses yielded multi‐gram quantities of EOE and EEO, in 80–85% yields, and with structural purities >99%. Thus, by careful selection of the thermodynamically more‐stable MAG or DAG precursors, the symmetrical EOE and non‐symmetrical EEO isomers could be readily synthesized, and their drop point and melting point values determined.
    DOI:
    10.1007/s11746-007-1056-2
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文献信息

  • Model studies and the ADMET polymerization of soybean oil
    作者:Qingping Tian、Richard C. Larock
    DOI:10.1007/s11746-002-0509-3
    日期:2002.5
    AbstractGrubbs' ruthenium catalyst 2 has been employed in model studies of the acyclic diene metathesis (ADMET) polymerization of soybean oil. In the presence of 0.1 mol% of catalyst 2, the ADMET polymerization of ethylene glycol dioleate afforded the isomerized (E)‐dioleate (27%), dimer (18%), trimer (13%), tetramer (7%), pentamer (5%), hexamer (4%), heptamer (4%), and 9‐octadecene (21%). Only a trace of any intramolecular cyclized product was formed. Under the same conditions, glycerol trioleate underwent ADMET polymerization to produce dimer, trimer, tetramer, pentamer, and monocyclic oligomers, with monocyclic oligomers predominating. The high number of repeat units in the monocyclic oligomers (n≅6, 10, and 21) in dicates that cross‐linking occurs readily in this process. Based on our model system studies, we have examined the ADMET polymerization of soybean oil and succeeded in producing polymeric materials ranging from sticky oils to rubbers.
  • Synthesis and Physical Properties of EOE and EEO, Triacylglycerols Containing Elaidic and Oleic Fatty Acids
    作者:R. O. Adlof、G. R. List
    DOI:10.1007/s11746-007-1056-2
    日期:2007.5.10
    AbstractSymmetrical and non‐symmetrical triacylglycerols (TAG) containing oleic (O; 9c‐18:1) and elaidic (E; 9t‐18:1) acids were required as part of a study relating the physical characteristics and functionality of trans‐containing TAG with the mouth feel, taste characteristics and related characteristics desired by consumers in frying oils and pastries. To replace the trans isomers in frying oils—a significant part of frying oils prepared by partial hydrogenation of vegetable oils—without loss of the sensory properties desired by consumers, required the initiation of a study relating the structure of trans‐containing TAG with such characteristics as melting range, drop points, and other crystalline properties. Elaidic acid was esterified to trielaidin (EEE), and the EEE partially converted (glycerol/p‐toluenesulfonic acid) to a mixture containing ca. 40% DAG (the 1,3‐ and 1,2‐isomers). The DAG fraction was separated by silica gel chromatography, the 1,3‐dielaidylglycerol (1,3EE‐DAG) isomer isolated (structural purity >99%) by crystallization from acetone and esterified with oleic acid (O) to yield EOE. The 1(3)O‐MAG was purchased commercially and esterified with E acid to prepare OEE. Both syntheses yielded multi‐gram quantities of EOE and EEO, in 80–85% yields, and with structural purities >99%. Thus, by careful selection of the thermodynamically more‐stable MAG or DAG precursors, the symmetrical EOE and non‐symmetrical EEO isomers could be readily synthesized, and their drop point and melting point values determined.
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