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1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine | 6931-84-6

中文名称
——
中文别名
——
英文名称
1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine
英文别名
1-palmitoyl-2-lineloylglycerophosphatidylcholine;1-palmitoyl-2-lineleoylphosphatidylcholine;1-palmitoyl-2-linoleoylphosphatidylcholine;1-palmitoyl-2-linoleoyl-phosphatidyl choline;[3-hexadecanoyloxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine化学式
CAS
6931-84-6
化学式
C42H80NO8P
mdl
——
分子量
758.073
InChiKey
JLPULHDHAOZNQI-AKMCNLDWSA-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

物化性质

  • 物理描述:
    DryPowder; Liquid
  • 颜色/状态:
    Color is nearly white when freshly made, but rapidly becomes yellow to brown in air
  • 气味:
    Odorless or slight nutlike odor; faint fatty odor
  • 味道:
    Bland
  • 熔点:
    236-237 °C
  • 溶解度:
    Insoluble in water
  • 密度:
    1.0305 at 24 °C/4 °C
  • 稳定性/保质期:
    Stable under recommended storage conditions.

计算性质

  • 辛醇/水分配系数(LogP):
    12.9
  • 重原子数:
    52
  • 可旋转键数:
    40
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.86
  • 拓扑面积:
    111
  • 氢给体数:
    0
  • 氢受体数:
    8

ADMET

毒理性
  • 毒性总结
鉴別和使用:当酸值约为20时,磷脂形成蜡状物质;当酸值为30左右时,为可倾倒的浓稠流体。它是一种可食用且可消化的天然来源的表面活性剂和乳化剂。用于人造黄油、巧克力和食品工业一般用途。此外,还用于药品和化妆品。它还有许多其他工业用途,包括处理皮革和纺织品。它还用作实验性药物。人类暴露和毒性:在临床刺激研究中,含有0.3%或3%磷脂65%(65%磷脂溶液)、含有0.83%磷脂粉的肥皂(在0.5%下测试)和磷脂脂质体的化妆品配方通常不会引起刺激。最严重的反应是几乎感觉不到的红斑。氢化磷脂也不是刺激物,且氢化磷脂(在凡士林中占15%)不是致敏剂。此外,含有3%磷脂65%的晒黑油、含有0.1%磷脂65%的睫毛膏和含有0.3%磷脂65%的粉底均不会引起过敏。以每天22至83克的剂量给人类受试者服用磷脂,持续两到四个月以改善工作能力,并未伴随任何不良反应。然而,被大豆蛋白污染并用作药物辅料的磷脂可能对大豆过敏的患者引起反应。含有0.3%磷脂65%(65%磷脂溶液)的粉底在人类受试者中不是光敏剂。动物研究:在单次封闭贴片试验(兔子)中,磷脂65%(65%磷脂溶液)的刺激性最小,含有3%磷脂65%的产品几乎不至轻度刺激,含有2.25%磷脂65%的产品对兔子的皮肤无刺激性。在一项豚鼠浸泡研究中,含有0.83%磷脂粉的肥皂0.5%的刺激性几乎可以忽略不计。磷脂65%(65%磷脂溶液)和含有2.25%或3.0%磷脂65%的产品对未冲洗的兔眼无至最小刺激性。含有0.83%磷脂粉的肥皂(在25%下测试)在德雷兹试验中刺激性中等,含有磷脂的脂质体几乎不刺激。将小鼠暴露于气溶胶化的磷脂4小时/天,持续2天后,肺出现局部内皮细胞肿胀和间质性水肿。一组小鼠被喂食含有糖的磷脂5至10毫克(以提高适口性),第二组被喂食磷脂(5至10毫克)和胆固醇(4至5毫克)。小鼠被繁殖,其后代按照相同的程序给药;给药持续到所有小鼠垂死或死亡。一个对照组随意喂食实验室饲料。分别喂食磷脂、磷脂和胆固醇或对照饲料的小鼠总数为166、212和360。动物被杀死并进行了脑剖检。在检查的73只喂食磷脂的动物中,有18只发现了脑神经细胞肿瘤,而在检查的88只喂食磷脂和胆固醇的动物中,有27只发现了脑神经细胞肿瘤,而在188只对照组动物中没有发现脑神经细胞肿瘤。
IDENTIFICATION AND USE: Lecithins forms a waxy mass when the acid value is about 20; pourable, thick fluid when the acid value is around 30. It is an edible and digestible surfactant and emulsifier of natural origin. Used in margarine, chocolate and in the food industry in general. In addition, it is used in pharmaceuticals and cosmetics. It has many other industrial uses, including treating leather and textiles. It is also used as experimental medication. HUMAN EXPOSURE AND TOXICITY: In clinical irritation studies, cosmetic formulations containing 0.3% or 3% lecithin 65% (solution of 65% lecithin), a soap containing 0.83% lecithin powder (tested at 0.5%), and lecithin liposomes were generally non-irritating. Barely perceptible erythema was the most severe reaction observed. Hydrogenated lecithin also was not an irritant, and hydrogenated lecithin (15% in petrolatum) was not a sensitizer. Additionally, a tanning oil containing 3% lecithin 65%, a mascara containing 0.1% lecithin 65%, and a foundation containing 0.3% lecithin 65% were non-sensitizing. Administration to human subjects of lecithin in daily doses varying from 22 to 83 g for two to four months to improve working capacity was not accompanied by any untoward reactions. However, lecithin contaminated by soy proteins and used as an excipient in drugs can cause reactions in patients with soy allergy. A foundation containing 0.3% lecithin 65% (solution of 65% lecithin) was not a photosensitizer in human subjects. ANIMAL STUDIES: In single-insult occlusive patch tests (rabbits), lecithin 65% (solution of 65% lecithin) was minimally irritating, products containing 3% lecithin 65% were practically non- to mildly irritating, and a product containing 2.25% lecithin 65% was non-irritating to the skin of rabbits. In a guinea pig immersion study, 0.5% of a soap containing 0.83% lecithin powder was practically non-irritating. Lecithin 65% (solution of 65% lecithin) and products containing 2.25% or 3.0% Lecithin 65% were non- to minimally irritating to unrinsed rabbit eyes. A soap containing 0.83% lecithin powder (tested at 25%) was moderately irritating, and lecithin-containing liposomes were practically nonirritating in a Draize test. After exposing mice to aerosolized lecithin 4 hr/day for 2 days, lungs showed focal endothelial cell swelling and interstitial edema. Mice were fed 5 to 10 mg lecithin mixed with sugar (for palatability), and a second group was fed lecithin (5 to 10 mg) and cholesterol (4 to 5 mg). The mice were bred and their offspring dosed following the same procedures; dosing continued until all mice became moribund or had died. A control group was given laboratory feed ad libitum. The total number of mice fed lecithin, lecithin and cholesterol, or control feed was 166, 212, and 360, respectively. Animals were killed and brain necropsies performed. Brain nerve cell tumors were found in 18 of 73 examined animals fed lecithin and in 27 of 88 examined animals fed lecithin and cholesterol, whereas, no brain nerve cell tumors were found in 188 control animals.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 在妊娠和哺乳期间的影响
◉ 母乳喂养期间使用总结:卵磷脂是一种混合物,包括胆碱、胆碱酯、脂肪酸、甘油、糖脂、三酸甘油酯、磷酸和磷脂,如磷脂酰胆碱,它们是人类母乳的正常成分。补充卵磷脂已被推荐作为治疗乳腺堵塞的治疗方法,并且作为添加到通过塑料管泵送给人乳喂养的早产儿的添加剂,以防止脂肪损失。关于高剂量卵磷脂补充在哺乳母亲或婴儿中的安全性和有效性,没有科学上有效的临床研究。卵磷脂的一个组成部分,磷脂酰胆碱的补充增加了胆碱,但并没有增加母乳中磷脂酰胆碱的浓度,而胆碱的补充增加了胆碱代谢物,但并没有增加母乳中的胆碱。一项荟萃分析发现,较高的母亲胆碱摄入量可能与更好的儿童神经认知和神经发育相关。卵磷脂通常耐受性良好,被美国食品药品监督管理局认为是“普遍认为安全”(GRAS)的。 膳食补充剂不需要美国食品药品监督管理局的广泛市场前批准。制造商负责确保安全,但在市场销售前不需要证明膳食补充剂的安全性和有效性。膳食补充剂可能含有多种成分,标签和实际成分或其数量之间常常存在差异。制造商可以与独立组织签订合同,以验证产品或其成分的质量,但这并不证明产品的安全或有效性。由于上述问题,一个产品的临床测试结果可能不适用于其他产品。关于膳食补充剂的更详细信息可以在LactMed网站的其它地方找到。 ◉ 对母乳喂养婴儿的影响:截至修订日期,没有找到相关的已发布信息。 ◉ 对泌乳和母乳的影响:截至修订日期,没有找到相关的已发布信息。
◉ Summary of Use during Lactation:Lecithin is a mixture of choline, choline esters, fatty acids, glycerol, glycolipids, triglycerides, phosphoric acid, and phospholipids, such as phosphatidylcholine that are normal components of human milk. Supplemental lecithin has been recommended as a treatment for plugged milk ducts, and as an additive to human milk that is given to preterm infants via pumping through plastic tubing in order to prevent fat loss. No scientifically valid clinical studies exist on the safety and efficacy of high-dose lecithin supplementation in nursing mothers or infants. Supplementation with one component of lecithin, phosphatidylcholine, increases choline, but not phosphatidylcholine concentrations in breastmilk and supplementation with choline increases choline metabolites, but not choline in breastmilk. A meta-analysis found that higher maternal choline intake was likely to be associated with better child neurocognition and neurodevelopment. Lecithin is usually well tolerated and is considered to be "generally recognized as safe" (GRAS) by the U.S. Food and Drug Administration. Dietary supplements do not require extensive pre-marketing approval from the U.S. Food and Drug Administration. Manufacturers are responsible to ensure the safety, but do not need to prove the safety and effectiveness of dietary supplements before they are marketed. Dietary supplements may contain multiple ingredients, and differences are often found between labeled and actual ingredients or their amounts. A manufacturer may contract with an independent organization to verify the quality of a product or its ingredients, but that does not certify the safety or effectiveness of a product. Because of the above issues, clinical testing results on one product may not be applicable to other products. More detailed information about dietary supplements is available elsewhere on the LactMed Web site. ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.
来源:Drugs and Lactation Database (LactMed)
毒理性
  • 解毒与急救
/SRP:/ 立即急救:确保已经进行了充分去污。如果患者停止呼吸,开始人工呼吸,最好使用需求阀复苏器、气囊面罩装置或口袋面罩,按培训操作。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。如果发生呕吐,让患者向前倾或放在左侧(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 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)
毒理性
  • 解毒与急救
/SRP:/ 基本治疗:建立专利气道(如有需要,使用口咽或鼻咽气道)。如有必要,进行吸痰。观察呼吸不足的迹象,如有需要,辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿,如有必要,进行治疗……。监测休克,如有必要,进行治疗……。预防癫痫发作,如有必要,进行治疗……。对于眼睛污染,立即用水冲洗眼睛。在运输过程中,用0.9%的生理盐水(NS)持续冲洗每只眼睛……。不要使用催吐剂。对于摄入,如果患者能吞咽、有强烈的干呕反射且不流口水,则用温水冲洗口腔,并给予5毫升/千克,最多200毫升的水进行稀释……。在去污后,用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 高级治疗:对于无意识、严重肺水肿或严重呼吸困难的病人,考虑进行口咽或鼻咽气管插管以控制气道。使用气囊阀面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛,考虑给予β受体激动剂,如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注5%葡萄糖水(D5W),并暂停其他输注。如果出现低血容量的迹象,使用0.9%生理盐水(NS)或乳酸林格氏液(LR)。对于伴有低血容量迹象的低血压,谨慎给予液体。注意观察液体过载的迹象……。使用地西泮(安定)或劳拉西泮(安定文)治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒物A和B/
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)

SDS

SDS:4fbde9356113b76350117dca64cf9e3e
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反应信息

  • 作为反应物:
    描述:
    乙酸酐1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine溶剂黄146 作用下, 以70%的产率得到1-palmitoyl-2-linoleoyl-3-acetylglycerol
    参考文献:
    名称:
    Monoacetyldiglycerides as new Ca2+ mobilizing agents in rat pancreatic acinar cells
    摘要:
    Several monoacetyldiglycerides were synthesized from glycerol in search fbr new Ca2+ mobilizing agent in vitro. All monoacetyldiglycerides except linolenoyl and phenlycyclopropylcarbonyl derivatives showed activity toward Ca2+ release in pancreatic acinar cells. Linoleoyl and docosahexaenoyl derivatives were chosen for further test and exhibited unique activity. (C) 1998 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0960-894x(98)00690-8
  • 作为产物:
    参考文献:
    名称:
    A Rapid Condensation between Lysophosphorylcholine and Fatty Acids with an Easily Separable Amine Base
    摘要:
    以2,6-Cl2C6H3COCl和1-甲基咪唑为原料,标题缩合反应在室温下12小时内完成,时间短于标准DCC/DMAP体系。通过色谱法容易地从粗产物中分离出1-甲基咪唑,是本试剂体系的额外优势。
    DOI:
    10.1055/s-2005-871973
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文献信息

  • Mass spectrometry of phospholipids. Some applications of desorption chemical ionization and fast atom bombardment
    作者:Eser Ayanoglu、Annemarie Wegmann、Olivier Pilet、G. Dean Marbury、J. Ronald Hass、Carl Djerassi
    DOI:10.1021/ja00330a035
    日期:1984.9
  • A Rapid Condensation between Lysophosphorylcholine and Fatty Acids with an Easily Separable Amine Base
    作者:Yuichi Kobayashi、Hukum P. Acharya
    DOI:10.1055/s-2005-871973
    日期:——
    With 2,6-Cl2C6H3COCl and 1-methylimidazole, the title condensation completed at room temperature within 12 hours, which is shorter time than that with the standard DCC/DMAP system. Use of easily separable 1-methylimidazole from the crude product by chromatography is an additional advantage of the present reagent system.
    以2,6-Cl2C6H3COCl和1-甲基咪唑为原料,标题缩合反应在室温下12小时内完成,时间短于标准DCC/DMAP体系。通过色谱法容易地从粗产物中分离出1-甲基咪唑,是本试剂体系的额外优势。
  • Monoacetyldiglycerides as new Ca2+ mobilizing agents in rat pancreatic acinar cells
    作者:So-Yeop Han、So-Hye Cho、So-Yeon Kim、Jeong-Taeg Seo、Seok-Jun Moon、Gil-Ja Jhon
    DOI:10.1016/s0960-894x(98)00690-8
    日期:1999.1
    Several monoacetyldiglycerides were synthesized from glycerol in search fbr new Ca2+ mobilizing agent in vitro. All monoacetyldiglycerides except linolenoyl and phenlycyclopropylcarbonyl derivatives showed activity toward Ca2+ release in pancreatic acinar cells. Linoleoyl and docosahexaenoyl derivatives were chosen for further test and exhibited unique activity. (C) 1998 Elsevier Science Ltd. All rights reserved.
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同类化合物

钙(2R)-2,3-二(棕榈酰氧基)丙基磷酸酯 辛酸(1R)-1-[(磷酰氧基)甲基]-1,2-乙二基酯单钠盐 血小板活化因子 (C18) 血小板-活化因子C18 苯甲醇,2-甲氧基-5-甲基-a-[1-(甲基氨基)乙基]- 苯甲基(2R)-2-(羟甲基)吡咯烷-1-羧酸酯 苯(甲)醛,2-甲基-4-硝基- 胞苷二磷酸甘油酯 胞苷-5’-二磷酸甘油酯二钠盐 肉豆蔻酰基溶血磷脂胆碱 聚乙二醇单甲醚-2000-二十八烷基磷脂酰乙醇胺 磷酸二氢1,3-羟基-2-丙酯 磷酸,单[3-(十八烷氧基)-2-(苯基甲氧基)丙基]单[2-(1-吡咯烷基)乙基]酯 磷酯酰乙醇胺 磷脂酰胆碱(大豆) 磷脂酰肌醇 磷脂酰乙醇胺(牛脑) 磷脂酰乙醇胺(大豆) 磷脂酰丝氨酸 硬脂酰溶血卵磷脂 甲氧基聚乙二醇-二棕榈酰磷酯酰乙醇胺 甘磷酸胆碱 甘油磷酸镁 甘油磷酸锌 甘油磷酸铁 甘油磷酸钾 甘油磷酸钾 甘油磷酸钠 甘油磷酸钙盐 甘油磷酸酯镍(2+)盐 甘油磷酸酯锰盐 甘油磷酸酯 甘油磷酸水和物 甘油磷酸-N-花生四烯酸乙醇胺 甘油磷酸-N-油酰基乙醇胺 甘油磷酸-N-棕榈酰乙醇胺 甘油磷酰丝氨酸 琥珀酸)氢21-羟基-5&#x3B2-孕烷-3,20-二酮21-( 焦磷酸甘油油酰甘油(铵盐) 溶血磷脂酰胆碱(鸡蛋) 溶血卵磷脂(猪或牛肝) 氨基甲酰-PAF(C16) 氢化磷脂酰胆碱 氢化卵磷脂 月桂酰溶血磷酰脂 心磷脂(钠盐或铵盐) 大豆卵磷脂 外消旋-1,2-二月桂酰-甘油-3-磷酰-胆碱 叔-丁氧基羰基-脯氨酰-氨基琥珀酰<丁二酰>-甘氨酰-丙氨酸甲基酯 反-N-(1-(2-乙氧基乙基)-3-甲基-4-哌啶基)-N-苯基苯酰胺