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大豆卵磷脂

中文名称
大豆卵磷脂
中文别名
卵磷脂;蛋黄卵磷脂;L-a-磷脂酰胆酰;多烯磷脂酰胆碱;L-A-卵磷脂;膦脂酰胆碱;L-Α-卵膦脂;L-α-磷脂酰胆碱;磷脂酰胆碱;大豆(卵)磷脂
英文名称
1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine
英文别名
PC 16:0/18:2;L-α-phosphatidylcholine;1-palmitoyl-2-linoleoylglycerylphosphatidylcholine;egg yolk lecithin;phosphatidylcholine;soy lecithin;lecithin;[(2R)-3-hexadecanoyloxy-2-octadeca-9,12-dienoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
大豆卵磷脂化学式
CAS
——
化学式
C42H80NO8P
mdl
——
分子量
758.073
InChiKey
JLPULHDHAOZNQI-RRHRGVEJSA-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):
    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
识别和使用:当酸值约为20时,卵磷脂形成蜡状团块;当酸值约为30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、巧克力和一般食品工业。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%卵磷脂65%(65%卵磷脂溶液)的化妆品配方、含有0.83%卵磷脂粉末的肥皂(在0.5%下测试)以及卵磷脂脂质体通常不具有刺激性。最严重的反应是几乎察觉不到的红斑。氢化卵磷脂也不具有刺激性,且氢化卵磷脂(含有15%的凡士林)不是致敏剂。此外,含有3%卵磷脂65%的晒黑油、含有0.1%卵磷脂65%的睫毛膏和含有0.3%卵磷脂65%的粉底均不具有致敏性。以每天22至83克的剂量给人类受试者服用卵磷脂,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,被大豆蛋白污染的卵磷脂作为药物辅料可能会引起大豆过敏患者的反应。含有0.3%卵磷脂65%(65%卵磷脂溶液)的粉底在人类受试者中不是光致敏剂。动物研究:在单次封闭贴片试验(兔子)中,卵磷脂65%(65%卵磷脂溶液)具有轻微刺激性,含有3%卵磷脂65%的产品几乎无至轻度刺激性,含有2.25%卵磷脂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%卵磷脂粉末的肥皂0.5%几乎无刺激性。卵磷脂65%(65%卵磷脂溶液)和含有2.25%或3.0%卵磷脂65%的产品对未冲洗的兔眼无至轻微刺激性。含有0.83%卵磷脂粉末的肥皂(在25%下测试)具有中等刺激性,而含有卵磷脂的脂质体在Draize试验中几乎无刺激性。将小鼠暴露于卵磷脂气溶胶4小时/天,持续2天后,肺部出现局部内皮细胞肿胀和间质性水肿。小鼠被喂食含有5至10毫克卵磷脂和糖的混合物(以提高适口性),第二组被喂食卵磷脂(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;继续给药直到所有小鼠垂死或死亡。对照组随意给予实验室饲料。总共喂食卵磷脂、卵磷脂和胆固醇或对照饲料的小鼠数量分别为166、212和360。动物被杀死并进行了脑部解剖。在大脑神经细胞肿瘤的检查中,在喂食卵磷脂的73只动物中发现了18只,在喂食卵磷脂和胆固醇的88只动物中发现了27只,而在188只对照组动物中没有发现大脑神经细胞肿瘤。
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
  • 解毒与急救
/SRP:/ 立即急救:确保已经进行了充分的中毒物清除。如果患者停止呼吸,开始人工呼吸,最好使用需求阀复苏器、袋阀面罩装置或口袋面罩,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。如果发生呕吐,让患者前倾或置于左侧卧位(如果可能的话,头部向下)以保持呼吸道畅通,防止吸入性肺炎。保持患者安静,维持正常体温。寻求医疗救助。 /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,协助通气。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……。预期癫痫发作,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,如果患者能够吞咽、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:对于昏迷、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。使用带有球囊-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激动剂,如沙丁胺醇(舒喘灵)……。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)。如果出现低血容量的迹象,使用0.9%盐水(NS)或乳酸钠林格氏液(LR)。对于伴有低血容量迹象的低血压,谨慎给予液体。注意液体过载的迹象……。使用地西泮(安定)或劳拉西泮(安定)治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒素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)
毒理性
  • 人类毒性摘录
在临床刺激研究中,含有0.3%或3%磷脂酰胆碱65%(65%磷脂酰胆碱溶液)、含有0.83%磷脂酰胆碱粉末(在0.5%浓度下测试)的肥皂和磷脂酰胆碱脂质体通常不具有刺激性。观察到的最严重反应是几乎感觉不到的红斑。氢化磷脂酰胆碱也不是刺激物,且氢化磷脂酰胆碱(在凡士林中占15%)不是致敏剂。此外,含有3%磷脂酰胆碱65%的晒黑油、含有0.1%磷脂酰胆碱65%的睫毛膏和含有0.3%磷脂酰胆碱65%的粉底均不具有致敏性。
/HUMAN EXPOSURE STUDIES/ 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.
来源:Hazardous Substances Data Bank (HSDB)

反应信息

  • 作为反应物:
    描述:
    大豆卵磷脂 在 soybean lipoxygenase 作用下, 反应 1.0h, 生成 1-palmitoyl-(13S)-hydroperoxyoctadeca-9-enoylglycerylphosphatidylcholine
    参考文献:
    名称:
    来自自由基终止的酪氨酸-脂质过氧化物加合物:对位偶联和分子内 Diels-Alder 环化
    摘要:
    多不饱和脂质与酪氨酸或酪氨酸的酚类类似物的自由基共氧化在胶束水溶液和有机溶液中产生脂质过氧化物-酪氨酸(苯酚)加合物。通过一维和二维核磁共振光谱以及质谱 (MS) 分离和表征了新的加合物。光谱数据表明多不饱和脂质过氧自由基只在酪氨酰(苯氧基)自由基的对位产生稳定的过氧化物偶联产物。由于苯酚衍生的环己二烯酮的交叉共轭羰基,这些加合物在 185 ppm 处具有特征 (13) C 化学位移。主要的过氧化物加合物随后进行分子内狄尔斯-阿尔德 (IMDA) 环化,提供了许多非对映异构三环加合物,它们在~198 ppm 处具有特征性的羰基 (13)C 化学位移。所有 NMR HMBC 和 HSQC 相关性都支持初级和 Diels-Alder 加合物的结构分配,MS 碰撞诱导解离数据也是如此。确定了 IMDA 反应的动力学速率常数和活化参数,并用亚铜离子还原初级加合物,得到苯酚衍生的 4-羟基环六-2,
    DOI:
    10.1021/ja106503a
  • 作为试剂:
    描述:
    4-硝基苯基乙酸酯 在 tris(hydroxymethyl)aminoethane buffer 、 大豆卵磷脂 作用下, 生成 对硝基苯酚 、 alkaline earth salt of/the/ methylsulfuric acid
    参考文献:
    名称:
    脂质体的动力学表征。
    摘要:
    DOI:
    10.1002/jps.2600690642
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文献信息

  • WO2008/44099
    申请人:——
    公开号:——
    公开(公告)日:——
  • Positively charged and neutral drug-loaded liposomes as the aerosolized formulations for the efficiency assessment of tumor metastases to lungs
    作者:Caiwei Jia、Yucheng Zhang、Yanyun Wang、Jiani Gao、Ali Raza、Takayo Ogawa、Satoshi Wada、Dong Xie、Jin-Ye Wang
    DOI:10.1016/j.jddst.2022.104081
    日期:2023.2
  • Tyrosine−Lipid Peroxide Adducts from Radical Termination: Para Coupling and Intramolecular Diels−Alder Cyclization
    作者:Roman Shchepin、Matias N. Möller、Hye-young H. Kim、Duane M. Hatch、Silvina Bartesaghi、Balaraman Kalyanaraman、Rafael Radi、Ned A. Porter
    DOI:10.1021/ja106503a
    日期:2010.12.15
    intramolecular Diels-Alder (IMDA) cyclization, affording a number of diastereomeric tricyclic adducts that have characteristic carbonyl (13)C chemical shifts at ~198 ppm. All of the NMR HMBC and HSQC correlations support the structure assignments of the primary and Diels-Alder adducts, as does MS collision-induced dissociation data. Kinetic rate constants and activation parameters for the IMDA reaction were
    多不饱和脂质与酪氨酸或酪氨酸的酚类类似物的自由基共氧化在胶束水溶液和有机溶液中产生脂质过氧化物-酪氨酸(苯酚)加合物。通过一维和二维核磁共振光谱以及质谱 (MS) 分离和表征了新的加合物。光谱数据表明多不饱和脂质过氧自由基只在酪氨酰(苯氧基)自由基的对位产生稳定的过氧化物偶联产物。由于苯酚衍生的环己二烯酮的交叉共轭羰基,这些加合物在 185 ppm 处具有特征 (13) C 化学位移。主要的过氧化物加合物随后进行分子内狄尔斯-阿尔德 (IMDA) 环化,提供了许多非对映异构三环加合物,它们在~198 ppm 处具有特征性的羰基 (13)C 化学位移。所有 NMR HMBC 和 HSQC 相关性都支持初级和 Diels-Alder 加合物的结构分配,MS 碰撞诱导解离数据也是如此。确定了 IMDA 反应的动力学速率常数和活化参数,并用亚铜离子还原初级加合物,得到苯酚衍生的 4-羟基环六-2,
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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