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lecithin | 8002-43-5

中文名称
——
中文别名
——
英文名称
lecithin
英文别名
1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine;PLPC;2-linoleoyl-1-palmitoyl-sn-glycero-3-phosphocholine;PC(16:0/18:2);L-alpha-lecithin;[(2R)-3-hexadecanoyloxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
lecithin化学式
CAS
8002-43-5
化学式
C42H80NO8P
mdl
——
分子量
758.073
InChiKey
JLPULHDHAOZNQI-ZTIMHPMXSA-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

  • 熔点:
    >145°C (dec.)
  • 密度:
    d424 1.0305
  • 闪点:
    57 °C
  • 溶解度:
    氯仿:0.1 g/mL,轻微混浊,淡黄色至深橙色
  • 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
  • 稳定性/保质期:

    不溶但能膨胀,在氯化钠溶液中则会形成胶体悬浮液。它还具有良好的乳化作用。

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刺激。最严重的反应是几乎察觉不到的红斑。氢化卵磷脂也不刺激,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%的粉底均不致敏。以每日剂量22至83克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,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卵磷脂可能对大豆过敏的患者产生反应。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)的刺激性最小,含有3%卵磷脂65%的产品几乎不至轻度刺激,含有2.25%卵磷脂65%的产品对兔子的皮肤不刺激。在一项豚鼠浸泡研究中,含有0.83%卵磷脂粉末的肥皂0.5%几乎不刺激。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非至最小刺激。含有0.83%卵磷脂粉末的肥皂(在25%下测试)中度刺激,卵磷脂脂质体在Draize试验中几乎不刺激。将小鼠暴露于气溶胶化卵磷脂4小时/天,持续2天后,肺脏显示局灶性内皮细胞肿胀和间质性肿。将小鼠喂食含有5至10毫克卵磷脂和糖的混合物(以提高适口性),第二组喂食卵磷脂(5至10毫克)和胆固醇(4至5毫克)。小鼠繁殖,其后代按相同程序给药;给药持续到所有小鼠垂死或死亡。对照组随意喂食实验室饲料。分别给服卵磷脂、卵磷脂胆固醇或对照饲料的小鼠总数为166、212和360。杀死动物并进行脑部解剖。在检查的73只喂食卵磷脂的动物中,有18只发现了脑神经细胞肿瘤,而在检查的88只喂食卵磷脂胆固醇的动物中,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、磷酸磷脂,如磷脂胆碱,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的科学有效的临床研究尚不存在。卵磷脂的一个组成部分,磷脂胆碱的补充增加了胆碱,但并未增加母乳中的磷脂胆碱浓度,而胆碱的补充增加了胆碱代谢物,但并未增加母乳中的胆碱。一项荟萃分析发现,较高的母体胆碱摄入量可能与儿童的神经认知和神经发展较好有关。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,但在市场营销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,未找到相关已发布信息。 ◉ 对泌乳和母乳的影响:截至修订日期,未找到相关已发布信息。
◉ 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,让患者向前倾或置于左侧(如果可能,头低脚高位),以保持呼吸道畅通,防止误吸。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,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。监测肺肿,如有必要,进行治疗……。监测休克,如有必要,进行治疗……。预期可能出现癫痫,如有必要,进行治疗……。对于眼睛污染,立即用冲洗眼睛。在转运过程中,用0.9%的生理盐(NS)连续冲洗每只眼睛……。不要使用催吐剂。对于摄入,如果患者能够吞咽、有强烈的呕吐反射且不流口,则用温冲洗口腔,并给予5毫升/千克,最多200毫升的进行稀释……。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肿……。对于严重的支气管痉挛,考虑给予β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%葡萄糖溶液(D5W),点滴。如果出现低血容量的迹象,使用0.9%生理盐(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……。使用丙美卡因盐酸协助眼部冲洗……。/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, administ