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蓖麻油 | 8001-79-4

中文名称
蓖麻油
中文别名
篦麻油;蓖麻(RICINUS COMMUNIS)籽油;麻油
英文名称
castor oil
英文别名
Optase;2,3-bis[[(Z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (Z)-12-hydroxyoctadec-9-enoate
蓖麻油化学式
CAS
8001-79-4
化学式
C57H104O9
mdl
——
分子量
933.447
InChiKey
ZEMPKEQAKRGZGQ-AAKVHIHISA-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:
    -10 °C
  • 沸点:
    313 °C(lit.)
  • 密度:
    0.955 g/mL at 25 °C
  • 闪点:
    >230 °F
  • 溶解度:
    Miscible with chloroform, diethyl ether, ethanol, glacial acetic acid, and methanol; freely soluble in ethanol (95%) and petroleum ether; practically insoluble in water; practically insoluble in mineral oil unless mixed with another vegetable oil.
  • 介电常数:
    4.8(14℃)
  • 物理描述:
    Castor oil appears as pale-yellow or almost colorless transparent viscous liquid with a faint mild odor and nauseating taste. Density 0.95 g / cm3. A mixture of glycerides, chiefly ricinolein (the glyceride of ricinoleic acid) .
  • 颜色/状态:
    Pale-yellowish or almost colorless, transparent, viscous liquid
  • 气味:
    Faint, mild odor
  • 味道:
    The crude oil tastes slightly acrid with a decidedly nauseating after-taste.
  • 稳定性/保质期:
    1. 如果按照规格使用和储存,则不会分解,避免接触氧化物。蓖麻油属于脂肪酸的三甘油酯,主要成分包括蓖麻油酸(87%)、油酸(7%)、亚油酸(3%)、棕榈酸(2%)、硬脂酸(1%)以及微量的二羟硬脂酸。受热时易燃。 2. 本品低毒,不可食用,用于医药作为泻剂。药用蓖麻油必须事先用水压机冷轧,温度不超过50℃,否则有害物质会进入油中而不能药用。
  • 旋光度:
    Dextrorotatory (undiluted in sodium light)
  • 自燃温度:
    840 °F (449 °C)
  • 粘度:
    At 25 °C: 6-8 poises, also expressed as U +/- 1/2 (Gardner-Holdt scale)
  • 表面张力:
    At 20 °C: 39.0 dynes/cm; at 80 °C: 35.2 dynes/cm
  • 折光率:
    Index of refraction: 1.473-1.477 at 25 °C/D; 1.466-1.473 at 40 °C/D

计算性质

  • 辛醇/水分配系数(LogP):
    17.8
  • 重原子数:
    66
  • 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:
    140
  • 氢给体数:
    3
  • 氢受体数:
    9

ADMET

代谢
蓖麻油是一种三酸甘油酯,在人类的小肠中被胰腺酶水解,导致甘油和蓖麻酸释放。
Castor Oil is a triglyceride that is hydrolyzed in the small intestine in humans by pancreatic enzymes, leading to the release of glycerol and Ricinoleic Acid.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在小肠内,胰腺脂肪酶将油脂水解为甘油和蓖麻酸。蓖麻酸盐与其他阴离子表面活性剂一样,减少了流体和电解质的净吸收并刺激肠道蠕动。蓖麻酸也被吸收并像其他脂肪酸一样被代谢。
Within the small intestine, ... pancreatic lipases hydrolyze the oil to glycerol and ricinoleic acid. Ricinoleate, like other anionic surfactants, reduces net absorption of fluid and electrolytes and stimulates intestinal peristalsis. Ricinoleic acid also is absorbed and metabolized like other fatty acids.
来源:Hazardous Substances Data Bank (HSDB)
代谢
蓖麻油通过灌胃的方式给予无菌大鼠和常规大鼠(数量未说明)。在24小时内每隔一段时间收集尿液。在无菌大鼠和常规大鼠的尿液中检测到以下环氧二羧酸:3,6-环氧辛二酸;3,6-环氧癸二酸;以及3,6-环氧十二烷二酸。在给大鼠灌胃蓖麻油之前收集的尿液中没有检测到这些酸,而且在蒸汽灭菌的蓖麻油中也没有检测到它们。无菌大鼠的结果表明,蓖麻油中的羟基脂肪酸——蓖麻酸环化形成环氧化合物的过程是在体内发生的,并不需要肠道细菌的存在。
Castor oil was administered intragastrically to germ-free and conventional rats (number not stated). Urine was collected at intervals over a 24-hr period. The following epoxydicarboxylic acids were detected in the urine of both germ-free and conventional rats: 3,6-epoxyoctanedioic acid; 3,6-epoxydecanedioic acid; and 3,6- epoxydodecanedioic acid. These acids were not detected in urine collected from the rats prior to dosing with castor oil, and they also were not detected in steam-sterilized castor oil. Results for the germ-free rat indicate that the cyclization of Ricinoleic Acid (hydroxy fatty acid in castor oil) to form an epoxy compound occurs endogenously and does not require the presence of intestinal bacteria.
来源:Hazardous Substances Data Bank (HSDB)
代谢
蓖麻油(10到15毫升)被三名健康受试者口服。在给药后2到8小时内收集尿液。尿液中含有以下三种环氧二羧酸:3,6-环氧辛二酸;3,6-环氧癸二酸;以及3,6-环氧十二烷二酸。
Castor oil (10 to 15 mL) /was administered/ orally to three healthy subjects. Urine was collected between 2 and 8 hr post dosing. The following three epoxydicarboxylic acids were excreted in the urine: 3,6-epoxyoctanedioic acid; 3,6-epoxydecanedioic acid; and 3,6-epoxydodecanedioic acid.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 在妊娠和哺乳期间的影响
哺乳期使用概述:麻子(蓖麻子)含有甘油三酯,主要由蓖麻酸酯组成,还含有少量的有毒物质蓖麻蛋白和蓖麻碱。压榨麻子产生麻油,麻油的净化过程可以消除蓖麻蛋白和蓖麻碱。麻油是一种强烈的刺激性泻药。麻子和麻子的顺势疗法制剂据说可以减少乳汁流量,但它也被报道用作催乳剂。麻叶的膏药据说也是催乳剂。在印度的某些地区,据说还会将麻油涂在乳房上以刺激泌乳。没有科学有效的临床试验支持这些用途,一些制剂可能对婴儿有毒。催乳剂不应替代影响乳汁产量的可改变因素的评估和建议。目前没有关于麻植物或麻油任何成分进入母乳的排泄数据,也没有关于它们在哺乳母亲或婴儿中的安全性和有效性的信息。然而,据认为肠道很少吸收活性蓖麻酸。由于缺乏信息,其他泻药可能更适合哺乳期母亲使用。 在传统印度文化中,麻油通常在新生儿出生后的头2到3天内给予,这常常导致不良反应。给新生儿服用麻油是危险的,应避免这样做。 膳食补充剂不需要美国食品和药物管理局的广泛市场前批准。制造商负责确保产品的安全性,但在产品上市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含量之间通常存在差异。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性和有效性。由于上述问题,一个产品的临床试验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。 对哺乳婴儿的影响:在印度农村,传统上会在新生儿出生后的头2到3天内给予麻油,以清除胎粪。这种做法可能导致麻痹性肠梗阻和吸入性肺炎。还报道了一名1.5个月大的婴儿,从出生第五天开始,祖母每天给他服用麻油,结果导致严重低蛋白血症、腹泻和营养不良。 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:Castor (Ricinus communis) beans contain triglycerides, mostly consisting of ricinoleic acid esters, and small amounts of the toxic ricin and ricine. Pressing of the beans produces castor oil and purification of the oil eliminates the ricin and ricine. Castor oil is a strong stimulant laxative. Castor beans as well as a homeopathic preparation of castor purportedly reduce milk flow, but it is also reportedly used as a galactogogue. A poultice of castor leaves is a purported galactogogue. In some parts of India, castor oil is also reportedly applied to the breasts to stimulate lactation. No scientifically valid clinical trials support any of these uses and some preparations may be toxic to the infant. Galactogogues should never replace evaluation and counseling on modifiable factors that affect milk production. No data exist on the excretion of any components of the castor plant or castor oil into breastmilk or on their safety and efficacy in nursing mothers or infants. However, little of the active ricinoleic acid is thought to be absorbed from the intestine. Because of a lack of information, other cathartics may be preferred in nursing mothers. In traditional Indian culture, castor oil has been administered to newborn infants during the first 2 to 3 days of life, often resulting in adverse effects. Administration of castor oil to newborns is dangerous and should be avoided. 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:In rural India, castor oil has been traditionally given to infants during the first 2 to 3 days of life to clear the intestine of meconium. This practice can result in paralytic ileus and aspiration pneumonia. Severe hypoalbuminemia was also reported in a 1.5-month-old infant whose grandmother gave him castor oil daily from the fifth day of life, resulting in diarrhea and malnutrition. ◉ 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
  • 摄入症状
腹痛。腹泻。恶心。呕吐。
Abdominal pain. Diarrhoea. Nausea. Vomiting.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
毒理性
  • 相互作用
肥皂已经保护了豚鼠免受破伤风和白喉毒素的致命剂量侵害。因此,胆汁皂化和碱性脂肪酸酯的形成是正常宿主防御机制的一部分,以对抗外毒素(本质上是蛋白质),但对内毒素(多糖)则无效。
The soap has protected guinea pigs against lethal doses of tetanus and diphtheria toxins. Thus, bile saponification and the formation of alkaline fatty acid esters are a normal host defense against exotoxins (protein in nature) but ineffective against endotoxins (polysaccharides).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 紧急急救: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、袋阀面罩装置或口袋面罩,按训练进行操作。如有必要,进行心肺复苏。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,让患者前倾或将其置于左侧(如果可能的话,头部向下),以保持呼吸道畅通并防止吸入。保持患者安静,维持正常体温。寻求医疗帮助。/碳氢化合物混合物、混合物及相关化合物/
/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. /Hydrocarbon Blends, Mixtures, and Related Compounds/
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,如有必要,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……。预见并治疗癫痫发作……。对于眼睛污染,立即用水冲洗眼睛。在转运过程中,用0.9%的生理盐水(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,有强烈的干呕反射,并且不流口水,则用水冲洗口腔,并给予5毫升/千克,最多200毫升的水进行稀释……。/碳氢化合物混合物、混合物及相关化合物/
/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 necessary Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema 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 m/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Hydrocarbon Blends, Mixtures, and Related Compounds/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
... 在肠道被清除之前,会吸收部分肠道代谢物。
... Some absorption of its intestinal metabolites occurs before the intestine is cleared.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
蓖麻油酸酯,像其他阴离子表面活性剂一样,减少流体和电解质的净吸收并刺激肠道蠕动。蓖麻油酸也被吸收并像其他脂肪酸一样被代谢。
Ricinoleate, like other anionic surfactants, reduces net absorption of fluid and electrolytes and stimulates intestinal peristalsis. Ricinoleic acid also is absorbed and metabolized like other fatty acids.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
两只兔子(体重=3公斤)在饮食中添加了6%的蓖麻油,持续了18天;粪便收集发生在最后十天。蓖麻油的利用效率(未对代谢脂肪进行校正)为92.1%,这被认为是高效的利用。对于两只兔子来说,粪便中脂肪的百分比是2.2%。
Two rabbits (weight = 3 kg) were fed 6% castor oil in the diet for 18 days; fecal collection occurred during the last ten days. The utilization (uncorrected for metabolic fat) of castor oil was 92.1%, which /was/ considered to be efficient utilization. For both rabbits, the percentage of fat in the feces was 2.2%.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
成年的大鼠(数量、体重和品种未说明)接受了一种含有48.4%蓖麻油的食物,持续4到6周。对照组的大鼠仅接受常规饲料。从三个接受蓖麻油饮食的大鼠那里收集了粪便。在饲养期结束时,切除的器官/组织被彻底研磨,从肝脏、小肠和肌肉中获得了磷脂脂肪酸样本;从肝脏和脂肪库中获得了甘油酯脂肪酸。没有任何动物出现泻药的迹象。磷脂脂肪酸中麻酸的平均百分比如下:肝脏(实验组:1.3 +/- 0.6% [9次分析];对照组:1.7 +/- 1.1% [7次分析]),小肠(实验组:4.9 +/- 1.7% [8次分析];对照组:6.0 +/- 4.4% [4次分析])和骨骼肌(实验组:3.6 +/- 2.9% [8次分析];对照组:4.0 +/- 1.7% [7次分析])。以下是在甘油酯和胆固醇酯中麻酸的平均百分比:脂肪库(实验组:6.8 +/- 4.2% [11次分析];对照组:0.5 +/- 0.5% [7次分析])和肝脏(实验组:7.2 +/- 2.4% [8次分析];对照组:5.6 +/- 4.1% [5次分析])。/得出的/结论是,喂食蓖麻油并没有导致小肠、肝脏和骨骼肌的磷脂中出现显著量的麻酸,也没有在肝脏的甘油酯中出现。此外,他们还得出结论,麻酸是脂肪库中甘油酯的一个组成酸,占总脂肪酸的7%。三只大鼠排出的脂肪酸分别占摄入的2.1%,2.2%和3.6%。这三只动物的总体脂肪也确定了,计算出吸收的麻酸中有1%到2%沉积在脂肪库中。/得出的/结论是,麻酸被迅速代谢。
Adult rats (number, weights, and strain not stated) received a diet containing 48.4% castor oil for 4 to 6 weeks. Control rats received stock ration only. Feces were collected from three rats on the castor oil diet. At the end of the feeding period, excised organs/tissues were ground thoroughly and samples of phospholipid fatty acids were obtained from the liver, small intestine, and muscle; glyceride fatty acids were obtained from the liver and fat depots. There was no evidence of catharsis in any of the animals. Average percentages of Ricinoleic Acid in the phospholipid fatty acids were as follows: liver (test: 1.3 +/- 0.6% [9 analyses]; controls: 1.7 +/- 1.1% [7 analyses]), small intestine (test: 4.9 +/- 1.7% [8 analyses]; controls: 6.0 +/- 4.4% [4 analyses]), and skeletal muscle (test: 3.6 +/- 2.9% [8 analyses]; controls: 4.0 +/- 1.7% [7 analyses]). The following values are average percentages of Ricinoleic Acid in glycerides and cholesterol esters: fat depots (test: 6.8 +/- 4.2% [11 analyses]; controls: 0.5 +/- 0.5% [7 analyses]) and liver (test: 7.2 +/- 2.4% [8 analyses]; controls: 5.6 +/- 4.1% [5 analyses]). /It was/ concluded that the feeding of castor oil did not lead to the appearance of significant amounts of Ricinoleic Acid in phospholipids of the small intestine, liver, and skeletal muscle, nor in glycerides of the liver. Additionally, they concluded that ricinoleic acid is a component acid of the glycerides in the fat depots, comprising 7% of the total fatty acids. The fatty acids excreted by each of three rats amounted to 2.1%, 2.2%, and 3.6% of those ingested. Total body fat in these three animals was also determined, and it was calculated that 1% to 2% of absorbed Ricinoleic Acid was deposited in the fat depots. /It was/ concluded that Ricinoleic Acid was rapidly metabolized.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • TSCA:
    Yes
  • 安全说明:
    S24/25
  • 海关编码:
    1515300000
  • RTECS号:
    FI4100000

制备方法与用途

蓖麻油简介

蓖麻油是从大戟科蓖麻属植物蓖麻的种子中榨取的脂肪油,常温下为几乎无色或微带黄色的透明粘稠液体。它具有微臭味且味道淡而后略显辛凉。不溶于水但能溶于乙醇、苯和二硫化碳,并且与无水乙醇、乙醚、氯仿或冰醋酸任意混合,而不溶于矿物油。相对密度0.956~0.969(25℃),折光率1.478~1.480,酸值≤2.0,皂化值176~186,碘值82~90。

主要由蓖麻醇酸(12-羟基十八碳-9-烯酸)和油酸组成的高级脂肪酸的甘油酯构成。分子中的R₁、R₂ 和 R₃ 可以相同也可以不同,其中含蓖麻醇酸80%~88%,油酸3%~9%,还含有棕榈酸(Palmitic acid)、硬脂酸(Stearic acid)、亚油酸(Linoleic acid)、亚麻酸(Linolenicacid)、二羟基硬脂酸(Dihydroxystearie acid)等,甘油酯的组成为三蓖麻酸酯68.2%、二蓖麻酸酯28.0%,一蓖麻酸酯2.9%及非蓖麻酸酯0.9%。灰分中含多量钙、铁、硅,另含无机元素铝、铜、镁及少量锰、钛、镍、锌等。

药理作用

蓖麻油是一种刺激性泻药,在十二指肠内受脂肪酶和胆汁的作用下被皂化成甘油与对小肠粘膜具有刺激性的蓖麻油酸钠,从而引起肠蠕动增强并有润肠作用。主要作用于小肠,服药后4~6小时排便。

临床应用

蓖麻油可应用于以下领域:

  1. 用于习惯性便秘
  2. 用于直肠镜检、肠外科手术及胃肠道X线检查前作泻剂,因为它能使肠道气体和粪便完全排空。
  3. 用作食物中毒时的导泻药物
生产方法

蓖麻油由大戟科一年生高大草本植物蓖麻(Ricinus communis)种子去壳后冷榨而得,籽含油约45%~60%。生产步骤如下:

  1. 将冷榨的蓖麻子油加入预先配制好的3%氢氧化钠溶液中,搅拌加热至60-65℃,以使游离脂肪酸充分皂化。
  2. 加入95-100℃热水淋洗,并静置分去洗涤水,反复洗涤数次后分离净的皂化洗涤液。
  3. 在105℃以下(7.98-14.63kPa)脱水,然后加入白陶土及活性炭搅拌半小时进行脱色处理。之后压滤得到药用蓖麻油。
特性

类别:易燃液体
毒性分级:中毒
急性毒性:口服-大鼠 LD50: 957 毫克/公斤
刺激数据

  • 皮肤 - 兔子100毫克/24小时,轻度
  • 眼睛 - 兔子500毫克,轻度

爆炸物危险特性:放置可氧化自行加热升温。
可燃性危险特性:遇高温、明火易燃;热分解产生辛辣刺激烟雾。
储运特性:库房需通风、低温干燥,并与食品原料分开储运,避免接触明火和高温。

灭火剂:干粉、水雾、泡沫、二氧化碳。

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    蓖麻油二甲基硫氧气臭氧 作用下, 生成 3-羟基壬醛
    参考文献:
    名称:
    Further study on the one‐pot synthesis of (E)‐2‐nonenal from castor oil
    摘要:
    摘要 本文介绍了一种以商用蓖麻油为原料,在甲醇中通过臭氧分解合成 (E)-2-nonenal 的一步法工艺,然后用二甲基硫醚还原臭氧产物,并将生成的中间产物暴露于稀硫酸中。所开发的工艺可以生产出产率为 80%、纯度为 95% 的醛。由于原料和还原剂价格低廉、溶剂可回收利用以及异常简单,该方法比之前报道的所有方法都更具优势。
    DOI:
    10.1007/bf02540671
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文献信息

  • The synthesis of PGF1α by re-structuring of castor oil
    作者:D. Ranganathan、S. Ranganathan、M.M. Mehrotra
    DOI:10.1016/0040-4020(80)80089-5
    日期:1980.1
    oil has been transformed—via methyl ricinoleate—to PGF1α by strategy wherein 16 of the 18 carbons of the castor oil backbone are incorporated in the C-20 PGF1α, involving, inter alia, a novel procedure for the regiospecific functionalisation of terminal olefins, a novel degradation of aldehyde to lower acid and strategies useful for the generation of the highly functionalised prostanoid system, which
    蓖麻油已被改造-经由蓖麻油酸甲酯到PGF 1个α由策略,其中所述18个碳原子的蓖麻油骨架的16中的C-20 PGF并入1 α,涉及,除其他外,对于区域专一性官能一种新颖的过程末端烯烃的合成,醛向低级酸的新降解以及可用于生成高度官能化的类前列腺素系统的策略,这些方法特别说明了MEM保护基在多种化学转化中的效用。此外,此工作描述了具有潜在效用和新颖的均PGP的合成合成子的制备1 α。
  • [EN] IODINATED PRODUCTS INTENDED FOR A USE FOR THE MEDICAL IMAGING AND THEIR METHODS OF PREPARATION<br/>[FR] PRODUITS IODÉS DESTINÉS À ÊTRE UTILISÉS POUR L'IMAGERIE MÉDICALE ET LEURS PROCÉDÉS DE PRÉPARATION
    申请人:UNIV STRASBOURG
    公开号:WO2013121284A1
    公开(公告)日:2013-08-22
    The present invention concerns an iodinated lipophilic compound of formula (I) or (II) : AG-R (I) or AG-X-R (II) wherein - AG represents an unsaturated or saturated (C8-C52) aliphatic hydrocarbon chain found in fatty acids having or not a double bond, an unsaturated or saturated aromatic cycle with an hydrocarbon chain, a sterol, an unsaturated or saturated (C8-C52) aliphatic hydrocarbon chain ended by an amino group having or not a double bound, - X represents a spacer such as a diacid, a diol (like aliphatic diol, polyethylene glycol comprising 1 to 50 ethylene glycol groups) or an amino acid, - R represents a benzene ring with one, two or three iodine atoms and a carboxylic group or an alcohol group.
    本发明涉及一种具有以下结构的碘化亲脂性化合物(I)或(II):AG-R(I)或AG-X-R(II),其中- AG代表脂肪酸中的不饱和或饱和(C8-C52)脂肪烃链,具有或不具有双键,带有碳氢链的不饱和或饱和芳香环,甾醇,由氨基结束的不饱和或饱和(C8-C52)脂肪烃链,- X代表间隔物,如二酸,二醇(如脂肪二醇,聚乙二醇,包含1至50个乙二醇基团)或氨基酸,- R代表一个苯环,带有一个、两个或三个碘原子和一个羧基或羟基。
  • Organosilicon ethers of ricinoleic acid
    作者:N. P. Shapkin、I. G. Khalchenko、N. V. Maslova、V. V. Gribova、V. G. Savchenko
    DOI:10.1007/s11172-020-2913-5
    日期:2020.7
    silicon-containing ethers depends on the content of crystallization water in sodium ricinoleate, and the concentration and nature of solvent. Thus, in the case of a mixture of absolute alcohol with ether and low content of crystallization water, the reaction proceeds by hydroxyl of alcohol to form salt-like compounds containing silicon. In the case of a salt with a high content of crystallization water, the reaction
    研究了乙烯基三氯硅烷与蓖麻油酸钠盐的相互作用。确定含硅醚的组成和结构取决于蓖麻油酸钠中结晶水的含量,以及溶剂的浓度和性质。因此,在无水醇与醚和低含量结晶水的混合物的情况下,反应通过醇的羟基进行,形成含硅的盐状化合物。在结晶水含量高的盐的情况下,反应沿着两个反应中心进行,同时形成醚和酯。所得化合物的组成和结构使用元素分析、IR、1H、13C NMR光谱和凝胶色谱法确定。
  • Synthesis of methyl 9,12‐epoxyoctadecanoate from castor oil
    作者:S. Y. Mhaskar、V. V. S. Mani
    DOI:10.1007/bf02540670
    日期:1994.5
    Abstract

    We report here the synthesis of methyl 9,12‐epoxyoctadecanoate (2‐[7‐methoxycarbonyl‐heptyl]‐5‐hexanyl‐tetrahydrofuran). Methyl ricinoleate (methyl 12‐hydroxy‐9‐cis‐octadecenoate), isolated from castor oil methyl esters was isomerized with diphenyl disulfide as radical initiator under ultraviolet radiation to give thetrans isomer, methyl ricinelaidate. The latter was cyclized by slow addition of 10% bromine solution in dichloromethane to give methyl 10‐bromo‐9,12‐epoxyoctadecanoate, which on hydrogenation with Pd/C catalyst gave the title compound, methyl 9,12‐epoxyoctadecanoate.

    摘要 我们在此报告 9,12-环氧十八烯酸甲酯(2-[7-甲氧羰基-庚基]-5-己基四氢呋喃)的合成。从蓖麻油甲酯中分离出的蓖麻油酸甲酯(12-羟基-9-顺式-十八烯酸甲酯)在紫外线辐射下以二苯基二硫化物作为自由基引发剂进行异构化,得到反式异构体蓖麻油酸甲酯。在二氯甲烷中缓慢加入 10%的溴溶液使后者环化,得到 10-溴-9,12-环辛基癸酸甲酯,在 Pd/C 催化剂作用下进行氢化,得到标题化合物--9,12-环辛基癸酸甲酯。
  • Esters from castor oil functionalized with aromatic amines as a potential lubricant
    作者:Laura de Andrade Souza、Denise Ramos Moreira、Nágila Maria Pontes Silva Ricardo、Martin Edmund Maier、Paulo Roberto Campos Flexa Ribeiro Filho、Francisco Murilo Tavares Luna、Cesar Liberato Petzhold
    DOI:10.1002/aocs.12648
    日期:2023.2
    acids prepared by transesterification (EHRO), epoxidation (TEPO), and oxirane ring opening with the aromatic amines aniline (ANIL) and p-anisidine (ANIS). The chemical structure of these oils was verified by 1H and 13C NMR analysis, and mass spectrometry. Measurements show that the presence of an aromatic amine increases the viscosity resulting in 172 (ANIL) and 199 (ANIS) cSt at 40°C, but reduces viscosity
    植物油由于其丰富、成本低、性能优异和环境友好,是非常有前途的化石润滑剂替代品。由于其多功能结构,蓖麻油是合成新型生物润滑剂的极佳前体。然而,它显示出较差的热氧化稳定性和较高的倾点。本研究使用通过酯交换 (EHRO)、环氧化 (TEPO) 和环氧乙烷开环与芳香胺苯胺 (ANIL) 和对茴香胺 (ANIS) 制备的蓖麻油脂肪酸。这些油的化学结构由1 H 和13验证C NMR分析和质谱分析。测量表明,芳香胺的存在会增加粘度,导致 40°C 下的粘度指数为 172 (ANIL) 和 199 (ANIS) cSt,但粘度指数分别降低至 16 和 1。此外,胺基可以清除自由基,增加它们的热稳定性和氧化稳定性。这些产品不会氧化铜,摩擦学分析显示 ANIS 具有最低的扭矩和磨损,相当于商业矿物润滑剂 NH-140。
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