蓖麻油酸甲酯 | 141-24-2

• 物质功能分类: 分析化学 - 标准品 - 食品和饮料标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 蓖麻油酸甲酯
• 中文别名: 蓖麻油酸甲酯(即12-羟基-9-十八碳烯酸甲酯)；蓖麻醇酸甲酯；12-羟基-9-十八碳烯酸甲酯
• 英文名称: methyl ricinoleate
• 英文别名: ricinoleic acid methyl ester；methyl (9Z,12R)-12-hydroxyoctadec-9-enoate；methyl (9Z,12R)-12-hydroxy-9-octadecenoate；methyl (R)-ricinoleate；(R,Z)-methyl 12-hydroxyoctadec-9-enoate；methyl (Z,12R)-12-hydroxyoctadec-9-enoate
• CAS: 141-24-2
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: XKGDWZQXVZSXAO-ADYSOMBNSA-N

物化性质

• 熔点：
  -29°C
• 沸点：
  170°C 1mm
• 密度：
  0,925 g/cm3
• 闪点：
  209 °C
• 溶解度：
  DMF：50mg/mL； DMSO：50mg/mL；乙醇：100mg/mL；乙醇:PBS (pH 7.2) (1:1): 0.5 mg/mL
• LogP：
  5.1 at 25℃
• 物理描述：
  Liquid
• 颜色/状态：
  Colorless liquid
• 蒸汽压力：
  6.85X10-8 mm Hg at 25 °C (est)
• 折光率：
  Index of refraction: 1.4628

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

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（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)

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……。预期可能出现癫痫，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，用干燥的灭菌敷料覆盖皮肤烧伤……。/毒物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……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸林格氏液。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……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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 or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：神经毒性/甲基麻风酸酯未能抑制在此测试浓度范围内（1.25×10^5至4×10^-4 M）的平滑肌抽搐反应。类似的结果也见于自发收缩的兔空肠。

/LABORATORY ANIMALS: Neurotoxicity/ Methyl ricinoleate failed to depress the smooth muscle twitch response over this range /1.25X10+5 to 4X10-4 M/ of test concentrations. Similar results were reported for spontaneously contracting rabbit jejunum.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

通过胃插管给予胸腔导管插管的大鼠甲基蓖麻油酸乙酯后，蓖麻油酸被更多地并入甘油酯中。在48小时内收集淋巴液。

Incorporation of ricinoleic acid into glycerides was increased after the administration of methyl ricinoleate by gastric intubation to thoracic duct-cannulated rats. Lymph was collected over a 48-hr period.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  TSCA listed
• WGK Germany：
  3
• 海关编码：
  2918199090
• 危险品运输编号：
  NONH for all modes of transport
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

用途
用于特殊有机化学品的制备。

生产方法
由蓖麻油酸和甲醇酯化制得。

反应信息

• 作为反应物：
  描述：

  蓖麻油酸甲酯 在 N-(2-aminoethyl)-3-aminopropyl-modified silica-alumina 作用下， 以 正己烷 为溶剂， 反应 12.0h， 生成 (Z)-2-戊基壬-2-烯醛
  参考文献：
  名称：

  Selective conversion of castor oil derived ricinoleic acid methyl ester into jet fuel

  摘要：

  将蓖麻油酸甲酯选择性转化为喷气燃料，而不损失脂肪酸链中的碳。

  DOI：

  10.1039/c6gc00942e
• 作为产物：
  描述：

  蓖麻油酸 以 甲醇 为溶剂， 生成 蓖麻油酸甲酯
  参考文献：
  名称：

  Polymeric formulations for drug delivery

  摘要：

  本文公开了由蓖麻油酸和天然脂肪二酸形成的聚酯酸酐或聚酯以及它们的制备方法，以及它们用于输送生物活性剂，包括小分子药物、肽和蛋白质、DNA和带阳离子脂质或聚合物或纳米和微粒子的DNA复合物。这些药物输送组合物以液态形式给患者使用，在体内粘度增加形成药物库或植入物，并能够持续释放所包含的生物活性剂达数周之久。在首选实施例中，药物输送配方通过注射给予。在一个实施例中，该组合物适用于将药物局部或区域性输送到疾病部位，例如治疗实体肿瘤和骨感染。在首选实施例中，药物输送组合物适用于针对实体肿瘤的特定部位化疗，包括头颈鳞状细胞癌（SCC）、前列腺癌和肉瘤的肿瘤内注射或插入。

  公开号：

  US20040161464A1

文献信息

• METHOD FOR THE SYNTHESIS OF DIACIDS OR DIESTERS FROM NATURAL FATTY ACIDS AND/OR ESTERS
  申请人：Dubois Jean-Luc

  公开号：US20100305354A1

  公开（公告）日：2010-12-02

  The invention relates to a process for the synthesis of diacids or diesters of general formula ROOC—(CH 2 ) x —COOR, in which n is an integer between 5 and 14, R is either H or an alkyl radical of 1 to 4 carbon atoms, from natural long-chain monounsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule of the general formula CH 3 —(CH 2 ) n —CHR 1 —CH 2 —CH═CH—(CH 2 ) p —COOR, in which R is H or an alkyl radical with 1 to 4 carbon atoms, R 1 is either H or OH, and n and p, which are equal or different and are indices between 2 and 11. The method comprises: during a first step, converting the natural fatty acid or ester by pyrolysis or by ethenolysis, into a ω-monounsaturated fatty acid or ester of the general formula CH 2 ═CH—(CH 2 ) m —COOR, in which m is equal to p or p+1, depending on the nature of the processed fatty acid/ester and the conversion used; during a second step, submitting the product thus obtained to a metathesis or homometathesis reaction for obtaining a compound of the general formula ROOC—(CH 2 ) m —CH═CH—(CH 2 ) m —COOR, or cross-metathesis with a compound of formula R 2 OOC—(CH 2 ) r —CH═CH—R 3 , in which R 2 is either H or an alkyl radical front with 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R 3 is H, CH 3 or COOR 2 , thus defining a cyclic or molecule or not, in order to obtain an unsaturated compound of the general formula ROOC—(CH 2 ) m —CH═CH—(CH 2 ) r —COOR 2 , and during a third step, converting the unsaturated compound into a saturated compound by hydrogenation of the double bond.

  这项发明涉及一种合成一般公式为ROOC—(CH2)x—COOR的二元酸或二元酯的过程，其中n是5到14之间的整数，R是H或1到4个碳原子的烷基自由基，从天然长链单不饱和脂肪酸或酯中合成，这些脂肪酸或酯每分子至少包括10个相邻的碳原子，其一般公式为CH3—(CH2)n—CHR1—CH2—CH═CH—(CH2)p—COOR，其中R是H或1到4个碳原子的烷基自由基，R1是H或OH，n和p相等或不同，是2到11之间的指数。该方法包括：在第一步中，通过热解或乙炔醇解将天然脂肪酸或酯转化为ω-单不饱和脂肪酸或酯，其一般公式为CH2═CH—(CH2)m—COOR，其中m等于p或p+1，具体取决于处理的脂肪酸/酯的性质和所使用的转化；在第二步中，将所得产物进行交叉代谢或同交叉代谢反应，以获得一般公式为ROOC—(CH2)m—CH═CH—(CH2)m—COOR的化合物，或与公式为R2OOC—(CH2)r—CH═CH—R3的化合物进行交叉代谢，其中R2是H或1到4个碳原子的烷基自由基，r是0或1或2，R3是H、CH3或COOR2，从而定义一个循环或不循环的分子，以获得一般公式为ROOC—(CH2)m—CH═CH—(CH2)r—COOR2的不饱和化合物；在第三步中，通过加氢双键将不饱和化合物转化为饱和化合物。
• METHOD FOR THE SYNTHESIS OF AN OMEGA-AMINO ACID OR ESTER STARTING FROM A MONOUNSATURATED FATTY ACID OR ESTER
  申请人：Dubois Jean-Luc

  公开号：US20110224454A1

  公开（公告）日：2011-09-15

  The invention relates to a method for the synthesis of ω-amino alkanoic acids or esters thereof starting from unsaturated natural fatty acids passing through an ω-unsaturated nitrile intermediate compound.

  该发明涉及一种从非饱和天然脂肪酸开始，通过一种ω-非饱和腈中间化合物来合成ω-氨基烷酸或其酯的方法。
• Amino acid preparation method comprising a step of hydroformylation of an unsaturated fatty nitrile
  申请人：ARKEMA FRANCE

  公开号：US10125221B2

  公开（公告）日：2018-11-13

  A process for synthesizing an ω-amino acid compound of formula HOOC—(CH2)r+2—CH2NH2, wherein 4≤r≤13 from a monounsaturated fatty nitrile compound of formula CH2═CH—(CH2)r—CN the process comprising: 1) a step of hydroformylation of the mono unsaturated fatty nitrile compound by reacting said nitrile with carbon monoxide and di hydrogen 5e-a5 to obtain a nitrile aldehyde compound of formula HOC—(CH2)r+2-CN, then 2) a step of oxidation, in the presence of dioxygen, of the nitrile aldehyde compound to obtain a corresponding nitrile acid compound of formula HOOC—(CH2)r+2-CN, and 3) a step of reduction of the nitrile acid compound to give an w-amino acid of formula HOOC—(CH2)r+2—CH2NH2.

  一种用于合成ω-氨基酸化合物公式 HOOC—(CH2)r+2—CH2NH2， 其中4≤r≤13，从单不饱和脂肪酸腈化合物公式 CH2═CH—(CH2)r—CN 该工艺包括：1）单不饱和脂肪酸腈化合物的氢甲酰化步骤，通过将所述腈与一氧化碳和二氢5e-a5反应，以获得腈醛化合物公式HOC—(CH2)r+2-CN，然后2）在 dioxygen 存在的情况下，氧化腈醛化合物以获得相应的腈酸化合物公式HOOC—(CH2)r+2-CN，以及3）将腈酸化合物还原为给出w-氨基酸的公式 HOOC—(CH2)r+2—CH2NH2.
• Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters
  作者：Anis Ahmad、Aiman Ahmad、Raja Sudhakar、Himani Varshney、Naidu Subbarao、Saba Ansari、Abdul Rauf、Asad U. Khan

  DOI：10.1080/07391102.2016.1255260

  日期：2017.11.18

  In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized

  在这项研究中，设计了一系列新的恶唑啉和噻唑啉作为白色念珠菌的细胞色素P450 14α-甾醇脱甲基酶（CYP51）和大肠杆菌的肽去甲酰基酶（PDF）的抑制剂。脂肪酸酯的长链二溴衍生物与尿素和硫脲反应后，分别得到了相应的恶唑啉和噻唑啉。所有化合物均通过其光谱数据（IR，1 H NMR，13NMR和MS），并通过圆盘扩散测定法测试其抗菌和抗真菌活性，并通过肉汤微稀释法测定其对革兰氏阳性和革兰氏阴性菌以及真菌菌株的最低抑菌浓度。抗菌筛选研究表明，所有化合物均为有效的抗菌剂。通过物质活性谱预测软件计算出化合物的相似药物特性后，Discovery Studio 2.5会计算与ADMET相关的描述符，以预测活性和生物利用度化合物的药代动力学特性。在大肠杆菌PDF和白色念珠菌CYP 450-14DM上进行了分子对接研究了解分子在受体活性位点的结合方式。化合物（2-氨基-5-（羰甲氧基辛基）-1,3-恶唑啉，2-氨基-5-（羧甲氧基辛基）-1
• [EN] NEW PROCESS OF PREPARATION OF POLYOLS AND POLYAMINES, AND PRODUCTS AS OBTAINED<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE POLYOLS ET DE POLYAMINES, ET PRODUITS OBTENUS
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2013072436A1

  公开（公告）日：2013-05-23

  The present invention relates to the use of a compound of formula (I) : wherein: - R represents –OH or –NH2;- A1 represents a divalent alkylene radical, straight or branched, having from 2 to 20 carbon atoms; - A2 represents a divalent alkylene radical, straight or branched, having from 1 to 20 carbon atoms; - X1 and X2 represent, independently of each other, –NH- or –O-;- A3 represents a divalent alkylene radical, straight or branched, having from 1 to 10 carbon atoms; - Z represents a hydrogen or a group of formula (A'): wherein A1, A3 and R are as defined above in formula (I), for the preparation of a polymer chosen among polyurethane, polyester and polyamide.

  本发明涉及使用公式（I）的化合物：其中：- R代表-OH或-NH2；- A1代表一个二价亚烷基基团，直链或支链，具有2到20个碳原子；- A2代表一个二价亚烷基基团，直链或支链，具有1到20个碳原子；- X1和X2分别独立地代表-NH-或-O-；- A3代表一个二价亚烷基基团，直链或支链，具有1到10个碳原子；- Z代表氢或公式（A'）的基团：其中A1、A3和R在公式（I）中如上定义，用于制备选自聚氨酯、聚酯和聚酰胺的聚合物。

表征谱图