methyl ricinoleate | 23224-20-6

• 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
• 英文名称: methyl ricinoleate
• 英文别名: 9-octadecenoic acid 12-hydroxy-methyl ester；methyl 12-hydroxy-9-octadecenoate；methyl 12-hydroxyoctadec-9-enoate；12-hydroxy-octadec-9-enoic acid methyl ester；12-Hydroxy-octadec-9-ensaeure-methylester；11-Hydroxy-heptadec-8-en-1-carbonsaeure-methylester
• CAS: 23224-20-6；141-24-2；7706-01-6；41989-07-5；67529-83-3；84799-82-6；84799-83-7；127062-53-7；127062-89-9
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: XKGDWZQXVZSXAO-UHFFFAOYSA-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
• 稳定性/保质期：
  在常温常压下，该物质是稳定的。

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、球囊阀面罩设备或口袋面罩，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。如果患者呕吐，让患者向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，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，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"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液。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……。 /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 /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/甲基蓖麻酸酯在这个测试浓度范围内（1.25×10^5到4×10^-4 M）未能抑制平滑肌的抽搐反应。在自发收缩的兔空肠中也报告了类似的结果。

/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

通过胃插管给予甲基麻风子酸酯后，麻风子酸被更多地整合到甘油酯中，这是在胸导管插管的 rats 中进行的。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
• 储存条件：
  -20°C条件下保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Methyl ricinelaidate
CAS-No. : 7706-01-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Ricinelaidic acid methyl ester
Methyl trans-12-hydroxy-9-octadecenoate
Formula : C19H36O3
Molecular Weight : 312,49 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
no data available
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature: -20 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. Use respirators and components tested and approved under
appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

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。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  蓖麻油酸	Ricinoleic acid	141-22-0	C18H34O3	298.466
  10-烯酸甲酯	Methyl 10-undecenoate	111-81-9	C12H22O2	198.305

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  12-羟基硬脂酸甲酯	methyl 12-hydroxyoctadecanoate	141-23-1	C19H38O3	314.509
  ——	methyl (Z)-10-cyano-9-decenoate	173602-45-4	C12H19NO2	209.288
  ——	methyl (E)-10-cyano-9-decenoate	173602-43-2	C12H19NO2	209.288
  亚油酸甲酯	Methyl linoleate	112-63-0	C19H34O2	294.478
  9顺,12反-十八碳二烯酸甲酯	methyl (9Z,12E)-9,12-octadecadienoate	20221-26-5	C19H34O2	294.478
  10-烯酸甲酯	Methyl 10-undecenoate	111-81-9	C12H22O2	198.305
  9-十八烯-1,12-二醇	octadec-9-ene-1,12-diol	1577-55-5	C18H36O2	284.483
  ——	methyl cis,cis-9,11-octadecadienoate	822-10-6	C19H34O2	294.478
  9C,11TR-共轭亚油酸甲酯	(9Z,11E)-methyl octadeca-9,11-dienoate	13058-52-1	C19H34O2	294.478
  (9E,11E)-9,11-十八碳二烯酸甲酯	octadeca-9,11-dienoic acid methyl ester	822-10-6	C19H34O2	294.478

反应信息

• 作为反应物：
  描述：

  methyl ricinoleate 在 乙酰氯 作用下， 生成 12-羟基硬脂酸
  参考文献：
  名称：

  Sigmund; Haas, Monatshefte fur Chemie, 1928, vol. 50, p. 364

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 蓖麻油酸 在 盐酸 作用下， 生成 methyl ricinoleate
  参考文献：
  名称：

  Walden, Chemische Berichte, 1903, vol. 36, p. 782

  摘要：

  DOI：

文献信息

• Hyperbranched polyesters by polycondensation of fatty acid-based AB_n-type monomers
  作者：Blandine Testud、Didier Pintori、Etienne Grau、Daniel Taton、Henri Cramail

  DOI：10.1039/c6gc02294d

  日期：——

  Widely available vegetable oils were readily derivatized into chemically pure ABn-type monomers (n = 2 or 3). Their polymerization led to unprecedented hyperbranched polyesters. Four different AB2/AB3-type monomers bearing one...

  广泛使用的植物油很容易衍生为化学纯的ABn型单体（n = 2或3）。他们的聚合反应导致了前所未有的超支化聚酯。四种不同的AB2 / AB3型单体带有一个...
• Synthesis of Enantiomerically Pure 2,3,4,6-Tetrasubstituted Tetrahydropyrans by Prins-Type Cyclization of Methyl Ricinoleate and Aldehydes
  作者：Ursula Biermann、Arne Lützen、Jürgen O. Metzger

  DOI：10.1002/ejoc.200500701

  日期：2006.6

  The AlCl3-catalyzed Prins-type cyclization of methyl ricinoleate (1), an enantiomerically pure renewable compound, with aldehydes such as heptanal (2a), isobutyraldehyde (2b), pivaldehyde (2c) and benzaldehyde (2d) is a simple reaction for the diastereoselective synthesis of enantiomerically pure 2,3,6-trialkyl-substituted 4-chlorotetrahydropyrans. The respective 4-hydroxytetrahydropyrans are obtained

  AlCl3 催化的蓖麻油酸甲酯 (1) 的 Prins 型环化反应是一种对映异构纯的可再生化合物，与醛类如庚醛 (2a)、异丁醛 (2b)、新戊醛 (2c) 和苯甲醛 (2d) 是一个简单的反应对映体纯 2,3,6-三烷基取代的 4-氯四氢吡喃的非对映选择性合成。相应的4-羟基四氢吡喃例如用醛2a和2d使用蒙脱石KSF/O作为催化剂获得。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Ruthenium–alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: a key step toward long-chain bifunctional and amino acid compounds
  作者：X. Miao、R. Malacea、C. Fischmeister、C. Bruneau、P. H. Dixneuf

  DOI：10.1039/c1gc15569e

  日期：——

  The ruthenium catalysed cross-metathesis of fatty-esters arising from plant oils with acrylonitrile is presented. The resulting linear nitrile ester products have potential as new intermediates for polyamides synthesis. A series of commercially available catalysts are able to promote the transformation of methyl 10-undecenoate 1, dimethyl octadec-9-en-1,18-dioate 5 and methyl ricinoleate 9 with acrylonitrile

  这 钌 催化交叉复分解 的 脂肪的--酯类 来自植物油的 丙烯腈被表达。结果线性腈 酯产品具有潜在的新中间体 聚酰胺纤维合成。一系列可商购的催化剂 能够促进变革 10-十一碳烯酸甲酯 1，octadec-9-en-1,18-diate的二甲基 5和甲基蓖麻油酸酯9与丙烯腈 和基于缓慢添加的协议 催化剂 允许交叉使用的TON高达1900（92％的收益）复分解 和 丙烯腈。这些交叉复分解 条件已应用于 丙烯酸甲酯 TON达到7600。
• Palladium Catalysed Acid‐Free Carboxytelomerisation of 1,3‐Butadiene with Alcohols Accessing Pelargonic Acid Derivatives Including Triglycerides under Selectivity Control
  作者：Dennis Vogelsang、Johanna Vondran、Kevin Hares、Kevin Schäfer、Thomas Seidensticker、Andreas J. Vorholt

  DOI：10.1002/adsc.201901383

  日期：2020.2.6

  100% atom economic manner. Effects of nucleophilicity and sterical demands were revealed for monoalcohols, di‐ and polyols. Whilst yields, chemoselectivity and E/Z‐selectivity of the pelargonic acid derivatives were excellent with up to 99%, selectivity towards mono‐, di‐ and triesters could be controlled successfully. Finally, the reaction profile of the carboxytelomerisation glycerol was uncovered

  钯催化的1,3-丁二烯与醇的羧基端聚反应以原子经济和直接的方式产生不饱和C 9-壬酸酯。尽管羧基端聚是当前关注的问题，但尚未充分研究适用的醇底物的局限性。在这里，我们提出的催化系统的转移包括乙酸钯和三- Ñ吡啶中的叔丁基膦与20种醇的亲核性和空间要求差异很大，以100％原子经济的方式产生相应的酯。一元醇，二元醇和多元醇显示出亲核性和空间需求的影响。壬酸衍生物的收率，化学选择性和E / Z选择性均极佳，最高可达99％，但对单酯，二酯和三酯的选择性仍可成功控制。最后，未发现羧基端粒化甘油的反应曲线，产生了高达97％的工业相关不饱和C 9-短链脂肪。
• Process for the synthesis of unsaturated alcohols
  申请人：Maughon R. Bob

  公开号：US20050080301A1

  公开（公告）日：2005-04-14

  A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.

  一种制备不饱和醇（烯醇）的过程，例如，保护羟基取代的不饱和脂肪酸或脂肪酸酯，例如来自种子油的甲基蓖麻油酸甲酯，形成羟基保护的不饱和脂肪酸或脂肪酸酯; 同型交换或交叉交换羟基保护的不饱和脂肪酸或脂肪酸酯，以产生含有羟基保护的不饱和交换产物的产物混合物; 并在足以制备不饱和醇的条件下去除羟基保护的不饱和交换产物。优选地，通过交叉或同型交换将甲基蓖麻油酸甲酯转化为同型烯丙基单醇1-癸烯-4-醇或同型烯丙基多醇9-十八烯-7,12-二醇。