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Cas Database

59044-32-5

59044-32-5

Identification

  • Product Name:erucic acid chloride

  • CAS Number: 59044-32-5

  • EINECS:

  • Molecular Weight:357.02

  • Molecular Formula: C22H41ClO

  • HS Code:

  • Mol File:59044-32-5.mol

Synonyms:

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. 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. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 8 Articles be found

Studies on the synthesis, surface activity and the ability to form pH-regulated wormlike micelles with surfactant containing carboxyl group

Yan, Zhihu,Qian, Feng,Sun, Haonan,Lu, Xia,Li, Yu,Lv, Haibin,Dai, Caili,Jiao, Minglian

, (2020)

In this article, a series of pH regulated surfactants with different hydrophobic chain length and carboxyl group molecular structure positions were designed and synthesized. The molecular structure of pH regulated surfactants was analyzed by mass spectrometry and 1H NMR spectroscopy. The results of the surface activity test show that the pH regulated surfactants have lower surface tension, which indicates that it is easier to adsorb directionally at the gas-liquid interface and to aggregate in solution. Both inorganic and organic counterions can improve the viscosity of the system to some extent, but the viscosity-increasing ability of organic counterions is much higher than that of inorganic counterions. The results of rheology and dynamic light scattering show the transition from spherical micelles to wormlike micelles was observed when pH increased from 5 to 8 in the Docos-13-enoylamino-acetic acid (Gly-22)/Trimethylstearylammonium chioride (ODAC) system. The results of Cryo-transmission electron microscopy verify this result directly. Also, the experimental results show that the Gly-22/ODAC system has excellent pH cycle regulation performance, which can significantly reduce the application cost of the system.

Synthesis and high-performance of a new sarcosinate anionic surfactant with a long unsaturated tail

Yao, Runchong,Qian, Jiasheng,Li, Huazhen,Yasin, Akram,Xie, Yongjun,Yang, Haiyang

, p. 2865 - 2872 (2014)

A new C22 tailed sarcosinate anionic surfactant, 2-(N-erucacyl-N-methyl amido) acetate (EMAA), has been synthesized by use of the erucic acid and a hydrotrope - sarcosine. In contrast to the common method, which blends the hydrotrope with a surfactant, the sarcosine has been introduced into the anionic surfactant through chemical modification. Interestingly, the resultant C22 tailed anionic surfactant shows excellent water solubility despite the ultra-long alkyl chain. Besides, the EMAA also exhibits high surface activity, and pH controllable micelles to vesicles transition (MVT). Rheology studies have revealed that the rheological properties of EMAA solutions are influenced by the concentration, temperature, salt, and pH dramatically. Aside from the excellent water solubility, the original feature highlighted in this work is that such a new C22 tailed sarcosinate anionic surfactant exhibits good temperature resistance. Compared to the potassium oleate (KOA), the zero-shear viscosity of the EMAA solution is nearly 3 orders of magnitude higher under the same conditions.

Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents

Hassan, Ahmed H.E.,Park, Hye Rim,Yoon, Yoon Mi,Kim, Hye In,Yoo, Sung Yeun,Lee, Kun Won,Lee, Yong Sup

, p. 444 - 455 (2019/01/03)

Sphingomyelins and glycerophospholipids are structurally related phospholipids. Nevertheless, glycerophospholipids analogs are known as antitumor agents while sphingomyelin analogs were reported as cytoprotective agents. Herein, we have addressed the development of 3-deoxysphingomyelin analogs as cytotoxic agents possessing modified sphingobases. Thus, pyrrolidine-based 3-deoxysphingomyelin analogs were synthesized and evaluated against a panel of cell lines representing four major types of cancers. Compounds 3d, 4d and 6d elicited better GI50 values than the FDA approved drug miltefosine. Investigation of their impact on Akt phosphorylation as a possible mechanism for the antiproliferative activity of this class of compounds revealed that these compounds might elicit a concentration-dependent mechanism via inhibition of Akt phosphorylation at the lower concentration. Molecular docking predicted their binding modes to Akt to involve polar head binding to the Pleckstrin homology domain and hydrophobic tail extension into a hydrophobic pocket connecting the Pleckstrin homology domain and the kinase domain. As a whole, the described work suggests compounds 3d, 4d and 6d as promising pyrrolidine-based 3-deoxysphingomyelin analogs for development of novel cancer therapies.

Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides

Vudhgiri, Srikanth,Koude, Dhevendar,Veeragoni, Dileep Kumar,Misra, Sunil,Prasad,Jala, Ram Chandra Reddy

supporting information, p. 3370 - 3373 (2017/07/07)

In the present study, the synthesis of 1, 3, 4-thiadiazole-based thioglycosides were accomplished in good yields with employing a convergent synthetic route. The starting material 5-amino-1, 3, 4-thiadiazole-2-thiol and followed by a series of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a–4j) were synthesized with different fatty acid chlorides. The glycosylation of compounds 4a–4j were achieved with trichloroacetimidate methodology. Antimicrobial and cytotoxicity activities of title compounds were evaluated. Among the entire compounds lauric acid and myristic acid derivatives showed good and moderate antimicrobial activity. In case of cytotoxicity results of compounds 8a–8j and 9a–9j, the acetate protected short chain (C6:0, C8:0, C10:0) compounds and the free hydroxyl long chain saturated (C16:0, C18:0) and unsaturated (C18:1, C22:1) compounds exhibited good activity against different cancer cell lines. Further, the free hydroxyl compounds 9a, 9c–9j did not show any toxicity towards normal CHO-K1 cell line whereas acylated compounds 8a–8j exhibited toxicity.

Screening of a selection of commercially available homogeneous Ru-catalysts in valuable olefin metathesis transformations

Caijo, Frederic,Tripoteau, Fabien,Bellec, Aurelien,Crevisy, Christophe,Basle, Olivier,Mauduit, Marc,Briel, Oliver

, p. 429 - 435 (2013/03/14)

A library of thirteen different commercially available Ru-based catalysts was evaluated in valuable metathesis reactions for the production of fragrance and bioactive molecule precursors. Rigorous library screening clearly illustrated the different catalytic behaviour of the catalyst selection and highlighted its significant advantage to provide efficiency in specific metathesis applications. Interestingly, this strategy offered substantial improvement over the state of the art, with the efficient synthesis of the macrocyclic Exaltolide 2 at low catalyst loading and dilution conditions. The Royal Society of Chemistry 2013.

Process route upstream and downstream products

Process route

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

Conditions
Conditions Yield
With thionyl chloride;
With oxalyl dichloride; for 3h;
With thionyl chloride; In dichloromethane; at 50 ℃; for 4h;
With oxalyl dichloride; In dichloromethane; Inert atmosphere;
With thionyl chloride; In toluene; at 80 ℃; for 2h;
With phosphorus trichloride; at 78 ℃; for 3h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere; Schlenk technique;
docos-13-enoic acid
1072-39-5

docos-13-enoic acid

docos-13-enoyl chloride
7459-29-2,59044-32-5

docos-13-enoyl chloride

Conditions
Conditions Yield
With thionyl chloride; In benzene; at 70 - 90 ℃;
Brassidic acid
506-33-2

Brassidic acid

docos-13-enoyl chloride
7459-29-2,59044-32-5

docos-13-enoyl chloride

Conditions
Conditions Yield
With thionyl chloride; brassidic acid chloride;
oxalyl dichloride
79-37-8

oxalyl dichloride

cis-13-docosenoic acid
112-86-7

cis-13-docosenoic acid

erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

Conditions
Conditions Yield
erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

pentadecanolide
106-02-5,81031-90-5

pentadecanolide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: dichloromethane / 2 h / 20 °C
2.1: cis-Caz-1 / toluene / 4 h / 80 °C
2.2: 20 °C / 760.05 Torr
With cis-Caz-1; In dichloromethane; toluene;
erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

Unislip 1753
112-84-5

Unislip 1753

Conditions
Conditions Yield
With ammonium hydroxide;
C<sub>18</sub>H<sub>13</sub>F<sub>17</sub>O<sub>2</sub>
1011483-45-6

C18H13F17O2

erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

C<sub>40</sub>H<sub>53</sub>F<sub>17</sub>O<sub>3</sub>

C40H53F17O3

Conditions
Conditions Yield
With triethylamine; In tetrahydrofuran; at 20 ℃; for 12h;
Vanillylamin
1196-92-5

Vanillylamin

erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

(Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-docos-13-enamide

(Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-docos-13-enamide

Conditions
Conditions Yield
In diethyl ether; N,N-dimethyl-formamide; Ambient temperature;
67%
erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

p-nitrophenyl erucate

p-nitrophenyl erucate

Conditions
Conditions Yield
With zinc(II) chloride; In dichloromethane; for 1h; Inert atmosphere; Reflux;
81%
erucic acid chloride
59044-32-5,7459-29-2

erucic acid chloride

3.6-dihydroxy-2-(heneicosen-(12<i>c</i>)-yl)-benzoquinone-(1.4)

3.6-dihydroxy-2-(heneicosen-(12c)-yl)-benzoquinone-(1.4)

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: petroleum ether; sodium peroxide; ice water
2: acetic acid; ethanol; petroleum ether / Behandeln einer Loesung des Reaktionsprodukts in Petrolaether mit Luft
With (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sodium peroxide; ethanol; acetic acid; Petroleum ether;
Multi-step reaction with 2 steps
1: petroleum ether; sodium peroxide; ice water
2: acetic acid; diethyl ether; petroleum ether
With (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sodium peroxide; diethyl ether; acetic acid; Petroleum ether;

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