亚麻酰基氯 | 59044-29-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 亚麻酰基氯
• 英文名称: cis,cis,cis-9,12,15-octadecatrienoyl chloride
• 英文别名: linolenoyl chloride；α-linolenoyl chloride；linolenic acid chloride；(9Z,12Z,15Z)-9,12,15-Octadecatrienoyl chloride；(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl chloride
• CAS: 59044-29-0
• 化学式: C₁₈H₂₉ClO
• 分子量: 296.881
• InChiKey: MRKXCQPDRPTZCG-PDBXOOCHSA-N

物化性质

• 沸点：
  382.9±21.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险类别码：
  R34
• 安全说明：
  S26,S36/37/39,S45
• 储存条件：
  请将商品存放在阴凉干燥处。

SDS

Name:	Linolenoyl Chloride (Pract) Material Safety Data Sheet
Synonym:	None known
CAS:	59044-29-0

Section 1 - Chemical Product MSDS Name:Linolenoyl Chloride (Pract) Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
59044-29-0	9,12,15-Octadecatrienoyl Chloride, (Z,	ca 100	261-572-7

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Corrosive.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. The toxicological properties of this substance have not been fully investigated.
Aspiration may lead to pulmonary edema. May cause systemic effects.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Discard contaminated shoes.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 59044-29-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: chlorine-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C18H29ClO
Molecular Weight: 296.88

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, chlorine, oxides of chlorine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 59044-29-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
9,12,15-Octadecatrienoyl Chloride, (Z,Z,Z)- - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3265
Packing Group: III
IMO
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 59044-29-0: No information available.
Canada
CAS# 59044-29-0 is listed on Canada's DSL List.
CAS# 59044-29-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 59044-29-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  亚麻酰基氯 在 Candida antarctica Lipase A 、 sodium chloride 、 zinc(II) chloride 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 异丙醇 为溶剂， 反应 1.0h， 生成 Γ-十八碳三烯酸
  参考文献：
  名称：

  通过半理性设计改变南极假丝酵母脂肪酶 A 的链长选择性以富集芥酸和贡多酸

  摘要：

  使用可再生材料作为起始底物的生物技术策略是用于分离不同脂肪酸的传统油脂化学工艺的有前途的替代方案。其中，长链单不饱和脂肪酸在工业脂质改性中尤其令人感兴趣，因为它们是多种经济相关产品的前体，包括洗涤剂、塑料和润滑剂。因此，本研究的目的是开发一种酶法，通过使用选择性脂肪酶来提高亚麻荠和海甘蓝油乙酯衍生物中长链单不饱和脂肪酸的百分比。具体来说，重点是分别从亚麻荠油和海甘蓝油衍生物中富集金刚烷酸(C20:1 cis Δ11) 和芥酸 (C22:1 cis Δ13)。实现这一目标需要几个步骤，包括：（i）选择合适的脂肪酶支架作为蛋白质工程模板（南极假丝酵母脂肪酶 A）；(ii) 鉴定潜在的氨基酸靶点以破坏适当位置处的结合隧道；(iii) 脂肪酶突变体文库的设计、创建和高通量筛选；(iv) 研究发现的最佳命中的不同链长对硝基苯基脂肪酸酯的选择性，以及分析每个氨基酸变化的贡献以及组合上述几种残基变化的结

  DOI：

  10.1002/adsc.201800889
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 亚麻酰基氯
  参考文献：
  名称：

  羟基与脂肪酸酯化对黄酮细胞毒性和抗氧化活性的影响

  摘要：

  由于体外研究的低细胞毒性，黄酮类化合物和多不饱和脂肪酸被认为是预防与氧化应激相关的疾病的潜在物质。我们研究了具有不同长度和饱和度的选定脂肪酸 (FA) 的新型 6-羟基黄烷酮和 7-羟基黄酮缀合物，并检查了它们的细胞毒性和抗氧化潜力。我们的研究结果表明，与 FA 的结合会影响两种原始黄酮类化合物的生物活性。6-羟基黄烷酮的结合增加了其对前列腺癌 PC3 细胞的细胞毒性。发现油酸结合物的效果最为显着。对于 7-羟基-黄酮缀合物也观察到了类似的趋势，其中对油酸盐和硬脂酸盐的影响最为明显。所有测试的缀合物的细胞毒性潜力对 PC3 没有特异性，因为人角质形成细胞 HaCaT 细胞的活力在暴露于所有缀合物后降低。此外，我们发现与原始化合物相比，两种黄酮类化合物的酯化降低了它们的抗氧化活性。在所有测试的化合物中，与原始化合物相比，只有 6-山梨黄烷酮的抗氧化能力略有增加。我们的数据表明，共轭类黄酮被更好地吸收并增强细胞毒性作用，但

  DOI：

  10.3390/molecules27020420

文献信息

• UNSATURATED FATTY ACID MONOESTERS AND DIESTERS ON ASCORBIC ACID AND COSMETIC USES THEREOF
  申请人：Poigny Stéphane

  公开号：US20120076744A1

  公开（公告）日：2012-03-29

  The present invention relates to a compound with the following general formula (I): in which: R 1 is a hydrocarbon chain of an unsaturated fatty acid from C 12 to C 24 including at least one unsaturation; and R 2 and R 3 are, independently or simultaneously: a hydrogen or a C 1 -C 3 alkyl or a phenyl; and R 4 : a hydrogen atom or COR 1′ , where R 1′ is a hydrocarbon chain of an unsaturated fatty acid from C 12 to C 24 including at least one unsaturation, advantageously 1 to 6 and preferably 1 to 4.

  本发明涉及具有以下一般式（I）的化合物： 其中：R1是来自C12到C24的不饱和脂肪酸的烃链，包括至少一个不饱和度；而R2和R3是独立或同时的：氢或C1-C3烷基或苯基；而R4：氢原子或COR1'，其中R1'是来自C12到C24的不饱和脂肪酸的烃链，有利地为1到6，优选为1到4。
• Amides of N-Deacetyllappaconitine and Unsaturated Fatty Acids
  作者：T. M. Gabbasov、E. M. Tsyrlina、S. G. Yunusova

  DOI：10.1007/s10600-018-2518-5

  日期：2018.9

  Amides were prepared from N-deacetyllappaconitine and unsaturated oleic, linoleic, α-linolenic, and γ-linolenic fatty acids.

  酰胺是由 N-脱乙酰基环乌头碱和不饱和油酸、亚油酸、α-亚麻酸和 γ-亚麻酸制备的。
• .gamma.-Aminobutyric acid esters. 2. Synthesis, brain uptake, and pharmacological properties of lipid esters of .gamma.-aminobutyric acid
  作者：James N. Jacob、Victor E. Shashoua、Alexander Campbell、Ross J. Baldessarini

  DOI：10.1021/jm00379a019

  日期：1985.1

  than that of free GABA. The results indicate that there is little or no blood-brain barrier for the GABA ester molecules at doses up to 0.36 mmol/kg. Both ester compounds, but neither free GABA nor the lipid components delivered systemically, demonstrated central nervous system depressant properties by inhibiting the general motor activity of mice. Brain tissue has esterase activity which can release

  合成了两种由U-14C标记和未标记的γ-氨基丁酸（GABA）制成的脂质酯，以测试类似于脂质双层膜正常成分的天然脂质类似物可以穿透血脑屏障并将外源GABA转运至大脑。1-亚油酰基-2,3-双（4-氨基丁酰基）丙烷-1,2,3-三醇和1,2-二亚油酰基-3-（4-氨基丁酰基）丙烷-1,2,3-三醇的吸收相对于肝脏，小鼠大脑的自由度分别比游离GABA高75倍和127倍。结果表明，剂量高达0.36 mmol / kg时，GABA酯分子几乎没有血脑屏障。既有酯化合物，也没有游离GABA或脂质成分，都是系统性递送的 通过抑制小鼠的一般运动活动，证明具有中枢神经系统抑制作用。脑组织具有酯酶活性，可以从这些化合物释放GABA。这表明这些化合物作为“前药”在中枢神经系统中释放GABA。
• Analysis of Intact Cholesteryl Esters of Furan Fatty Acids in Cod Liver
  作者：Simon Hammann、Christine Wendlinger、Walter Vetter

  DOI：10.1007/s11745-015-4019-7

  日期：2015.6

  Furan fatty acids (F-acids) are a class of natural antioxidants with a furan moiety in the acyl chain. These minor fatty acids have been reported to occur with high proportions in the cholesteryl ester fraction of fish livers. Here we present a method for the direct analysis of intact cholesteryl esters with F-acids and other fatty acids in cod liver lipids. For this purpose, the cholesteryl ester

  呋喃脂肪酸（F-酸）是一类天然抗氧化剂，在酰基链中具有呋喃部分。据报道，这些次要脂肪酸在鱼肝的胆固醇酯部分中以高比例存在。在这里，我们提出了一种直接分析完整的胆固醇酯与鳕鱼肝脂质中的F-酸和其他脂肪酸的方法。为此，通过固相萃取（SPE）分离胆固醇酯馏分，然后使用柱上冷却入口通过气相色谱质谱分析（GC / MS）进行分析。用胆固醇酯化的十五烷酸用作内标。F-酸胆固醇酯的GC / MS光谱显示了胆固醇和F-酸部分的分子离子以及特征性碎片离子。所有研究的鳕鱼肝样本（n = 8）均显示F-酸的胆甾醇酯，以及较低程度的常规脂肪酸。通过GC / MS-SIM，样品中最多可以测定十种F-酸胆固醇酯。胆甾醇酸酯与常规脂肪酸的浓度总计为78-140 mg / 100 g脂质（平均97 mg / 100 g脂质），而F-酸胆甾醇酯的含量为47-270 mg / 100 g脂质（平均130 mg / 100克脂质）。
• [EN] GEMCITABINE AMPHIPHILE PRODRUGS<br/>[FR] PROMÉDICAMENTS AMPHIPHILES À BASE DE GEMCITABINE
  申请人：NANOMED HOLDINGS PTY LTD

  公开号：WO2019204869A1

  公开（公告）日：2019-10-31

  The present invention relates to improved prodrugs, and compositions thereof. In particular, it relates to amphiphilic gemcitabine prodrugs or amphiphilic prodrugs of other biologically active molecules with the capacity to make liquid crystalline nanostructured nanoparticles, and uses thereof to treat animals, including humans.

  本发明涉及改进的前药及其组合物。具体而言，涉及两性的吉西他滨前药或其他生物活性分子的两性前药，具有制备液晶纳米结构纳米颗粒的能力，以及用途包括治疗动物，包括人类。