花生四烯酸甲酯 | 2566-89-4

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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: 花生四烯酸甲酯
• 中文别名: 花生四烯酸甲基酯
• 英文名称: methyl arachidonate
• 英文别名: arachidonic acid methyl ester；5,8,11,14-eicosatetraenoic acid methyl ester；methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 2566-89-4
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: OFIDNKMQBYGNIW-ZKWNWVNESA-N

物化性质

• 沸点：
  200-205℃ (1-2 Torr)
• 密度：
  0.9168 g/cm3
• 溶解度：
  氯仿：50 mg/mL，澄清，无色
• LogP：
  7.466 (est)
• 保留指数：
  2231;2231;2231;2225.1
• 稳定性/保质期：
  1. 如果遵照规格使用和储存，则不会分解。 2. 它存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  4.2
• 危险品标志：
  Xn,F,N
• 安全说明：
  S16,S29,S33,S60,S61,S62,S9
• 危险类别码：
  R19
• WGK Germany：
  2,3
• 危险品运输编号：
  UN 3183 4
• 海关编码：
  2916190090
• 包装等级：
  I
• 危险类别：
  4.2
• 危险标志：
  GHS07,GHS08,GHS09
• 危险性描述：
  H304,H315,H336,H410
• 危险性防范说明：
  P261,P273,P301 + P310,P331,P501
• 储存条件：
  充氩密封，在-18℃及以下干燥避光条件下保存。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Methyl arachidonate
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 2566-89-4
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
Classification according to Regulation (EC) No 1272/2008
Self-heating substances and mixtures (Category 2), H252
For the full text of the H-Statements mentioned in this Section, see Section 16.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H252 Self-heating in large quantities; may catch fire.
Precautionary statement(s)
P235 + P410 Keep cool. Protect from sunlight.
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : Arachidonic acid methyl ester
Formula : C21H34O2
Molecular weight : 318,49 g/mol
CAS-No. : 2566-89-4
No components need to be disclosed according to the applicable regulations.
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult 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
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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 firefighting if necessary.
Further information
Use water spray to cool unopened containers.

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13).
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Keep away from sources of ignition - No smoking.
For precautions see section 2.2.
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
Air and moisture sensitive.
Storage class (TRGS 510): Pyrophoric and self-heating hazardous materials
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
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.
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
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: light yellow
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) Auto-ignition Self-heating in large quantities; may catch fire.
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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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 sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. 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: 3183 IMDG: 3183 IATA: 3183
UN proper shipping name
ADR/RID: SELF-HEATING LIQUID, ORGANIC, N.O.S. (Methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-
tetraenoate)
IMDG: SELF-HEATING LIQUID, ORGANIC, N.O.S. (Methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-
tetraenoate)
IATA: Self-heating liquid, organic, n.o.s. (Methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate)
Transport hazard class(es)
ADR/RID: 4.2 IMDG: 4.2 IATA: 4.2
Packaging group
ADR/RID: III IMDG: III IATA: III
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

制备方法

生化研究和气相色谱分析标准。

用途简介 用途

生化研究和气相色谱分析标准。

反应信息

• 作为反应物：
  描述：

  花生四烯酸甲酯 在 异丙醇 、 2-巯基乙醇 作用下， 生成 全反式花生四烯酸甲酯
  参考文献：
  名称：

  Synthesis of all-trans arachidonic acid and its effect on rabbit platelet aggregation

  摘要：

  A simple and high-yielding method to convert natural all-cis PUFA derivatives to the corresponding all-trans geometrical isomers is described. The method is based on the thiyl radical-catalyzed cis-trans isomerization. The all-trans isomer of arachidonic acid was found to cause rabbit platelet aggregation at concentrations higher than 0.1 mM and inhibition of PAF-induced platelet aggregation in a concentration dependent manner with an IC50 in the micromolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.109
• 作为产物：
  描述：

  花生四烯酸 以 氯仿 为溶剂， 反应 5.0h， 生成 花生四烯酸甲酯
  参考文献：
  名称：

  1,1′-OXALYLDIIMIDAZOLE, A NEW REAGENT FOR ACTIVATION OF CARBOXYLIC ACID

  摘要：

  羧酸及其盐通过标题试剂转变为1-酰基咪唑。这一反应被应用于脂肪酸的酯化过程。

  DOI：

  10.1246/cl.1983.1819

文献信息

• Structural Requirements for Binding of Anandamide-Type Compounds to the Brain Cannabinoid Receptor
  作者：Tzviel Sheskin、Lumir Hanuš、Joram Slager、Zvi Vogel、Raphael Mechoulam

  DOI：10.1021/jm960752x

  日期：1997.2.1

  inactive or less active than comparable compounds in the n-6 series. Alkylation or dialkylation of the alpha carbon adjacent to the carbonyl group retains the level of binding in the case of anandamide (compounds 48, 49); however, alpha-monomethylation or alpha,alpha-dimethylation of N-propyl derivatives (50-53) potentiates binding and leads to the most active compounds seen in the present work (Ki values

  为了建立与脑大麻素受体（CB1）结合的结构要求，我们合成了许多脂肪酸酰胺，乙醇酰胺和一些相关的简单衍生物，并确定了它们的Ki值。还检查了一些α-甲基或α，α-二甲基花生四烯酰基烷基酰胺。在20：4，n-6系列中，未取代的酰胺是惰性的；N-单烷基化，至少直至分支的戊基，导致显着的结合。N，N-二烷基化，在一个烷基上具有或不具有羟基化，导致活性的消除。在ω碳原子上的N-单烷基的羟基化保持活性。在20x，n-6序列中，x必须为3或4；否则，x为3。只有两个双键的存在会导致失活。在n-3系列中 报告的有限数据表明，衍生的乙醇酰胺比n-6系列中的同类化合物无活性或活性较低。对于邻氨基苯甲酰胺（化合物48、49），与羰基相邻的α碳的烷基化或二烷基化保持结合水平。但是，N-丙基衍生物（50-53）的α-单甲基化或α，α-二甲基化可增强结合并导致本研究中活性最高的化合物（Ki值为6.9 +/- 0.7至8
• [EN] PKC ACTIVATORS AND COMBINATIONS THEREOF<br/>[FR] ACTIVATEURS DE PKC ET DES COMBINAISONS DE CEUX-CI
  申请人：BRNI NEUROSCIENCES INST

  公开号：WO2013071282A1

  公开（公告）日：2013-05-16

  The present disclosure relates to PKC activators and combinations thereof. The disclosure further relates to compositions, kits, uses, and methods thereof.

  本公开涉及PKC激活剂及其组合物。本公开进一步涉及其组成物、试剂盒、用途和方法。
• Cannabimimetic lipid amides as useful medications
  申请人：University of Connecticut

  公开号：US07161016B1

  公开（公告）日：2007-01-09

  Novel analogs of arachidonylethanolamide are presented which have higher affinities for the cannabinoid CB1 and/or CB2 receptor sites. Further, most of the analogs exhibit greater metabolic stability than arachidonylethanolamide. The improved receptor affinity and selectivity and/or greater metabolic stability make these analogs therapeutically useful as medications for relief of pain caused by cancer and nausea caused by chemotherapy, as well as for peripheral pain. The compounds may also be useful as oral and topical contraceptives, in suppression of the immune system, enhancement of appetite and in treatment of psychomotor disorders, multiple sclerosis and hypertension.

  新型的花生四烯酰乙醇胺类似物具有更高的亲和力，适用于大麻素CB1和/或CB2受体位点。此外，大多数类似物表现出比花生四烯酰乙醇胺更高的代谢稳定性。改善的受体亲和力和选择性和/或更高的代谢稳定性使这些类似物在作为药物用于缓解癌症引起的疼痛和化疗引起的恶心，以及外周疼痛方面具有治疗用途。这些化合物也可能用于口服和局部避孕药、免疫系统抑制、增强食欲以及治疗精神运动障碍、多发性硬化和高血压。
• Pharmacological and behavioral evaluation of alkylated anandamide analogs
  作者：Irma B. Adams、William Ryan、Michael Singer、Raj K. Razdan、David R. Compton、Billy R. Martin

  DOI：10.1016/0024-3205(95)00187-b

  日期：1995.5

  examined structure-activity relationships in alkylated anandamide analogs. The analogs were evaluated for their ability to displace [3H]CP-55,940 in a filtration binding assay using rat brain membranes in the presence and absence of the enzyme inhibitor phenylmethylsulfonyl fluoride (PMSF). Behavioral activity was assessed by the ability of the analogs to produce hypomotility and antinociception. Methylations

  从猪脑中分离出的Anandamide（花生四烯基乙醇酰胺）已在药理学分析中与大麻素受体结合并产生大麻素活性。这项研究检查了烷基化的anandamide类似物的构效关系。在存在和不存在酶抑制剂苯基甲基磺酰氟（PMSF）的情况下，使用大鼠脑膜在过滤结合试验中评估了类似物置换[3H] CP-55,940的能力。通过类似物产生动力不足和抗伤害感受的能力来评估行为活性。在不存在PMSF的情况下，碳2和1处的甲基化可稳定形成化合物，其亲和力和行为活性与Anandamide类似。在这些位置或氮甲基化处添加较大的烷基会降低受体亲和力和行为能力。这些结果表明在anandamide的特定碳甲基化赋予体外稳定性。
• A Facile Method for Activation of Carboxylic Acids
  作者：Shizuaki Murata

  DOI：10.1246/bcsj.57.3597

  日期：1984.12

  1,1′-Oxalyldiimidazole, -1,2,4-triazole, and -1,2,3,4-tetrazole were prepared in situ from oxalyl dichloride and corresponding 1H-azoles. The 1,1′-oxalyldiazoles converted carboxylic acids and their salts into 1-acylazoles.

  1,1'-草酰二咪唑、-1,2,4-三唑和-1,2,3,4-四唑由草酰二氯和相应的1H-唑原位制备。1,1'-草酰二唑将羧酸及其盐转化为 1-酰基唑。

表征谱图