亚油醇乙醇胺 | 68171-52-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 亚油醇乙醇胺
• 英文名称: N-linoleoylethanolamine
• 英文别名: linoleoyl ethanolamide；LEA；(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide；linoleyl ethanolamide；N-linoleoylethanolamide
• CAS: 68171-52-8
• 化学式: C₂₀H₃₇NO₂
• 分子量: 323.519
• InChiKey: KQXDGUVSAAQARU-HZJYTTRNSA-N

物化性质

• 熔点：
  38-40 °C
• 沸点：
  499.1±38.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)
• 闪点：
  14 °C
• 溶解度：
  DMF:25.0(最大浓度 mg/mL);77.27(最大浓度 mM)DMSO:25.0(最大浓度 mg/mL);77.27(最大浓度 mM)乙醇:50.0(最大浓度 mg/mL);154.55(最大浓度 mM)
• LogP：
  6.003 (est)
• 物理描述：
  Solid
• 碰撞截面：
  187.8 Ų [M+H]+ [CCS Type: TIMS, Method: single field calibrated]
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  F,Xi
• 危险类别码：
  R36/37/38,R11
• 危险品运输编号：
  UN 1170 3/PG 2
• 安全说明：
  S16,S26,S36
• 储存条件：
  存放在阴凉干燥处，并密封于-20 ºC的环境中。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Linoleyl ethanolamide
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. : 68171-52-8
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
Flammable liquids (Category 2), H225
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
F Highly flammable R11
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H225 Highly flammable liquid and vapour.
Precautionary statement(s)
P210 Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s) F Highly flammable
R-phrase(s)
R11 Highly flammable.
S-phrase(s)
S16 Keep away from sources of ignition - No smoking.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Mixtures
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
Do NOT induce vomiting. 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, Metal oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting 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. Remove all sources of ignition.
Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations.
Vapours can accumulate in low 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
Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
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
Specific end use(s)
A part 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, Flame retardant antistatic protective 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
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 14 °C - closed cup
h) Evapouration 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 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks. Extremes of temperature and direct sunlight.
Incompatible materials
Oxidizing agents, Alkali metals, Ammonia, Peroxides
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.
Heart - Irregularities - Based on Human Evidence (Ethanol)

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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: 1170 IMDG: 1170 IATA: 1170
UN proper shipping name
ADR/RID: ETHANOL
IMDG: ETHANOL
IATA: Ethanol
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: II IMDG: II IATA: II
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

合成制备方法：

以下是详细步骤：

• (此处内容为空)

反应信息

• 作为反应物：
  描述：

  亚油醇乙醇胺 在 四氮唑 、 盐酸 、 双氧水 作用下， 生成 C₂₀H₃₆NO₅P^(2-)
  参考文献：
  名称：

  轻松合成含有不饱和脂肪酸链的溶血磷脂

  摘要：

  由于不饱和部分对磷酸酯脱保护中所用条件的敏感性，有效合成多不饱和磷脂具有挑战性。我们在这里讨论三种独立的方法来解决此问题，并使一系列不饱和溶血磷脂酸模拟物的合成，以发展对该系列中结构-活性关系的更全面的了解。

  DOI：

  10.1016/0040-4039(96)01802-3
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 草酰氯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.25h， 生成 亚油醇乙醇胺
  参考文献：
  名称：

  Novel Analogues of Arachidonylethanolamide (Anandamide):  Affinities for the CB1 and CB2 Cannabinoid Receptors and Metabolic Stability

  摘要：

  Several analogues of the endogenous cannabinoid receptor ligand arachidonylethanolamide (anandamide) were synthesized and evaluated in order to study (a) the structural requirements for high-affinity binding to the CB1 and CB2 cannabinoid receptors and (b) their hydrolytic stability toward anandamide amidase. The series reported here was aimed at exploring structure-activity relationships (SAR) primarily with regard to stereoelectronic requirements of ethanolamido headgroup for interaction with the cannabinoid receptor active site. Receptor affinities, reported as K-i values, were obtained by a standard receptor binding assay using [H-3]CP-55,940 as the radioligand, while stability toward the amidase was evaluated by comparing the K-i of each analogue in the presence and absence of phenylmethanesulfonyl fluoride (PMSF), a serine protease blocker and inhibitor of anandamide amidase. Introduction of a methyl group in the 1'- and 2'-positions or substitution of the ethanolamido headgroup with a butylamido group gave analogues with vastly improved biochemical stability. This is accomplished in some cases with increased receptor affinity. Conversely, oxazolyl and methyloxazolyl headgroups led to low-affinity analogues. Substitution of the hydroxyl group with electronegative substituents such as fluoro, chloro, allyl, and propargyl groups significantly increased receptor affinity but did not influence the biochemical stability. The 2'-chloro analogue of anandamide was found to have the highest affinity for CB1. Additionally, reversing the positions of the carbonyl and NH in the amido group produces retro-anandamides possessing considerably higher metabolic stability. Replacement of the arachidonyl tail with oleyl or linoleyl results in analogues with low affinities for both receptors. All of the analogues in this study showed high selectivity for the CB1 receptor over the peripheral CB2 receptor. The most potent analogues were tested for their ability to stimulate the binding of [S-35]GTP gamma S to G-proteins and were shown to be potent cannabimimetic agonists. The results are discussed in terms of pharmacophoric features affecting receptor affinity and enzymatic stability.

  DOI：

  10.1021/jm970257g

文献信息

• METHODS AND COMPOSITIONS FOR TREATING INFLAMMATION
  申请人：UNIVERSITY OF MASSACHUSETTS

  公开号：US20200138756A1

  公开（公告）日：2020-05-07

  Disclosed herein are methods and compositions for treating neutrophil-mediated inflammation by targeting, in any combination, the pro-inflammatory MRP2/HXA3 pathway and/or the anti-inflammatory P-gp/endocannabinoid pathway and/or the anti-inflammatory MRP 1/L-AMEND pathway, comprising administering to the subject a therapeutically effective amount of (a) one or more first compound that inhibits the activity and/or level of one or more of multidrug resistance protein 2 (MRP2) and hepoxilin A3 (HXA3) synthase, and/or (b) one or more second compound that increases the level and/or activity of one or more N-acylethanolamines (NAEs), and/or (c) one or more third compound that increases the level and/or activity of multidrug resistance protein 1 (MRP1), wherein the therapeutic amount of the first, second, and third compounds reduces migration of neutrophils into the target tissue.

  本文披露了一种治疗中性粒细胞介导炎症的方法和组合物，通过以任何组合方式靶向抗炎 MRP2/HXA3 途径和/或抗炎 P-gp/内源性大麻素途径和/或抗炎 MRP 1/L-AMEND 途径，包括向受试者施用治疗有效量的（a）抑制一种或多种多药耐药蛋白2（MRP2）和肝过氧化脂酸A3（HXA3）合酶的活性和/或水平的一种或多种第一化合物，和/或（b）增加一种或多种N-乙酰基乙醇胺（NAEs）的水平和/或活性的一种或多种第二化合物，和/或（c）增加一种或多种多药耐药蛋白1（MRP1）的水平和/或活性的一种或多种第三化合物，其中第一、第二和第三化合物的治疗量减少中性粒细胞向目标组织的迁移。
• [EN] STORE OVERLOAD-INDUCED CALCIUM RELEASE INHIBITORS AND METHODS FOR PRODUCING AND USING THE SAME<br/>[FR] INHIBITEURS DE LIBÉRATION DU CALCIUM INDUITE PAR UNE SURCHARGE DU STOCK CALCIQUE ET LEURS MÉTHODES DE PRODUCTION ET D'UTILISATION
  申请人：UTI LIMITED PARTNERSHIP

  公开号：WO2015031914A1

  公开（公告）日：2015-03-05

  The present invention provides compounds having store overload-induced Ca2+ release (SOICR) inhibitory activity and methods for producing and using the same. In particular, compounds of the invention is of the formula: R1-X1-L-X2-R2, wherein R1, X1, L, X2, and R2 are those defined herein.

  本发明提供了具有存储过载诱导的Ca2+释放（SOICR）抑制活性的化合物以及生产和使用这些化合物的方法。特别是，本发明的化合物具有如下通式：R1-X1-L-X2-R2，其中R1、X1、L、X2和R2如本文所定义。
• A Convenient Protocol for the Synthesis of Fatty Acid Amides
  作者：Jens Nolsøe、Silje Johansson、Tonje Johannessen、Christiane Ellefsen、Mali Ristun、Simen Antonsen、Trond Hansen、Yngve Stenstrøm

  DOI：10.1055/s-0037-1611939

  日期：2019.1

  Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical,

  已经从哺乳动物和植物来源报道了几类生物存在的脂肪酸酰胺。许多与哺乳动物来源的脂肪酸结合的酰胺表现出对个体受体的特异性激活。它们作为药理学工具或作为开发新疗法的先导化合物的潜力引起了人们极大的兴趣。因此，需要在不影响敏感功能的几何形状或位置的情况下，通过实用、高产和可扩展的协议来获取此类酰胺。满足所有这些要求的方案包括用羰基二咪唑 (CDI) 活化相应的酸，然后与所需的胺或其盐酸盐反应。已经以通常高产率制备了五十多种化合物。
• Radiosynthesis, in vitro and in vivo evaluation of 123I-labeled anandamide analogues for mapping brain FAAH
  作者：Leonie wyffels、Sylvie De Bruyne、Peter Blanckaert、Didier M. Lambert、Filip De Vos

  DOI：10.1016/j.bmc.2008.11.019

  日期：2009.1

  Fatty acid amide hydrolase (FAAH) is one of the main enzymes responsible for terminating the signaling of endocannabinoids, including anandamide. This paper is the first report of the synthesis, [123I]-labeling and in vitro and in vivo evaluation of anandamide analogues as potential metabolic trapping radioligands for in vivo evaluation of brain FAAH. N-(2-Iodoethyl)linoleoylamide (2) and N-(2-iod

  脂肪酸酰胺水解酶（FAAH）是负责终止包括anandamide在内的大麻素信号传导的主要酶之一。本文是合成，[ 123 I]标记和anandamide类似物体外和体内评价的首次报道，anandamide类似物可作为潜在的代谢捕获放射性配体用于体内FAAH的脑评价。N-（2-碘乙基）亚油酰基酰胺（2）和N-（2-碘乙基）花生四烯酰胺（4）以两步法从它们各自的酸开始以良好的产率（分别为75％和86％）合成。使用重组大鼠FAAH和[ 3 H] -anandamide进行的体外分析显示2和3的相互作用。4与FAAH（IC 50个5.78μM和3.14μM，分别的值）。合成了[ 123 I] -2和[ 123 I] -4，其放射化学产率分别为21％和12％，放射化学纯度> 90％。小鼠的生物分布研究表明，两种示踪剂均能吸收大脑（对于[ 123 I] -2，在pi 3 min时最大值为1.23％ID /
• Optimized synthesis and characterization of N-acylethanolamines and O-acylethanolamines, important family of lipid-signalling molecules
  作者：Roberta Ottria、Silvana Casati、Pierangela Ciuffreda

  DOI：10.1016/j.chemphyslip.2012.06.010

  日期：2012.10

  VA) is the only identified new member of the endocannabinoid family that is characterised by an ester linkage between acylic acid and ethanolamine instead of the amide linkage found in AEA and others non-cannabinoid N-acylethanolamines. It has been reported, as a cautionary note for lipid analyses, that VA can be produced nonenzymatically from AEA (and vice versa) as consequence of O,N-acyl migrations

  内源性大麻素大麻酚（N-花生四烯酰乙醇胺，AEA）是一种在CB1和CB2受体上发生的生理活性生物活性化合物，具有多种生理功能。 自发现AEA以来，已从哺乳动物组织中鉴定出其他非大麻类内源性化合物，例如N-棕榈酰乙醇胺（PEA）和N-油酰乙醇胺（OEA）。Virodhamine（O-花生四烯酸乙醇胺，VA）是内源性大麻素家族中唯一被鉴定的新成员，其特征是酰基酸和乙醇胺之间存在酯键，而不是AEA和其他非大麻N-酰基乙醇胺中发现的酰胺键。作为脂质分析的注意事项，据报道，由于O，N-酰基迁移，VA可以非酶法从AEA生产（反之亦然）。O，N-酰基迁移在合成有机化学文献中有充分的文献记载，但是关于脂质分离或脂质酶研究的方法并未得到很好的描述或认可。 我们在这里报告了一种经济有效的方案，用于大规模合成和表征某些N-和O-酰基乙醇胺，这些化合物可以用作参考标准，以研究它们在生物膜中的可能形成，并具有潜在的有趣生物学特性。