硬脂酰胺MEA | 111-57-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 硬脂酰胺MEA
• 中文别名: N-(2-羟基乙基)硬脂酰胺
• 英文名称: N-stearoylethanolamine
• 英文别名: stearoyl ethanolamide；N-(2-Hydroxyethyl)octadecanamide
• CAS: 111-57-9
• 化学式: C₂₀H₄₁NO₂
• mdl: MFCD00045971
• 分子量: 327.551
• InChiKey: OTGQIQQTPXJQRG-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: ethanol (64-17-5))
• 沸点：
  486.0±28.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：>2mg/mL； DMSO：>100μg/ml；乙醇：>2mg/mL； PBS pH 7.2：>100 μg/ml
• LogP：
  4.46 at 20℃
• 物理描述：
  DryPowder; Liquid; OtherSolid; PelletsLargeCrystals
• 碰撞截面：
  198.93 Ų [M+H]+ [CCS Type: TIMS, Method: single field calibrated]
• 保留指数：
  2347.1

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  23
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  2
• 海关编码：
  2924199090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Stearoyl ethanolamide
CAS-No. : 111-57-9
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
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C20H41NO2
Molecular Weight : 327,55 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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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, nitrogen oxides (NOx)
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 dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. 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
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
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
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., 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 is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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: crystalline
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.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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

生物活性

Stearoylethanolamide 是一种具有促细胞凋亡活性的内源性大麻素类化合物。

靶点

• 人类内源代谢物

体外研究显示，Stearoylethanolamide (SEA) 在人类、大鼠和小鼠的大脑中存在，并且其含量与内源性大麻素anandamide (arachidonoylethanolamide; AEA) 相当。Stearoylethanolamide 是一种具有促凋亡作用的类似内源性大麻素的化合物，它通过一氧化氮（NO）进行调节，并且其调节方式与AEA相反。

反应信息

• 作为反应物：
  描述：

  硬脂酰胺MEA 在 palladium on activated charcoal sodium hydroxide 、 二氯二茂锆 、 氢气 、 silver perchlorate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of a 2-Acetamido-2-deoxy-β-D-mannuronic Acid-Containing Artificial Glycolipid Corresponding to the Repeating Unit of a Teichuronic Acid fromMicrococcus luteus

  摘要：

  我们利用一种容易获得的结构单元--2-（苯甲酰氧基）亚氨基糖苷酸甲酯作为糖基供体，合成了一种由 2-乙酰氨基-2-脱氧-β-D-甘露糖酸构成的新型人工糖脂。供体的立体定向 β-糖苷化与随后的（苯甲酰氧基）亚氨基功能的立体定向还原一样顺利。经过异构活化、连接间隔物（2-氨基乙醇）-连接硬脂酸和最终解锁，就得到了所设计的糖脂，而且总收率很高。

  DOI：

  10.1246/cl.1993.1567
• 作为产物：
  描述：

  2-氨基乙基硬脂酸酯 生成 硬脂酰胺MEA
  参考文献：
  名称：

  Desnuelle; Naudet; Sambuc, Bulletin de la Societe Chimique de France, 1949, p. 651

  摘要：

  DOI：

文献信息

• POLYETHYLENE GLYCOL DERIVATIVES OF PALMITOYLETHANOLAMIDE AND ANALOGOUS ACYLETHANOLAMIDES
  申请人：EPITECH GROUP S.r.l.

  公开号：US20150157733A1

  公开（公告）日：2015-06-11

  The synthesis of a series of Polyethylene glycol conjugates (esters and carbonates) of PEA and its analogous acylethanolamides, have higher water solubility and good hydrophilic/lipophilic balance, resulting in (i) improved accumulation in tissues (particularly skin and mucosae), (ii) prolonged release, and (iii) increased bioavailability. Improvement of PEA and analogous acylethanolamides levels in the tissues—particularly in the skin and mucosae—and their prolonged release is due to the improved bioavailability of related conjugates. Conjugates are able to extend the time frame in which PEA and analogous acylethanolamides exert their pharmacological effects.

  一系列聚乙二醇酯和碳酸酯的PEA及其类似的酰乙醇胺共轭物具有更高的水溶性和良好的亲水/疏水平衡，导致（i）在组织中（特别是皮肤和粘膜）的积累增加，（ii）释放延长，以及（iii）生物利用度增加。PEA和类似的酰乙醇胺在组织中（特别是皮肤和粘膜）的水平提高以及它们的延长释放是由于相关共轭物生物利用度的提高。共轭物能够延长PEA和类似的酰乙醇胺发挥药理效应的时间范围。
• Design and synthesis of silicon-containing fatty acid amide derivatives as novel peroxisome proliferator-activated receptor (PPAR) agonists
  作者：Daisuke Kajita、Masaharu Nakamura、Yotaro Matsumoto、Minoru Ishikawa、Yuichi Hashimoto、Shinya Fujii

  DOI：10.1016/j.bmcl.2015.05.045

  日期：2015.8

  We recently reported that diphenylsilane structure can function as a cis-stilbene mimetic. Here, we investigate whether silyl functionality can also serve as a mimetic of aliphatic cis-olefin. We designed and synthesized various silyl derivatives of oleoylethanolamide (OEA: 8), an endogenous cis-olefin-containing PPARα agonist, and evaluated their PPARα/δ/γ agonistic activity. We found that diethylsilyl

  我们最近报道了二苯基硅烷结构可以充当顺式-苯乙烯模拟物。在这里，我们研究甲硅烷基官能团是否也可以用作脂肪族顺式烯烃的模拟物。我们设计和合成了油酰乙醇酰胺（OEA：8）的各种甲硅烷基衍生物，一种内源性含顺式烯烃的PPARα激动剂，并评估了它们的PPARα/δ/γ激动活性。我们发现二乙基甲硅烷基衍生物20表现出PPARα/δ激动活性，我们还获得了PPARδ选择性激动剂32。我们的结果表明，甲硅烷基官能团的结合是生物活性化合物结构开发的有用选择。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• Structure and Reactivity in Langmuir Films of Amphiphilic Alkyl and Thio-alkyl Esters of α-Amino Acids at the Air/Water Interface
  作者：Ran Eliash、Isabelle Weissbuch、Markus J. Weygand、Kristian Kjaer、Leslie Leiserowitz、Meir Lahav

  DOI：10.1021/jp049381j

  日期：2004.6.1

  occurring in an isotropic environment. The alkyl esters of phenylalanine and tyrosine did not form 2D crystallites at the air/water interface, and, upon polycondensation, they yielded only dipeptides. The enantiomeric disorder within the 2D crystallites of the monomers of the alkyl esters and thioesters of racemic serine was absent. Polycondensation of these esters, however, yielded only dipeptides and

  作为我们对可能与产生纯手性益生元肽相关的机制研究的一部分，已经研究了在空气/水界面自组装的几种 α-氨基酸的烷基酯的结构和反应性。水表面上外消旋和对映纯烷基酯和丙氨酸硫酯单分子层的掠入射 X 射线衍射 (GIXD) 研究表明，这些外消旋体以混合固溶体的形式自组装，因为二维 (2D) 微晶内的两种对映异构体（对映异构体紊乱）。对从空气/水界面收集的产物进行基质辅助激光解吸电离飞行时间质谱 (MALDI-TOF MS) 分析表明形成了低分子量寡肽（主要是二聚体），并且，在一些硫酯的情况下，少量的三聚体和四聚体。从氘对映体标记的单体开始，对寡肽的非对映异构分布的质谱研究证明了二项式统计，例如在各向同性环境中发生的反应。苯丙氨酸和酪氨酸的烷基酯不会在空气/水界面形成二维微晶，并且在缩聚时，它们仅产生二肽。不存在外消旋丝氨酸的烷基酯和硫酯单体的二维微晶内的对映异构体紊乱。然而，这些酯的缩聚仅产生二肽
• Stannyl ceramides as efficient acceptors for synthesising β-galactosyl ceramides
  作者：José Antonio Morales-Serna、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1039/b809570a

  日期：——

  β-Galactosyl ceramides have been obtained in excellent yields and stereoselectivities by reacting disarmed glycosyl donors with stannyl ethers. The broad compatibility of stannyl ethers with various leaving group–promoter pairs is demonstrated.

  β-半乳糖苷神经酰胺通过将非活性糖苷供体与锡醚反应获得了优异的产率和立体选择性。证明了锡醚与各种离去基–促进剂配对的广泛相容性。

表征谱图