(9Z,12Z)-N-(2-ヒドロキシエチル)-9,12-オクタデカジエンアミド
N-Linoleoylethanolamine
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基本情報
- CAS
68171-52-8- 標準SMILES
CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO- InChIKey
KQXDGUVSAAQARU-HZJYTTRNSA-N- 分子式
- C20H37NO2
- 平均分子量
- 323.5 g/mol
- 単同位体質量
- 323.28242942
概要
Linoleoyl ethanolamide is an N-acylethanolamine 18:2 that is the ethanolamide of linoleic acid. It has a role as an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor. It is functionally related to a linoleic acid.
名称と識別子
- 優先名称
- N-Linoleoylethanolamine
- IUPAC
- (9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide
- 現地名
- (9Z,12Z)-N-(2-ヒドロキシエチル)-9,12-オクタデカジエンアミド
- 英語名
- LINOLEOYLETHANOLAMIDE
- 分子式
- C20H37NO2
- 分子量
- 323.51
名称と別名
Linoleoyl ethanolamide68171-52-8n-linoleoylethanolamineLinoleic ethanolamide(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamideLinoleoyl monoethanolamidelinoleic monoethanolamideMonoethanolamine linoleic acid amide9,12-Octadecadienamide, N-(2-hydroxyethyl)-, (9Z,12Z)-889DYX0816N-cis-9-cis-12-OctadecadienoylethanolamineN-(2-Hydroxyethyl)-9,12-octadecadienamide
名称をさらに表示
(9Z,12Z)-N-(2-ヒドロキシエチル)オクタデカ-9,12-ジエナミド(9Z,12Z)-N-(2-ヒドロキシエチル)-9,12-オクタデカジエンアミドリノレイルエタノールアミド(9Z,12Z)-N-(2-ヒドロキシエチル)-9,12-オクタデカジエン酸アミドN-リノレオイルエタノールアミンジホモ-γ-リノレノイルエタノールアミド(9Z,12Z)-N-(2-ヒドロキシエチル)オクタデカ-9,12-ジエンアミドN-リノレオイルエタノールアミドLEAODNHETOHEinecs 269-029-6Anandamide (18:2,n6)Linoleic ethanolamineN-lineleoyl Ethanolamide (LEA)
CHEBI:64032RefChem:799235Linoleamide MEALinoleylethanolamideLinoleyl ethanolamideLinoleoylethanolamideN-(2-Hydroxyethyl)linoleamideAnandamide (18:2, n-6)
物性
構造計算による物性補完中
- XLogP
- 5.6
- 極性表面積
- 49.3 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 2
- 回転可能結合数
- 16
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 311
実験および物理化学的性質
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Cosmetics
Cosmetic ingredients (Linoleamide MEA) -> CIR (Cosmetic Ingredient Review)
Antistatic; Foam boosting; Hair conditioning; Viscosity controlling
Personal care product
Physical Description
Other Solid
Solid
Collision Cross Section187.8 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]
物理化学的性質
- 融点
- 38 · 38-40 °C
- 沸点
- 499.1 · 499.1±38.0 °C(Predicted)
- 比重(密度)
- 0.926 · 0.926±0.06 g/cm3(Predicted)
- 闪点
- 14 °C · 14 °C
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 25 · DMF:25.0(Max Conc. mg/mL);77.27(Max Conc. mM)DMSO:25.0(Max Conc. mg/mL);77.27(Max Conc. mM)Ethanol:50.0(Max Conc. mg/mL);154.55(Max Conc. mM)
- 外見
- エタノール溶液
- 酸解離定数(Pka)
- 14.49 · 14.49±0.10(Predicted)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
危険有害性情報
Regulatory Information
9,12-Octadecadienamide, N-(2-hydroxyethyl)-, (9Z,12Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9,12-Octadecadienamide, N-(2-hydroxyethyl)-, (9Z,12Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
9,12-Octadecadienamide, N-(2-hydroxyethyl)-, (9Z,12Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
毒性情報
Toxicity Summary
The CIR Expert Panel concluded that the ethanolamides listed subsequently are safe in the present practices of use and concentration described in this safety assessment when formulated to be non-irritating. The Expert Panel cautioned that these ingredients should not be used in cosmetic products in which N-nitroso compounds may be formed...Linoleamide MEA...
Safe for use in cosmetics, with qualifications
安全データ
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 1170 3/PG 2
- risk_code
- 11-36/37/38
- hazard_code
- F,Xi
- safety_code
- 16-26-36
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2
- ストレージクラス
- 3 - Flammable liquids
化学と産業
薬理情報
Cellular LocationsExtracellular
用途と製造
UsesCIR ingredient: Linoleamide MEA
U.S. Production2023: <50,000 lb
Consumer UsesSurfactant (surface active agent)
Industry UsesSurfactant (surface active agent)
Household ProductsInformation on 1 consumer products that contain Linoleamide MEA in the following categories is provided:
Use ClassificationCosmetics -> Antistatic; Foam boosting; Hair conditioning; Viscosity controlling
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
9,12-Octadecadienamide, N-(2-hydroxyethyl)-, (9Z,12Z)-: ACTIVE
応用分野
使用N-Linoleoylethanolamine reduces lipopolysaccharide-induced inflammation in macrophages and reduces inflammation in ameliorates 2,4-dinitrofluorobenzene-induced contact dermatitis. N-Linoleoylethanolamine inhibits NF-κB signaling and may be used as a therapeutic agent against contact dermatitis.Linoleoyl ethanolamide is an endocannabinoid detected in porcine brain.
補足説明
定義ChEBI: An N-(long-chain-acyl)ethanolamine that is the ethanolamide of linoleic acid.
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