CAS 111-58-0 Oleoylethanolamide (HCID 5283454)

概要

Oleoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. It has a role as a geroprotector, a PPARalpha agonist and an EC 3.5.1.23 (ceramidase) inhibitor. It is a N-acylethanolamine 18:1, a N-(long-chain-acyl)ethanolamine and an endocannabinoid. It is functionally related to an oleic acid.

名称と識別子

優先名称: Oleoylethanolamide
IUPAC: (Z)-N-(2-hydroxyethyl)octadec-9-enamide
現地名: N-(2-ヒドロキシエチル)オレイン酸アミド
英語名: Oleoyl Ethanolamide
分子式: C20H39NO2
分子量: 325.53

名称と別名

oleoylethanolamide111-58-0N-(2-Hydroxyethyl)oleamideOleoyl Ethanolamide(Z)-N-(2-hydroxyethyl)octadec-9-enamideOleoyl monoethanolamideOLEIC MONOETHANOLAMIDEN-(9Z-octadecenoyl)-ethanolamine1HI5J9N8E69-Octadecenamide, N-(2-hydroxyethyl)-DTXSID1044516N-(cis-9-octadecenoyl) ethanolamine

名称をさらに表示

2-(オレオイルアミノ)エタノール(Z)-N-(2-ヒドロキシエチル)-9-オクタデセンアミドオレイルエタノールアミドN-(2-ヒドロキシエチル)オレイン酸アミドオレオイルエタノールアミドN-オレオイルエタノールアミンN-(2-ヒドロキシエチル)オレインアミドN-オレオイルエタノールアミド(9Z)-N-(2-ヒドロキシエチル)-9-オクタデセンアミドN-（2-ヒドロキシエチル)オレオアミド（9Z）-N-（2-ヒドロキシエチル）オクタデカ-9-エンアミドN-(2-ヒドロキシエチル)オレアミドODAOEAOleoylethanolamide(OEA)OLEAMIDE MEAN-(Hydroxyethyl)oleamideAM-3101UNII-1HI5J9N8E6

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-CHEBI:71466RefChem:856533DTXCID9024516203-884-8Oleoylethanolaminen-oleoylethanolamineOleylethanolamide

データベース識別子

CAS: 111-58-0
PubChem CID: 5283454
DTXSID: DTXSID1044516
ChEMBL: CHEMBL280065
ChEBI: CHEBI:71466
UNII: 1HI5J9N8E6
EC Number: 203-884-8、921-073-3
Nikkaji: J193.596H

物性

構造計算による物性

XLogP: 6.3
極性表面積: 49.3 Å²
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: 17
重原子数: 23
形式電荷: 0
複雑度: 277

実験および物理化学的性質

LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]

Cosmetics · 3 件

Cosmetic ingredients (Oleamide MEA) -> CIR (Cosmetic Ingredient Review)

Personal care product

Antistatic; Viscosity controlling; Foam boosting

Physical Description · 2 件

Other Solid

Solid

Collision Cross Section192.94 Å² [M+H]+ [CCS Type: TIMS; Method: single field calibrated]

物理化学的性質

融点: 63 · 63-64 °C
沸点: 496.4 · 496.4±38.0 °C(Predicted)
比重(密度): 0.915 · 0.915±0.06 g/cm3(Predicted)
貯蔵温度: -20 °C · -20°C
溶解性: DMSO (最大 25mg/ml) またはエタノール (最大 35mg/ml) に可溶
外見: 白い固体
酸解離定数(Pka): 14.49 · 14.49±0.10(Predicted)
色: 白い
安定性: -20 °Cで最大1か月保存できます。 · DMSO溶液またはエタノール溶液で-20°Cで最大1か月保存できます。
化粧品成分の機能: 粘度制御帯電防止界面活性剤 - 泡立ち促進剤
InChI: InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-
InChIKey: BOWVQLFMWHZBEF-KTKRTIGZSA-N
SMILES: C(NCCO)(=O)CCCCCCC/C=C\CCCCCCCC
LogP: 6.406 · 6.406 (est)
CAS データベース: 111 · 111-58-0(CAS DataBase Reference)
EPAの化学物質情報: 9 · 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- (111-58-0)

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 205 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: 9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)-

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- 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)

Status: Active Update: 11-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19715

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

毒性情報

Toxicity Summary · 2 件

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...Oleamide MEA...

Safe for use in cosmetics, with qualifications

安全データ

wgk: 2
tsca: TSCA listed
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
hazard_class: IRRITANT
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Mechanism of Action · 1 件

Oleoylethanolamide (OEA) is a major N-acylethanolamine and an endogenous ethanolamide fatty acid. Although it is an endocannabinoids-like compound, it does not bind to cannabinoid receptors. Instead, this lipid sensor is an agonist at peroxisome proliferator-activated receptor-α (PPAR-α) agonist while also being an inhibitor of ceramidase and thereby the sphingolipid signaling pathway.

Tissue LocationsPlacenta

Cellular LocationsExtracellular

用途と製造

UsesCIR ingredient: Oleamide MEA

U.S. Production2023: 75,000 - <500,000 lb

Consumer UsesSurfactant (surface active agent)

Industry UsesSurfactant (surface active agent)

Use ClassificationCosmetics -> Antistatic; Viscosity controlling; Foam boosting

General Manufacturing Information · 2 件

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: ACTIVE

応用分野 · 3 件

説明Oleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate. It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation. OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay. Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice. These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.

使用N-Oleoyl Ethanolamide is an agonist of peroxisome proliferator-activated receptor-α (PPAR-α). N-Oleoyl Ethanolamide generates an intestinal signal that stimulates central dopamine activity establishing a link between caloric-homeostatic and hedonic-homeostatic controllers. Oleoyl Ethanolamide has been implicated as the molecular mechanism associated with gastric bypass success. N-Oleoyl Ethanolamide is a selective GPR55 agonist.

一般的な説明Oleoylethanolamide (OEA) is an endogenous fatty acid ethanolamine. Small intestine cells, adipose tissues, neurons and astrocytes produces OEA.

上流・下流製品情報

上流原料

オレオイルクロリドオレイン酸 2-アミノエタノールリノール酸水和物ヘキサン

サプライヤー100 社

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]

山东天微医药科技有限公司+86-18653895227 · [email protected]

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

上海毕合生物化学技术有限公司13816464724 · [email protected]

補足説明 · 1 件

定義ChEBI: Oleoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. It has a role as a PPARalpha agonist, an EC 3.5.1.23 (ceramidase) inhibitor and a geroprotector. It is a N-(long-chain-acyl)ethanolamine, an endocannabinoid and a N-acylethanolamine 18:1. It is functionally related to an oleic acid.

化合物ノート

読み込み中…

N-(2-ヒドロキシエチル)オレイン酸アミド

基本情報

概要