CAS 111-58-0 Oleoylethanolamide (HCID 5283454)

개요

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.

이름 및 식별자

우선 이름: Oleoylethanolamide
IUPAC: (Z)-N-(2-hydroxyethyl)octadec-9-enamide
현지명: 올레아마이드엠이에이
영어명: Oleoyl Ethanolamide
분자식: C20H39NO2
분자량: 325.53

이름 및 동의어

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

이름 더 보기

올레아마이드엠이에이ODAOEAOleoylethanolamide(OEA)OLEAMIDE MEAN-(Hydroxyethyl)oleamideAM-3101UNII-1HI5J9N8E6

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 6.3
극성 표면적: 49.3 Å²
수소 결합 공여자 수: 2
수소 결합 수용자 수: 2
회전 가능 결합 수: 17
무거운 원자 수: 23
형식 전하: 0
복잡도: 277

실험 및 물리화학적 성질

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

Cosmetics · 3건

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

Personal care product

Antistatic; Viscosity controlling; Foam boosting

Physical Description · 2건

Other Solid

Solid

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

물리화학적 성질

녹는점: 63 · 63-64 °C
끓는 점: 496.4 · 496.4±38.0 °C(Predicted)
밀도: 0.915 · 0.915±0.06 g/cm3(Predicted)
저장 조건: -20 °C · -20°C
용해도: DMSO(최대 25mg/ml) 또는 에탄올(최대 35mg/ml)에 용해됩니다.
물리적 상태: 흰색 고체
산도 계수 (pKa): 14.49 · 14.49±0.10(Predicted)
색상: 하얀색
안정성: 2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 1개월 동안 보관할 수 있습니다.
화장품 원료 기능: 점도 조절대전방지제계면활성제 - 거품 증진제
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)
EPA: 9 · 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- (111-58-0)

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Regulatory Information · 4건

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%)

독성 정보

Toxicity Summary · 2건

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

안전 데이터

wgk: 2
tsca: TSCA listed
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
위험 등급: IRRITANT
기존화학 물질: KE-20537
스토리지 클래스: 11 - Combustible Solids

화학 및 산업

약리 정보

Mechanism of Action · 1건

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

용도 및 제조

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 · 2건

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

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

응용 분야 · 3건

개요Oleoyl 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.

용도N-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.

일반 설명Oleoylethanolamide (OEA) is an endogenous fatty acid ethanolamine. Small intestine cells, adipose tissues, neurons and astrocytes produces OEA.

상·하류 제품 정보

상류 원료

공급사100 곳

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]

추가 설명 · 1건

정의ChEBI: 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.

화합물 노트

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올레아마이드엠이에이

기본 정보

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