기본 정보
- 표준 SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O- InChIKey
JAZBEHYOTPTENJ-JLNKQSITSA-N- 분자식
- C20H30O2
- 평균 분자량
- 302.5 g/mol
- 단동위원소 질량
- 302.2245802
이름 및 식별자
- 우선 이름
- Icosapent
- IUPAC
- (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
- 영어명
- EPA
- 분자식
- C20H30O2
- 분자량
- 302.45
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
10417-94-4- PubChem CID
- 446284
- DTXSID
DTXSID9041023- ChEMBL
CHEMBL460026- ChEBI
CHEBI:28364- UNII
- AAN7QOV9EA
- EC Number
- 600-528-7
- Nikkaji
- J343.473G
물성
구조 계산 물성
- XLogP
- 5.6
- 극성 표면적
- 37.3 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 13
- 무거운 원자 수
- 22
- 형식 전하
- 0
- 복잡도
- 398
실험 및 물리화학적 성질
Collision Cross Section
180.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
178.53 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
물리화학적 성질
- 녹는점
- 54 · −54-−53 °C(lit.)
- 끓는 점
- 439 ℃ · 439℃
- 밀도
- 0.943 g/mL · 0.943 g/mL at 25 °C(lit.)
- 굴절률
- 20 · n20/D 1.4977(lit.)
- 인화점
- 93 °C · 93 °C
- 저장 조건
- -20 °C · -20°C
- 용해도
- 메탄올에 용해됨
- 물리적 상태
- 액체
- 산도 계수 (pKa)
- 4.75 · 4.75±0.10(Predicted)
- 색상
- 무색~담황색
- 생물학적 소스
- fish oil
- Merck
- 14 · 14,3531
- BRN
- 1714433 · 1714433
- 안정성
- 1 · 공급된 상태로 1년 동안 안정적입니다(미개봉). 개봉 후에는 EPA를 -80°C의 불활성 가스 환경에서 보관해야 합니다. DMSO 또는 에탄올 용액도 불활성 가스 하에 보관해야 하며 -80°C에서 최대 2개월 동안 보관할 수 있습니다.
- 화장품 원료 기능
- 피부 컨디셔닝피부 컨디셔닝 - 보습제
- InChIKey
- RRGOKSYVAZDNKR-ARJAWSKDSA-N
- SMILES
- CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
- LogP
- 6.232 · 6.232 (est)
화학적 성질
Colorless Oil
안전 및 규제
GHS 분류
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 92 reports by companies from 1 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
규제 정보
안전 데이터
- wgk
- 3
- ridadr
- UN 3265 8/PG 3
- HS 번호
- 29161900
- risk_code
- 34
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- 위험 등급
- 8
- F 고인화성물질
- 8-10-23
- 스토리지 클래스
- 10 - Combustible liquids
화학 및 산업
약리 정보
Pharmacodynamics
Eicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.
Mechanism of Action
The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40.
용도 및 제조
응용 분야
용도cis-5,8,11,14,17-Eicosapentaenoic acid has been used:to test pharmacologic effect on steatosis in hepatocytesas an analytical standard in Raman spectra measurements to characterize human breast cancer samplesin lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies
일반 설명Eicosapentaenoic acid (cis-5,8,11,14,17), also known as EPA, is a long-chain omega-3 fatty acid. Studies suggests that EPA as well as other fatty acids can serve as biomarkers for cardiovascular disease, and nutritional and metabolic disorders. This certified solution standard is suitable for use as starting material in the preparation of linearity standards, calibrators, or controls in mass spectrometry-based EPA testing applications such as assessment of cardiovasculardisease risk and fatty acid deficiency, and detection and quantification of EPA in nutraceuticals and dietary supplements.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.
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