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顺式-5,8,11,14,17-二十碳五烯酸(EPA)

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货号 (SKU) 包装规格 是否现货 价格 数量
E122277-25mg
 25mg 现货 Stock Image
E122277-100mg
 100mg 现货 Stock Image
E122277-500mg
 500mg 现货 Stock Image
E122277-1g
 1g 现货 Stock Image
E122277-5g
 5g 现货 Stock Image
E122277-25g
 25g 现货 Stock Image
E122277-100g
 100g 现货 Stock Image
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Coenzymes (8) Endogenous Metabolite (978) Histone Demethylase (97) Histone Modification (3105) Metabolic Enzyme/Protease (4889) 代谢物 (8911) 羧酸 (2181) 羧酸封端剂 (20) 表观遗传学 (1497)
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基本描述

别名 二十碳五烯酸 | 花生五烯酸 | 全顺-5,8,11,14,17-二十碳五烯酸
英文别名 EPA | all cis-5,8,11,14,17-Eicosapentaenoic Acid | all cis-5,8,11,14,17-Icosapentaenoic Acid
规格或纯度 Moligand™, ≥95%
英文名称 cis-5,8,11,14,17-Eicosapentaenoic acid (EPA)
生化机理 5 - 脂氧合酶抑制剂，降低血栓素A2的生产。
储存温度 -20°C储存,充氩
运输条件 超低温冰袋运输
产品介绍

天然以其甘油酯的形式存在于海鱼的肉、脂肪中，尤其是深海鱼的眼窝周围脂肪中含量更丰富。本品易氧化，易对光、热、氧敏感，氧化后颜色变深。通常加入维生素E及儿茶酚等抗氧化剂。是一种多烯不饱和脂肪酸。

Eicosapentaenoic acid is a polyunsaturated fatty acid (PUFAs) and is synthesized from linolenic acid. It is distributed in phospholipid bilayers of the cell membrane, synaptic membranes of the brain and retina.It is obtained majorly from fish oil, seaweed, phytoplankton, and camelina.Being an Omega-3 fatty acid, it shows cis-trans conformations.

cis-5,8,11,14,17-Eicosapentaenoic acid has been used:

· to test pharmacologic effect on steatosis in hepatocytes

· as an analytical standard in Raman spectra measurements to characterize human breast cancer samples

· in lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies
纯度 ≥95%

产品属性

ALogP 5.6

关联靶点（人）

F2 Tclin Thrombin (11687 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PGR Tclin Progesterone receptor (8562 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
AR Tclin Androgen Receptor (11781 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
VDR Tclin Vitamin D receptor (26531 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CYP19A1 Tclin Cytochrome P450 19A1 (6099 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
KCNH2 Tclin HERG (29587 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
RXRA Tclin Retinoid X receptor alpha (3637 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PDE4A Tclin Phosphodiesterase 4A (1943 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
MDA-MB-468 (9477 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HCT-116 (91556 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
POLL Tbio DNA polymerase lambda (184 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
OXER1 Tchem Oxoeicosanoid receptor 1 (131 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SREBF2 Tchem Sterol regulatory element-binding protein 2 (50 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
F7 Tchem Coagulation factor VII/tissue factor (740 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
EA.hy 926 (491 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

关联靶点（其它种属）

Trypsin (394 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Ppard Peroxisome proliferator-activated receptor delta (358 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Mus musculus (284745 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Hepatitis C virus (23859 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
RAW264.7 (28094 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
RBL-2H3 (1162 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

作用机制

作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献

名称和识别符

分子类型 小分子
IIUPAC Name (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
INCHI 1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChi Key JAZBEHYOTPTENJ-JLNKQSITSA-N
Smiles CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Isomeric SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
UN Number 3265
分子量 302.45
Beilstein号 1714433
Reaxy-Rn 8989326
Reaxys-RN link address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8989326&ln=

化学和物理性质

溶解性 Soluble in methanol
密度 0.943
敏感性 对光，空气和热敏感
折光率 1.4977
闪点(℉) 199.4 °F
闪点(℃) 93℃
熔点 -54--53°C
分子量 302.500 g/mol
XLogP3 5.600
氢键供体数Hydrogen Bond Donor Count 1
氢键受体数Hydrogen Bond Acceptor Count 2
可旋转键计数Rotatable Bond Count 13
精确质量Exact Mass 302.225 Da
单同位素质量Monoisotopic Mass 302.225 Da
拓扑极表面积Topological Polar Surface Area 37.300 Ų
重原子数Heavy Atom Count 22
形式电荷Formal Charge 0
复杂度Complexity 398.000
同位素原子数Isotope Atom Count 0
定义的原子立体中心计数Defined Atom Stereocenter Count 0
未定义的原子立体中心计数Undefined Atom Stereocenter Count 0
定义的键立体中心计数Defined Bond Stereocenter Count 5
未定义的键立体中心计数Undefined Bond Stereocenter Count 0
所有立体化学键的总数The total count of all stereochemical bonds 5
共价键合单元计数Covalently-Bonded Unit Count 1

安全和危险性（GHS）

象形图 GHS05
信号词 危险
危险声明

H314: 造成严重的皮肤灼伤和眼睛损伤
预防措施声明

P260: 不要吸入灰尘/烟雾/气体/雾/蒸汽/喷雾。

P264: 处理后要彻底洗手。

P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。

P321: 特殊处理（请参阅此标签上的...）。

P363: 再次使用之前，请清洗受污染的衣物。

P301+P330+P331: 如误吞咽：漱口。不要诱导呕吐。

P304+P340: 如误吸入：将人转移到空气新鲜处，保持呼吸舒适体位。

P405: 密闭存放

P501: 将内容物/容器处理到。。。

P305+P354+P338: 如果进入眼睛：立即用水冲洗几分钟。取下隐形眼镜（如果有的话），并且操作简单。继续冲洗。

P302+P361+P354: 如果接触皮肤：立即脱掉所有被污染的衣服。立即用水冲洗几分钟。

P316: 立即寻求紧急医疗救助。
WGK Germany 3
Merck Index 3531
个人防护装备 Faceshields,full-face respirator (US),Gloves,Goggles,multi-purpose combination respirator cartridge (US),type ABEK (EN14387) respirator filter

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I2509349 分析证书 E122277
I2509350 分析证书 E122277
I2509351 分析证书 E122277
I2509352 分析证书 E122277
I2509327 分析证书 E122277
I2509328 分析证书 E122277
D2315697 分析证书 E122277
L2110072 分析证书 E122277
D2524168 分析证书 E122277
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D2524170 分析证书 E122277
D2524171 分析证书 E122277
D2524172 分析证书 E122277
D2524173 分析证书 E122277
J2422373 分析证书 E122277
J2422374 分析证书 E122277
J2422376 分析证书 E122277
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J2422378 分析证书 E122277
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E2428609 分析证书 E122277
E2428610 分析证书 E122277
E2428611 分析证书 E122277
C2407222 分析证书 E122277
C2407219 分析证书 E122277
A2425017 分析证书 E122277
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F2411074 分析证书 E122277
A2104180 分析证书 E122277
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引用文献

1. C Calzada,E Véricel,M Lagarde.  (1992-07-29)  Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid..  Biochimica et biophysica acta,  1127  ((2)): (147-152).  [PMID:1643099]
2. I Hafström,B Ringertz,H Gyllenhammar,J Palmblad,M Harms-Ringdahl.  (1988-05-01)  Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis..  Arthritis and rheumatism,  31  ((5)): (585-592).  [PMID:2837251]
3. W Herrmann,J Beitz.  (1987-03-01)  [Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet]..  Zeitschrift fur die gesamte innere Medizin und ihre Grenzgebiete,  42  ((5)): (117-122).  [PMID:3035811]
4. S Sipka,I Dey,C Buda,J Csongor,G Szegedi,T Farkas.  (1996-06-01)  The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes..  Clinical immunology and immunopathology,  79  ((3)): (224-228).  [PMID:8635279]
5. R Luostarinen,T Saldeen.  (1996-09-01)  Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release..  Prostaglandins, leukotrienes, and essential fatty acids,  55  ((3)): (167-172).  [PMID:8931114]
6. M Lagarde,M Croset,E Véricel,C Calzada.  (1989-01-01)  Effects of small concentrations of eicosapentaenoic acid on platelets..  Journal of internal medicine. Supplement,  731  (177-179).  [PMID:2539831]
7. M Takenaga,A Hirai,T Terano,Y Tamura,H Kitagawa,S Yoshida.  (1986-02-01)  Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid..  Thrombosis research,  41  ((3)): (373-384).  [PMID:3010490]
8. R Andrew,S A Best,D G Watson,J M Midgley,J L Reid,I B Squire.  (1993-11-01)  Analysis of biogenic amines in plasma of hypertensive patients and a control group..  Neurochemical research,  18  ((11)): (1179-1182).  [PMID:8255371]
9. G Sato,T Aoki,S Hosokawa,F Sagami,K Tsukidate.  (2001-06-13)  Protection from drug-induced hepatocellular changes by pretreatment with conjugating enzyme inhibitors in rats..  Life sciences,  68  ((24)): (2665-2673).  [PMID:11400910]
10. V I Hereliuk.  (2001-06-27)  [The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis]..  Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994),  46  ((6)): (112-115).  [PMID:11424554]
11. R C Gillis,B J Daley,B L Enderson,M D Karlstad.  (2002-10-18)  Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells..  The Journal of surgical research,  107  ((1)): (145-153).  [PMID:12384078]
12. Richard J Woodman,Trevor A Mori,Valerie Burke,Ian B Puddey,Anne Barden,Gerald F Watts,Lawrence J Beilin.  (2002-12-17)  Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients..  Atherosclerosis,  166  ((1)): (85-93).  [PMID:12482554]
13. Cindy A Francois,Sonja L Connor,Linda C Bolewicz,William E Connor.  (2002-12-25)  Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk..  The American journal of clinical nutrition,  77  ((1)): (226-233).  [PMID:12499346]
14. M K Sim,X S Qui.  (2003-03-01)  Angiotensins in plasma of hypertensive rats and human..  Regulatory peptides,  111  ((1-3)): (179-182).  [PMID:12609766]
15. Tatsuya Ide,Takashi Okamura,Ryukichi Kumashiro,Yuriko Koga,Teruko Hino,Akiko Hisamochi,Kei Ogata,Kazuo Tanaka,Reiichiro Kuwahara,Ritsuko Seki,Michio Sata.  (2003-05-09)  A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C..  International journal of molecular medicine,  11  ((6)): (729-732).  [PMID:12736713]
16. Saleh Abdelhamid,Roland Blomer,Gerhard Hommel,Doris Haack,Sabina Lewicka,Peter Fiegel,Bernd Krumme.  (2003-07-10)  Urinary tetrahydroaldosterone as a screening method for primary aldosteronism: a comparative study..  American journal of hypertension,  16  ((7)): (522-530).  [PMID:12850384]
17. Hyeon Ho Kim,Chung Min Shin,Chi-Hyun Park,Kyu Han Kim,Kwang Hyun Cho,Hee Chul Eun,Jin Ho Chung.  (2005-06-03)  Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts..  Journal of lipid research,  46  ((8)): (1712-1720).  [PMID:15930517]
18. Vigdis Aas,Merethe H Rokling-Andersen,Eili Tranheim Kase,G Hege Thoresen,Arild C Rustan.  (2005-11-23)  Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells..  Journal of lipid research,  47  ((2)): (366-374).  [PMID:16301737]
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