A3611
花生四烯酸
from non-animal source, ≥98.5% (GC)
别名:
二十碳-5Z,8Z,11Z,14Z-四烯酸, 全顺式-5,8,11,14-二十碳四烯酸, 花生四烯酸
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关于此项目
线性分子式:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
化学文摘社编号:
分子量:
304.47
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
EC Number:
208-033-4
Beilstein/REAXYS Number:
1713889
产品名称
花生四烯酸, from non-animal source, ≥98.5% (GC)
InChI
1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
SMILES string
OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
InChI key
YZXBAPSDXZZRGB-DOFZRALJSA-N
biological source
non-animal source
assay
≥98.5% (GC)
form
liquid
refractive index
n20/D 1.4872 (lit.)
bp
169-171 °C/0.15 mmHg (lit.)
mp
−49 °C (lit.)
density
0.922 g/mL at 25 °C (lit.)
functional group
carboxylic acid
lipid type
omega FAs
shipped in
dry ice
storage temp.
−20°C
Quality Level
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Application
<ul>
<li><strong>长链n-3 PUFA在结直肠癌中抑制作用相关的分子机制：</strong>本研究探讨了花生四烯酸等长链多不饱和脂肪酸对结直肠癌发病机制的影响。本研究的重点是通过调节脂质代谢和信号传导途径来发挥抗炎和癌症抑制作用 （Jayathilake et al., 2024）。</li>
<li><strong>Zhiline Formula通过AHR/NF-Bp65轴抑制炎症和肠道屏障功能障碍来缓解DSS诱导的结肠炎：</strong>本文介绍了花生四烯酸在抑制炎症和恢复肠道屏障功能中的作用，这对于理解炎症性疾病和制定治疗策略至关重要（ (Zhou et al., 2024）.</li>
<li><strong>5,6-diHETE内酯（EPA-L）通过激活内皮GPR-PLC-IP（3）信号通路介导高血压微血管扩张:</strong> 探讨了花生四烯酸代谢物对心血管的影响，特别是它们在微血管反应中的作用，这可能会影响高血压的治疗策略（Asulin et al., 2024）。</li>
</ul>
<li><strong>长链n-3 PUFA在结直肠癌中抑制作用相关的分子机制：</strong>本研究探讨了花生四烯酸等长链多不饱和脂肪酸对结直肠癌发病机制的影响。本研究的重点是通过调节脂质代谢和信号传导途径来发挥抗炎和癌症抑制作用 （Jayathilake et al., 2024）。</li>
<li><strong>Zhiline Formula通过AHR/NF-Bp65轴抑制炎症和肠道屏障功能障碍来缓解DSS诱导的结肠炎：</strong>本文介绍了花生四烯酸在抑制炎症和恢复肠道屏障功能中的作用，这对于理解炎症性疾病和制定治疗策略至关重要（ (Zhou et al., 2024）.</li>
<li><strong>5,6-diHETE内酯（EPA-L）通过激活内皮GPR-PLC-IP（3）信号通路介导高血压微血管扩张:</strong> 探讨了花生四烯酸代谢物对心血管的影响，特别是它们在微血管反应中的作用，这可能会影响高血压的治疗策略（Asulin et al., 2024）。</li>
</ul>
Biochem/physiol Actions
花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸，是细胞膜磷脂的组分。在炎症反应中，水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后，AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷，被脂氧合酶代谢为白三烯和脂氧素，以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合，抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。
花生四烯酸及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。
花生四烯酸可刺激MDA-MB-435人转移癌细胞与细胞外基质分子（胶原蛋白IV和玻连蛋白）的粘附 。
Packaging
密封安瓿包装
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
Abdulaziz M S Alsaad et al.
Drug metabolism reviews, 45(2), 173-195 (2013-04-23)
A plethora of studies have demonstrated the expression of cytochrome P450 (CYP) and soluble epoxide hydrolase (sEH) enzymes in the heart and other cardiovascular tissues. In addition, the expression of these enzymes is altered during several cardiovascular diseases (CVDs), including
Alma M Astudillo et al.
Biochimica et biophysica acta, 1821(2), 249-256 (2011-12-14)
The development of mass spectrometry-based techniques is opening new insights into the understanding of arachidonic acid (AA) metabolism. AA incorporation, remodeling and release are collectively controlled by acyltransferases, phospholipases and transacylases that exquisitely regulate the distribution of AA between the
Tamás Decsi et al.
The American journal of clinical nutrition, 98(2), 543S-548S (2013-07-05)
We summarize data on the potential interaction of trans isomeric fatty acids [trans fatty acids (TFAs)] with the availability of long-chain polyunsaturated fatty acids (LC-PUFAs) in the perinatal period. Today, TFA intakes in pregnant and lactating women can be estimated
Jesmond Dalli et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(7), 2573-2583 (2013-03-19)
Maresins are produced by macrophages from docosahexaenoic acid (DHA) and exert potent proresolving and tissue homeostatic actions. Maresin 1 (MaR1; 7R,14S-dihydroxy-docosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid) is the first identified maresin. Here, we investigate formation, stereochemistry, and precursor role of 13,14-epoxy-docosahexaenoic acid, an intermediate
Peter Willatts et al.
The American journal of clinical nutrition, 98(2), 536S-542S (2013-06-21)
Evidence is accumulating that a dietary supply of long-chain polyunsaturated fatty acids (LC-PUFAs) enhances the development of attention and efficient information processing in infants. However, it is uncertain whether LC-PUFAs in infancy influence cognitive development in later childhood. The objective
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