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A3611

Sigma-Aldrich

花生四烯酸

from non-animal source, ≥98.5% (GC)

同義詞:

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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About This Item

線性公式:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS號碼:
506-32-1
分子量：:
304.47
Beilstein:
1713889
EC號碼:
208-033-4
MDL號碼:
MFCD00004417
分類程式碼代碼:
12352211
PubChem物質ID:
329770839
NACRES:
NA.25
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生物源

non-animal source

品質等級

300

化驗

≥98.5% (GC)

形狀

liquid

折射率

n20/D 1.4872 (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

mp

−49 °C (lit.)

密度

0.922 g/mL at 25 °C (lit.)

官能基

carboxylic acid

脂質類型

omega FAs

運輸包裝

dry ice

儲存溫度

−20°C

SMILES 字串

OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

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-

InChI 密鑰

YZXBAPSDXZZRGB-DOFZRALJSA-N

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相關類別

應用

<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>

生化／生理作用

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 。

包裝

密封安瓿包装

象形圖

Exclamation mark
GHS07

訊號詞

Warning

危險聲明

H315,H319

危險分類

Eye Irrit. 2 - Skin Irrit. 2

儲存類別代碼

10 - Combustible liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

235.4 °F - closed cup

閃點（°C）

113 °C - closed cup

從最近期的版本中選擇一個：

分析證明 (COA)

Lot/Batch Number
0000429322
0000429322
0000421082
0000421082
0000407633

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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
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
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
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Questions

1–7 of 7 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is the solubility of item A3611, Arachidonic acid?

    1 answer

    1. This product is soluble in DMSO (100 mg/ml), DMF (100 mg/ml), 100% ethanol (50 mg/ml), methanol (50 mg/ml), chloroform (50 mg/ml), dichloromethane, hexane, acetonitrile, and ether.

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  4. what is the volume in the 10mg ampule for A3611- arachidonic acid?

    1 answer

    1. Based on the density of 0.922 g/mL, the volume of the 10 mg package is approximately 0.011mL.

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  5. What is the volume in microL of arachidonic acid (A3611-100 mg) in vial? Please specify the purity (PCode 1003455023).

    1 answer

    1. There is 108 uL in the 100mG pack size. The exact purity will be listed on the Certificate of Analysis. Please see the sample Certificate of Analysis: https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/A3611-1G-PWSLCQ3577.pdf

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  6. May I know the Molarity (M) of the Arachidonic Acid A3611? It was not stated in the SDS.

    1 answer

    1. The concentration for this product will be lot specific as purity changes with each batch. The concentration of this material can be calculated by the following equation: density x 1000 x purity percent divided by the molecular weight. For example, lot SLCQ3577 on the sample certificate of analysis will have a concentration of about 3.01 M

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  7. Hi, I'm used to ordering AA with this same catalogue nr at 10mg in powder form. Now only 100mg in liquid form is available. In which solvent is this?

    1 answer

    1. This is pure arachadonic acid - it is not in any solvent. Its melting point is at -49 deg C. At temperatures above, it will be in its liquid physical state. You can determine the amount by using the density for a calculation. 0.922 g/mL at 25 °C (lit.)

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