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A3611

Sigma-Aldrich

Arachidonic acid

from non-animal source, ≥98.5% (GC)

Sinonimo/i:

cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte

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10 MG
CHF 93.60
100 MG
CHF 178.00
1 G
CHF 1’160.00

CHF 93.60

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Cambia visualizzazione
10 MG
CHF 93.60
100 MG
CHF 178.00
1 G
CHF 1’160.00

About This Item

Formula condensata:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
Numero CAS:
506-32-1
Peso molecolare:
304.47
Beilstein:
1713889
Numero CE:
208-033-4
Numero MDL:
MFCD00004417
Codice UNSPSC:
12352211
ID PubChem:
329770839
NACRES:
NA.25

CHF 93.60

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Origine biologica

non-animal source

Livello qualitativo

300

Saggio

≥98.5% (GC)

Stato

liquid

Indice di rifrazione

n20/D 1.4872 (lit.)

P. ebollizione

169-171 °C/0.15 mmHg (lit.)

Punto di fusione

−49 °C (lit.)

Densità

0.922 g/mL at 25 °C (lit.)

Gruppo funzionale

carboxylic acid

Tipo di lipide

omega FAs

Condizioni di spedizione

dry ice

Temperatura di conservazione

−20°C

Stringa SMILE

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-
YZXBAPSDXZZRGB-DOFZRALJSA-N

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Categorie correlate

Applicazioni

<ul>
<li><strong>Molecular Mechanisms Associated with the Inhibitory Role of Long Chain n-3 PUFA in Colorectal Cancer:</strong> This study discusses the effects of long-chain polyunsaturated fatty acids, like arachidonic acid, on colorectal cancer mechanisms. The research focuses on the anti-inflammatory and cancer inhibitory roles through the modulation of lipid metabolism and signal transduction pathways (Jayathilake et al., 2024).</li>
<li><strong>Zhilining Formula alleviates DSS-induced colitis through suppressing inflammation and gut barrier dysfunction via the AHR/NF-Bp65 axis:</strong> This article presents arachidonic acid′s role in the suppression of inflammation and restoration of gut barrier function, crucial for understanding inflammatory diseases and developing therapeutic strategies (Zhou et al., 2024).</li>
<li><strong>5,6-diHETE lactone (EPA-L) mediates hypertensive microvascular dilation by activating the endothelial GPR-PLC-IP(3) signaling pathway:</strong> Explores the cardiovascular implications of arachidonic acid metabolites, specifically their role in microvascular responses, which could influence hypertension treatment strategies (Asulin et al., 2024).</li>
</ul>

Azioni biochim/fisiol

Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Confezionamento

Sealed ampule

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

235.4 °F - closed cup

Punto d’infiammabilità (°C)

113 °C - closed cup

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Certificati d'analisi (COA)

Lot/Batch Number
0000429322
0000429322
0000421082
0000421082
0000407633

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Sigma-Aldrich

C0733

Cyclooxygenase 1 from sheep

Arachidonic-5,6,8,9,11,12,14,15-d8 acid &#8805;98 atom % D, &#8805;98% (CP)

Sigma-Aldrich

735000

Arachidonic-5,6,8,9,11,12,14,15-d8 acid

Acido linoleico liquid, BioReagent, suitable for cell culture

Sigma-Aldrich

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Acido linoleico

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
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
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
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
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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

      Helpful?

  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

      Helpful?

  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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