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10931

Arachidonic acid

>95.0% (GC)

Synonym(s):

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

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250 mg
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$206.00
1 g
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$515.00

About This Item

Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
506-32-1
Molecular Weight:
304.47
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
57646859
EC Number:
208-033-4
Beilstein/REAXYS Number:
1713889
MDL number:
MFCD00004417

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biological source

fungus

Quality Segment

100

assay

>95.0% (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

SMILES string

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 key

YZXBAPSDXZZRGB-DOFZRALJSA-N

Application

Arachidonic acid has been used:
  • in calibration curve generation in Raman spectroscopy and atomic force microscopy (AFM) in normal and breast cancer samples
  • as a polyunsaturated fatty acid supplement to the reconstituted synthetic bile (RSB) in drug resistance analysis
  • for the activation of mechanistic target of rapamycin 1 (mTOR1) and mTOR2

Biochem/physiol Actions

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) .

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This Item
A3611181198735000
Arachidonic acid >95.0% (GC)

Sigma-Aldrich

10931

Arachidonic acid

Arachidonic acid from non-animal source, ≥98.5% (GC)

Sigma-Aldrich

A3611

Arachidonic acid

Arachidonic Acid Precursor for prostaglandins, prostacyclin, and thromboxane.

Sigma-Aldrich

181198

Arachidonic Acid

Arachidonic-5,6,8,9,11,12,14,15-d8 acid ≥98 atom % D, ≥97% (CP)

Sigma-Aldrich

735000

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

assay

>95.0% (GC)

assay

≥98.5% (GC)

assay

≥99% (TLC and GC)

assay

≥97% (CP)

biological source

fungus

biological source

non-animal source

biological source

-

biological source

-

functional group

carboxylic acid

functional group

carboxylic acid

functional group

-

functional group

-

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−70°C

storage temp.

−20°C

form

liquid

form

liquid

form

oil

form

liquid

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)

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Questions

1–5 of 5 Questions  

  1. 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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. 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

      Helpful?

  3. IS THIS IN A SOLID FORM? HOW CAN THIS BE DILUTED

    1 answer

    1. TS Final Answer: This product is a neat or pure liquid that has a melting point of −49 °C. This material is soluble in ethanol, DMSO, or dimethyl formamide at 100 mg/ml, and in chloroform or methanol at 50 mg/ml. Additional information may be accessed in the product datasheet for item A3555, available at the link below. This product is an identical compound but is tested for use in cell culture.
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/239/399/a3555pis.pdf

      Helpful?

  4. What is the solubility of item 10931, Arachidonic acid?

    1 answer

    1. Arachidonic acid is almost insoluble in water; it is soluble in ethanol, ether, acetone. The exact concentrations at which the material can be solubilized has not been determined.

      Helpful?

  5. Is this supplied in a bottle with a septa such that the headspace can be flushed with Nitrogen?

    1 answer

    1. This material is packaged in a glass bottle with a screw-type cap. It does not include a septa.

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