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44864

cis-5,8,11,14,17-Eicosapentaenoic acid

analytical standard

Synonym(s):

EPA, Timnodonic acid

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About This Item

Linear Formula:
CH3(CH2CH=CH)5(CH2)3CO2H
CAS Number:
Molecular Weight:
302.45
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1714433
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biological source

fish oil

Quality Level

grade

analytical standard

assay

≥98.5% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

refractive index

n20/D 1.4977 (lit.)

mp

−54-−53 °C (lit.)

density

0.943 g/mL at 25 °C (lit.)

format

neat

functional group

carboxylic acid

storage temp.

−20°C

SMILES string

CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O

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

General description

cis-5,8,11,14,17-Eicosapentaenoic acid belongs to the class of long-chain omega-3 polyunsaturated fatty acids. It is synthesized in the human body from the essential fatty acid alpha-linolenic acid.

Application

This analyticalstandard can also be used as follows:

  • Optimization of capillary zone electrophoresis procedurecoupled with direct absorption UV detection (CZE-UV) to determine eicosapentaenoicacid and docosahexaenoic acids after their methylation in 10 different samplesof commercial omega-3 supplements
  • Simultaneous determination of eicosapentaenoic acid,docosahexaenoic acid, and arachidonic acid in human plasma samples by high-performanceliquid chromatography-electrochemical detection (HPLC-ECD)
  • Separation, identification, and quantification of eicosapentaenoicacid, docosahexaenoic acid, and arachidonic acid in human plasma samples by high-performanceliquid chromatography combined with tandem mass spectrometry (HPLC-MS/MS)

Biochem/physiol Actions

5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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This Item
E20116220016413
technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

-

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

format

neat

format

-

format

neat

format

neat

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

grade

analytical standard

grade

-

grade

analytical standard

grade

analytical standard

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

assay

≥98.5% (GC)

assay

≥99%

assay

≥98.5% (GC)

assay

≥96.0% (HPLC)


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Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

200.1 °F - closed cup

flash_point_c

93.4 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter



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I Hafström et al.
Arthritis and rheumatism, 31(5), 585-592 (1988-05-01)
Fourteen patients with rheumatoid arthritis (RA) were studied before, during, and after a 1-week total fast. Disease activity decreased, as did the neutrophil release of lysozyme induced by the ionophore A23187. The ability of zymosan-activated RA patient serum to aggregate
J A Dunstan et al.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology, 34(8), 1237-1242 (2004-08-10)
Breast milk contains many immunomodulatory factors (soluble CD14 (sCD14), IgA and cytokines) with the potential to influence infant immune development. To determine if changes in breast milk omega-3 polyunsaturated fatty acid (n-3 PUFA) composition as a result of maternal dietary
Vigdis Aas et al.
Journal of lipid research, 47(2), 366-374 (2005-11-23)
This study was conducted to evaluate the chronic effects of eicosapentaenoic acid (EPA) on fatty acid and glucose metabolism in human skeletal muscle cells. Uptake of [14C]oleate was increased >2-fold after preincubation of myotubes with 0.6 mM EPA for 24



Global Trade Item Number

SKUGTIN
44864-100MG04061832312675
44864-500MG04061832312682

Questions

1–2 of 2 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?

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