5(Z),11(Z),14(Z)-Eicosatrienoic Acid

Cayman Chemical Item Number 10009999

5,11,14,20:3; Sciadonic Acid (CAS 7019-85-4)

5(Z),11(Z),14(Z)-Eicosatrienoic Acid (CAS 7019-85-4)

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Description

5(Z),11(Z),14(Z)-Eicosatrienoic acid is a polyunsaturated fatty acid found in various natural sources including maritime pine (Pinus pinaster) seed oil (MPSO), gymnospermae leaves and seeds, and freshwater gastropods.1,2,3 A diet containing MPSO lowered high-density lipoprotein and ApoA1 levels in transgenic mice expressing human ApoA1. MPSO was found to diminish cholesterol efflux in vitro.1 5(Z),11(Z),14(Z)-Eicosatrienoic acid methyl ester, when topically applied, reduces inflammatory processes, potentially by displacing arachidonic acid from phospholipid pools and reducing downstream inflammatory products such as prostaglandin E2 and leukotrienes.4

1 Asset, G., Leroy, A., Bauge, E., et al. Effects of dietary maritime pine (Pinus pinaster)-seed oil on high-density lipoprotein levels and in vitro cholesterol efflux in mice expressing human apolipoprotein A-I. Br J Nutr 84 353-360 (2000).

2 Mongrand, S., Badoc, A., Patouille, B., et al. Taxonomy of gymnospermae: Multivariate analyses of leaf fatty acid composition. Phytochem 58 101-115 (2001).

3 Go, J.V., Rezanka, T., Srebnik, M., et al. Variability of fatty acid components of murine and freshwater gastropod speices from the littoral zone of the Red Sea, Mediterranean Sea, and Sea of Galilee. Biochem Syst Ecol 30 819-835 (2002).

4 Berger, A., Monnard, I., Baur, M., et al. Epidermal anti-inflammatory properties of 5,11,14 20:3: Effects on mouse ear edema, PGE2 levels in cultured keratinocytes, and PPAR activation. Lipids Health Dis 1(5) 1-12 (2002).

Synonyms
  • 5,11,14,20:3
  • Sciadonic Acid
Formal Name 5Z,​11Z,​14Z-​eicosatrienoic acid
CAS Number 7019-85-4
Molecular Formula C20H34O2
Formula Weight 306.5
Formulation A solution in ethanol
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\CCCC/C=C\CCCC(=O)​O
InCHI Code
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​1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)​22/h6-7,9-10,15-16H,2-5,8,11-14,17-19H2,1H3,(H,21,22)​/b7-6-,10-9-,16-15-
InCHI Key
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PRHHYVQTPBEDFE-URZBRJKDSA-N

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5(Z),11(Z),14(Z)-Eicosatrienoic Acid is available in the following screening library:

Size Price Quantity Subtotal
100 µg $55.00 $0.00
500 µg $193.00 $0.00
1 mg $358.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-21. Prices are subject to change without notice.

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