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H7898

Sigma-Aldrich

15(S)-Hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoic acid

~100 μg/mL in ethanol, ~98%

Synonym(s):

15(S)-HEPE

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About This Item

Empirical Formula (Hill Notation):
C20H30O3
CAS Number:
86282-92-0
Molecular Weight:
318.45
MDL number:
MFCD00065817
UNSPSC Code:
12352211
PubChem Substance ID:
24895813

Assay

~98%

form

liquid

concentration

~100 μg/mL in ethanol

functional group

carboxylic acid

storage temp.

−20°C

SMILES string

CC\C=C/C[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI

1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h3-5,8-11,13-14,17,19,21H,2,6-7,12,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,13-3-,17-14+/t19-/m0/s1

InChI key

WLKCSMCLEKGITB-DBVSHIMFSA-N

Packaging

Packaged under Argon.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Aude Le Bail et al.
BMC molecular biology, 9, 75-75 (2008-08-20)
Brown algae are plant multi-cellular organisms occupying most of the world coasts and are essential actors in the constitution of ecological niches at the shoreline. Ectocarpus siliculosus is an emerging model for brown algal research. Its genome has been sequenced
Nguyen Dang Hung et al.
British journal of pharmacology, 162(5), 1119-1135 (2010-11-26)
Lysophosphatidylcholines (lysoPCs) with polyunsaturated acyl chains are known to exert anti-inflammatory actions. 15-Lipoxygeanation is crucial for anti-inflammatory action of polyunsaturated acylated lysoPCs. Here, the anti-inflammatory actions of 1-(15-hydroxyeicosapentaenoyl)-lysoPC (15-HEPE-lysoPC) and its derivatives were examined in a mechanistic analysis. Anti-inflammatory actions
Christopher P Thomas et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 67(1), 156-165 (2007-02-03)
Unexpected enhancement of the topical delivery of eicosapentaenoic acid (EPA) across porcine skin was observed previously when fish oil was co-formulated with ketoprofen. In the current work depth profile analysis was used to probe the epidermal conversion of EPA to
K Fogh et al.
Biomedical & environmental mass spectrometry, 17(6), 459-461 (1988-12-01)
A direct mass spectrometric method for 15-hydroxy metabolites of arachidonic acid and of eicosapentaenoic acid is described. 15-Hydroxyeicosanoids have the capacity to inhibit the formation of leukotrienes, potent mediators of inflammation formed by the 5-lipoxygenase pathway of arachidonic acid metabolism
M Tsunomori et al.
Biochimica et biophysica acta, 1300(3), 171-176 (1996-05-20)
The effect of 15-hydroperoxy-5,8,11,13,15-eicosapentaenoic acid (15-HPEPE), a hydroperoxy adduct of eicosapentaenoic acid (EPA), on the formation of 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE), thromboxane (TX) B2 and 12-hydroxy-5,8,10-heptadecatrienoic acid (HHT) from exogenous arachidonic acid in washed rabbit platelets was examined. 15-HPEPE inhibited 12-HETE
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