Oxylipins

4-hydroxy Nonenal Mercapturic Acid
4-HNE is cleared rapidly from the plasma and undergoes enterohepatic circulation as a glutathione conjugate in the rat,with about two thirds of an administered dose of 4-HNE is excreted within 48 hours in the urine, primarily in the form of mercapturic acid conjugates.
Katalog # CAS Nummer Summenformel Menge
sc-205121 146764-24-1 C₁₄H₂₅NO₅S 1 mg/10 mg
4-hydroxy Nonenal Mercapturic Acid-d3
4-hydroxy Nonenal mercapturic acid-d3 contains three deuterium atoms at the terminal methyl position. It is used for an internal standard for quantification of 4-hydroxy nonenal mercapturic acid by GC- or LC-mass spectrometry. Peroxidation of common ω-6 polyunsaturated fatty acids (PUFAs) such as linoleic acid, DGLA, and arachidonic acid can give rise to 4-HNE. 4-HNE is cleared rapidly from the plasma and undergoes enterohepatic circulation as a glutathione conjugate in the rat. About two thirds of an administered dose of 4-HNE is excreted within 48 hours in the urine, primarily in the form of mercapturic acid conjugates. The C-1 aldehyde of 4-HNE is reduced to an alcohol in about half of these metabolites. The remainder are C-1 aldehydes that have been oxidized to C-1 carboxylic acids. These aldehydes and carboxylic acids can also form γ-lactols and γ-lactones, producing at least four or five end urinary metabolites of 4-HNE in vivo.
Katalog # CAS Nummer Summenformel Menge
sc-220938 n.n. C₁₄H₂₂D₃NO₅S 50 µg/100 µg
4-hydroxy Nonenal-d3
4-hydroxy Nonenal-d3 (4-HNF-d3) contains three deuterium atoms at the terminal methyl position. It is used as an internal standard for the quantification of 4-HNE by GC- or LC-mass spectrometry. 4-HNE is a lipid peroxidation product derived from oxidized ω-6 polyunsaturated fatty acids such as arachidonic acid. 4-HNE is widely used as a marker of lipid peroxidation. It exhibits many biological activities such as cytotoxicity, genotoxicity, growth inhibiting activity, and chemotactic activity. 4-HNE inhibits pro-oxidant-induced Ca²⁺ release from mitochondria at 10-50 µM.
Katalog # CAS Nummer Summenformel Menge
sc-220939 n.n. C₉H₁₃D₃O₂ 50 µg/100 µg
(±)4-HDoHE
An autoxidation product of docosahexaenoic acid (DHA) in vitro. Also, it is produced from incubations of DHA in rat brain, intestinal microsomes and liver. It is a potential marker of oxidative stress in brain and retina where DHA is abundant.
Katalog # CAS Nummer Summenformel Menge
sc-205120 90906-40-4 C₂₂H₃₂O₃ 25 µg/50 µg
(±)5-HEPE
Produced by non-enzymatic oxidation of EPA resulting in a racemic mixture of 5-HEPE.
Katalog # CAS Nummer Summenformel Menge
sc-205135 83952-40-3 C₂₀H₃₀O₃ 25 µg/50 µg
(±)5-HETE
This compound is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid, and it is a racemic mixture. It induces the aggregation of isolated neutrophils with an IC₅₀ value of 200 nM.
Katalog # CAS Nummer Summenformel Menge
sc-205136 73307-52-5 C₂₀H₃₂O₃ 25 µg/50 µg
(±)5-HETE methyl ester
One of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid, where the methyl ester of (±)5-HETE has no distinguishing biological activity and is supplied as a standard. Oxidatively degraded polyunsaturated fatty acid (PUFA) methyl esters may contain (±)5-HETE methyl ester.
Katalog # CAS Nummer Summenformel Menge
sc-205137 73279-38-6 C₂₁H₃₄O₃ 25 µg/50 µg
(±)5,6-DHET
Epoxide hydrolases convert the EETs into vicinal diols, with concurrent loss of much of their biological activity. It is a substrate for sheep seminal vesicle COX, producing 5,6-dihydroxy prostaglandin E1 and F1α metabolites in vitro.
Katalog # CAS Nummer Summenformel Menge
sc-221046 213382-49-1 C₂₀H₃₄O₄ 25 µg/50 µg
(±)5,6-DHET lactone
Epoxide hydrolases convert EETs into vicinal diols, with concurrent loss of their biological activity. (±)5,(6)-DHET can be transformed to the 1,5-lactone as an artifact during extraction.
Katalog # CAS Nummer Summenformel Menge
sc-221047 213126-92-2 C₂₀H₃₂O₃ 25 µg/50 µg
(±)5(6)-EET
(±)5(6)-EET is biosynthesized in rabbit and rat liver microsomes by cCYP450. In neuroendocrine cells, such as the anterior pituitary and pancreatic islet, (±)5(6)-EET has been used in the mobilization of Ca²⁺ and hormone secretion.
Katalog # CAS Nummer Summenformel Menge
sc-221068 n.n. C₂₀H₃₂O₃ 25 µg/50 µg
(±)5(6)-EET methyl ester
(±)5(6)-EET is biosynthesized in rat and rabbit liver microsomes by CYP450. In neuroendocrine cells, such as the anterior pituitary and pancreatic islet, (±)5(6)-EET has been implicated in mobilization of Ca²⁺ and hormone secretion. Since (±)5(6)-EET is highly unstable, (±)5(6)-EET methyl ester is used for bulk storage and small amounts are converted to free acid before use.
Katalog # CAS Nummer Summenformel Menge
sc-221070 122799-12-6 C₂₁H₃₄O₃ 25 µg/50 µg
5(6)-EpETE methyl ester
A chemically less reactive derivative of 5(6)-Epoxy eicosatetraenoic acid; an epoxygenase metabolite of EPA.
Katalog # CAS Nummer Summenformel Menge
sc-205147 127716-49-8 C₂₁H₃₂O₃ 25 µg/100 µg
5(R)-HETE
A rare lipoxygenase product of arachidonic acid. Nearly all plant and animal 5-LOs produce 5(S)-HETE, but the presence of a 5(R)-LO and the synthesis of 5(R)-HpETE and 5(R)-HETE have been established in oocytes of the bivalve mollusk, S. solidissima.1 5(R)-HETE is more potent than the (S)-enantiomer as a chemotactic agent for human neutrophils.2
Katalog # CAS Nummer Summenformel Menge
sc-205148 61641-47-2 C₂₀H₃₂O₃ 25 µg/50 µg
5(S)-HEPE
Produced by the 5-lipoxygenase catalyzed oxidation of eicosapentaenoic acid (EPA), this chemical is synthesized from tissue homogenates. The biological activity is poorly documented and it remains to be determined whether this activity differs substantially from that of 5(S)-HETE.
Katalog # CAS Nummer Summenformel Menge
sc-205149 92008-51-0 C₂₀H₃₀O₃ 25 µg/50 µg
5(S)-HETE lactone
Cyclic ester formed by acid-catalyzed nucleophilic addiction of the C-5 hydroxyl to the C-1 carboxyl of 5(S)-HETE. The ability of (±)5-HETE lactone to inhibit rat basophilic leukemia cell 5-lipoxygenase (IC₅₀ = 27 µM) may be entirely due to the 5(S) isomer, but the enantiomers have not been tested separately.
Katalog # CAS Nummer Summenformel Menge
sc-205150 127708-42-3 C₂₀H₃₀O₂ 25 µg/100 µg
5(S),14(R)-Lipoxin B4
A positional isomer of LXA4 produced by the metabolism of 15-HETE or 15-HpETE by human leukocytes.
Katalog # CAS Nummer Summenformel Menge
sc-205151 98049-69-5 C₂₀H₃₂O₅ 25 µg/50 µg
5(S),6(R)-11-trans DiHETE
5(S),6(R)-11-trans DiHETE is a C-11 double bond isomer of 5(S),6(R)-DiHETE that is formed by the enzymatic isomerization of 5(S),6(R)-DiHETE by a membrane bound factor. 5(S),6(R)-11-trans DiHETE has been found in rat kidney homogenates and is potentially formed by the epoxide hydrolase pathway in this tissue. The isomerase activity responsible for the conversion of leukotriene B4 (LTB4) to 6-trans LTB4 in rat kidney homogenates has been implicated in its formation. 5(S),6(R)-11-trans DiHETE is not a substrate for soybean lipoxygenase. The biological activity of 5(S),6(R)-11-trans DiHETE has not been reported yet.
Katalog # CAS Nummer Summenformel Menge
sc-221075 n.n. C₂₀H₃₂O₄ 25 µg/50 µg
5(S),6(R)-Lipoxin A4 methyl ester
A more lipid soluble, prodrug formulation of the transcellular metabolite LXA4; equipotent to leukotriene B4 (LTB4) in inducing superoxide generation in human neutrophils.
Katalog # CAS Nummer Summenformel Menge
sc-205152 97643-35-1 C₂₁H₃₄O₅ 25 µg/50 µg
5(S),6(S)-DiHETE
One of the four diastereomeric 5,6-dihydroxy acids produced from the non-enzymatic hydrolysis of LTA4,1 yet does not have significant leukotriene-like activity.2
Katalog # CAS Nummer Summenformel Menge
sc-205153 82948-87-6 C₂₀H₃₂O₄ 25 µg/50 µg
(±)7-HDoHE
An autoxidation product of docosahexaenoic acid (DHA) in vitro. Also, it is produced from incubations of DHA in rat brain, intestinal microsomes and liver. It is a potential marker of oxidative stress in brain and retina where DHA is abundant.
Katalog # CAS Nummer Summenformel Menge
sc-205168 90780-55-5 C₂₂H₃₂O₃ 25 µg/50 µg
(±)8-HDoHE
An autoxidation product of docosahexaenoic acid (DHA) in vitro. Also, it is produced from incubations of DHA in rat brain, intestinal microsomes and liver. It is a potential marker of oxidative stress in brain and retina where DHA is abundant.
Katalog # CAS Nummer Summenformel Menge
sc-205170 90780-54-4 C₂₂H₃₂O₃ 25 µg/50 µg
(±)8-HEPE
(±)8-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 8(S)-HEPE and 8(R)-HEPE. (±)8-HEPE can induce hatching of E. modestus and B. balanoides eggs. This is probably due to the presence of the 8(R) isomer within the racemic mixture.
Katalog # CAS Nummer Summenformel Menge
sc-221131 n.n. C₂₀H₃₀O₃ 25 µg/50 µg
(±)8-HETE
One of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid, where the biological activity is likely to resemble that of its constituent enantiomers.
Katalog # CAS Nummer Summenformel Menge
sc-205171 79495-84-4 C₂₀H₃₂O₃ 25 µg/50 µg
(±)8,9-DHET
Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity. The 8(S),9(R)-EET isomer is metabolized by platelet COX to form 8(S),9(R),11(R)-THETA, a trihydroxy fatty acid which may act as a renal vasoconstrictor.
Katalog # CAS Nummer Summenformel Menge
sc-221155 192461-96-4 C₂₀H₃₄O₄ 25 µg/50 µg
8,9-EE-14(Z)-E
A potent vasodilator in bovine coronary arteries. The synthesis of this analog involves the formation of the epoxide at the 14,15 double bond, yet, epoxidation can also occur at the 8,9 double bond 2. It is a minor product from the synthesis of 14,15-EE-8(Z)-E. This compound has not been reported in the literature, and its biological activity is not known. It may serve as a tool to verify that the parent compound, 14,15-EE-8(Z)-E, is pure and does not contain the 8,9 epoxy regioisomer.
Katalog # CAS Nummer Summenformel Menge
sc-221156 n.n. C₂₀H₃₆O₃ 25 µg/50 µg
(±)8(9)-EET
Biosynthesized in rat and rabbit liver microsomes by CYP450.1,2 It is a major P450 metabolite in the renal cortex.3 (±)8(9)-EET reduces GFR through cyclooxygenase-dependent preglomerular vasoconstriction.4
Katalog # CAS Nummer Summenformel Menge
sc-221158 n.n. C₂₀H₃₂O₃ 25 µg/50 µg
(±)8(9)-EET methyl ester
Biosynthesized in rat and rabbit liver microsomes by CYP450.1,2 This compound is a major CYP450 metabolite in the renal cortex.3 (±)8(9)-EET reduces GFR through cyclooxygenase-dependent preglomerular vasoconstriction.4 (±)8(9)-EET methyl ester is a more stable form used for long-term storage. It can be readily hydrolyzed to the free acid as needed.
Katalog # CAS Nummer Summenformel Menge
sc-221160 n.n. C₂₁H₃₄O₃ 25 µg/50 µg
8(R)-HETE
8(R)-HETE is biosynthesized by lipoxygenation of arachidonic acid in marine invertebrates such as gorgonian corals and starfish.
Katalog # CAS Nummer Summenformel Menge
sc-205180 105500-09-2 C₂₀H₃₂O₃ 25 µg/50 µg
8(S)-HEPE
8(S)-HEPE is a monohydroxy fatty acid produced by lipoxygenase oxidation of EPA. It acts to promote hatching of barnacle eggs at 10 nM, although it is not clearly identified as the natural egg hatching factor.
Katalog # CAS Nummer Summenformel Menge
sc-205181 118492-81-2 C₂₀H₃₀O₃ 25 µg/50 µg
8(S)-HETrE
A monohydroxy polyunsaturated fatty acid produced by rabbit neutrophil lipoxygenase when dihomo-γ-linolenic acid is used as a substrate.1 Although the biological activities of 8(S)-HETrE have not been well characterized, it is hypothesized to behave similarly to 8(S)-HETE.
Katalog # CAS Nummer Summenformel Menge
sc-221162 n.n. C₂₀H₃₄O₃ 25 µg/50 µg
(±)9-HEPE
Produced by non-enzymatic oxidation of EPA. Contains equal amounts of 9(S)-HEPE and 9(R)-HEPE. The biological activity has not been clearly documented.
Katalog # CAS Nummer Summenformel Menge
sc-221166 n.n. C₂₀H₃₀O₃ 25 µg/50 µg
(±)9-HODE
One of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in plasma and mitochondrial membranes of rabbit reticulocytes. Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.
Katalog # CAS Nummer Summenformel Menge
sc-205184 98524-19-7 C₁₈H₃₂O₃ 100 µg/500 µg
(±)9-HODE cholesteryl ester
Originally extracted from atherosclerotic lesions and shown to be produced by Cu2+-catalyzed oxidation of LDL. Studies later determined that 15-LO from rabbit reticulocytes and human monocytes were able to metabolize cholesteryl linoleate, a major component of LDL, to 9-HODE cholesteryl ester.
Katalog # CAS Nummer Summenformel Menge
sc-205185 33783-76-5 C₄₅H₇₆O₃ 25 µg/50 µg
9-OxoODE
Results from oxidation of the allylic hydroxyl of either 9(S)- or 9(R)-HODE.
Katalog # CAS Nummer Summenformel Menge
sc-205187 54232-59-6 C₁₈H₃₀O₃ 25 µg/50 µg
9-OxoOTrE
9-OxoOTrE is produced by the oxidation of 9-HpOTrE.1 9-OxoOTrE and exhibits antimicrobial activity against plant pathogenic microorganisms including bacteria and fungi.2
Katalog # CAS Nummer Summenformel Menge
sc-205188 125559-74-2 C₁₈H₂₈O₃ 25 µg/100 mg
(±)9,10-DiHOME
The 9(10) epoxide of linoleic acid, created by neutrophils during the oxidative burst.
Katalog # CAS Nummer Summenformel Menge
sc-205189 263399-34-4 C₁₈H₃₄O₄ 25 µg/50 µg
(±)9,10-DiHOME-d4
Contains four deuterium atoms at the 9, 10, 12, and 13 positions. Used as an internal standard for the quantification of (±)9,10-DiHOME by GC- or LC-mass spectrometry (MS). The unstable compound Leukotoxin is rapidly degraded by epoxide hydrolases to form the diol, 9,10-DiHOME.4 Mitochondrial dysfunction, vasodilation, and apoptosis are features of leukotoxin toxicity. In renal proximal tubular cells, the diol hydrolysis products of leukotoxin, such as 9,10-DiHOME, have been directly implicated as the cytotoxic agent responsible for cell death.5
Katalog # CAS Nummer Summenformel Menge
sc-221168 263399-34-4 (unlabeled) C₁₈H₃₀D₄O₄ 25 µg/50 µg
(±)9(10)-EpOME
The 9,10-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst. The compound has been recovered from the lungs of hyperoxic rats and from humans with acute respiratory distress syndrome. Mitochondrial dysfunction is the main feature of (±)9(10)-EpOME cytotoxicity, which may be due to the diol metabolites as well as the parent epoxide.
Katalog # CAS Nummer Summenformel Menge
sc-221169 6814-52-4 C₁₈H₃₂O₃ 25 µg/50 µg
(±)9(10)-EpOME-d4
Contains four deuterium atoms at the 9, 10, 12, and 13 positions. Used as an internal standard for the quantification of latanoprost by GC- or LC-mass spectrometry (MS).
Katalog # CAS Nummer Summenformel Menge
sc-221170 n.n. C₁₈H₂₈D₄O₃ 25 µg/50 µg
9(R)-HODE
Produced by both human umbilical vein endothelial cells and bovine aorta endothelial cells when incubated with linoleic acid.
Katalog # CAS Nummer Summenformel Menge
sc-205192 10075-11-3 C₁₈H₃₂O₃ 25 µg/50 µg
9(R)-HODE cholesteryl ester
This compound was originally extracted from atherosclerotic lesions. It remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation. It can be used as a standard for analysis of chiral HODE cholesteryl esters.
Katalog # CAS Nummer Summenformel Menge
sc-221171 n.n. C₄₅H₇₆O₃ 25 µg/50 µg
9(S)-HEPE
A monohydroxy fatty acid derived from EPA where the biological activity of 9(S)-HEPE has not yet been documented.
Katalog # CAS Nummer Summenformel Menge
sc-221172 n.n. C₂₀H₃₀O₃ 25 µg/50 µg
9(S)-HETE
9(S)-HETE is an enantiomer which makes up 50% of (±)9-HETE. There are no reports of 9(S)-HETE occurring as an enzymatic lipoxygenation product. While 12(S)-HETE promotes adhesion of several cell lines to endothelial cell monolayes, 9(S)-HETE and other positional HETEs are without effect.
Katalog # CAS Nummer Summenformel Menge
sc-205193 107656-13-3 C₂₀H₃₂O₃ 25 µg/50 µg
9(S)-HODE
Produced by the lipoxygenation of linoleic acid in both animals and plants. The compound has been detected in oxidized LDL particles and in atherosclerotic plaques as an esterified component of membrane phospholipids.
Katalog # CAS Nummer Summenformel Menge
sc-205194 73543-67-6 C₁₈H₃₂O₃ 100 µg/500 µg
9(S)-HODE cholesteryl ester
This compound was originally extracted from atherosclerotic lesions.1 It remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation.2 It can be used as a standard for analysis of chiral HODE cholesteryl esters.
Katalog # CAS Nummer Summenformel Menge
sc-221173 n.n. C₄₅H₇₆O₃ 25 µg/50 µg
9(S)-HODE-d4
This compound contains four deuterium atoms at the 9, 10, 12, and 13 positions. It is intended for use as an internal standard for the quantification of 9(S)-HODE by GC- or LC-mass spectrometry. 9(S)-HODE is produced by the lipoxygenation of linoleic acid in both plants and animals. It has been detected in atherosclerotic plaques, as an esterified component of membrane phospholipids and in oxidized low-density lipoproteins particles.
Katalog # CAS Nummer Summenformel Menge
sc-221174 98524-19-7 (unlabeled) C₁₈H₂₈D₄O₃ 25 µg/50 µg
9(S)-HpODE
Produced by the action of arachidonate 5-LO on linoleic acid. Can be further metabolized by potato hydroperoxide dehydratase to colneleic acid.
Katalog # CAS Nummer Summenformel Menge
sc-205196 29774-12-7 C₁₈H₃₂O₄ 100 µg/500 µg
9(S)-HpOTrE
A monohydroperoxy polyunsaturated fatty acid produced by the action of 5-lipoxygenase (5-LO) on α-linolenic acid; serves as a substrate for further oxidation by both soybean and potato LOs.
Katalog # CAS Nummer Summenformel Menge
sc-205197 111004-08-1 C₁₈H₃₀O₄ 100 µg/500 µg
(±)10-HDoHE
An autoxidation product of docosahexaenoic acid (DHA) in vitro. Also, it is produced from incubations of DHA in rat brain, intestinal microsomes and liver. It is a potential marker of oxidative stress in brain and retina where DHA is abundant.
Katalog # CAS Nummer Summenformel Menge
sc-204959 90780-50-0 C₂₂H₃₂O₃ 25 µg/50 µg
(±)11-HEPE
Produced by non-enzymatic oxidation of eicosapentaenoic acid and it contains equal amounts of 11(S)-HEPE and 11(R)-HEPE. The biological activity of (±)11-HEPE has not been clearly documented.
Katalog # CAS Nummer Summenformel Menge
sc-204969 99217-78-4 C₂₀H₃₀O₃ 25 µg/50 µg
(±)11-HETE
One of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. Using chiral phase HPLC, the individual R and S isomers of racemic HETEs have been separated and identified. The racemic HETEs have been quantified as an index of lipid peroxidation using GC/MS.
Katalog # CAS Nummer Summenformel Menge
sc-204970 73804-65-6 C₂₀H₃₂O₃ 25 µg/50 µg
(±)11,12-DHET
Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity. 11,12-DHET relaxes U-46619-contracted arterial rings with approximately 70% of the magnitude of 11,12-EET.
Katalog # CAS Nummer Summenformel Menge
sc-220577 n.n. C₂₀H₃₄O₄ 25 µg/50 µg
(±)11(12)-EET methyl ester
Biosynthesized in rat and rabbit liver microsomes by CYP450. Has been shown, along with (±)8(9)-EET, to play a role in the recovery of depleted Ca²⁺ pools in cultured smooth muscle cells. It can be readily hydrolyzed to the free acid as needed.
Katalog # CAS Nummer Summenformel Menge
sc-220581 73799-06-1 C₂₁H₃₄O₃ 25 µg/50 µg
11(R)-HETE
Biosynthesized by the 11(R)-LOs of the sea urchin, S. purpuratus, and the fresh water hydra, H. vulgaris. The biological activity relates to oocyte maturation and tentacle regeneration, respectively, in these two species. Also produced when aspirin-treated recombinant COX-2 is incubated with arachidonic acid.
Katalog # CAS Nummer Summenformel Menge
sc-204974 73347-43-0 C₂₀H₃₂O₃ 25 µg/50 µg
11(S)-HEDE
Isolated by the chromatographic resolution of (±)11-HEDE. There are no reports of biological activity associated with 11(S)-HEDE in the literature.
Katalog # CAS Nummer Summenformel Menge
sc-220583 330800-90-3 C₂₀H₃₆O₃ 25 µg/50 µg
Traumatic Acid
A product of the hydroperoxide lyase pathway in plants. A wound healing agent that stimulates cell division near a wound site to form a protective callus.
Katalog # CAS Nummer Summenformel Menge
sc-205532 6402-36-4 C₁₂H₂₀O₄ 500 mg/1 g
11(S)-HEPE
A monohydroxy fatty acid derived from EPA, theoretically by the action of COX. Although its arachidonate derived congener 11(S)-HETE has been isolated from cultured neutrophils, it is not known if similar incubations with EPA can produce 11(S)-HEPE.
Katalog # CAS Nummer Summenformel Menge
sc-220584 n.n. C₂₀H₃₀O₃ 25 µg/50 µg
11(S)-HETE
Synthesis by rat PMNL has been recorded, but the stereochemistry is not defined. There are no definitive reports of a mammalian 11(S)-LO.
Katalog # CAS Nummer Summenformel Menge
sc-204975 54886-50-9 C₂₀H₃₂O₃ 25 µg/50 µg
(±)12-HEPE
Inhibits platelet aggregation with the same potency as 12-HETE; inhibits U46619-induced contraction of rat aorta.
Katalog # CAS Nummer Summenformel Menge
sc-204981 81187-21-5 C₂₀H₃₀O₃ 25 µg/50 µg
(±)12-HETE
(±)12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. The biological activity of (±)12-HETE is similar to that of its constituent enantiomers. It aggregates neutrophils with an EC₅₀ value of 40 nM.
Katalog # CAS Nummer Summenformel Menge
sc-204982 71030-37-0 C₂₀H₃₂O₃ 25 µg/50 µg
(±)12-HpETE
One of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid and consists of an equivalent mixture of the R and S isomers. Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (±)12-HETE. The biological activity of (±)12-HpETE has not been documented.
Katalog # CAS Nummer Summenformel Menge
sc-204983 71030-35-8 C₂₀H₃₂O₄ 25 µg/50 µg
(±)12,13-DiHOME
The diol resulting from the soluble epoxide hydrolase opening of (±)12,13-EpOME; the mixture of the methyl ester of this diol and the 9,10 isomer are more cytotoxic than the methyl ester epoxides in renal proximal tubular cells.
Katalog # CAS Nummer Summenformel Menge
sc-204985 263399-35-5 C₁₈H₃₄O₄ 25 µg/50 µg
(±)12(13)-EpOME
The 12,13-cis epoxide of linoleic acid, generated by neutrophils during the oxidative burst. The toxicity and biosynthesis of (±)12(13)-EpOME have not been well differentiated from (±)9(10)-EpOME, but are assumed to be essentially the same.
Katalog # CAS Nummer Summenformel Menge
sc-220590 n.n. C₁₈H₃₂O₃ 25 µg/50 µg
12(S)-HEPE
A monohydroxy fatty acid; unstimulated neutrophils metabolize 12(S)-HEPE to 12(S),20-diHEPE.
Katalog # CAS Nummer Summenformel Menge
sc-204986 116180-17-7 C₂₀H₃₀O₃ 25 µg/50 µg
12(S)-HETE-d8
Katalog # CAS Nummer Summenformel Menge
sc-204987 84807-90-9 C₂₀H₂₄D₈O₃ 25 µg/50 µg
12(S)-HpEPE
12(S)-HpEPE is a monohydroperoxy polyunsaturated fatty acid produced by the action of 12-lipoxygenase on eicosapentaenoic acid. Although the biological activities of 12(S)-HpEPE have not been well characterized, it is expected to behave similarly to 12(S)-HpETE.
Katalog # CAS Nummer Summenformel Menge
sc-204988 103239-14-1 C₂₀H₃₀O₄ 25 µg/50 µg
12(S)-hydroxy-16-Heptadecynoic Acid
12(S)-hydroxy-16-Heptadecynoic acid is a mechanism-based inhibitor of cytochrome P450 ω-hydroxylase. It inhibits prostaglandin ω-hydroxylase with a Ki value of 1.8 µM.
Katalog # CAS Nummer Summenformel Menge
sc-223157 148019-74-3 C₁₇H₃₀O₃ 1 mg/5 mg
(±)13-HDoHE
An autoxidation product of docosahexaenoic acid (DHA) in vitro. Also, it is produced from incubations of DHA in rat brain, intestinal microsomes and liver. It is a potential marker of oxidative stress in brain and retina where DHA is abundant.
Katalog # CAS Nummer Summenformel Menge
sc-204990 90780-53-3 C₂₂H₃₂O₃ 25 µg/50 µg
(±)13-HODE
One of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. It is the principle hydroxylated fatty acid in human psoriatic skin scales, with a mean concentration of 17 ng/mg.
Katalog # CAS Nummer Summenformel Menge
sc-204991 73804-64-5 C₁₈H₃₂O₃ 100 µg/500 µg
(±)13-HODE cholesteryl ester
Originally extracted from atherosclerotic lesions and shown to be produced by Cu2+-catalyzed oxidation of LDL. Later studies showed 15-LO from rabbit reticulocytes and human monocytes were able to metabolize cholesteryl linoleate, a major component of LDL, to 13-HODE cholesteryl ester.
Katalog # CAS Nummer Summenformel Menge
sc-204992 167354-91-8 C₄₅H₇₆O₃ 25 µg/50 µg
13-OxoODE
Poduced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa; stimulates cell proliferation when instilled intrarectally in rats.
Katalog # CAS Nummer Summenformel Menge
sc-204993 54739-30-9 C₁₈H₃₀O₃ 25 µg/50 µg
13(R)-HODE
13(R)-HODE is the opposite enantiomer of the 13(S)-HODE produced when linoleic acid is incubated with soybean lipoxygenase. The existence of 13(R)-HODE in the supernatants and membranes of cultured bovine endothelial cells has been attributed to COX metabolism. 13(R)-HODE is a weak (IC₅₀ = 2.7 µM) inhibitor of U-46619-induced platelet aggregation.
Katalog # CAS Nummer Summenformel Menge
sc-205004 10219-69-9 C₁₈H₃₂O₃ 25 µg/50 µg
13(R)-HODE cholesteryl ester
Originally extracted from atherosclerotic lesions. and it remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation. Can be used as a standard for analysis of chiral HODE cholesteryl esters.
Katalog # CAS Nummer Summenformel Menge
sc-220601 n.n. C₄₅H₇₆O₃ 25 µg/50 µg
13(S)-HODE
Produced by incubation of linoleic acid with plant and mammalian lipoxygenases. Shown to inhibit the adhesion of tumor cells to the endothelium at concentrations around 1 µM,1,2 and down regulates the expression of the IRGpIIb/IIIa receptor.3
Katalog # CAS Nummer Summenformel Menge
sc-205005 29623-28-7 C₁₈H₃₂O₃ 100 µg/500 µg
13(S)-HODE cholesteryl ester
Originally extracted from atherosclerotic lesions. and it remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation. Can be used as a standard for analysis of chiral HODE cholesteryl esters.
Katalog # CAS Nummer Summenformel Menge
sc-220603 n.n. C₄₅H₇₆O₃ 25 µg/50 µg
13(S)-HODE-d4
Produced by incubation of linoleic acid along with plant and mammalian lipoxygenases; intended for use as an internal standard for the quantification of 13(S)-HODE by GC- or LC-mass spectrometry.
Katalog # CAS Nummer Summenformel Menge
sc-205006 139408-39-2 C₁₈H₂₈D₄O₃ 25 µg/100 µg
13(S)-HOTrE(γ)
The 15-LO product of γ-linolenic acid that is synthesized in human platelets, yet its specific function is unknown.
Katalog # CAS Nummer Summenformel Menge
sc-205007 74784-20-6 C₁₈H₃₀O₃ 25 µg/100 µg
13(S)-HpOTrE
A monohydroperoxy polyunsaturated fatty acid made in soybeans by the action of soybean LO-2 on esterified α-linolenic acid.1 Treatment of tomato leaves with 13-HpOTrE causes induction of proteinase inhibitors, simulating the normal response to wounding.5 This data suggests that in plants, 13(S)-HpOTrE may take part in a lipid-based signalling system initiated by insect and pathogen attack.
Katalog # CAS Nummer Summenformel Menge
sc-205008 67597-26-6 C₁₈H₃₀O₄ 100 µg/500 µg
(±)14,15-DHET
Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity. (±)14,(15)-DHET is the urinary metabolite of (±)14,(15)-EET that has been documented by GC-MS to be elevated in pregnancy-induced hypertension.
Katalog # CAS Nummer Summenformel Menge
sc-220605 n.n. C₂₀H₃₄O₄ 25 µg/50 µg
14,15-EE-(5Z)-E
This product antagonizes EpETrE-induced relaxation of vascular smooth muscle.
Katalog # CAS Nummer Summenformel Menge
sc-205011 519038-92-7 C₂₀H₃₆O₃ 25 µg/50 µg
(±)14(15)-EET methyl ester
Biosynthesized in rat and rabbit liver microsomes by CYP450.1,2 Dramatic increases in urinary (±)14,15-DiHETrE, a (±)14(15)-EET metabolite, have been documented by GC/MS in pregnancy induced hypertension.3 A more stable form used for long-term storage which can be readily hydrolyzed to the free acid as needed.
Katalog # CAS Nummer Summenformel Menge
sc-220612 n.n. C₂₁H₃₄O₃ 25 µg/50 µg
14(15)-EpETE
The ω-3 homolog of 14(15)-EpETrE, derived via epoxidation of the 14,15-double bond of EPA. The EDHF activity of 14(15)-EpETE has not yet been determined.
Katalog # CAS Nummer Summenformel Menge
sc-205015 131339-24-7 C₂₀H₃₀O₃ 25 µg/100 µg
(±)15-HEDE
Produced by the non-enzymatic oxidation of 11,14-eicosadienoic acid, yet there are no reports of biological activity associated with (±)15-HEDE.
Katalog # CAS Nummer Summenformel Menge
sc-205021 77159-57-0 C₂₀H₃₆O₃ 25 µg/50 µg
(±)15-HEPE
Produced by non-enzymatic oxidation of EPA, it contains equal amounts of 15(S) and 15(R)-HEPE. Specific biological activity attributed to this chemical has not been documented.
Katalog # CAS Nummer Summenformel Menge
sc-205022 88852-33-9 C₂₀H₃₀O₃ 25 µg/50 µg
(±)15-HETE
One of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid, where the biological activity of (±)15-HETE is similar to that of its constituent enantiomers.
Katalog # CAS Nummer Summenformel Menge
sc-205023 73836-87-0 C₂₀H₃₂O₃ 25 µg/50 µg
15-OxoEDE
15-OxoEDE is produced by the oxidation of 15-HEDE. 15-OxoEDE inhibits 5-LO from RBL-1 cells with an IC₅₀ of 55 µM, which is about 2-fold lower than 15(S)-HEDE. A related oxo-eicosanoid, 5-oxoETE, is biosynthesized from 5(S)-HETE by a specific dehydrogenase and has potent inflammatory activity.
Katalog # CAS Nummer Summenformel Menge
sc-205026 105835-44-7 C₂₀H₃₄O₃ 25 µg/50 µg
15(R)-HEDE
Isolated by the chromatographic resolution of (±)15-HEDE. There are no reports of biological activity associated with 15(R)-HEDE in the literature.
Katalog # CAS Nummer Summenformel Menge
sc-220627 n.n. C₂₀H₃₆O₃ 25 µg/50 µg
15(R)-HETE
This compound is produced when aspirin-inhibited COX-2 is incubated with arachidonic acid.The clinical significance and its potential downstream metabolites is the subject of current investigations.
Katalog # CAS Nummer Summenformel Menge
sc-205032 83603-31-0 C₂₀H₃₂O₃ 25 µg/50 µg
15(S)-HETrE
The hydroxy-trienoic acid resulting from 15-lipoxygenation of DGLA. It is an inhibitor of 5-LO in human PMNL with an IC₅₀ value of 4.6 µM. It inhibits 5-LO in RBL cells, but is about 1/20 as potent as 15(S)-HpETE.
Katalog # CAS Nummer Summenformel Menge
sc-205043 92693-02-2 C₂₀H₃₄O₃ 25 µg/50 µg
15(S)-HpEDE
The biological activities of 15(S)-HpEDE have not been well characterized, but it is expected to behave similarly to 15(S)-HpETE (sc-200966).
Katalog # CAS Nummer Summenformel Menge
sc-205044 145375-41-3 C₂₀H₃₆O₄ 25 µg/100 µg
(±)16-HDoHE
An autoxidation product of docosahexaenoic acid (DHA) in vitro. Also, it is produced from incubations of DHA in rat brain, intestinal microsomes and liver. It is a potential marker of oxidative stress in brain and retina where DHA is abundant.
Katalog # CAS Nummer Summenformel Menge
sc-205046 90780-51-1 C₂₂H₃₂O₃ 25 µg/50 µg
(±)17-HDoHE
Shown to inhibit U-46619-induced rabbit and rat aortic smooth muscle contraction; An autoxidation product of docosahexaenoic acid in vitro.
Katalog # CAS Nummer Summenformel Menge
sc-205059 90780-52-2 C₂₂H₃₂O₃ 25 µg/50 µg
17(18)-EpETE
The epoxygenase pathway is one of the three major branches of eicosanoid biosynthesis(1,2). Cytochrome P450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied relative to arachidonate epoxygenase metabolites. 17(18)-EpETE is biosynthesized by stereospecific epoxidation of the ω-3 bond of EPA. 17(18)-EpETE at 100 nM was found to be a potent and selective activator of BK-type calcium activated potassium ion channels in vascular smooth muscle cells(3). It is possible that some of the physiologic effects of fish oil-enhanced diets could be due to this epoxygenase metabolite.
Katalog # CAS Nummer Summenformel Menge
sc-220653 n.n. C₂₀H₃₀O₃ 25 µg/50 µg
17(R)-HDoHE
The primary oxygenation product of DHA when exposed to aspirin-inhibited cyclooxygenase-2; serves as an inhibitor of TNFα-induced IL-1β expression in human glioma cells.
Katalog # CAS Nummer Summenformel Menge
sc-205063 155976-53-7 C₂₂H₃₂O₃ 25 µg/50 µg
17(S)-HpDoHE
17(S)-HpDoHE is a mono-oxygenation product of docosahexaenoic acid in human leukocytes, human whole blood, human glial cells, and murine brain. 17(S)-HpDoHE is generally reduced to 17(S)-HDoHE, a compound that serves as a precursor to 17(S)-resolvins. 17(S)-HDoHE has been shown to inhibit TNF-α-induced interleukin-1β expression in human glioma cells and inhibit TNF-α-induced leukocyte trafficking to the murine air pouch.
Katalog # CAS Nummer Summenformel Menge
sc-220655 n.n. C₂₂H₃₂O₄ 25 µg/50 µg
(±)18-HEPE
(±)18-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 18(S)-HEPE and 18(R)-HEPE. Specific biological activity attributed to (±)18-HEPE has not been documented.
Katalog # CAS Nummer Summenformel Menge
sc-205067 141110-17-0 C₂₀H₃₀O₃ 25 µg/100 µg
19(20)-EpDPE
EDHF (endothelium-derived hyperpolarizing factor) is an unidentified mediator released from vascular endothelial cells in response to acetylcholine and bradykinin which is distinct from the NOS- (nitric oxide) and COX-derived (prostacyclin) vasodilators(1,2). Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids produces epoxides such as 14(15)-EpETrE which are prime candidates for the actual active mediator(3). However, the CYP450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied compared to arachidonate epoxygenase metabolites. 19(20)-EpDPE is a DHA epoxygenase metabolite, that is derived via epoxidation of the ω-3 double bond of DHA. EDHF activity of 19(20)-EpDPE has not been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model(4).
Katalog # CAS Nummer Summenformel Menge
sc-220658 183012-99-9 C₂₂H₃₂O₃ 25 µg/50 µg
19(R)-HETE
Potent vasodilator of renal preglomerular vessels; completely blocks 20-HETE-induced vasoconstriction of renal arterioles.
Katalog # CAS Nummer Summenformel Menge
sc-204615 115461-39-7 C₂₀H₃₂O₃ 25 µg/50 µg
(±)20-HDoHE
An autoxidation product of docosahexaenoic acid (DHA) in vitro. Also, it is produced from incubations of DHA in rat brain, intestinal and liver microsomes. It is a potential marker of oxidative stress in brain and retina where DHA is abundant.
Katalog # CAS Nummer Summenformel Menge
sc-205101 90906-41-5 C₂₂H₃₂O₃ 25 µg/50 µg
20-HETE
A cytochrome P450 (CYP450) metabolite postulated to play an autacoid role in the cerebral and renal vasculature.
Katalog # CAS Nummer Summenformel Menge
sc-205102 79551-86-3 C₂₀H₃₂O₃ 25 µg/50 µg
Cholesteryl Linoleate Hydroperoxides
Derived from the autoxidation of cholesteryl linoleate and contain a mixture of racemic 9- and 13-HpODE cholesteryl esters. Oxidative modification of LDL is suggested to play an important role in atherosclerosis. Studies determined that 15-LO, from rabbit reticulocytes and activated human monocytes, oxygenates cholesteryl linoleate to both 9- and 13-hydroperoxy linoleate cholesteryl esters. Cholesteryl ester hydroperoxides may be transferred from LDL to HDL, reduced to the corresponding hydroxides, and cleared via the liver.
Katalog # CAS Nummer Summenformel Menge
sc-223886 n.n. C₄₅H₇₆O₄ 100 µg/500 µg
FOG9
Formed through the conjugation of 5-oxoETE with glutathione in a 1,6 Michael addition at C-9. The biological activity of FOG9 has not been determined.
Katalog # CAS Nummer Summenformel Menge
sc-221623 n.n. C₃₀H₄₇N₃O₉S 25 µg/50 µg
Lipoxin A5
Produced by enzymatic transformation of EPA by leukocytes. LXA5 slowly contracts pulmonary parenchymal strips from guinea pig with similar potency to that of LXA4 and LXB4. However, LXA5 does not employ the vasodilatory effects on aortic smooth muscle exhibited by LXA4 and LXB4.
Katalog # CAS Nummer Summenformel Menge
sc-221859 110657-98-2 C₂₀H₃₀O₅ 25 µg/50 µg
n-Triacontanol
A plant growth regulator found in the plant cuticle waxes and in beeswax as the palmitate ester. Has been reported to have growth enhancing properties when applied to the leaves of growing plants.
Katalog # CAS Nummer Summenformel Menge
sc-205411 593-50-0 C₃₀H₆₂O 25 mg/50 mg
PPOH
A selective inhibitor of the epoxygenation reactions catalyzed by specific CYP450 isozymes; inhibits the formation of arachidonate 11,12 epoxides by CYP4A2 and CYP4A3 enzymes.
Katalog # CAS Nummer Summenformel Menge
sc-205442 206052-01-9 C₁₅H₁₈O₃ 1 mg/5 mg
tetranor-12(R)-HETE
Metabolism of 12(R)-HETE in corneal tissue produces predominantly the compound resulting from the loss of four carbon atoms through β-oxidation from C-1. This metabolite is 8(R)-hydroxy hexadecatrienoic acid (8(R)-HHxTrE) or 2,3,4,5-tetranor 12(R)-HETE.
Katalog # CAS Nummer Summenformel Menge
sc-205520 135271-51-1 C₁₆H₂₆O₃ 25 µg/100 µg
trans-4,5-epoxy-2(E)-Decenal
An aldehyde compound responsible for the pungent metallic flavor of decomposed lipids. Has been shown to react with nucleophiles on proteins, resulting in a loss of cell function and viability. Useful tool in demonstrating the effects (acute and gradual) of peroxidative damage in experimental models.
Katalog # CAS Nummer Summenformel Menge
sc-204922 134454-31-2 C₁₀H₁₆O₂ 1 mg/10 mg