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Arachidonic acid (20:4, n-6)

Eicosanoid precursor and second messenger
BML-FA003-0100 100 mg 113.00 USD
BML-FA003-1000 1 g 322.00 USD
Do you need bulk/larger quantities?
Replaces Prod. #: ALX-340-004

Precursor to a large family of eicosanoids. Acts as a second messenger independent of metabolism. Retrograde messenger in long-term potentiation in the nervous system. Inhibits ras-GAP. Activator for several protein kinase C (PKC) isotypes.

Product Details

Alternative Name:5Z,8Z,11Z,14Z-Eicosatetraenoic acid
MI:14: 765
Purity:≥99% (TLC)
Appearance:Colorless oil.
Solubility:100mg/ml soluble in DMSO or dimethyl formamide; soluble in 100% ethanol (50mg/ml); sparingly soluble in basic aqueous buffers (1.7mg/ml). To prevent oxidation, the solvent should be purged with an inert gas.
Long Term Storage:-20°C
Use/Stability:Stable for 12 months after receipt when stored at -20°C. Keep aqueous solutions on ice and use within 12 hours.
Handling:Protect from light and oxygen.
Regulatory Status:RUO - Research Use Only
BML-FA003 structure
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BML-FA003 structure

Product Literature References

Ca2+-mediated mitochondrial inner membrane permeabilization induces cell death independently of Bax and Bak: G. Quarato, et al.; Cell Death Differ. 29, 1318 (2022), Abstract;
Influence of low‐dose aspirin, resistance exercise, and sex on human skeletal muscle PGE2/COX pathway activity: M. Naruse, et al.; Physiol. Rep. 9, 14790 (2021), Abstract;
Low-dose aspirin and COX inhibition in human skeletal muscle: W. Fountain, et al.; J. Appl. Physiol. 129, 1477 (2020), Abstract;
Discovery of a small-molecule protein kinase Cδ-selective activator with promising application in colon cancer therapy: C. Bessa, et al.; Cell Death Dis. 9, 23 (2018), Abstract; Full Text
Selective inhibition of 12-lipoxygenase protects islets and beta cells from inflammatory cytokine-mediated beta cell dysfunction: D.A. Taylor-Fishwick, et al.; Diabetologia 58, 549 (2015), Application(s): Cell Culture, Abstract;
Arachidonic acid and free fatty acids as second messengers and the role of protein kinase C: W.A. Khan, et al.; Cell. Signal. 7, 171 (1995), Abstract;
Covalent binding of arachidonate to G protein alpha subunits of human platelets: H. Hallak, et al.; J. Biol. Chem. 269, 4713 (1994), Abstract; Full Text
Arachidonic acid-induced Ca2+ release from isolated sarcoplasmic reticulum: C. Dettbarn & P. Palade; Biochem. Pharmacol. 45, 1301 (1993), Abstract;
Nitric oxide and arachidonic acid modulation of calcium currents in postganglionic neurones of avian cultured ciliary ganglia: G. Khurana & M.R. Bennett; Br. J. Pharmacol. 109, 480 (1993), Abstract;
Role of fatty acids in signal transduction: modulators and messengers: C. Sumida, et al.; Prostaglandins Leukot. Essent. Fatty Acids 48, 117 (1993), Abstract;
The immediate activator of the NADPH oxidase is arachidonate not phosphorylation: L.M. Henderson, et al.; Eur. J. Biochem. 211, 157 (1993), Abstract;
A unique pool of free arachidonate serves as substrate for both cyclooxygenase and lipoxygenase in platelets: F. Chevy, et al.; Lipids 26, 1080 (1991), Abstract;
Arachidonic acid as a second messenger. Interactions with a GTP-binding protein of human neutrophils: S.B. Abramson, et al.; J. Immunol. 147, 231 (1991), Abstract;
Is arachidonic acid a retrograde messenger in long-term potentiation?: M.A. Lynch, et al.; Biochem. Soc. Trans. 19, 391 (1991), Abstract;
Regulation of Ras-GAP and the neurofibromatosis-1 gene product by eicosanoids: J.W. Han, et al.; Science 252, 576 (1991), Abstract;
Characterization of the L-arginine:nitric oxide pathway in human platelets: M.W. Radomski, et al.; Br. J. Pharmacol. 101, 325 (1990), Abstract;
The control of free arachidonic acid levels: R.D. Burgoyne & A. Morgan; TIBS 15, 365 (1990), Abstract;
The LDL receptor pathway delivers arachidonic acid for eicosanoid formation in cells stimulated by platelet-derived growth factor: A.J.R. Habenicht, et al.; Nature 345, 634 (1990), Abstract;
Kinetic analysis of the Ca2+-dependent, membrane-bound, macrophage phospholipase A2 and the effects of arachidonic acid: M.D. Lister, et al.; J. Biol. Chem. 263, 7506 (1988), Abstract; Full Text
Handbook of Eicosanoids: A.L. Willis (ed.); CRC Press, Boca Raton (1987),
Arachidonic acid metabolism: P. Needleman, et al.; Ann. Rev. Biochem. 55, 69 (1986), Abstract;

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