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Arachidonic acid (20:4, n-6)

BML-FA003

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Eicosanoid precursor and second messenger

Essential precursor for leukotrienes, prostaglandins, and thromboxanes
Used in cancer, cardiovascular, cell signaling, immunology, and metabolism studies amongst others

Arachidonic acid is an essential fatty acid and a precursor to a large family of eicosanoids. Arachidonic acid acts as a second messenger independent of metabolism and a retrograde messenger in long-term potentiation in the nervous system. Arachidonic acid activates several protein kinase C (PKC) isotypes and inhibits ras-GAP.

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Product Details

Alternative Name	5Z,8Z,11Z,14Z-Eicosatetraenoic acid
Appearance	Colorless oil.
CAS	506-32-1
Couple Target	PKC, Ras-GAP
Couple Type	Activator, Inhibitor
Formula	C₂₀H₃₂O₂
MI	14: 765
MW	304.5
Purity	≥99% (GLC, TLC)
RTECS	CE6675000
Solubility	Soluble in DMF (100mg/ml), DMSO (100mg/ml), or 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.

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended. 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.
Long Term Storage	-20°C
Shipping	Ambient Temperature

Regulatory Status	RUO – Research Use Only

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
Synthesis and structure-activity relationship studies of 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide derivatives as potent and selective inhibitors of 12-lipoxygenase: Luci, D. K., Jameson, J. B., et al.; J. Med. Chem. 57, 495 (2014), Abstract
Discovery of potent and selective inhibitors of human platelet-type 12- lipoxygenase: Kenyon, V., Rai, G., et al.; J. Med. Chem. 54, 5485 (2011), 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
Role of fatty acids in signal transduction: modulators and messengers: C. Sumida, et al.; Prostaglandins Leukot. Essent. Fatty Acids 48, 117 (1993), Abstract