ALEXIS Biochemicals: 4-Oxatetradecanoic acid

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ALX-340-004

Revised 18-Aug-08

Arachidonic acid
SYNONYMS	5Z,8Z,11Z,14Z-Eicosatetraenoic acid
PRODUCT LINE	Inflammation
PRODUCT CATEGORY	Arachidonic Acid / Related Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-340-004-M100		100 mg	147.00 USD

Product Specification

FORMULA:	C₂₀H₃₂O₂
MW:	304.5
CAS NUMBER:	506-32-1
MERCK INDEX:	14: 765
RTECS:	CE6675000
CONCENTRATION:	100mg/ml
PURITY:	≥98%
FORMULATION:	Liquid. Solution in ethanol containing 0.1% BHT.
SOLUBILITY:	100mg/ml soluble in DMSO or dimethyl formamide; sparingly soluble in basic aqueous buffers (1.7mg/ml). To prevent oxidation, the solvent should be purged with an inert gas.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stable for at least 6 months after receipt when stored at -20°C. Keep aqueous solutions on ice and use within 12 hours.
HANDLING:	Protect from light and oxygen.
HAZARD:	TOXIC.

Product Description

Precursor to a large family of eicosanoids. Activator for several protein kinase C (PKC) isotypes.

Product Specific Literature References

Arachidonic acid metabolism: P. Needleman, et al.; Ann. Rev. Biochem. 55, 69 (1986) 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
Characterization of the L-arginine:nitric oxide pathway in human platelets: M.W. Radomski, et al.; Br. J. Pharmacol. 101, 325 (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
The control of free arachidonic acid levels: R.D. Burgoyne & A. Morgan; TIBS 15, 365 (1990) 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
Regulation of Ras-GAP and the neurofibromatosis-1 gene product by eicosanoids: J.W. Han, et al.; Science 252, 576 (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
The immediate activator of the NADPH oxidase is arachidonate not phosphorylation: Henderson, et al.; Eur. J. Biochem. 211, 157 (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
Arachidonic acid-induced Ca2+ release from isolated sarcoplasmic reticulum: C. Dettbarn & P. Palade; Biochem. Pharmacol. 45, 1301 (1993) 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

General Information

BACKGROUND/TECHNICAL INFORMATION

To change the solvent, evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.

Further Categories Containing This Product:

PKC Activators • Nitric Oxide Pathway Other Products • Fatty Acids

ALX-581-210

Revised 14-Feb-07

Cord Factor (endotoxin-free grade)
SYNONYMS	Trehalose 6,6’-dimycolate (endotoxin-free grade) TDM (endotoxin-free grade)
PRODUCT LINE	Immunology
PRODUCT CATEGORY	Immunomodulators Other Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-581-210-M001		1 mg	235.00 USD

Product Specification

CAS NUMBER:	61512-20-7
SOURCE/HOST:	Isolated from M. tuberculosis.
PURITY:	Single spot (TLC)
FORMULATION:	Lyophilized.
ENDOTOXIN CONTENT:	<0.002EU/µg (LAL test; BioWhittaker)
SOLUBILITY:	Soluble in chloroform:methanol:water (90:10:1) (5mg/ml), hexane or isopropanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Immunomodulatory compound. Induces activation of macrophages independent of TLR2 or TLR4.

Product Specific Literature References

The chemical structure of the cord factor of Mycobacterium tuberculosis: H. Noll, et al.; Biochim. Biophys. Acta 20, 299 (1956) Abstract
Development of a trehalose 6,6’-dimycolate model which explains cord formation by Mycobacterium tuberculosis: C.A. Behling, et al.; Infect. Immun. 61, 2296 (1993) Abstract
Extravascular coagulation and fibrinolysis in murine lung inflammation induced by the mycobacterial cord factor trehalose-6,6’-dimycolate: R.L. Perez, et al.; Am. J. Respir. Crit. Care Med. 149, 510 (1994) Abstract
Immunological properties of trehalose dimycolate (cord factor) and other mycolic acid-containing glycolipids: R. Ryll, et al.; Microbiol. Immunol. 45, 801 (2001), Review Abstract
Mycobacterial glycolipid cord factor trehalose 6,6’-dimycolate causes a decrease in serum cortisol during the granulomatous response: J.K. Actor, et al.; Neuroimmunomodulation 10, 270 (2002) Abstract
Influence of trehalose 6,6’-dimycolate (TDM) during mycobacterial infection of bone marrow macrophages: J. Indrigo, et al.; Microbiology 148, 1991 (2002) Abstract
Cord factor trehalose 6,6’-dimycolate (TDM) mediates trafficking events during mycobacterial infection of murine macrophages: J. Indrigo, et al.; Microbiology 149, 2049 (2003) Abstract
Failure of CD1D-/- mice to elicit hypersensitive granulomas to mycobacterial cord factor trehalose 6,6’-dimycolate: T.V. Guidry, et al.; J. Interferon Cytokine Res. 24, 362 (2004) Abstract
Requisite role for complement C5 and the C5a receptor in granulomatous response to mycobacterial glycolipid trehalose 6,6’-dimycolate: C.W. Borders, et al.; Scand. J. Immunol. 62, 123 (2005) Abstract
In vivo activity of released cell wall lipids of Mycobacterium bovis bacillus Calmette-Guerin is due principally to trehalose mycolates: R.E. Geisel, et al.; J. Immunol. 174, 5007 (2005) Abstract
Macrophage scavenger receptor down-regulates mycobacterial cord factor-induced proinflammatory cytokine production by alveolar and hepatic macrophages: Y. Ozeki, et al.; Microb. Pathog. 40, 171 (2006) Abstract
Interferon-gamma independent formation of pulmonary granuloma in mice by injections with trehalose dimycolate (cord factor), lipoarabinomannan and phosphatidylinositol mannosides isolated from Mycobacterium tuberculosis: H. Takimoto, et al.; Clin. Exp. Immunol. 144, 134 (2006) Abstract

General Information

BACKGROUND/TECHNICAL INFORMATION

In vitro stimulation of macrophages
Purified Cord Factor was used to stimulate either mouse RAW 264.7 cells or bone marrow-derived macrophages. Cord Factor was suspended at a concentration of 1mg/ml in isopropanol and sonicated in a bath sonicator for 5 min. This suspension was incubated at 60°C for 10 min. and sonication repeated. The resulting solution was layered onto 24-well tissue culture plates at the indicated concentrations and incubated at 37°C in order to ensure complete evaporation of the solvent. Control wells were layered with solvent without Cord Factor and incubated at 37°C. To this layer of Cord Factor, either RAW 264.7 cells or bone marrow-derived macrophages were added at a concentration of 10⁶ cells in 100µl of medium and incubated at 37°C for 24 hours before activation e.g. TNF-α production was measured in the supernatant.
Alternatively, Cord Factor was suspended at a concentration of 0.2 or 2mg/ml in hexane. Of the resulting solution 50µl were layered onto 96-well tissue culture plates at the indicated concentrations of 1 or 10µg/well, respectively and the solvent completely evaporated. Control wells were layered with solvent without Cord Factor and incubated at 37°C. To this layer of Cord Factor, either RAW 264.7 cells or bone marrow-derived macrophages were added at a concentration of 10⁶ cells in 100µl of medium and incubated at 37°C for 24 hours before activation e.g. TNF-α production was measured in the supernatant.

In vivo pulmonary granuloma formation in mice
For in vivo experiments 10µg Cord Factor per mouse were applied i.v. in a water/oil/water emulsion.

Please also see our Product Flyer "Cord Factor - Endotoxin-free grade".

Further Categories Containing This Product:

Fatty Acids

ALX-300-148

Revised 11-Jul-08

Docosatetraenylethanolamide
SYNONYMS	N-(2-Hydroxyethyl)-7Z,10Z,13Z,16Z-docosatetraenamide DEA
PRODUCT LINE	Neurobiology
PRODUCT CATEGORY	Endocannabinoids

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-300-148-M005		5 mg	63.00 USD

Product Specification

FORMULA:	C₂₄H₄₁NO₂
MW:	375.6
CAS NUMBER:	150314-35-5
PURITY:	≥98%
FORMULATION:	Liquid. Solution in ethanol.
SOLUBILITY:	10mg/ml soluble in DMSO or dimethyl formamide; 8mg/ml soluble in 1:2 solution of ethanol:PBS (pH 7.2) (dilute the ethanol solution with PBS).
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stable for at least 1 year after receipt when stored at -20°C. We do not recommend storing aqueous solutions for more than one day.
HANDLING:	Protect from light.

Product Description

Endocannabinoid. Also inhibits adenylate cyclase (IC₅₀=117nM). Does also bind to TRPV1 (K_i=5.63µM).

Product Specific Literature References

Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor: L. Hanus, et al.; J. Med. Chem. 36, 3032 (1993) Abstract
Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction: C.C. Felder, et al.; PNAS 90, 7656 (1993) Abstract
Cannabinomimetic behavioral effects of and adenylate cyclase inhibition by two new endogenous anandamides: J. Barg, et al.; Eur. J. Pharmacol. 287, 145 (1995) Abstract
Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens: R.A. Ross, et al.; Br. J. Pharmacol. 132, 631 (2001) Abstract
Astrocytes in culture produce anandamide and other acylethanolamides: L. Walter, et al.; J. Biol. Chem. 277, 20869 (2002) Abstract

General Information

BACKGROUND/TECHNICAL INFORMATION

To change the solvent, evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.

Further Categories Containing This Product:

Adenylyl Cyclase Inhibitors • TRPV1 Agonists and Antagonists / Related Products • Fatty Acids

ALX-300-132

Revised 04-Feb-05

2-Fluoropalmitic acid
PRODUCT LINE	Obesity & Adipokines
PRODUCT CATEGORY	Fatty Acids

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-300-132-M001		1 mg	15.00 USD
ALX-300-132-M005		5 mg	60.00 USD

Product Specification

FORMULA:	C₁₆H₃₁FO₂
MW:	274.4
CAS NUMBER:	89270-22-4
PURITY:	≥98%
APPEARANCE:	White solid.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Inhibitor of palmityl-CoA biosynthesis resulting in blockade of protein palmitoylation.

Product Specific Literature References

D,L-alpha-Fluoropalmitic acid inhibits sphingosine base formation and accumulates in membrane lipids of cultured mammalian cells: R.M. Soltysiak, et al.; Biochim. Biophys. Acta 792, 214 (1984) Abstract
All ras proteins are polyisoprenylated but only some are palmitoylated: J.F. Hancock, et al.; Cell 57, 1167 (1989) Abstract
Activation of p56lck through mutation of a regulatory carboxy-terminal tyrosine residue requires intact sites of autophosphorylation and myristylation: N.E. Abraham & A. Veillette; Mol. Cell. Biol. 10, 5197 (1990) Abstract
The G protein alpha s subunit incorporates [3H]palmitic acid and mutation of cysteine-3 prevents this modification: M.Y. Degtyarev, et al.; Biochemistry 32, 8057 (1993) Abstract
Lipid modifications of G proteins: alpha subunits are palmitoylated: M.E. Linder, et al.; PNAS 90, 3675 (1993) Abstract
A novel N-terminal motif for palmitoylation of G-protein alpha subunits: M. Parenti, et al.; Biochem. J. 291, 349 (1993) Abstract

ALX-300-131

Revised 04-Feb-05

2-Hydroxymyristic acid
SYNONYMS	2-Hydroxy-tetradecanoic acid
PRODUCT LINE	Obesity & Adipokines
PRODUCT CATEGORY	Fatty Acids

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-300-131-M025		25 mg	35.00 USD

Product Specification

FORMULA:	C₁₄H₂₈O₃
MW:	244.4
CAS NUMBER:	2507-55-3
PURITY:	≥97%
APPEARANCE:	White solid.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

Selective inhibitor of protein myristoylation in cells, able to distinguish myristoylation from palmitoylation. Metabolic activation appears to be required. Myristoylation takes place on glycine residues at the N-terminus of proteins and provides a strong membrane anchor for the modified proteins, many of which require myristoylation for full activity.

Product Specific Literature References

Activation of p56lck through mutation of a regulatory carboxy-terminal tyrosine residue requires intact sites of autophosphorylation and myristylation: N. Abraham & A. Veillette; Mol. Cell. Biol. 10, 5197 (1990) Abstract
Metabolic activation of 2-substituted derivatives of myristic acid to form potent inhibitors of myristoyl CoA:protein N-myristoyltransferase: L.A. Paige, et al.; Biochemistry 29, 10566 (1990) Abstract
The G protein connection: molecular basis of membrane association [published erratum appears in TIBS 17, 177 (1992)]: A.M. Spiegel, et al.; TIBS 16, 338 (1991), (Review) Abstract
Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck: M.J.S. Nadler, et al.; Biochemistry 32, 9250 (1993) Abstract
Reversible palmitoylation of the protein-tyrosine kinase p56lck: L.A. Paige, et al.; J. Biol. Chem. 268, 8669 (1993) Abstract; Full Text
Inhibition of varicella-zoster virus replication by an inhibitor of protein myristoylation: D.R. Harper, et al.; J. Gen. Virol. 74, 1181 (1993) Abstract

ALX-300-138

Revised 28-Jan-05

Oleic acid (high purity)
SYNONYMS	cis-9-Octadecenoic acid 18:1
PRODUCT LINE	Obesity & Adipokines
PRODUCT CATEGORY	Fatty Acids

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-300-138-G001		1 g	25.00 USD

Product Specification

FORMULA:	C₁₈H₃₄O₂
MW:	282.5
CAS NUMBER:	112-80-1
MERCK INDEX:	14: 6828
PURITY:	≥99%
APPEARANCE:	Colorless liquid.
SOLUBILITY:	Soluble in chloroform or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Keep under inert gas. Protect from light and oxygen.
HAZARD:	IRRITANT.

Product Description

Unsaturated fatty acid that has been shown to activate protein kinase C (PKC) in hepatocytes. Inhibitor of glucose production and food intake. Upregulates the expression of uncoupling protein-3 (UCP-3) in L6 myotubes.

Product Specific Literature References

Oleic acid promotes changes in the subcellular distribution of protein kinase C in isolated hepatocytes: M.J. Diaz-Guerra; J. Biol. Chem. 266, 23568 (1991) Abstract; Full Text
Spinal cord of the rat contains more lipoprotein lipase than other brain regions: D.H. Bessesen, et al.; J. Lipid Res. 34, 229 (1993) Abstract
Free fatty acid-induced alterations in the steroid-binding properties of rat androgen-binding protein: F. Felden, et al.; BBRC 190, 602 (1993) Abstract
Chronic feline leukemia virus infection alters arachidonic acid proportions in vivo and in vitro: L.L. Williams, et al.; Proc. Soc. Exp. Biol. Med. 202, 239 (1993) Abstract
Central administration of oleic acid inhibits glucose production and food intake: S. Obici, et al.; Diabetes 51, 271 (2002) Abstract; Full Text
Effects of rosiglitazone and oleic acid on UCP-3 expression in L6 myotubes: A. Costello, et al.; Diabetes Obes. Metab. 5, 136 (2003) Abstract

Further Categories Containing This Product:

PKC Activators • Obesity & Diabetes Other Products

ALX-300-134

Revised 06-Feb-05

4-Oxatetradecanoic acid
PRODUCT LINE	Obesity & Adipokines
PRODUCT CATEGORY	Fatty Acids

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-300-134-M010		10 mg	110.00 USD

Product Specification

FORMULA:	C₁₃H₂₆O₃
MW:	230.3
CAS NUMBER:	4720-16-8
PURITY:	≥98%
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Analog of myristate with same chain length but a polar oxygen atom incorporated in place of a methylene group, resulting in reduced hydrophobicity. Inhibits HIV replication. Acts as fungicide against Cryptococcus neoformans. May exert its effects by inhibiting the activity of N-myristoyltransferase or by altering the physiology of proteins which have incorporated this analog in place of myristic acid.

Product Specific Literature References

4-oxatetradecanoic acid is fungicidal for Cryptococcus neoformans and inhibits replication of human immunodeficiency virus I: C.A. Langner, et al.; J. Biol. Chem. 267, 17159 (1992) Abstract; Full Text

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