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M3525 Sigma

Myristoleic acid

≥99% (capillary GC)

Synonym: cis-9-Tetradecenoic acid

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Properties

Related Categories Biochemicals and Reagents, Fatty Acids and conjugates, Fatty Acyls, Lipids, Monoenoic fatty acids,
assay   ≥99% (capillary GC)
refractive index   n20/D 1.4562(lit.)
bp   144 °C/0.6 mmHg(lit.)
mp   −4.5-−4 °C(lit.)
density   0.9 g/mL at 25 °C(lit.)
storage temp.   −20°C

Description

Packaging

Sealed ampule.

Application

Myristoleic acid (C14:1) is a mono-unsaturated medium-chain fatty acid used as a model substrate for enzymes such as the cytochrome P450 enzyme CYP102D1; the aromatic peroxygenase from Agrocybe aegerita and oleate hydratase from Lysinibacillus fusiformis.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M3525.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
RIDADR 
UN 1993 / PGIII
WGK Germany 
3
Flash Point(F) 
143.6 °F
Flash Point(C) 
62 °C

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Production of 10-hydroxystearic acid from oleic acid and olive oil hydrolyzate by an oleate hydratase from Lysinibacillus fusiformis. Kim BN, Joo YC, Kim YS, et al. Appl. Microbiol. Biotechnol. 95(4), 929-37, (2012)

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Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces Choi KY, Jung E, Jung DH, et al. FEBS J. 279, 1650-1662, (2012)

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Regioselective oxygenation of fatty acids, fatty alcohols and other aliphatic compounds by a basidiomycete heme-thiolate peroxidase. Gutiérrez A, Babot ED, Ullrich R, et al. Arch. Biochem. Biophys. 514, 33-43, (2011)

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Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. Jiang J, Wolk A, and Vessby B Am. J. Clin. Nutr. 70(1), 21-7, (1999)

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HMDB: a knowledgebase for the human metabolome. Wishart DS, Knox C, Guo AC, et al. Nucleic Acids Res. 37(Database issue), D603-10, (2009)

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Dual fatty acyl modification determines the localization and plasma membrane targeting of CBL/CIPK Ca2+ signaling complexes in Arabidopsis. Batistic O, Sorek N, Schültke S, et al. Plant Cell 20(5), 1346-62, (2008)

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The human serum metabolome. Psychogios N, Hau DD, Peng J, et al. PLoS ONE 6(2), e16957, (2011)

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Different properties of two isoforms of annexin XIII in MDCK cells. Lecat S, Verkade P, Thiele C, et al. J. Cell Sci. 113 ( Pt 14), 2607-18, (2000)

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Biosynthesis of the pyoverdine siderophore of Pseudomonas aeruginosa involves precursors with a myristic or a myristoleic acid chain. Hannauer M, Schäfer M, Hoegy F, et al. FEBS Lett. 586(1), 96-101, (2012)

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Antagonizing potencies of saturated and unsaturated long-chain free fatty acids to isoflurane in goldfish. Hanada R, Tatara T, and Iwao Y J. Anesth. 18(2), 89-93, (2004)

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Exploitation of eukaryotic subcellular targeting mechanisms by bacterial effectors. Hicks SW and Galán JE Nat. Rev. Microbiol. 11(5), 316-26, (2013)

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The emergence of competition between model protocells. Chen IA, Roberts RW, and Szostak JW Science 305(5689), 1474-6, (2004)

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Structural basis for Arl3-specific release of myristoylated ciliary cargo from UNC119. Ismail SA, Chen YX, Miertzschke M, et al. EMBO J. 31(20), 4085-94, (2012)

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Sunitinib induces apoptosis and growth arrest of medulloblastoma tumor cells by inhibiting STAT3 and AKT signaling pathways. Yang F, Jove V, Xin H, et al. Mol. Cancer Res. 8(1), 35-45, (2010)

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Experimental models of primitive cellular compartments: encapsulation, growth, and division. Hanczyc MM, Fujikawa SM, and Szostak JW Science 302(5645), 618-22, (2003)

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Sulfoquinovosylmonoacylglycerol inhibitory mode analysis of rat DNA polymerase beta. Kasai N, Mizushina Y, Murata H, et al. FEBS J. 272(17), 4349-61, (2005)

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Peptides modified by myristoylation activate eNOS in endothelial cells through Akt phosphorylation. Krotova K, Hu H, Xia SL, et al. Br. J. Pharmacol. 148(5), 732-40, (2006)

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Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid. Liao S, Lin J, Dang MT, et al. Arch. Dermatol. Res. 293(4), 200-5, (2001)

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Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Iguchi K, Okumura N, Usui S, et al. Prostate 47(1), 59-65, (2001)

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Dietary intake of specific fatty acids and breast cancer risk among postmenopausal women in the VITAL cohort. Sczaniecka AK, Brasky TM, Lampe JW, et al. Nutr. Cancer 64(8), 1131-42, (2012)

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Fatty acid composition of adipose tissue triglycerides after weight loss and weight maintenance: the DIOGENES study. Kunešová M, Hlavatý P, Tvrzická E, et al. Physiol. Res. 61(6), 597-607, (2012)

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Elo1p-dependent carboxy-terminal elongation of C14:1Delta(9) to C16:1Delta(11) fatty acids in Saccharomyces cerevisiae. Schneiter R, Tatzer V, Gogg G, et al. J. Bacteriol. 182(13), 3655-60, (2000)

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Aspergillus nidulans ArfB plays a role in endocytosis and polarized growth. Lee SC, Schmidtke SN, Dangott LJ, et al. Eukaryotic Cell 7(8), 1278-88, (2008)

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The effects of topical application of various fatty acids on pheromone and glandular lipid biosynthesis in the moth Heliothis virescens. Foster SP Insect Biochem. Mol. Biol. 34(5), 467-75, (2004)

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PACE-1, a novel protein that interacts with the C-terminal domain of ezrin. Sullivan A, Uff CR, Isacke CM, et al. Exp. Cell Res. 284(2), 224-38, (2003)

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Computational analysis and structure predictions of CHH-related peptides from Litopenaeus vannamei. Nagaraju GP, Kumari NS, Prasad GL, et al. Integr. Biol. (Camb.) 3(3), 218-24, (2011)

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The nuclear lamina in Heidelberg and Würzburg: a personal view. Krohne G, Benavente R, Scheer U, et al. Eur. J. Cell Biol. 84(2-3), 163-79, (2005)

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Exogenous myristoylated-G(i2)alpha subunits of GTP-binding proteins are mitogens following their internalization by astrocytes in culture. Sánchez-Blázquez P, De Antonio I, Montero C, et al. Brain Res. Mol. Brain Res. 110(1), 15-26, (2003)

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Type A behavior and adipose tissue linoleic acid: implications for stress management. Mamalakis G, Kafatos A, and Board S J. Am. Coll. Nutr. 13(3), 292-7, (1994)

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Striatal dopamine in the response of brain and liver unsaturated and saturated free fatty acids following administration of C75 in CD-1 mice. Binienda ZK, Ross IA, Gough B, et al. Neurosci. Lett. 469(3), 324-7, (2010)

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Unexpected tails of a Ca2+ sensor. Haynes LP and Burgoyne RD Nat. Chem. Biol. 4(2), 90-1, (2008)

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Beil. 2,II,423

Corp MSDS 1 (2), 2482:C / FT-IR 2 (1), 783:B / FT-NMR 1 (1), 782:A / RegBook 1 (1), 549:H / Sigma FT-IR 1 (1), 1426:B / Structure Index 1, 78:C:1 / Vapor Phase 3, 587:C

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