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M3525

Sigma-Aldrich

Myristoleic acid

≥99% (capillary GC)

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Synonym(s):
cis-9-Tetradecenoic acid
Linear Formula:
CH3(CH2)3CH=CH(CH2)7CO2H
CAS Number:
Molecular Weight:
226.36
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

plant

Assay

≥99% (capillary GC)

form

liquid

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.)

functional group

carboxylic acid

lipid type

unsaturated FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCC\C=C/CCCCCCCC(O)=O

InChI

1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-

InChI key

YWWVWXASSLXJHU-WAYWQWQTSA-N

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This Item
M3650M3128V0384
Myristoleic acid ≥99% (capillary GC)

Sigma-Aldrich

M3525

Myristoleic acid

Methyl myristoleate ≥98.5% (capillary GC), liquid

Sigma-Aldrich

M3650

Methyl myristoleate

Myristic acid Sigma Grade, ≥99%

Sigma-Aldrich

M3128

Myristic acid

cis-Vaccenic acid ≥97% (capillary GC), oil

Sigma-Aldrich

V0384

cis-Vaccenic acid

assay

≥99% (capillary GC)

assay

≥98.5% (capillary GC)

assay

≥99%

assay

≥97% (capillary GC)

form

liquid

form

liquid

form

powder or flakes

form

oil

refractive index

n20/D 1.4562 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.459 (lit.)

bp

144 °C/0.6 mmHg (lit.)

bp

-

bp

250 °C/100 mmHg (lit.)

bp

150 °C/0.03 mmHg (lit.)

mp

−4.5-−4 °C (lit.)

mp

-

mp

52-54 °C (lit.)

mp

14-15 °C (lit.)

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.

Packaging

Sealed ampule.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Stuart W Hicks et al.
Nature reviews. Microbiology, 11(5), 316-326 (2013-04-17)
Several bacterial species have evolved specialized secretion systems to deliver bacterial effector proteins into eukaryotic cells. These effectors have the capacity to modulate host cell pathways in order to promote bacterial survival and replication. The spatial and temporal context in
S Lecat et al.
Journal of cell science, 113 ( Pt 14), 2607-2618 (2000-06-23)
Annexins form a family of proteins that are widely expressed and known to bind membranes in the presence of calcium. Two isoforms of the annexin XIII subfamily are expressed in epithelia. We previously reported that annexin XIIIb is apically localized
Ana Gutiérrez et al.
Archives of biochemistry and biophysics, 514(1-2), 33-43 (2011-08-26)
Reaction of fatty acids, fatty alcohols, alkanes, sterols, sterol esters and triglycerides with the so-called aromatic peroxygenase from Agrocybe aegerita was investigated using GC-MS. Regioselective hydroxylation of C(12)-C(20) saturated/unsaturated fatty acids was observed at the ω-1 and ω-2 positions (except
Mélissa Hannauer et al.
FEBS letters, 586(1), 96-101 (2011-12-17)
Pyoverdine I (PVDI) is the major siderophore produced by Pseudomonas aeruginosa to import iron. Biosynthesis of this chelator involves non-ribosomal peptide synthetases and other enzymes. PvdQ is a periplasmic enzyme from the NTN hydrolase family and is involved in the
Martin M Hanczyc et al.
Science (New York, N.Y.), 302(5645), 618-622 (2003-10-25)
The clay montmorillonite is known to catalyze the polymerization of RNA from activated ribonucleotides. Here we report that montmorillonite accelerates the spontaneous conversion of fatty acid micelles into vesicles. Clay particles often become encapsulated in these vesicles, thus providing a

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