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M3525

Sigma-Aldrich

Myristoleic acid

≥99% (capillary GC)

Synonym(s):

cis-9-Tetradecenoic acid

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About This Item

Linear Formula:
CH3(CH2)3CH=CH(CH2)7CO2H
CAS Number:
544-64-9
Molecular Weight:
226.36
EC Number:
208-876-8
MDL number:
MFCD00004436
UNSPSC Code:
12352211
PubChem Substance ID:
24896849
NACRES:
NA.25

biological source

plant

Quality Level

200

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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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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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