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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Bi-Na Kim et al.
Applied microbiology and biotechnology, 95(4), 929-937 (2011-12-23)
A recombinant enzyme from Lysinibacillus fusiformis was expressed, purified, and identified as an oleate hydratase because the hydration activity of the enzyme was the highest for oleic acid (with a k (cat) of 850 min(-1) and a K (m) of 540 μM)
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
Karina Krotova et al.
British journal of pharmacology, 148(5), 732-740 (2006-05-23)
1. Myristoylated pseudosubstrate of PKCzeta (mPS) - a synthetic myristoylated peptide with a sequence (13 amino acids) mimicking the endogenous PKCzeta pseudosubstrate region -- is considered a selective cell-permeable inhibitor of PKCzeta. We present strong evidence that in endothelial cells
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