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Merck
CN

M3525

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

Key Documents

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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

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Certificates of Analysis (COA)

Lot/Batch Number
0000448026
0000448026
0000424277
0000424276
0000424276

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Kwon-Young Choi et al.
The FEBS journal, 279(9), 1650-1662 (2011-12-23)
Among 33 cytochrome P450s (CYPs) of Streptomyces avermitilis, CYP102D1 encoded by the sav575 gene is naturally a unique and self-sufficient CYP. Since the native cyp102D1 gene could not be expressed well in Escherichia coli, its expression was attempted using codon-optimized
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
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
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
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
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