Structure Database (LMSD)

Common Name
SFE 1:0/14:1(9Z)
Systematic Name
Methyl 9Z-tetradecenoate
Synonyms
  • WE(1:0/14:1(9Z))
LM ID
LMFA07010493
Formula
C15H28O2
Exact Mass
Calculate m/z
240.20893
Sum Composition
SFE 15:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Short fatty esters [FA0710]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

Myristoleic acid is a cytotoxic component from the fruit extract of S. repens.1 It induces apoptosis and necrosis in human prostate cancer LNCaP cells at a rate of 8.8% and 8.1%, respectively.1 Furthermore, myristoleic acid found in the by-products for making cheese is one of three fatty acids that are most active at inhibiting Candida albicans germination.2 It has a minimal inhibitory concentration (MIC) of 9 µM in vivo.3 Myristoleic acid methyl ester is a more hydrophobic form of the free acid.

This information has been provided by Cayman Chemical

References

1. Umehara, T., Sudoh, M., Yasui, F., et al. Serine palmitoyltransferase inhibitor suppresses HCV replication in a mouse model. Biochem. Biophys. Res. Commun. 346(1), 67-73 (2006).
2. Clément, M., Tremblay, J., Lange, M., et al. Whey-derived free fatty acids suppress the germination of Candida albicans in vitro. FEMS Yeast Res. 7(2), 276-285 (2007).
3. Iguchi, K., Okumura, N., Usui, S., et al. Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Prostate 47(1), 59-65 (2001).

References

Comments
Pherobase Semiochemicals

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Apidae (#7458)
Insecta (#50557)
Biogenetic pattern of straight chain marking compounds in male bumble bees,
Comp Biochem Physiol B, 1987

String Representations

InChiKey (Click to copy)
RWIPSJUSVXDVPB-SREVYHEPSA-N
InChi (Click to copy)
InChI=1S/C15H28O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17-2/h6-7H,3-5,8-14H2,1-2H3/b7-6-
SMILES (Click to copy)
O=C(CCCCCCC/C=C\CCCC)OC

Other Databases

CHEBI ID
143579
PubChem CID
5352674
Cayman ID
10008581

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 0
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 280.36
Topological Polar Surface Area 26.30
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 4.64
Molar Refractivity 73.00

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Created at
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Updated at
9th Apr 2025