Structure Database (LMSD)
Common Name
Methyl 9Z-tetradecenoate
Systematic Name
Methyl 9Z-tetradecenoate
Synonyms
- WE(1:0/14:1(9Z))
3D model of Methyl 9Z-tetradecenoate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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
Admin
Created at
-
Updated at
6th Jun 2022