Structure Database (LMSD)

Common Name
ethyl 9Z-hexadecenoate
Systematic Name
ethyl 9Z-hexadecenoate
Synonyms
  • WE(2:0/16:1(9Z))
LM ID
LMFA07010502
Formula
C18H34O2
Exact Mass
Calculate m/z
282.25588
Sum Composition
SFE 18:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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

Palmitoleic acid ethyl ester (ethyl palmitoleate) is a more lipophilic form of the free acid. It is one of the fatty acid ethyl esters that increase cytosolic Ca2+ concentration leading to pancreatic acinar cell injury due to excessive consumption of ethanol. Ethyl palmitoleate (10-100 µM) in addition to 850 mM ethanol resulted in sustained, concentration-dependent increases in Ca2+ that caused cell death.1 This fatty acid ethyl ester is also a potential biomarker for fetal exposure to alcohol.2

This information has been provided by Cayman Chemical

References

1. Criddle, D.N., Raraty, M.G.T., Neoptolemos, J.P., et al. Ethanol toxicity in pancreatic acinar cells: Mediation by nonoxidative fatty acid metabolites. Proc. Natl. Acad. Sci. USA 101(29), 10738-10743 (2004).
2. Moore, C., Jones, J., Lewis, D., et al. Prevalence of fatty acid ethyl esters in meconium specimens. Clin. Chem. 49(1), 133-136 (2003).

References

Comments
Pherobase Semiochemicals

String Representations

InChiKey (Click to copy)
JELGPLUONQGOHF-KTKRTIGZSA-N
InChi (Click to copy)
InChI=1S/C18H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20-4-2/h9-10H,3-8,11-17H2,1-2H3/b10-9-
SMILES (Click to copy)
O=C(CCCCCCC/C=C\CCCCCC)OCC

Other Databases

CHEBI ID
84934
PubChem CID
6436624
Cayman ID
10008204

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 332.26
Topological Polar Surface Area 26.30
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 6.09
Molar Refractivity 87.34

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Created at
-
Updated at
6th Jun 2022