Structure Database (LMSD)

Common Name
Methyl nonanoate
Systematic Name
methyl nonanoate
Synonyms
LM ID
LMFA07010963
Formula
C10H20O2
Exact Mass
Calculate m/z
172.14633
Sum Composition
SFE 10:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Short fatty esters [FA0710]

Biological Context

Nonanoic acid methyl ester is an esterified form of nonanoic acid. It is found as a volatile component following thermal oxidation of conjugated linoleic acid methyl ester but not linoleic acid methyl ester.1 It is cytotoxic to A549 lung carcinoma cells with an LC50 value of 104.09 µg/ml.2 Nonanoic acid methyl ester enhances the penetration of minoxidil into isolated hamster ventral ear skin when applied at a 10% concentration ex vivo.3 It is a substrate for the E. coli alkane hydroxylase system (AlkBGT), which oxidizes nonanoic acid methyl ester to produce 9-hydroxy methyl nonanoate, an ω-hydroxy fatty acid ester that can be used in the production of sustainable polymers.4

This information has been provided by Cayman Chemical

References

1. Cossignani, L., Giua, L., Simonetti, M.S., et al. Volatile compounds as indicators of conjugated and unconjugated linoleic acid thermal oxidation. Eur. J. Lipid Sci. Technol. 116(4), 407-412 (2014).
2. Bordoloi, M., Saikia, S., Kolita, B., et al. Volatile inhibitors of phosphatidylinositol-3-kinase (PI3K) pathway: Anticancer potential of aroma compounds of plant essential oils. Anticancer Agents Med. Chem. 18(1), 87-109 (2018).
3. Chukwumerije, O., Nash, R.A., Matias, J.R., et al. Studies on the efficacy of methyl esters of n-alkyl fatty acids as penetration enhancers. J. Invest. Dermatol. 93(3), 349-352 (1989).
4. van Nuland, Y.M., Eggink, G., and Weusthuis, R.A. Application of AlkBGT and AlkL from Pseudomonas putida GPo1 for selective alkyl ester ω-oxyfunctionalization in Escherichia coli. Appl. Environ. Microbiol. 82(13), 3801-3807 (2016).

String Representations

InChiKey (Click to copy)
IJXHLVMUNBOGRR-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C10H20O2/c1-3-4-5-6-7-8-9-10(11)12-2/h3-9H2,1-2H3
SMILES (Click to copy)
CCCCCCCCC(OC)=O

Other Databases

HMDB ID
HMDB0031264
CHEBI ID
44499
PubChem CID
15606
Cayman ID
26719
PDB ID
NON

Calculated Physicochemical Properties

Heavy Atoms 12
Rings 0
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 196.50
Topological Polar Surface Area 26.30
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 2.91
Molar Refractivity 50.01

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Created at
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Updated at
6th Jun 2022