Structure Database (LMSD)

Common Name
Petroselaidic acid
Systematic Name
6E-octadecenoic acid
Synonyms
  • trans-6-octadecenoic acid
  • C18:1n-12
LM ID
LMFA01030067
Formula
C18H34O2
Exact Mass
Calculate m/z
282.25588
Sum Composition
FA 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 Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Octadecanoids [FA02]

Biological Context

trans-Petroselinic acid is the trans isomer of petroselinic acid and an isomer of oleic acid that has been found in cow, goat, and ewe milk fat as well as human breast milk.1,2 In HepG2 cells, trans-petroselinic acid (100 μM) increases cellular content of triacylglycerols and cholesterol esters and upregulates transcription of genes involved in fatty acid synthesis, including SREBP-1c, ACACA, FASN, and SCD1, and cholesterol synthesis, including HMGCR, HMGCS1, FDFT1, and SREBP-2.3

This information has been provided by Cayman Chemical

References

1. Precht, D., Molkentin, J., Destaillats, F., et al. Comparative studies on individual isomeric 18:1 acids in cow, goat, and ewe milk fats by low-temperature high-resolution capillary gas-liquid chromatography. Lipids 36(8), 827-832 (2001).
2. Hauff, S., and Vetter, W. Quantitation of cis- and trans-monounsaturated fatty acids in dairy products and cod liver oil by mass spectrometry in the selected ion monitoring mode. J. Agric. Food Chem. 57(9), 3423-3430 (2009).
3. Vahmani, P., Meadus, W.J., Duff, P.T., et al. Comparing the lipogenic and cholesterolgenic effects of individual trans -18:1 isomers in liver cells. Eur. J. Lipid Sci. Technol. 119(3), 1600162 (2017).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
CNVZJPUDSLNTQU-OUKQBFOZSA-N
InChi (Click to copy)
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)/b13-12+
SMILES (Click to copy)
C(CCCCCCCC)CC/C=C/CCCCC(=O)O

Other Databases

CHEBI ID
30829
LIPIDBANK ID
DFA0106
PubChem CID
5282754
PlantFA ID
10072
Cayman ID
20026

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 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 6.11
Molar Refractivity 87.09

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Created at
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Updated at
25th Apr 2022