Structure Database (LMSD)

Common Name
Petroselinic acid
Systematic Name
6Z-octadecenoic acid
Synonyms
  • 6-octadecylenic acid
  • Petroselic acid
  • 5-heptadecylene-1-carboxylic acid
  • delta-5-octadecylenic acid
  • cis-6-octadecenoic acid
  • C18:1n-12
LM ID
LMFA01030066
Formula
C18H34O2
Exact Mass
Calculate m/z
282.255881
Sum Composition
FA 18:1
Status
Curated
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Classification

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

Biological Context

cis-Petroselinic acid is a monounsaturated fatty acid and isomer of oleic acid that is a component of plant lipids.1 Arachidonic acid levels decrease, while linoleic acid levels increase, in the heart, liver, and blood of rats fed a diet containing petroselinic acid.2 It has been used in a composite membrane as a model of plant partitioning to study the uptake of hydrophobic organic contaminants and polycyclic aromatic hydrocarbons.1 It has also been used as a substrate for the synthesis of new sophorolipids, which could have biological activities similar to natural biosurfactants.3

This information has been provided by Cayman Chemical

References

1. Delbeke, E.I.P., Everaert, J., Uitterhaegen, E., et al. Petroselinic acid purification and its use for the fermentation of new sophorolipids. AMB Express. 6(1), 28 (2016).
2. Li, X., Zhu, Y., Wu, T., et al. Using a novel petroselinic Acid embedded cellulose acetate membrane to mimic plant partitioning and in vivo uptake of polycyclic aromatic hydrocarbons. Environ. Sci. Technol. 44(1), 297-301 (2010).
3. Weber, N., Richter, K.D., Schulte, E., et al. Petroselinic acid from dietary triacylglycerols reduces the concentration of arachidonic acid in tissue lipids of rats. J. Nutr. 125(6), 1563-1568 (1995).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Petroselinum crispum (#4043)
Magnoliopsida (#3398)
Über Petroselinsäure, eine neue Ölsäure,
Berichte der Deutschen Chemischen Gesellschaft, 1909

String Representations

InChiKey (Click to copy)
CNVZJPUDSLNTQU-SEYXRHQNSA-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(=C/CCCCCCCCCCC)/CCCCC(=O)O

Other Databases

Wikipedia
Petroselinic_acid
KEGG ID
C08363
CHEBI ID
28194
LIPIDBANK ID
DFA0105
PubChem CID
5281125
PlantFA ID
10552
SwissLipids ID
SLM:000001201
Cayman ID
20024
PDB ID
4I1

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
7th Jan 2025