Structure Database (LMSD)

Common Name
Etheroleic acid
Systematic Name
12-(1'E-Hexaenyloxy)-9Z,11E-dodecadienoic acid
Synonyms
LM ID
LMFA10000008
Formula
C18H30O3
Exact Mass
Calculate m/z
294.219496
Sum Composition
FA 18:3;O
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 ethers [FA10]

Biological Context

Etheroleic acid is a divinyl ether oxylipin.1,2 It is a metabolite of linolenic acid that is formed in plants via 13-lipoxygenase-mediated formation of 13(S)-HpODE or (±)13-HpODE followed by conversion to the divinyl ether by divinyl ether synthase. Etheroleic acid (30 µM) is fungicidal against the powdery mildew B. graminis on the second leaves of barley seedlings.3

This information has been provided by Cayman Chemical

References

1. Grechkin, A.N., Ilyasov, A.V., and Hamberg, M. On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 245(1), 137-142 (1997).
2. Hamberg, M. Biosynthesis of new divinyl ether oxylipins in Ranunculus plants. Lipids 37(4), 427-433 (2002).
3. Cowley, T., and Walters, D. Local and systemic effects of oxylipins on powdery mildew infection in barley. Pest Manag. Sci. 61(6), 572-576 (2005).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Allium sativum (#4682)
Magnoliopsida (#3398)
The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins.,
FEBS Lett, 1995
Pubmed ID: 7672118

String Representations

InChiKey (Click to copy)
NQNHRHWFZHFAAH-XSWVPMOFSA-N
InChi (Click to copy)
InChI=1S/C18H30O3/c1-2-3-4-13-16-21-17-14-11-9-7-5-6-8-10-12-15-18(19)20/h9,11,13-14,16-17H,2-8,10,12,15H2,1H3,(H,19,20)/b11-9-,16-13+,17-14+
SMILES (Click to copy)
C(CCCCCCC/C=C\C=C\O/C=C/CCCC)(=O)O

Other Databases

CHEBI ID
133329
PubChem CID
25246008
Cayman ID
10005119

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 335.77
Topological Polar Surface Area 46.53
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 5.59
Molar Refractivity 87.98

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Created at
10th Aug 2020
Updated at
9th Jun 2022