Divinylether fatty acids contain a fatty acid chemically combined with a doubly unsaturated carbon chain linked by an oxygen atom (

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

). Fatty acid hydroperoxides generated by plant lipoxygenases from

linoleic Linoleic acid (LA) is an organic compound with the formula . Both alkene groups () are ''cis''. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 ''cis''-9,12. A linoleate is a salt or ester of this acid. Linoleic acid is a polyunsatu ...

and

linolenic acid Linolenic acid is a type of naturally-occurring fatty acid. It can refer to either of two octadecatrienoic acids (i.e. with an 18-carbon chain and three double bonds, which are found in the '' cis'' configuration), or a mixture of the two. Lino ...

s are known to serve as substrates for a

divinyl ether synthase 1,3-Butadiene () is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two ...

which produces divinyl ether fatty acids. Divinyl ethers were detected only within the plant kingdom. The discovery of that class of compounds dates to 1972, when the structures of two ether C18 fatty acids generated by homogenates of the potato tuber were described. These compounds, named

colneleic acid Divinylether fatty acids contain a fatty acid chemically combined with a doubly unsaturated carbon chain linked by an oxygen atom (ether). Fatty acid hydroperoxides generated by plant lipoxygenases from linoleic acid, linoleic and α-Linolenic ac ...

(from linoleic acid) and colnelenicacid (from linolenic acid), could be also produced in potato leaves and tomato roots by rearrangement of 9-hydroperoxides. Isomers of colneleic acid and colnelenic acid were isolated from homogenates of leaves of ''

Clematis vitalba ''Clematis vitalba'' (also known as old man's beard and traveller's joy) is a shrub of the family Ranunculaceae. Description ''Clematis vitalba'' is a climbing shrub with branched, grooved Plant stem, stems, deciduous leaves, and scented green ...

'' (

Ranunculaceae Ranunculaceae (, buttercup or crowfoot family; Latin "little frog", from "frog") is a family (biology), family of over 2,000 known species of flowering plants in 43 genera, distributed worldwide. The largest genera are ''Ranunculus'' (600 spec ...

). Similarly, 13-lipoxygenase-generated hydroperoxides serve as precursor of other divinyl ether fatty acids which are produced in bulbs of

garlic Garlic (''Allium sativum'') is a species of bulbous flowering plants in the genus '' Allium''. Its close relatives include the onion, shallot, leek, chives, Welsh onion, and Chinese onion. Garlic is native to central and south Asia, str ...

or Ranunculus leaves. These compounds were named etheroleic and etherolenic acids. Etheroleic acid has systematic name 12- ′E-hexenyloxy9Z,11Z-dodecadienoic acid. Etherolenic acid has systematic name (9Z,11E,1'E,3'Z)-12-(1',3'-Hexadienyloxy)-9,11-dodecadienoic acid. The physiological significance of divinyl ethers is still not fully studied. As infection of potato leaves leads to increased levels of

, it was suggested that this pathway could be of importance in the defense of plants against attacking pathogens. Similar structures have been discovered in the brown alga ''

Laminaria sinclairii ''Laminaria sinclairii'' is a species of brown algae (class Phaeophyceae), in the family Laminariaceae. It is native to the lower intertidal zone of the northeastern Pacific Ocean from British Columbia southwards to California. Description This ...

'', with 18 or 20 carbons and 4, 5 or 6 double bonds, and in the red alga ''

Polyneura latissima ''Polyneura'' is a cicada genus from Southeast Asia. The type species is '' Polyneura ducalis'' with type material from India.Hayashi, M. 1978. The Cicadidae (Homoptera, Auchenorrhyncha) from east and central Nepal (Part II). Bulletin of the Nati ...

'', with 20 carbons and 5 double bonds.

References

{{Reflist Carboxylic acids Ethers