Nervonic acid (24:1, n−9) is a

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

. It is a monounsaturated analog of

lignoceric acid Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula . It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid (1 ...

(24:0). It is also known as selacholeic acid and ''cis''-15-tetracosenoic acid. Its name derives from the

Latin Latin ( or ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken by the Latins (Italic tribe), Latins in Latium (now known as Lazio), the lower Tiber area aroun ...

word '' nervus'', meaning nerve or sinew. It exists in nature as an elongation product of

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is cl ...

(18:1 Δ9). Its immediate precursor is

erucic acid Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the chemical formula: . It is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high erucic acid rapese ...

. Nervonic acid is particularly abundant in the white matter of animal brains and in peripheral nervous tissue where nervonyl sphingolipids are enriched in the myelin sheath of nerve fibers. This acid is among the group of cerebrosides, which are fatty acids of the glycosphingolipids group, which are components of muscles and the nervous system, accounting for approximately 40% of the total fatty acids in sphingolipids.

Structure

As it is defined as a

monounsaturated In biochemistry and nutrition, a monounsaturated fat is a fat that contains a monounsaturated fatty acid (MUFA), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being s ...

fatty acid, it has one double bond in the fatty acid chain and all the remaining

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms are single-bonded. It is classified in the sub-group of very long chain fatty acids (VLCFA), which includes molecules containing more than 20 carbon atoms. It has specifically 24-carbon backbone and the sole C=C double bond originating from the methyl end is in n-9 or omega-9 (ω-9).

Functions

Nervonic acid may be involved in the growth and maintenance of nerve tissue as a regulator of Ca²⁺

ion channel Ion channels are pore-forming membrane proteins that allow ions to pass through the channel pore. Their functions include establishing a resting membrane potential, shaping action potentials and other electrical signals by Gating (electrophysiol ...

s in the cell membranes of nerve tissue.

Sources

Nervonic acid occurs in

seed oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oi ...

of plants, where significant amounts are contained. Indeed, more than 10% of the lipids contain nervonic acid, usually in the form of

triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...

s. The seed oils of ''

Lunaria ''Lunaria'' is a genus of flowering plants in the family Brassicaceae. It is native to Europe and has been introduced to North America and elsewhere. Species include: *'' L. annua'' ( syn. ''L. biennis''), annual or biennial *'' L. rediviva ...

'' species (''

Lunaria biennis ''Lunaria annua'', commonly called honesty or annual honesty, is a species of flowering plant in the cabbage and mustard family Brassicaceae. It is native plant, native to southern Europe, and cultivated throughout the temperate climate, temperat ...

'' or ''

Lunaria annua ''Lunaria annua'', commonly called honesty or annual honesty, is a species of flowering plant in the cabbage and mustard family Brassicaceae. It is native to southern Europe, and cultivated throughout the temperate world. Description It is an ...

'', for example) are a quite important source of this long chain fatty acid, since they contain over 20% of it in the triglyceride lipid. Nervonic acid is also found in '' Cardamine gracea'', '' Heliophila longifola'', and '' Malania oleifera''. In all these species, 24:1 usually is esterified at the sn-1 and sn-3 positions on the glycerol backbone. Other sources can be the

mold A mold () or mould () is one of the structures that certain fungus, fungi can form. The dust-like, colored appearance of molds is due to the formation of Spore#Fungi, spores containing Secondary metabolite#Fungal secondary metabolites, fungal ...

s '' Neocallimastix frontalis'', the bacterium '' Pseudomonas atlantica'', the yeast ''

Saccharomyces cerevisiae ''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungal microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have be ...

'', and the marine diatom '' Nitzschia cylindrus''. Nervonic acid was first isolated from the brains of sharks and its molecular structure was determined over a century ago; due to this, the acid is also known as shark oil acid. Scientists found that shark brains could repair themselves quickly after being damaged, suggesting that nervonic acid had the ability to promote the repair and regeneration of nerve fibers in damaged brain tissue.

References

Additional references

* Appelqvist (1976) Lipids in Cruciferae. In: Vaughan JG, Macleod AJ (Eds), ''The Biology and the Chemistry of Cruciferae''. Academic Press, London, UK, pp. 221–277. {{Fatty acids Fatty acids Alkenoic acids