Nervonic acid Chemical Properties

Melting point:

42-43 °C (lit.)

Boiling point:

459.84°C (rough estimate)

Density 

0.9009 (rough estimate)

refractive index 

1.4806 (estimate)

Flash point:

>230 °F

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Hexanes (Very Slightly)

pka

4.78±0.10(Predicted)

form 

Liquid

color 

White to Pale Yellow

BRN 

1728551

InChI

InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-

InChIKey

GWHCXVQVJPWHRF-KTKRTIGZSA-N

SMILES

C(O)(=O)CCCCCCCCCCCCC/C=C\CCCCCCCC

LogP

10.890 (est)

CAS DataBase Reference

506-37-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8-10

HS Code 

2916.19.3000

MSDS

• Language:English Provider:cis-15-Tetracosenoic acid
• Language:English Provider:SigmaAldrich

Nervonic acid Usage And Synthesis

Description

Nervonic acid, also known as shark oil acid, is a monounsaturated omega-9 fatty acid that exists in nerve tissue and fish oil. It was first discovered in shark brain and is a component of cerebroside, the main source of in shark brain and shark oil. It is also found in the sphingolipids of white matter in human brain. It is the only dual-action miracle substance that can repair nerve fibers that unblock damaged nerve pathways in the brain and promote nerve cell regeneration. Nervonic acid has been identified as important in the biosynthesis of nerve cell myelin. It is used in the treatment of disorders involving demyelination, such as adrenoleukodystrophy and multiple sclerosis where there is a decreased level of nervonic acid in sphingolipids.

Occurrence

Nervonic acid is abundant in King Salmon ( Chinook ) with 140 mg/100g, yellow mustard seed 83 mg/100g , flax seed 64 mg/ 100g, Sockeye salmon 40 mg/100g, sesame seed 35mg/100g, and macademia nuts 18 mg/100g.

Uses

Found in sphingolipids of the white matter of the human brain, neuronic acid is the only magical substance with a dual role in brain development, repairing nerve fibers, unblocking damaged neural pathways in the brain, and promoting nerve cell regeneration. Neuroic acid is very important in the biosynthesis of nerve cell myelin, which together with lignoceric acid accounts for 60% of the acylated fatty acids in white matter sphingomyelin. In demyelinating diseases such as adrenoleukodystrophy and multiple sclerosis, the amount of neuronic acid acylated to sphingolipids is highly reduced, and supplements rich in this fatty acid have been used to help treat these demyelinating diseases.

Definition

ChEBI: Nervonic Acid is a monounsaturated fatty acid with a 24-carbon backbone and the sole double bond originating from the 9th carbon from the methyl end, with this bond in the cis- configuration. It is a metabolite found in the aging mouse brain.

Preparation

Nervonic acid was shown to be identical with selachaleic acid isolated from whale oils. It is obvious that nervonic acid is probably the cis form of erucylacetic acid. Erucylacetic acid has been prepared from erucyl alcohol through the bromide and malonic ester synthesis and has been shown to be identical with nervonic acid obtained from hydrolysis of the cerebroside isolated from human brains.
Nervonic acid is also produced from oleic acid, that undergoes three consecutive chain elongation steps, catalyzed by elongases.Two carbon units are added in each step, with production of gadoleic acid, erucic acid, and finally, nervonic acid.

benefits

Nervonic acid (NA, a monounsaturated long-chain fatty acid) has been found to alleviate neurodegeneration. In humans, abnormal NA levels are closely associated with a higher risk of developing neurological or psychiatric disorders such as psychosis, schizophrenia, or attention deficit disorder. Studies have shown that NA treatment can improve cognitive function, prevent demyelination and oligodendrocyte loss or apoptosis, improve cerebral blood flow, and upregulate brain-derived neurotrophic factor and myelin basic protein genes. In addition, NA can not only stimulate adipogenesis by regulating signaling pathways in human MSCs, but also improve the results of fat transplantation by reducing inflammation and stimulating angiogenesis.

General Description

Nervonic acids are the products of desaturation and elongation processes of various fatty acids such as palmitic acid, stearic acid, oleic acid, etc.

Biochem/physiol Actions

Nervonic acid (C24:1), a component of membrane sphingolipids and phosphatidylethanolamines, may be a useful predictor of chronic kidney disease mortality and diabetes. Nervonic acid oils are being studied for pharmaceutical, nutraceutical and industrial applications. Nervonic acid is a major component of Lunaria oil.

Source

Sources of Nervonic acid include oil crop seeds, oil-producing microalgae and other microorganisms. Transgenic technology can also be used to improve the source and production of Nervonic acid.

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