506-37-6 Usage
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 506-37-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 6 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 506-37:
(5*5)+(4*0)+(3*6)+(2*3)+(1*7)=56
56 % 10 = 6
So 506-37-6 is a valid CAS Registry Number.
InChI:InChI=1/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-
506-37-6Relevant articles and documents
A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids
Hamberg, Mats
, p. 489 - 494 (2021/04/19)
Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese-based Wurtz type coupling of alkyl bromides. 22-Bromo-3(Z),6(Z),9(Z),12(Z),15(Z),18(Z)-docosahexaene, easily prepared from 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenoic acid, was coupled to homologous ω-bromoesters by stirring for 4 hours at 40°C in the presence of manganese powder, a nickel catalyst and terpyridine. This afforded in yields of 70–75% a series of ω3-hexaenoates of chain lengths of 32–40 carbons. The corresponding fatty acids of >98% purity were obtained following saponification and final purification. By using methyl [2,2,3,3,4,4-2H6]10-bromodecanoate as coupling partner it was possible to prepare a very long chain fatty acid in isotopically labeled form, i.e., [2,2,3,3,4,4-2H6]14(Z),17(Z),20(Z),23(Z),26(Z),29(Z)-dotriacontahexaenoic acid. Also prepared were the monounsaturated long chain fatty acids 15(Z)-octadecenoic acid and 15(Z)-tetracosenoic acid. Very long chain fatty acids have been isolated from retina and other tissues and are of biological relevance. The methodology described will assist in further analytical and biological studies in this field.
NOVEL PHOSPHOLIPIDS WITH UNSATURATED ALKYL AND ACYL CHAINS
-
Page/Page column 15, (2010/02/11)
The invention relates to phospholipid-like compounds having defined apolar constituents and to the use of such compounds as liposomes, active ingredients, and solubilizers.
