Nervonic Acid

Base Information

• Chemical Name: Nervonic Acid
• CAS No.: 506-37-6
• Molecular Formula: C24H46 O2
• Molecular Weight: 366.628
• Hs Code.: DERIVATION
• European Community (EC) Number: 610-549-3
• UNII: 91OQS788BE
• ChEMBL ID: CHEMBL1173379
• DSSTox Substance ID: DTXSID801009308
• Metabolomics Workbench ID: 525
• NCI Thesaurus Code: C68395
• Nikkaji Number: J11.357C
• Wikidata: Q414231
• Wikipedia: Nervonic_acid
• Mol file: 506-37-6.mol

Synonyms:nervonic acid;nervonic acid, potassium salt(Z)-isomer;nervonic acid, sodium salt, (Z)-isomer;trans-tetracos-15-enoic acid

Chemical Property of Nervonic Acid

Chemical Property:

• Appearance/Colour: clear to yellowish crystalline powder
• Vapor Pressure: 1.68E-10mmHg at 25°C
• Melting Point: 42 - 44 C
• Refractive Index: 1.4806 (estimate)
• Boiling Point: 479.2ºC
• PKA: 4.78±0.10(Predicted)
• Flash Point: >110 ºC
• PSA: 37.30000
• Density: 0.887g/cm³
• LogP: 8.44910
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Hexanes (Very Slightly)
• XLogP3: 9.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 21
• Exact Mass: 366.349780706
• Heavy Atom Count: 26
• Complexity: 309

Purity/Quality:

90% GC, ^*data from raw suppliers

Nervonic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCC=CCCCCCCCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O
• 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.
• 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.

Technology Process of Nervonic Acid

There total 15 articles about Nervonic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

1-hydroxy-cis-15-tetracosene (50995-29-4) → Nervonic acid (506-37-6)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃; for 7h;

Reference yield:

methyl cis-tetracos-15-enate (2733-88-2) → Nervonic acid (506-37-6)

Guidance literature:

With sodium hydroxide; In ethanol; at 60 ℃; for 1h; Inert atmosphere;

DOI:10.1002/aocs.12484

Reference yield:

(Z)-22-bromo-9-docosene (111924-39-1) + sodium diethylmalonate (996-82-7) → Nervonic acid (506-37-6) + tetracos-15t-enoic acid (115863-91-7)

Guidance literature:

With ethanol; Verseifen des Reaktionsprodukts mit siedender alkoh.KOH und Erhitzen der erhaltenen Dicarbonsaeure auf 175-210grad; die Trennung der beiden Stereoisomeren erfolgt durch fraktionierte Krystallysation aus Aethanol oder Aceton;

upstream raw materials:

(Z)-22-bromo-9-docosene

sodium diethylmalonate

cis-Octadecenoic acid

erucyl alcohol

Downstream raw materials:

pentadecanedioic acid

n-tetracosanoic acid

tetracos-15t-enoic acid

nonanoic acid

Refernces

• 1、 -. "Preparation method of nervonic acid and nervonic acid". . . Retrieved 2020/07/27.