Methyl (Z)-tetracos-15-enoate

Base Information

• Chemical Name: Methyl (Z)-tetracos-15-enoate
• CAS No.: 2733-88-2
• Molecular Formula: C25H48 O2
• Molecular Weight: 380.655
• Hs Code.: 2916190090
• European Community (EC) Number: 220-352-0
• DSSTox Substance ID: DTXSID701311780
• Nikkaji Number: J109.457B
• Wikidata: Q76305309
• Mol file: 2733-88-2.mol

Synonyms:2733-88-2;Nervonic acid methyl ester;Methyl nervonate;Methyl (Z)-tetracos-15-enoate;METHYL CIS-15-TETRACOSENOATE;(Z)-Methyl tetracos-15-enoate;15-Tetracosenoic acid, methyl ester, (Z)-;EINECS 220-352-0;Nervonic acid-methyl ester 10 microg/mL in Cyclohexane;NERVONICACIDMETHYLESTER;MFCD00056324;(Z)-Methyltetracos-15-enoate;SCHEMBL2191853;AINIZSBLAFHZCP-KHPPLWFESA-N;CHEBI:143592;DTXSID701311780;CAA73388;HY-N8064;Methyl (15Z)-15-tetracosenoate #;cis-15-Tetracosenoic acidmethyl ester;AKOS024386319;cis-15-Tetracosenoic acid, methyl ester;CS-0139592;Methyl cis-15-tetracosenoate, analytical standard;J-016742

Chemical Property of Methyl (Z)-tetracos-15-enoate

Chemical Property:

• Vapor Pressure: 2.66E-08mmHg at 25°C
• Melting Point: 14-15℃ (acetone )
• Refractive Index: 1.4563 (589.3 nm 23℃)
• Boiling Point: 450.3°Cat760mmHg
• Flash Point: 81°C
• PSA: 26.30000
• Density: 0.868g/cm³
• LogP: 8.53750
• Storage Temp.: −20°C
• XLogP3: 10.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 22
• Exact Mass: 380.365430770
• Heavy Atom Count: 27
• Complexity: 322

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl Nervonate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCCCCCCCC(=O)OC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)OC
• Description: Nervonic acid (24:1n-9) is a very long chain fatty acid produced by elongation of oleic acid (18:1n-9) and derived from erucic acid (22:1n-9) . It is enriched in nervous tissue and is particularly abundant in sphingolipids, such as sphingomyelin in the myelin sheath of nerve fibers. Nervonic acid is poorly produced in demyelinating disorders, including multiple sclerosis and adrenoleukodystrophy, suggesting that dietary supplementation may be beneficial. Nervonic Acid methyl ester is an ester version of the free acid which may be more suitable for the formulation of fatty acid-containing diets and dietary supplements.
• Uses: Nervonic Acid methyl ester is an ester version of?Nervonic Acid (N390110), a fatty acid that can be found?in the white matter of animal brains and in peripheral nervous tissue.?Nervonic Acid?is one of the major fatty acids in brain sphingolipids, normally accounting for approximately 40% of the total fatty acids in sphingolipids.

Technology Process of Methyl (Z)-tetracos-15-enoate

There total 17 articles about Methyl (Z)-tetracos-15-enoate 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: 75.0%

methanol (67-56-1) + (Z)-1-bromo-9-octadecene (13044-38-7,62871-05-0,6110-53-8) + 6-bromohexanoic acid (4224-70-8) → methyl cis-tetracos-15-enate (2733-88-2)

Guidance literature:

(Z)-1-bromo-9-octadecene; With magnesium; In tetrahydrofuran; ethylene dibromide; at 60 ℃; for 0.5h; Inert atmosphere;

6-bromohexanoic acid; With 1-methyl-pyrrolidin-2-one; tert-butylmagnesium chloride; buta-1,3-diene; nickel dichloride; In tetrahydrofuran; at -78 - 0 ℃; for 1.16667h; under 760.051 Torr; Inert atmosphere;

methanol; With hydrogenchloride; thionyl chloride; Inert atmosphere;

DOI:10.1002/chem.201204222

Reference yield:

methanol (67-56-1) + soybean oil (8001-22-7) → methyl trans-2-octadecenoate (14663-11-7) + 5,8,11-Eicosatrienoic acid, methyl ester + heneicosapentaenoic acid methyl ester + eicosadienoic acid methyl ester (88400-02-6) + docosapentaenoic acid methyl ester + docosatetraenoic acid methyl ester + docosadienoic acid methyl ester + palmitelaidic acid methyl ester (10030-74-7,3913-63-1) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + methyl cis-13-docosenoate (1120-34-9) + methyl cis-tetracos-15-enate (2733-88-2) + methyl myristoate (124-10-7) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + methyl tetracosanoate (2442-49-1) + methyl (2E)-eicosenoate (10305-59-6) + methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate (37929-05-8) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0)

Guidance literature:

With potassium hydroxide; at 48 - 52 ℃; for 4h;

Reference yield:

methanol (67-56-1) + canola oil → methyl trans-2-octadecenoate (14663-11-7) + 5,8,11-Eicosatrienoic acid, methyl ester + heneicosapentaenoic acid methyl ester + eicosadienoic acid methyl ester (88400-02-6) + docosapentaenoic acid methyl ester + docosatetraenoic acid methyl ester + docosadienoic acid methyl ester + palmitelaidic acid methyl ester (10030-74-7,3913-63-1) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + methyl cis-13-docosenoate (1120-34-9) + methyl cis-tetracos-15-enate (2733-88-2) + methyl myristoate (124-10-7) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + methyl tetracosanoate (2442-49-1) + methyl (2E)-eicosenoate (10305-59-6) + methyl (9Z,12Z,15E)-octadeca-9,12,15-trienoate (37929-05-8) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0)

Guidance literature:

With potassium hydroxide; at 48 - 52 ℃; for 4h;

upstream raw materials:

cis-Octadecenoic acid

methanol

soybean oil

sodium methylate

Downstream raw materials:

1,2,3-tris(cis-15-tetracosenoyl)glycerol

Nervonic acid

Refernces

• 1、 -. "Preparation method of nervonic acid and nervonic acid". . . Retrieved 2020/07/27.
• 2、 Goyal, Sandeep,Banerjee, Shibdas,Mazumdar, Shyamalava. "Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27". . p. 7880 - 7890. Retrieved 2013/01/15.