trans-Vaccenic acid

Base Information

• Chemical Name: trans-Vaccenic acid
• CAS No.: 693-72-1
• Molecular Formula: C18H34 O2
• Molecular Weight: 282.467
• European Community (EC) Number: 211-758-9
• UNII: GQ72OGU4EV
• DSSTox Substance ID: DTXSID301009341
• Metabolomics Workbench ID: 510
• NCI Thesaurus Code: C68438
• Nikkaji Number: J6.936A,J327.304K
• Wikidata: Q419047
• Wikipedia: Vaccenic_acid
• Mol file: 693-72-1.mol

Synonyms:11-octadecenoic acid;11-octadecenoic acid, (E)-isomer;trans-vaccenic acid;vaccenic acid

Chemical Property of trans-Vaccenic acid

Chemical Property:

• Vapor Pressure: 1.81E-06mmHg at 25°C
• Melting Point: 44℃
• Refractive Index: 1.4472 (589.3 nm 50℃)
• Boiling Point: 369.4°C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 113 °C
• PSA: 37.30000
• Density: 0.899g/cm³
• LogP: 6.10850
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 282.255880323
• Heavy Atom Count: 20
• Complexity: 234

Purity/Quality:

99.00% ^*data from raw suppliers

VaccenicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCC=CCCCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCC/C=C/CCCCCCCCCC(=O)O
• Recent ClinicalTrials: A Study Of Different Doses Of UK-453, 061 Plus Truvada Compared To Efavirenz Plus Truvada In Patients Who Have Not Been Previously Treated For HIV-1
• Uses: Vaccenic Acid is a fatty acid found in Artemia salina that shows antimicrobial activity against a variety of microorganisms except Escherichia coli, Micrococcus luteus and Salmonella enteritidis.

Technology Process of trans-Vaccenic acid

There total 24 articles about trans-Vaccenic 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: 99.0%

C14H25BrO2 (1448529-14-3) + butyl magnesium bromide (693-04-9) → trans-Vaccenic acid (693-72-1)

Guidance literature:

C₁₄H₂₅BrO₂; With tert-butylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

butyl magnesium bromide; With 1-methyl-pyrrolidin-2-one; buta-1,3-diene; nickel dichloride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201204222

Reference yield: 94.0%

methyl vaccenate (1937-63-9,52380-33-3,6198-58-9) → trans-Vaccenic acid (693-72-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 48 ℃;

DOI:10.1016/j.tet.2006.03.006

Reference yield:

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → Elaidic acid (112-79-8,2027-47-6) + cis-10-octadecenoic acid (2442-70-8) + trans-10-octadecenoic acid (5684-82-2) + cis-vaccenic acid (506-17-2) + trans-Vaccenic acid (693-72-1) + stearic acid (57-11-4)

Guidance literature:

With hydrogen; silica gel; nickel; In neat (no solvent); at 139.9 ℃; under 300 Torr; Product distribution; Mechanism; var. pressure, temperature and catalyst, other reaction products also present;

DOI:10.1007/BF02525461

upstream raw materials:

cis-vaccenic acid

methyl 12-tridecenoate

methyl (Z)-vaccenate

linoleic acid

Downstream raw materials:

undecanedioic acid

methyl vaccenate

(4R,5S)-3-((E)-(R)-2-Hydroxy-octadec-11-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

(4R,5S)-4-Methyl-3-((E)-octadec-11-enoyl)-5-phenyl-oxazolidin-2-one

Refernces

• 1、 -. "CATALYSTS AND CATALYTIC PROCESSES". Paragraph 0088. . Retrieved 2017/05/28.
• 2、 Reaume, Stephen J.,Ellis, Naoko. "Optimizing reaction conditions for the isomerization of fatty acids and fatty acid methyl esters to their branch chain products". experimental part. p. 661 - 671. Retrieved 2012/01/31.