(E)-11-methyldodec-2-enoic acid

Base Information

• Chemical Name: (E)-11-methyldodec-2-enoic acid
• CAS No.: 677354-24-4
• Molecular Formula: C13H24O2
• Molecular Weight: 212.3
• DSSTox Substance ID: DTXSID601347871
• Metabolomics Workbench ID: 119259
• Wikidata: Q27159410
• Mol file: 677354-24-4.mol

Synonyms:677354-24-4;(E)-11-methyldodec-2-enoic acid;trans-delta2-11-methyl-Dodecenoic Acid;trans-11-methyl-2-dodecenoic acid;11-Methyl-2E-dodecenoic acid;SCHEMBL301125;SCHEMBL1470217;CHEBI:87153;SNTXNGAQYNSTHI-PKNBQFBNSA-N;11-Methyl-2(E)-Dodecenoic acid;DTXSID601347871;HMS3650A16;JM085;trans-11-methyldodec-2-enoic acid;trans-2-11-Methyl-dodecenoic acid;(2E)-11-Methyl-2-dodecenoic acid;(2E)-11-methyldodec-2-enoic acid;MFCD09263532;AKOS025295622;PD019925;trans- delta 2-11-methyl-Dodecenoic Acid;trans-.DELTA.2-11-Methyldodecenoic Acid;SR-01000946260;SR-01000946260-1;Q27159410

Chemical Property of (E)-11-methyldodec-2-enoic acid

Chemical Property:

• Appearance/Colour: a crystalline solid
• Boiling Point: 322.3±11.0 °C(Predicted)
• PKA: 4.79±0.10(Predicted)
• PSA: 37.30000
• Density: 0.916±0.06 g/cm3(Predicted)
• LogP: 4.01390
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 212.177630004
• Heavy Atom Count: 15
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

trans-Δ2-11-methyl-Dodecenoic Acid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCCCCCC=CC(=O)O
• Isomeric SMILES: CC(C)CCCCCCC/C=C/C(=O)O
• Description: Both prokaryotes and eukaryotes depend on small signalling molecules for cell-cell communication. trans-Δ2-11-methyl-Dodecenoic acid is the conformational isomer of cis-Δ2-11-methyl-dodecenoic acid, a diffusible signal factor (DSF) in extracellular microbial and fungal communication systems. In a DSF bioassay, the minimum concentration of cis-Δ2-11-methyl-dodecenoic acid required for induction of a DSF biosensor was about 0.5 μM, which is 200-fold lower than that of trans-Δ2-11-methyl-dodecenoic acid and 20,000-fold lower than that of the corresponding saturated fatty acid (11-methyl-dodecanoic acid).

Technology Process of (E)-11-methyldodec-2-enoic acid

There total 12 articles about (E)-11-methyldodec-2-enoic 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: 89.0%

11-methyldodec-2-ynoic acid → (Z)-11-methyldodec-2-enoic acid (677354-23-3,677354-24-4)

Guidance literature:

With hydrogen; In dichloromethane; for 72h; under 3102.97 Torr;

DOI:10.1016/j.tetlet.2018.04.071

Reference yield: 88.3%

C14H26Br2O → (Z)-11-methyldodec-2-enoic acid (677354-23-3,677354-24-4)

Guidance literature:

C₁₄H₂₆Br₂O; With sodium hydroxide; water; for 6 - 8h;

With hydrogenchloride; In water;

Reference yield: 58.0%

C15H28O2 → (Z)-11-methyldodec-2-enoic acid (677354-23-3,677354-24-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃; for 16h;

DOI:10.1016/j.tetlet.2018.04.071

upstream raw materials:

9-methyldecan-1-ol

(3-methylbutyl)magnesium bromide

1-Heptyne

5-bromopentan-1-ol

Refernces

• 1、 Kumar, Vydyula P.,Gupta, Manoj K.,Horgan, Conor,O'Sullivan, Timothy P.. "Synthesis of the quorum sensing molecule Diffusible Signal Factor using the alkyne zipper reaction". supporting information. p. 2193 - 2195. Retrieved 2018/05/08.