2-Dodecenoic acid

Base Information

• Chemical Name: 2-Dodecenoic acid
• CAS No.: 32466-54-9
• Molecular Formula: C12H22 O2
• Molecular Weight: 198.305
• Hs Code.: 2916190090
• European Community (EC) Number: 224-569-1,603-308-9,836-106-6
• DSSTox Substance ID: DTXSID401343611
• Nikkaji Number: J98.064A,J98.065J
• Wikidata: Q27117056,Q27117632
• NCI Thesaurus Code: C68354
• Metabolomics Workbench ID: 1128
• ChEMBL ID: CHEMBL4281333
• Mol file: 32466-54-9.mol

Synonyms:2-dodecenoic acid;cis-2-dodecenoic acid

Chemical Property of 2-Dodecenoic acid

Chemical Property:

• Melting Point: 19°C
• Boiling Point: 311.7±11.0 °C(Predicted)
• PKA: 4.79±0.10(Predicted)
• Flash Point: 216.6oC
• PSA: 37.30000
• Density: 0,92 g/cm3
• LogP: 3.76790
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 198.161979940
• Heavy Atom Count: 14
• Complexity: 162

Purity/Quality:

98%Min ^*data from raw suppliers

trans-2-Dodecenoic Acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC=CC(=O)O
• Isomeric SMILES: CCCCCCCCC/C=C/C(=O)O
• Uses: (2E)-2-Dodecenoic acid is used in a biological study that assesses bacterial cell-cell communication signals with cross-kingdom structural analogues.

Technology Process of 2-Dodecenoic acid

There total 19 articles about 2-Dodecenoic 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: 97.0%

tert-butyl (E)-dodec-2-enoate → (E)-2-dodecenoic acid (32466-54-9,4412-16-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2018.09.013

Reference yield: 96.0%

ethyl (E)-dodec-2-enoate (42778-95-0,78217-11-5,28290-90-6) → (E)-2-dodecenoic acid (32466-54-9,4412-16-2)

Guidance literature:

With sodium hydroxide; In water; tert-butyl alcohol; at 60 ℃; for 6h;

DOI:10.1039/c8ob01268g

Reference yield: 89.0%

lauric acid (143-07-7) → (E)-2-dodecenoic acid (32466-54-9,4412-16-2)

Guidance literature:

lauric acid; With Zn(2,2,6,6-tetramethylpiperidine)_2*2LiCl; zinc(II) chloride; In tetrahydrofuran; at -40 ℃; for 1.5h; Inert atmosphere; Sealed tube;

With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate; In tetrahydrofuran; at -40 - 60 ℃; for 12h; diastereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201706893

upstream raw materials:

caprinaldehyde

malonic acid

(E)-tridec-3-en-2-one

2-bromododecanoic acid

Downstream raw materials:

dodec-2-enoic acid ethyl ester

methyl (E)-dodec-2-enolate

1-decanoic acid

caprinaldehyde

Refernces

• 1、 Corcilius, Leo,Liu, Dennis Y.,Ochoa, Jessica L.,Linington, Roger G.,Payne, Richard J.. "Synthesis and evaluation of analogues of the glycinocin family of calcium-dependent antibiotics". . p. 5310 - 5320. Retrieved 2018/08/03.
• 2、 Brodl, Eveline,Ivkovic, Jakov,Tabib, Chaitanya R.,Breinbauer, Rolf,Macheroux, Peter. "Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases". . p. 1487 - 1495. Retrieved 2017/02/18.