cis-beta-Octenoic acid

Base Information

• Chemical Name: cis-beta-Octenoic acid
• CAS No.: 5169-51-7
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.198
• UNII: 54ZLT8D16E
• Nikkaji Number: J1.554.520H
• Wikidata: Q27261250
• Metabolomics Workbench ID: 454
• Mol file: 5169-51-7.mol

Synonyms:(Z)-3-octenoic acid;cis-beta-octenoic acid;3-Octenoic acid, (3Z)-;3Z-octenoic acid;cis-3-octenoic acid;5169-51-7;UNII-54ZLT8D16E;3-OCTENOIC ACID, CIS;54ZLT8D16E;C8:1n-5;(Z)-oct-3-enoic acid;cis-oct-3-enoic acid;(3Z)-3-octenoic acid;SCHEMBL5375230;3-OCTENOIC ACID, CIS-;3-OCTENOIC ACID, (Z)-;CHEBI:180314;IWPOSDLLFZKGOW-WAYWQWQTSA-N;FEMA NO. 4362, Z-;LMFA01030019;AKOS006222555;Q27261250

Chemical Property of cis-beta-Octenoic acid

Chemical Property:

• PSA: 37.30000
• LogP: 2.20750
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC=CCC(=O)O
• Isomeric SMILES: CCCC/C=C\CC(=O)O

Technology Process of cis-beta-Octenoic acid

There total 6 articles about cis-beta-Octenoic 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:

1-hepten-3-ol (4938-52-7) + carbon monoxide (201230-82-2) → cis-3-octenoic acid (1577-19-1,5163-67-7,5169-51-7) + (E)-oct-3-enoic acid (5163-67-7)

Guidance literature:

With dmap; palladium diacetate; acetic anhydride; triethylamine; triphenylphosphine; at 60 ℃; for 24h; under 7500.75 Torr; Overall yield = 26 percent; Overall yield = 2.4 g; Autoclave; Inert atmosphere;

Reference yield:

cis-3-octen-1-ol (18185-81-4,20125-84-2,20125-85-3) → cis-3-octenoic acid (1577-19-1,5163-67-7,5169-51-7)

Guidance literature:

With sodium periodate; potassium dichromate; nitric acid; In water; acetonitrile; at 0 - 10 ℃;

DOI:10.1002/anie.201107317

Reference yield:

(Z)-deca-1,5-dien-3-ol (78693-34-2) → cis-3-octenoic acid (1577-19-1,5163-67-7,5169-51-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; water; In dimethyl sulfoxide; at 20 ℃; pH=4.3;

DOI:10.1021/acs.jafc.6b04780

upstream raw materials:

oct-3-ynoic acid

hexenylmagnesium bromide

oct-3-yn-1-ol

cis-3-octen-1-ol

Refernces

• 1、 Schelwies, Mathias,Paciello, Rocco,Pelzer, Ralf,Siegel, Wolfgang,Breuer, Michael. "Palladium-Catalyzed Low Pressure Carbonylation of Allylic Alcohols by Catalytic Anhydride Activation". supporting information. p. 9263 - 9266. Retrieved 2021/05/27.
• 2、 Lorber, Katja,Zeh, Gina,Regler, Johanna,Buettner, Andrea. "Structure-Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids". . p. 2334 - 2343. Retrieved 2018/03/21.