(2Z,4E)-hexa-2,4-dienoic acid

Base Information

• Chemical Name: (2Z,4E)-hexa-2,4-dienoic acid
• CAS No.: 5309-56-8
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• NSC Number: 263484
• Nikkaji Number: J1.363.916G,J9.860D
• Wikidata: Q27117553
• Metabolomics Workbench ID: 55839
• Mol file: 5309-56-8.mol

Synonyms:(2Z,4E)-hexa-2,4-dienoic acid;5309-57-9;(2Z,4E)-2,4-hexadienoic acid;(2Z,4E)-sorbic acid;(2Z,4E)-SA;5309-56-8;z,e-sorbic acid;(Z,E)-Sorbic acid;(2Z)-2,4-Hexadienoic acid;CHEBI:38360;BBL011617;NSC263484;STK802469;AKOS005613170;NSC-263484;VS-02986;Q27117553;F2191-0241

Chemical Property of (2Z,4E)-hexa-2,4-dienoic acid

Chemical Property:

• Boiling Point: 233°Cat760mmHg
• Flash Point: 139.9°C
• Density: 1.024g/cm³
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 123

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2Z,4E)-hexa-2,4-dienoic acid

There total 21 articles about (2Z,4E)-hexa-2,4-dienoic 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: 86.0%

pyran-2-one (504-31-4) + methylmagnesium bromide (75-16-1) → sorbic acid (5309-56-8,91751-55-2)

Guidance literature:

With iron(III)-acetylacetonate; In diethyl ether; at -30 ℃; Inert atmosphere;

DOI:10.1002/asia.201900865

Reference yield: 79.0%

(but-2-enylidene)malonic acid (4423-18-1) → (2Z,4E)-hexa-2,4-dienoic acid (110-44-1,5309-56-8,5309-57-9,22500-92-1,30361-30-9,91751-55-2)

Guidance literature:

With quinoline; at 130 ℃; for 3h;

DOI:10.1021/ja020635t

Reference yield: 54.0%

3-butenoic acid 1-methyl-2-propen-1-yl ester → (2Z,4E)-hexa-2,4-dienoic acid (110-44-1,5309-56-8,5309-57-9,22500-92-1,30361-30-9,91751-55-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydride; In toluene; mineral oil; at 65 ℃; for 4.5h;

DOI:10.1002/anie.202106250

upstream raw materials:

hex-4c-en-2-ynoic acid

pyran-2-one

methylmagnesium bromide

pyridine

Downstream raw materials:

Hexa-2,4-diensaeure-amid

hexa-2c,4t-dienoic acid isobutylamide

(2Z,4E)-Hexa-2,4-dienoic acid [(S)-((2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-hydroxy-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl)-(4-methoxy-benzyloxy)-methyl]-amide

(2Z,4E)-Hexa-2,4-dienoic acid [(S)-((2E,8E,10Z,14E)-(1R,5R,17R)-3,11-dimethyl-19-methylene-7,13-dioxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl)-(4-methoxy-benzyloxy)-methyl]-amide