cis,trans-Muconic acid

Base Information

• Chemical Name: cis,trans-Muconic acid
• CAS No.: 1119-73-9
• Molecular Formula: C6H6O4
• Molecular Weight: 142.111
• UNII: 10Z8SOV21M
• DSSTox Substance ID: DTXSID101304080
• Metabolomics Workbench ID: 51412
• Nikkaji Number: J784.052G
• Wikidata: Q27103253
• Mol file: 1119-73-9.mol

Synonyms:cis,trans-muconic acid;(2Z,4E)-hexa-2,4-dienedioic acid;1119-73-9;Muconic acid, (E,Z)-;Muconic acid (2E,4Z)-form [MI];2,4-Hexadienedioic acid, (2E,4Z)-;10Z8SOV21M;(E,Z)-Muconic acid;(2E,4Z)-2,4-hexadienedioic acid;UNII-10Z8SOV21M;cis-muconic acid;cis,trans muconic acid;starbld0020403;cis,trans-Hexadienedioate;cis,trans-MuconsA currencyure;SCHEMBL820982;CHEBI:27671;TXXHDPDFNKHHGW-HSFFGMMNSA-N;DTXSID101304080;AKOS040758777;2,4-HEXADIENEDIOIC ACID, CIS,TRANS;C03647;Q27103253

Chemical Property of cis,trans-Muconic acid

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 142.02660867
• Heavy Atom Count: 10
• Complexity: 168

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of cis,trans-Muconic acid

There total 9 articles about cis,trans-Muconic 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: 63.0%

methanol (67-56-1) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → cis,cis-Muconic acid (1119-72-8) + (2Z,4E)-2,4-hexadienedioic acid (1119-73-9) + (2Z,4Z)-5-methoxycarbonyl-2,4-pentadieonic acid (61186-96-7) + (2Z,4E)-5-methoxycarbonyl-2,4-pentadienoic acid (105136-07-0) + (2Z,4Z)-6-(2-hydroxyphenoxy)-6-oxohexa-2,4-dienoic acid (1447970-90-2) + (2Z,4E)-6-(2-hydroxyphenoxy)-6-oxohexa-2,4-dienoic acid (1447970-89-9)

Guidance literature:

With Iron(III) nitrate nonahydrate; nitrogen; ammonium acetate; tris[(2-pyridylmethyl)amine]; at 50 ℃; for 4h; under 7500.75 Torr; Reagent/catalyst; Pressure; Temperature; Autoclave;

DOI:10.1039/c4cy01562b

Reference yield: 10.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → cis,cis-Muconic acid (1119-72-8) + (2Z,4E)-2,4-hexadienedioic acid (1119-73-9)

Guidance literature:

With peracetic acid; In acetic acid;

DOI:10.1080/00397919908086126

Reference yield:

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → cis,cis-Muconic acid (1119-72-8) + (2Z,4E)-2,4-hexadienedioic acid (1119-73-9) + maleic acid (110-16-7,26099-09-2) + trans,trans-muconic acid (3588-17-8)

Guidance literature:

With dihydrogen peroxide; at 23 ℃; for 1h; pH=6.2; Further byproducts given; UV-irradiation;

DOI:10.1016/0043-1354(95)00060-X

upstream raw materials:

benzene-1,2-diol

salicylaldehyde

2-methoxy-phenol

phenol

Downstream raw materials:

Adipic acid

adipic acid monomethyl ester

dimethyl 1,4-cyclohexane dicarboxylate

cyclohex-1-ene-1,4-dicarboxylic acid

Refernces

• 1、 Jastrzebski, Robin,Van Den Berg, Emily J.,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.. "Sustainable production of dimethyl adipate by non-heme iron(iii) catalysed oxidative cleavage of catechol". . p. 2103 - 2109. Retrieved 2015/04/14.
• 2、 Giurg, Miroslaw,Kowal, Ewa,Muchalski, Hubert,Syper, Ludwik,Mlochowski, Jacek. "Catalytic oxidative domino degradation of alkyl phenols towards 2- and 3-substituted muconolactones". experimental part. p. 251 - 266. Retrieved 2009/04/07.