trans,trans-Muconic acid

Base Information

• Chemical Name: trans,trans-Muconic acid
• CAS No.: 1119-72-8
• Molecular Formula: C6H6O4
• Molecular Weight: 142.111
• Hs Code.: 29171990
• European Community (EC) Number: 222-724-8,208-017-7
• NSC Number: 227902,66486,16627
• UNII: 3KD92ZL2KH
• DSSTox Substance ID: DTXSID9052848
• Nikkaji Number: J73.682A,J208.691C
• Wikipedia: Muconic_acid
• Wikidata: Q2252158
• NCI Thesaurus Code: C173419
• Metabolomics Workbench ID: 2034
• ChEMBL ID: CHEMBL1922185
• Mol file: 1119-72-8.mol

Synonyms:cis,cis-muconate;muconic acid;muconic acid, (E,E)-isomer;trans,trans-muconic acid;trans-beta-hydromuconic acid

Chemical Property of trans,trans-Muconic acid

Chemical Property:

• Appearance/Colour: yellow-beige crystalline powder
• Vapor Pressure: 1.1E-05mmHg at 25°C
• Melting Point: 194-195 °C(lit.)
• Refractive Index: 1.4434 (estimate)
• Boiling Point: 345.4 °C at 760 mmHg
• PKA: 3.57±0.25(Predicted)
• Flash Point: 176.9 °C
• PSA: 74.60000
• Density: 1.365 g/cm³
• LogP: 0.26800
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• 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:

98%,99%, ^*data from raw suppliers

cis,cis-Muconic acid ≥97.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• 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 trans,trans-Muconic acid

There total 43 articles about trans,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: 88.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → cis,cis-Muconic acid (1119-72-8)

Guidance literature:

With methyltrifluoromethyldioxirane; In acetone; at -20 ℃; for 1h;

DOI:10.1016/0040-4039(91)80054-A

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:

phenol (108-95-2,27073-41-2) → o-Phenoxyphenol (2417-10-9) + 2,2'-dihydroxybiphenyl (1806-29-7) + cis,cis-Muconic acid (1119-72-8) + 2,4'-dihydroxybiphenyl (611-62-1) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + hydroquinone (123-31-9,8027-02-9)

Guidance literature:

With sodium hydroxide; ozone; at 0 - 20 ℃; Kinetics; Mechanism; Product distribution; dependence from NaOH concn.;

DOI:10.1007/BF00965412

upstream raw materials:

Perbenzoic acid

cis,cis-2,4-hexadienedial

chloroform

cis,cis-dimethyl muconate

Downstream raw materials:

hexa-2c,4c-dienedioic acid dibenzhydryl ester

Adipic acid

(2E,4E)-2,4-hexadienedioic acid

4-Hydroxy-2-hexenedioic Acid γ-lactone

Refernces

• 1、 Jiang, Yun,Yang, Xianglong,Liu, Bin,Zhao, Huabing,Cheng, Qiuxiang,Cai, Baoli. "Catechol 2,3-dioxygenase from Pseudomonas sp. strain ND6: Gene sequence and enzyme characterization". . p. 1798 - 1800. Retrieved 2004.
• 2、 Konstantinova, M. L.,Razumovskii, S. D.,Zaikov, G. E.. "KINETICS AND MECHANISM OF THE REACTION OF OZONE WITH PHENOL IN ALKALINE MEDIA". . p. 266 - 270. Retrieved 1991.
• 3、 McKague, A. Bruce. "Synthesis of muconic acids peracetic acid oxidation of catechols". . p. 1463 - 1475. Retrieved 1999.
• 4、 Roig, Benoit,Gonzalez,Thomas. "Monitoring of phenol photodegradation by ultraviolet spectroscopy". . p. 303 - 307. Retrieved 2003.
• 5、 Kaneko, Aya,Ishii, Yoshitaka,Kirimura, Kohtaro. "High-yield production of cis,cis-muconic acid from catechol in aqueous solution by biocatalyst". . p. 381 - 383. Retrieved 2011.
• 6、 Caglio, Raffaella,Pessione, Enrica,Valetti, Francesca,Giunta, Carlo,Ghibaudi, Elena. "An EPR, thermostability and pH-dependence study of wild-type and mutant forms of catechol 1,2-dioxygenase from Acinetobacter radioresistens S13". . p. 75 - 84. Retrieved 2013.
• 7、 Altamura,Fusco,D'Accolti,Mello,Prencipe,Curci. "Oxidation of catechol and of 2,6-di-tert butylphenol by dioxiranes". . p. 5445 - 5448. Retrieved 1991.
• 8、 Jaroszewski, Jerzy W.,Grossen, Peter,Mohr, Peter,Tamm, Christoph. "Ionization Shifts in 1H-NMR Spectra of α,β-Unsaturated Carboxylic Acids". . p. 718 - 725. Retrieved 1986.
• 9、 Coupé, Florentin,Petitjean, Laurène,Anastas, Paul T.,Caijo, Frédéric,Escande, Vincent,Darcel, Christophe. "Sustainable oxidative cleavage of catechols for the synthesis of muconic acid and muconolactones including lignin upgrading". supporting information. p. 6204 - 6211. Retrieved 2020/10/18.