cis,cis-muconic acid

Names

[ Name ]:
cis,cis-muconic acid

[Synonym ]:
(2Z,4Z)-hexa-2,4-dienedioic acid
muconic acid
MUCONIC ACID, (Z,Z)-
MFCD00085266
2,4-Hexadienedioic acid, (Z,Z)-
(Z,Z)-hexa-2,4-dienedioic acid
(Z,Z)-Muconic acid
cis,cis-Muconic acid
(Z,Z)-butadiene-1,4-dicarboxylic acid
cis,cis-2,4-Hexadienedioic Acid
2,4-Hexadienedioic acid, (2Z,4Z)-
(Z,Z)-2,4-hexadienedioic acid
(2Z,4Z)-2,4-Hexadienedioic acid

Biological Activity

[Description]:

cis,cis-Muconic acid, a metabolic intermediate of Klebsiella pneumonia, can be converted to adipic acid and terephthalic acid, which are important monomers of synthetic polymers. cis,cis-Muconic acid is also a biochemical material that can be used for the production of various plastics and polymers and is particularly gaining attention as an adipic acid precursor for the synthesis of nylon-6,6[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Jung HM, et al. Metabolic engineering of Klebsiella pneumoniae for the production of cis,cis-muconic acid. Appl Microbiol Biotechnol. 2015;99(12):5217-5225.

[2]. Shin WS, et al. Characterization of a non-phosphotransferase system for cis,cis-muconic acid production in Corynebacterium glutamicum. Biochem Biophys Res Commun. 2018;499(2):279-284.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
345.4±15.0 °C at 760 mmHg

[ Melting Point ]:
194-195ºC(lit.)

[ Molecular Formula ]:
C₆H₆O₄

[ Molecular Weight ]:
142.109

[ Flash Point ]:
176.9±16.9 °C

[ Exact Mass ]:
142.026611

[ PSA ]:
74.60000

[ LogP ]:
-0.21

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.549

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2917190090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2917190090

[ Summary ]:
2917190090 acyclic polycarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

Extending shikimate pathway for the production of muconic acid and its precursor salicylic acid in Escherichia coli.

Metab. Eng. 23 , 62-9, (2014)

cis,cis-Muconic acid (MA) and salicylic acid (SA) are naturally-occurring organic acids having great commercial value. MA is a potential platform chemical for the manufacture of several widely-used co...

Small-angle X-ray scattering and in silico modeling approaches for the accurate functional annotation of an LysR-type transcriptional regulator.

Biochim. Biophys. Acta 1834(3) , 697-707, (2013)

Xylella fastidiosa is a xylem-limited, Gram-negative phytopathogen responsible for economically relevant crop diseases. Its genome was thus sequenced in an effort to characterize and understand its me...

Tandem anion and cation exchange solid phase extraction for the enrichment of micropollutants and their transformation products from ozonation in a wastewater treatment plant.

Anal. Bioanal. Chem 408 , 4219-32, (2016)

The presence of organic micropollutants and their transformation products (TPs) from biotic and abiotic processes in aquatic environments is receiving intense public and scientific attention. Yet a su...