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3588-17-8

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3588-17-8 Usage

Description

trans,trans-Muconic acid, also known as trans,trans-1,3-Butadiene-1,4-dicarboxylic acid, is a metabolite found in urine that serves as a biological exposure index for workers exposed to benzene.

Uses

Used in Occupational Health Monitoring:
trans,trans-Muconic acid is used as a biomarker for assessing the exposure levels of workers to benzene, a hazardous chemical substance. This helps in monitoring the health risks associated with benzene exposure and ensuring the safety of workers in various industries.

Purification Methods

Crystallise the diacid from H2O. [Beilstein 2 IV 2298.]

Check Digit Verification of cas no

The CAS Registry Mumber 3588-17-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,8 and 8 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3588-17:
(6*3)+(5*5)+(4*8)+(3*8)+(2*1)+(1*7)=108
108 % 10 = 8
So 3588-17-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/p-2/b3-1+,4-2+

3588-17-8 Well-known Company Product Price

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  • Alfa Aesar

  • (L03987)  trans,trans-1,3-Butadiene-1,4-dicarboxylic acid, 98+%   

  • 3588-17-8

  • 1g

  • 169.0CNY

  • Detail
  • Alfa Aesar

  • (L03987)  trans,trans-1,3-Butadiene-1,4-dicarboxylic acid, 98+%   

  • 3588-17-8

  • 5g

  • 747.0CNY

  • Detail

3588-17-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name trans,trans-muconic acid

1.2 Other means of identification

Product number -
Other names MUCONIC ACID

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3588-17-8 SDS

3588-17-8Relevant articles and documents

Molecular design and polymer structure control based on polymer crystal engineering. Topochemical polymerization of 1,3-diene mono- and dicarboxylic acid derivatives bearing a naphthylmethylammonium group as the countercation

Matsumoto, Akikazu,Nagahama, Sadamu,Odani, Toru

, p. 9109 - 9119 (2000)

The topochemical polymerization of the alkylammonium salts of (Z,Z)-, (E,Z)-, and (E,E)-1,3-diene mono- or dicarboxylic acids, i.e., of the muconic and sorbic acid derivatives, is described from the viewpoint of polymer crystal engineering. Not only the (Z,Z)- but also the (E,E)-derivatives polymerize to give a high molecular weight polymer in the crystalline state under UV irradiation when a naphthylmethylammonium moiety is introduced to these monomers as the countercation. NMR spectroscopy confirms the formation of the stereoregular meso- or erythro-diisotactic-trans-2,5-polymer during the polymerization, irrespective of the configuration of the monomers and the structure of the substituents. The single-crystal structure analysis of the naphthylmethylammonium salt of sorbic acid reveals the stacking of the diene moieties in the columns formed in the crystals, favorable for the topochemical polymerization. The photopolymerization reactivity and the stereochemistry of the resulting polymers are determined by the molecular packing in the crystals during the topochemical polymerization of the diene monomers.

Muconic acid production from methane using rationally-engineered methanotrophic biocatalysts

Henard, Calvin A.,Akberdin, Ilya R.,Kalyuzhnaya, Marina G.,Guarnieri, Michael T.

, p. 6731 - 6737 (2019)

Here, we demonstrate bioconversion of methane to muconic acid, a dicarboxylic acid that can be upgraded to an array of platform chemicals, by three gammaproteobacterial methanotrophs. All engineered methanotrophs expressing a heterologous dihydroxyshikimate dehydratase, protocatechuate decarboxylase, and catechol dioxygenase produced muconic acid from methane, with the highest titer (12.4 mg MA per L), yield (2.8 mg MA per g CH4), and specific productivity (1.2 mg MA per g dcw, 48 hr) synthesized by Methylotuvimicrobium buryatense, Methylococcus capsulatus, and Methylotuvimicrobium alcaliphilium, respectively. Methylotuvimicrobium alcaliphilum genome-scale model-guided strain engineering predicted that disruption of the pyruvate dehydrogenase or shikimate dehydrogenase would significantly enhance flux to the heterologous muconic acid pathway in this organism. However, knock-out of these targets caused a growth defect, and coupled with similar muconic acid titers (~1 mg L-1), resulted in minimal flux enhancement to muconic acid in these genetically-modified strains. The shikimate dehydrogenase mutant's ability to grow without aromatic amino acid supplementation revealed that M. alcaliphilum likely encodes an unidentified enzyme or pathway with shikimate biosynthetic capacity, which prevents maximal flux through the synthetic muconic acid pathway. This study expands the suite of products that can be generated from methane using methanotrophic biocatalysts, lays the foundation for green production of muconic acid-derived polymers from methane, and highlights the need for further analysis of methanotroph biosynthetic potential to guide refinement of metabolic models and strain engineering.

Solvent-driven isomerization of: cis, cis -muconic acid for the production of specialty and performance-advantaged cyclic biobased monomers

Carraher, Jack M.,Carter, Prerana,Cochran, Eric W.,Forrester, Michael J.,Pfennig, Toni,Rao, Radhika G.,Shanks, Brent H.,Tessonnier, Jean-Philippe

, p. 6444 - 6454 (2020/11/09)

The quest for green plastics calls for new routes to aromatic monomers using biomass as a feedstock. Suitable feedstock molecules and conversion pathways have already been identified for several commodity aromatics through retrosynthetic analysis. However, this approach suffers from some limitations as it targets a single molecule at a time. A more impactful approach would be to target bioprivileged molecules that are intermediates to an array of commodity and specialty chemicals along with novel compounds. Muconic acid (MA) has recently been identified as a bioprivileged intermediate as it gives access to valuable aliphatic and cyclic diacid monomers including terephthalic acid (TPA), 1,4-cyclohexanedicarboxylic acid (CHDA), and novel monounsaturated 1,4-cyclohexenedicarboxylic acids (CH1DA, CH2DA). However, accessing these cyclic monomers from MA requires to first isomerize biologically-produced cis,cis-MA to Diels-Alder active trans,trans-MA. A major impediment in this isomerization is the irreversible ring closing of MA to produce lactones. Herein, we demonstrate a green solvent-mediated isomerization using dimethyl sulfoxide and water. The mechanistic understanding achieved here elucidates the role of low concentrations of water in reducing the acidity of the system, thereby preventing the formation of lactones and improving the selectivity to trans,trans-MA from less than 5% to over 85%. Finally, a Diels-Alder reaction with trans,trans-MA is demonstrated with ethylene. The monounsaturated cyclic diacid obtained through this reaction (CH1DA) can be converted in a single step into TPA and CHDA, or can be directly copolymerized with adipic acid and hexamethylenediamine to tailor the thermal and mechanical properties of conventional Nylon 6,6.

N,N,O-Coordinated tricarbonylrhenium precatalysts for the aerobic deoxydehydration of diols and polyols

Klein Gebbink, Robertus J. M.,Li, Jing,Lutz, Martin

, p. 3782 - 3788 (2020/06/22)

Rhenium complexes are well known catalysts for the deoxydehydration (DODH) of vicinal diols (glycols). In this work, we report on the DODH of diols and biomass-derived polyols using L4Re(CO)3as precatalyst (L4Re(CO)3= tricarbonylrhenium 2,4-di-tert-butyl-6-(((2-(dimethylamino)ethyl)(methyl)amino)methyl)phenolate). The DODH reaction was optimized using 2 mol% of L4Re(CO)3as precatalyst and 3-octanol as both reductant and solvent under aerobic conditions, generating the active high-valent rhenium speciesin situ. Both diol and biomass-based polyol substrates could be applied in this system to form the corresponding olefins with moderate to high yield. Typical features of this aerobic DODH system include a low tendency for the isomerization of aliphatic external olefin products to internal olefins, a high butadiene selectivity in the DODH of erythritol, the preferential formation of 2-vinylfuran from sugar substrates, and an overall low precatalyst loading. Several of these features indicate the formation of an active species that is different from the species formed in DODH by rhenium-trioxo catalysts. Overall, the bench-top stable and synthetically easily accessible, low-valent NNO-rhenium complex L4Re(CO)3represents an interesting alternative to high-valent rhenium catalysts in DODH chemistry.

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