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Merck
CN

M90003

trans,trans-Muconic acid

95%

Synonym(s):

trans,trans-1,3-Butadiene-1,4-dicarboxylic acid, trans,trans-2,4-Hexadienedioic acid

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About This Item

Linear Formula:
HO2CCH=CHCH=CHCO2H
CAS Number:
3588-17-8
Molecular Weight:
142.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24897302
EC Number:
222-724-8
Beilstein/REAXYS Number:
1722248
MDL number:
MFCD00002702

Key Documents

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Product Name

trans,trans-Muconic acid, 95%

InChI

1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+

InChI key

TXXHDPDFNKHHGW-ZPUQHVIOSA-N

SMILES string

OC(=O)\C=C\C=C\C(O)=O

assay

95%

form

powder

bp

320 °C (lit.)

mp

290 °C (dec.) (lit.)

Quality Level

100

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Application

trans,trans-Muconic acid can be used as a:
  • Reactant to produce aromatic monomers via Diels-Aldercycloaddition.
  • Biomarker for benzene exposure.

General description

trans,trans-Muconic acid is a polyunsaturated dicarboxylic acid characterized by its conjugated double bonds and reactive dicarboxylic groups. It serves primarily as a key precursor to monomers in the synthesis of polyamides and polyesters.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8059
MKCZ6172
MKCT6100
MKCQ2490
MKCP5988

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Francesco Marchetti et al.
Environmental health perspectives, 120(2), 229-234 (2011-11-17)
Benzene is an industrial chemical that causes blood disorders, including acute myeloid leukemia. We previously reported that occupational exposures near the U.S. Occupational Safety and Health Administration permissible exposure limit (8 hr) of 1 ppm was associated with sperm aneuploidy.
Nancy B Hopf et al.
International archives of occupational and environmental health, 85(3), 261-271 (2011-06-15)
Characterize ethylbenzene and xylene air concentrations, and explore the biological exposure markers (urinary t,t-muconic acid (t,t-MA) and unmetabolized toluene) among petroleum workers offshore. Offshore workers have increased health risks due to simultaneous exposures to several hydrocarbons present in crude oil.
A Bartczak et al.
Journal of toxicology and environmental health, 42(3), 245-258 (1994-07-01)
Muconic acid (MA) is a urinary metabolite of benzene and has been used as a biomarker of exposure to benzene in humans exposed to levels as low as 1 ppm. We have modified a high-pressure liquid chromatography (HPLC) based assay
Sirirat Chanvaivit et al.
Mutation research, 626(1-2), 79-87 (2006-11-11)
Exposure to benzene can cause DNA damage and the subsequent development of cancer. In this study, study subjects were 31 laboratory workers at a petrochemical factory and 31 gasoline service attendants. Control subjects were 34 workers from a mail sorting
Stephen S Hecht
Carcinogenesis, 23(6), 907-922 (2002-06-26)
Measurement of human urinary carcinogen metabolites is a practical approach for obtaining important information about tobacco and cancer. This review presents currently available methods and evaluates their utility. Carcinogens and their metabolites and related compounds that have been quantified in
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