Muconic acid is a dicarboxylic acid. There are three

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

ic forms designated ''trans,trans''-muconic acid, ''cis,trans''-muconic acid, and ''cis,cis''-muconic acid which differ by the geometry around the

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

s. Its name is derived from

mucic acid Mucic acid, C6H10O8 or HOOC-(CHOH)4-COOH (also known as galactaric or meso-galactaric acid) is an aldaric acid obtained by nitric acid oxidation of galactose or galactose-containing compounds such as lactose, dulcite, quercite, and most varieties ...

. : ''trans,trans''-Muconic acid is a

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

of benzene in humans. The determination of its concentration in urine is therefore used as a

biomarker In biomedical contexts, a biomarker, or biological marker, is a measurable indicator of some biological state or condition. Biomarkers are often measured and evaluated using blood, urine, or soft tissues to examine normal biological processes, ...

of occupational or environmental exposure to benzene. Synthetically, ''trans,trans''-muconic acid can be prepared from

adipic acid Adipic acid or hexanedioic acid is the organic compound with the formula (CH2)4(COOH)2. From an industrial perspective, it is the most important dicarboxylic acid: about 2.5 billion kilograms of this white crystalline powder are produced annually, ...

. ''cis,cis''-Muconic acid is produced by some bacteria by the enzymatic degradation of various

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

chemical compounds. The bioproduction of muconic acid is of interest because of its potential use as a platform chemical for the production of several valuable consumer

bioplastics Bioplastics are plastic materials produced from renewable biomass sources, such as vegetable fats and oils, corn starch, straw, woodchips, sawdust, recycled food waste, etc. Some bioplastics are obtained by processing directly from natural ...

including nylon-6,6,

polyurethane Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethan ...

, and

polyethylene terephthalate Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods ...

.{{cite journal, vauthors=Curran KA, Leavitt JM, Karim AS, Alper HS, title=Metabolic engineering of muconic acid production in Saccharomyces cerevisiae., journal=Metab. Eng., pmid=23164574, doi=10.1016/j.ymben.2012.10.003, volume=15, year=2013, pages=55–66

Notes

Dicarboxylic acids

See also

Notes