| 词条 | Muconic acid | |||||||||
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 437115148 | Reference =[1][2] | Name =trans,trans-Muconic acid | ImageFile1 = muconic acid EE.png | ImageSize1 = | IUPACName = (2E,4E)-Hexa-2,4-dienedioic acid | OtherNames = (E,E)-Muconic acid |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 3588-17-8 | PubChem = 5356793 | SMILES = OC(\\C=C/C=C\\C(O)=O)=O | EINECS = 222-724-8 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4512358 | InChI = 1/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+ | InChIKey = TXXHDPDFNKHHGW-ZPUQHVIOBF | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = TXXHDPDFNKHHGW-ZPUQHVIOSA-N | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 27036 |Section2={{Chembox Properties | C=6 | H=6 | O=4 | Appearance = Crystalline prisms | Density = 1.366 g/mL | MeltingPtC = 194 to 195 | MeltingPt_notes = (cis,cis-form, prisms from ethanol), 301 °C (trans,trans-form, prisms from water), 190–191 °C (cis,trans-form, needles from hot water)[3] | BoilingPtC = 345 | Solubility = 1 g/L |Section3={{Chembox Hazards | MainHazards = Irritant | FlashPt = | AutoignitionPt = }} Muconic acid is a dicarboxylic acid. There are three isomeric forms designated trans,trans-muconic acid, cis,trans-muconic acid, and cis,cis-muconic acid which differ by the geometry around the double bonds.
cis,cis-Muconic acid is produced by some bacteria by the enzymatic degradation of various aromatic 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 including nylon-6,6, polyurethane, and polyethylene terephthalate (PET).[7] See also
Notes1. ^Merck Index, 11th Edition, 6210 2. ^trans,trans-Muconic acid at Sigma-Aldrich 3. ^Merck Index, 12th Edition (1996), 6381, p.1079 4. ^{{cite journal |vauthors=Wiwanitkit V, Soogarun S, Suwansaksri J |title=A correlative study on red blood cell parameters and urine trans, trans-muconic acid in subjects with occupational benzene exposure |journal=Toxicologic pathology |volume=35 |issue=2 |pages=268–9 |year=2007 |pmid=17366320 |doi=10.1080/01926230601156278}} 5. ^{{cite journal |vauthors=Weaver VM, Davoli CT, Heller PJ, etal |title=Benzene exposure, assessed by urinary trans,trans-muconic acid, in urban children with elevated blood lead levels |journal=Environ. Health Perspect. |volume=104 |issue=3 |pages=318–23 |year=1996 |pmid=8919771 |doi=10.2307/3432891 |pmc=1469300 |jstor=3432891 |publisher=Brogan &}} 6. ^{{cite journal|journal=Organic Syntheses|volume=26|page=57|year=1946|authors=P. C. Guha, D. K. Sankaran|doi=10.15227/orgsyn.026.0057}} 7. ^{{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}} 1 : Dicarboxylic acids |
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