ISODEHYDROACETIC ACID

Base Information

• Chemical Name: ISODEHYDROACETIC ACID
• CAS No.: 480-65-9
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 29329900
• European Community (EC) Number: 207-554-4
• NSC Number: 408066,34551
• UNII: Y755M7L6DC
• DSSTox Substance ID: DTXSID80197386
• Nikkaji Number: J13.182B
• Wikidata: Q83070266
• ChEMBL ID: CHEMBL1892918
• Mol file: 480-65-9.mol

Synonyms:Coumalicacid, 4,6-dimethyl- (6CI);Glutaconic acid, 4-(1-hydroxyethylidene)-3-methyl-, d-lactone (7CI);2-Pentenedioicacid, 4-(1-hydroxyethylidene)-3-methyl-, d-lactone;4,6-Dimethylcoumalic acid;Acetic acid,isodehydro-;Isodehydracetic acid;Isodehydroacetic acid;NSC 34551;NSC 408066;

Chemical Property of ISODEHYDROACETIC ACID

Chemical Property:

• Vapor Pressure: 0.000215mmHg at 25°C
• Melting Point: 154-156 °C
• Refractive Index: 1.4530 (estimate)
• Boiling Point: 303.4 °C at 760 mmHg
• Flash Point: 125.8 °C
• PSA: 67.51000
• Density: 1.326 g/cm³
• LogP: 0.95480
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 309

Purity/Quality:

NLT 98% ^*data from raw suppliers

4,6-DIMETHYL-2-OXO-2H-PYRAN-5-CARBOXYLIC ACID ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC(=C1C(=O)O)C

Technology Process of ISODEHYDROACETIC ACID

There total 8 articles about ISODEHYDROACETIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (41264-06-6) → isodehydracetic acid (480-65-9)

Guidance literature:

With sulfuric acid; at 80 ℃; for 120h;

DOI:10.1271/bbb.64.530

Reference yield: 8.0%

ethyl isodehydroacetate (3385-34-0) → isodehydracetic acid (480-65-9) + 2,6-dimethyl-terephthalic acid-1-ethyl ester (116934-84-0)

Guidance literature:

With dipotassium hydrogenphosphate; sodium dihydrogenphosphate; In ethanol; water; for 480h; fermentation process;

Reference yield:

acetoacetic acid methyl ester (105-45-3) → isodehydracetic acid (480-65-9) + methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (41264-06-6)

Guidance literature:

With sulfuric acid;

upstream raw materials:

ethyl acetoacetate

acetoacetic acid methyl ester

ethyl isodehydroacetate

sulfuric acid

Downstream raw materials:

methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

2,4-Dimethyl-6-oxo-1-ureido-1,6-dihydro-pyridine-3-carboxylic acid

1-(4-chlorophenylamino)-5-carboxy-4,6-dimethyl-2(1H)-pyridone

1-(4-nitrophenylamino)-5-carboxy-4,6-dimethyl-2(1H)-pyridone

Refernces

• 1、 Watanabe, Kenji,Mie, Takashi,Ichihara, Akitami,Oikawa, Hideaki,Honma, Mamoru. "Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates". . p. 530 - 538. Retrieved 2007/10/03.
• 2、 Sakurai, Ikuo,Miyajima, Hisae,Akiyama, Katsuyoshi,Shimizu, Sakae,Yamamoto, Yuzuru. "Studies on Metabolites of Macrophoma commelinae. IV. Substrate Specificity in the Biotransformation of 2-Pyrones to Substituted Benzoic Acids". . p. 2003 - 2011. Retrieved 2007/10/02.