Xylaric acid

Base Information

• Chemical Name: Xylaric acid
• CAS No.: 10158-64-2
• Molecular Formula: C₅H₈O₇
• Molecular Weight: 180.114
• DSSTox Substance ID: DTXSID30144027
• Nikkaji Number: J668.235I
• Wikidata: Q77564477
• Metabolomics Workbench ID: 103935
• Mol file: 10158-64-2.mol

Synonyms:gamma-pyrone-3-acetic acid;L 741,494;L 741494;L-741,494;L-741494

Chemical Property of Xylaric acid

Chemical Property:

• Vapor Pressure: 2.03E-07mmHg at 25°C
• Boiling Point: 397.2°Cat760mmHg
• Flash Point: 174.3°C
• PSA: 67.51000
• Density: 1.391g/cm³
• LogP: 0.26690
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 154.02660867
• Heavy Atom Count: 11
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=COC=C(C1=O)CC(=O)O

Technology Process of Xylaric acid

There total 65 articles about Xylaric 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: 49.67%

D-xylose (58-86-6) → xylaric acid (488-31-3,608-54-8,608-55-9,6703-05-5,10158-64-2,20869-04-9,33012-62-3) + disodium 2,2,3,3-tetrahydroxybutane-1,4-dioate (866-17-1,51083-10-4)

Guidance literature:

With oxygen; nitric acid; sodium nitrite; In water; at 35 ℃; for 4.5h;

DOI:10.1080/07328303.2012.745550

Reference yield:

5-keto-D-gluconic acid (5287-64-9) + nitric acid (7697-37-2,78989-43-2) → DL-tartaric acid (133-37-9,138508-61-9) + xylaric acid (488-31-3,608-54-8,608-55-9,6703-05-5,10158-64-2,20869-04-9,33012-62-3) + 2,2-bis(hydroxyl)methylpropionic acid (55833-34-6) + Glyoxilic acid (298-12-4)

Guidance literature:

Reference yield:

D-xylose (58-86-6) → D-xylonic acid (488-30-2,526-91-0,526-92-1,608-53-7,642-98-8,4172-43-4,4172-44-5,13171-74-9,13752-83-5,17812-24-7,17828-56-7,20663-19-8,28223-40-7) + xylaric acid (488-31-3,608-54-8,608-55-9,6703-05-5,10158-64-2,20869-04-9,33012-62-3)

Guidance literature:

With platinum on carbon; oxygen; In water; at 80 ℃; under 10501.1 Torr; pH=2.5;

DOI:10.1002/cssc.201800494

upstream raw materials:

Mucin

Reactive blue 19 alcohol

2,3,4,5,6-pentahydroxy-hexanal

D-gluconic acid

Downstream raw materials:

dl-trioxyglutaric acid

cis-cyclohexane-1,2-diamine

1,5-pentanedioic acid

Refernces

• 1、 Hardegger et al.. "". . p. 958,961. Retrieved 1952.
• 2、 Iwadare. "". . . Retrieved 1942.
• 3、 Gao, Chuan-Zhu,Wang, Tian-Shuai,Chen, Jia,Fei, Fan,Zhang, Yan,Yang, Bo. "Efficient chiral resolution of (±)-cyclohexane-1,2-diamine". . p. 490 - 492. Retrieved 2014.
• 4、 Cantrell,C.E. et al.. "-". . p. 3562 - 3567. Retrieved 1977.
• 5、 Ferreira, M.,Figueiredo, J. L.,Fonseca, A. M.,Güney, S.,Ku?niarska-Biernacka, I.,Neves, I. C.,Parpot, P.,Pereira, M. F. R.,Soares, O. S. G. P.. "Electrochemical oxidation of diclofenac on CNT and M/CNT modified electrodes". . p. 12622 - 12633. Retrieved 2021/07/25.
• 6、 Ding, Jie,Jin, Xin,Lai, Linyi,Liu, Mengyuan,Sun, Yu,Wang, Jinyao,Xia, Qi,Yan, Hao,Yang, Chaohe,Zhang, Guangyu,Zhang, Wenxiang. "Bimetallic AuPt/TiO2Catalysts for Direct Oxidation of Glucose and Gluconic Acid to Tartaric Acid in the Presence of Molecular O2". . p. 10932 - 10945. Retrieved 2020/11/23.