Comanic Acid

Base Information

• Chemical Name: Comanic Acid
• CAS No.: 499-05-8
• Molecular Formula: C6H4O4
• Molecular Weight: 140.095
• Hs Code.: 2932999099
• European Community (EC) Number: 679-617-8
• UNII: FEF84NM2E9
• DSSTox Substance ID: DTXSID00486729
• Nikkaji Number: J6.115H
• Wikidata: Q82328109
• Mol file: 499-05-8.mol

Synonyms:Comanic Acid;499-05-8;4-Oxo-4H-pyran-2-carboxylic Acid;4-OXOPYRAN-2-CARBOXYLIC ACID;4H-Pyran-2-carboxylic acid, 4-oxo-;MFCD00059958;COMANICACID;FEF84NM2E9;SCHEMBL546936;gamma-Pyrone-2-carboxylic Acid;DTXSID00486729;UFMDRPPBUAPWBK-UHFFFAOYSA-N;AMY19765;ZB0605;AKOS006227995;AS-40793;BP-10232;SY026770;CS-0100194;FT-0703985;4-Oxo-4H-pyran-2-carboxylic acid, AldrichCPR;A847468;J-650350

Chemical Property of Comanic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 253-254 °C
• Boiling Point: 354.54°C at 760 mmHg
• PKA: 1.79±0.20(Predicted)
• Flash Point: 160.049°C
• PSA: 67.51000
• Density: 1.542g/cm³
• LogP: 0.33800
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 140.01095860
• Heavy Atom Count: 10
• Complexity: 236

Purity/Quality:

98%,99%, ^*data from raw suppliers

Comanic Acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=COC(=CC1=O)C(=O)O
• Uses: Comanic Acid has a curative effect in mice infected with skin leishmaniosis and trypanosomiasis.

Technology Process of Comanic Acid

There total 16 articles about Comanic 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: 94.0%

1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid (62133-77-1,67919-37-3,83023-73-8,85165-61-3,95722-13-7,98301-58-7,103730-05-8,104195-04-2) → comanic acid (499-05-8)

Guidance literature:

With triethylamine; In acetic anhydride; at 100 ℃; for 5h;

DOI:10.1016/S0040-4039(00)85407-6

Reference yield: 76.3%

(2S,3S,4S,5R,6R)-3,4,5,6-tetraacetoxytetrahydro-2H-pyran-2-carboxylic acid (83023-73-8) → comanic acid (499-05-8) + 1,2,3-tri-O-acetyl-4-deoxy-β-L-threo-4-hexenopyranuronic acid (95722-14-8)

Guidance literature:

With triethylamine; In acetic anhydride; at 100 ℃; for 16h;

DOI:10.1016/S0040-4039(00)85407-6

Reference yield: 73.4%

1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid (62133-77-1,67919-37-3,83023-73-8,85165-61-3,95722-13-7,98301-58-7,103730-05-8,104195-04-2) → comanic acid (499-05-8) + (2S,3R,4S)-2,3,4-triacetoxy-3,4-dihydro-2H-pyran-6-carboxylic acid (110454-51-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetic anhydride; for 16h; Ambient temperature;

DOI:10.1016/S0040-4039(00)85407-6

upstream raw materials:

ethyl 4-oxo-4H-2-pyran-carboxylate

chelidonic acid

D-glucuronic acid

acetic anhydride

Downstream raw materials:

methyl 4-oxotetrahydro-2H-pyran-2-carboxylate

Refernces

• 1、 Tajima, Kiyohiko. "ANOMER-SPECIFICITY IN THE DEGRADATION REACTION OF D-GLUCOPYRANURONIC ACID TETRAACETATE LEADING TO COMANIC ACID IN THE ACETIC ANHYDRIDE-BASE SYSTEM". . p. 6095 - 6098. Retrieved 2007/10/02.