Lobaric acid

Base Information

• Chemical Name: Lobaric acid
• CAS No.: 522-53-2
• Molecular Formula: C25H28 O8
• Molecular Weight: 456.493
• DSSTox Substance ID: DTXSID30200238
• Nikkaji Number: J11.718H
• Wikidata: Q27165242
• Pharos Ligand ID: GVP8QRMW2MSU
• Metabolomics Workbench ID: 142525
• ChEMBL ID: CHEMBL551842
• Mol file: 522-53-2.mol

Synonyms:lobaric acid;lobaric acid, monopotassium salt

Chemical Property of Lobaric acid

Chemical Property:

• Vapor Pressure: 9.53E-19mmHg at 25°C
• Melting Point: 196～197℃
• Boiling Point: 667.9°Cat760mmHg
• PKA: 2.60±0.20(Predicted)
• Flash Point: 225.7°C
• PSA: 119.36000
• Density: 1.265g/cm³
• LogP: 5.52950
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 456.17841785
• Heavy Atom Count: 33
• Complexity: 694

Purity/Quality:

99%, ^*data from raw suppliers

Lobaric Acid ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=C(C(=CC2=C1OC3=CC(=CC(=C3C(=O)O2)C(=O)CCCC)OC)O)C(=O)O
• Uses: antibacterial

Technology Process of Lobaric acid

There total 19 articles about Lobaric 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: 90.0%

C32H34O8 → lobaric acid (522-53-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 12h; under 760.051 Torr;

DOI:10.1021/acs.jnatprod.8b00227

Reference yield:

5-methoxyisobenzofuran-1,3-dione (28281-76-7) → lobaric acid (522-53-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper(l) chloride / tetrahydrofuran / -20 - 20 °C / Inert atmosphere

2.1: [bis(acetoxy)iodo]benzene; iodine; palladium diacetate / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere

3.1: potassium phosphate; copper(l) iodide / dimethyl sulfoxide / 12 h / 110 °C / Inert atmosphere

4.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 760.05 Torr

5.1: caesium carbonate / methanol / 0.17 h / 20 °C / Inert atmosphere

5.2: 18 h / 20 °C / Inert atmosphere

6.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12.5 h / 20 °C / Inert atmosphere

7.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 760.05 Torr

With dmap; potassium phosphate; copper(l) iodide; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; iodine; palladium diacetate; caesium carbonate; dicyclohexyl-carbodiimide; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.1: |Ullmann Condensation;

DOI:10.1021/acs.jnatprod.8b00227

Reference yield:

3-butyl-3-hydroxy-5-methoxyisobenzofuran-1-(3H)-one → lobaric acid (522-53-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: [bis(acetoxy)iodo]benzene; iodine; palladium diacetate / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere

2.1: potassium phosphate; copper(l) iodide / dimethyl sulfoxide / 12 h / 110 °C / Inert atmosphere

3.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 760.05 Torr

4.1: caesium carbonate / methanol / 0.17 h / 20 °C / Inert atmosphere

4.2: 18 h / 20 °C / Inert atmosphere

5.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12.5 h / 20 °C / Inert atmosphere

6.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 760.05 Torr

With dmap; potassium phosphate; copper(l) iodide; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; iodine; palladium diacetate; caesium carbonate; dicyclohexyl-carbodiimide; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: |Ullmann Condensation;

DOI:10.1021/acs.jnatprod.8b00227

upstream raw materials:

5-methoxyisobenzofuran-1,3-dione

4-hydroxysalicylic acid

benzyl 2,4-bis(benzyloxy)benzoate

benzyl 4,6-bis(benzyloxy)-3-formyl-2-pentylbenzoate

Downstream raw materials:

lobarin

C₂₅H₃₂O₆

2-(2,4-dihydroxy-6-pentyl-phenoxy)-4-methoxy-6-valeryl-benzoic acid

3-((Ξ)-butylidene)-7-hydroxy-5-methoxy-phthalide

Refernces

• 1、 Kim, Tai Kyoung,Kim, Joung Eun,Youn, Ui Joung,Han, Se Jong,Kim, Il-Chan,Cho, Cheon-Gyu,Yim, Joung Han. "Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum". . p. 1460 - 1467. Retrieved 2018/06/29.