Toralactone

Base Information

• Chemical Name: Toralactone
• CAS No.: 41743-74-2
• Molecular Formula: C15H12 O5
• Molecular Weight: 272.25
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID20194576
• Nikkaji Number: J516.545H
• Metabolomics Workbench ID: 48240
• ChEMBL ID: CHEMBL4457748
• Mol file: 41743-74-2.mol

Synonyms:toralactone

Chemical Property of Toralactone

Chemical Property:

• Vapor Pressure: 7.63E-10mmHg at 25°C
• Melting Point: 250-252 °C
• Boiling Point: 480.2°Cat760mmHg
• PKA: 4.65±0.20(Predicted)
• Flash Point: 184.8°C
• PSA: 79.90000
• Density: 1.432g/cm³
• LogP: 2.67440
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.06847348
• Heavy Atom Count: 20
• Complexity: 432

Purity/Quality:

99%+, ^*data from raw suppliers

Toralactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=CC3=CC(=CC(=C3C(=C2C(=O)O1)O)O)OC

Technology Process of Toralactone

There total 5 articles about Toralactone 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: 85.0%

10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone (71602-63-6) → Toralactone (41743-74-2)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 7h;

DOI:10.1021/jo034223u

Reference yield:

cassiaside C (119170-52-4) → Toralactone (41743-74-2)

Guidance literature:

With β-glucosidase; In water; at 37 ℃; for 20h;

Reference yield:

2,4-dimethoxy-6-methylbenzoic acid (3686-57-5) → Toralactone (41743-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; cyclohexane / 0.33 h / -78 °C

1.2: 32 percent / tetrahydrofuran; cyclohexane / -78 - 20 °C

2.1: 85 percent / BBr₃ / CH₂Cl₂ / 7 h / 20 °C

With boron tribromide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/jo034223u

upstream raw materials:

cassiaside C

isotoraslactone

10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone

2,4-dimethoxy-6-methylbenzoic acid

Downstream raw materials:

toralactone 9-O-yl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-glucopyranoside

toralactone 9-O-yl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside

toralactone 9-O-yl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside

cassiaside C

Refernces

• 1、 Tang, Liying,Wu, Hongwei,Su, Huijuan,Zhou, Xidan,Zhou, Guohong,Wang, Ting,Kou, Zhenzhen,Wang, Zhuju. "Four new glycosides from the seeds of Cassia obtusifolia". . p. 81 - 84. Retrieved 2015.
• 2、 Kitanaka, Susumu,Takido, Michio. "Studies on the Constituents of the Seeds of Cassia obtusifolia L. The Structures of Two Naphthopyrone Glycosides". . p. 3980 - 3984. Retrieved 2007/10/02.