Terreic acid

Base Information

• Chemical Name: Terreic acid
• CAS No.: 121-40-4
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.122
• European Community (EC) Number: 635-585-7
• NSC Number: 294734
• UNII: XM2Y0DRJ7D
• DSSTox Substance ID: DTXSID40879070
• Nikkaji Number: J5.338D
• Wikidata: Q27293905
• Metabolomics Workbench ID: 118527
• ChEMBL ID: CHEMBL1455300
• Mol file: 121-40-4.mol

Synonyms:terreic acid;terreic acid, (+-)-isomer;terreic acid, (1S)-isomer;versilin

Chemical Property of Terreic acid

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Vapor Pressure: 9.63E-06mmHg at 25°C
• Melting Point: 127-127.5°
• Refractive Index: 1.618
• Boiling Point: 333.6 °C at 760 mmHg
• PKA: 4.5(at 25℃)
• Flash Point: 147.4 °C
• PSA: 66.90000
• Density: 1.613 g/cm³
• LogP: -0.26240
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: soluble10mg/mL
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 154.02660867
• Heavy Atom Count: 11
• Complexity: 289

Purity/Quality:

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

Terreic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=O)C2C(C1=O)O2)O
• Isomeric SMILES: CC1=C(C(=O)[C@H]2[C@@H](C1=O)O2)O
• Uses: Terreic Acid is an inhibitor of the catalytic activity of BTK. It is used in the method for treating SWI/SNF complex-deficient cancers comprising glutathione (GSH) metabolic pathway inhibitor.

Technology Process of Terreic acid

There total 5 articles about Terreic 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: 84.0%

2-tert-butoxy-5,6-epoxy-3-methylcyclohex-2-ene-1,4-dione (124175-65-1) → (+/-)-terreic acid (15255-24-0,121-40-4)

Guidance literature:

With trifluoroacetic acid; at 0 ℃;

DOI:10.1021/jo00291a015

Reference yield:

2-tert-butoxy-3-methylcyclohexa-2,5-diene-1,4-dione (124175-64-0) → (+/-)-terreic acid (15255-24-0,121-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / t-BuOOH, triton B / 2,2,4-trimethyl-pentane; ethanol; dioxane; methanol / 0.17 h / Ambient temperature

2: 84 percent / TFA / 0 °C

With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; trifluoroacetic acid; In 1,4-dioxane; methanol; 2,2,4-trimethylpentane; ethanol;

DOI:10.1021/jo00291a015

Reference yield:

3-tert-butoxy-2-methyl-5-(trimethylsilyl)cyclohexa-2,5-diene-1,4-dione (124175-84-4) → (+/-)-terreic acid (15255-24-0,121-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / t-BuOOH, triton B / 2,2,4-trimethyl-pentane; ethanol; dioxane; methanol / 1 h / Ambient temperature

2: 84 percent / TFA / 0 °C

With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; trifluoroacetic acid; In 1,4-dioxane; methanol; 2,2,4-trimethylpentane; ethanol;

DOI:10.1021/jo00291a015

upstream raw materials:

2-tert-butoxy-5,6-epoxy-3-methylcyclohex-2-ene-1,4-dione

2-tert-butoxy-3-methylcyclohexa-2,5-diene-1,4-dione

3-tert-butoxy-2-methyl-5-(trimethylsilyl)cyclohexa-2,5-diene-1,4-dione

2-tert-butoxy-3-methyl-5-(trimethylsilyl)cyclohexa-2,5-diene-1,4-dione

Refernces