CID 5281560

Base Information

• Chemical Name: CID 5281560
• CAS No.: 78824-30-3
• Molecular Formula: C₃₈H₅₀O₆
• Molecular Weight: 602.811
• European Community (EC) Number: 616-656-1
• Metabolomics Workbench ID: 70325
• Wikidata: Q105104463
• Mol file: 78824-30-3.mol

Synonyms:cambogin;camboginol;garcinol

Chemical Property of CID 5281560

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 132 °C
• Refractive Index: 1.563
• Boiling Point: 710.763 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 397.609 °C
• PSA: 111.90000
• Density: 1.114 g/cm³
• LogP: 8.91460
• Storage Temp.: ?20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• XLogP3: 10.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 602.36073931
• Heavy Atom Count: 44
• Complexity: 1300

Purity/Quality:

20%, ^*data from raw suppliers

Garcinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1CC2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)C(C2=O)(C1(C)C)CC=C(C)C)CC(CC=C(C)C)C(=C)C)C
• Isomeric SMILES: CC(=CC[C@@H]1C[C@@]2(C(=O)/C(=C(\C3=CC(=C(C=C3)O)O)/O)/C(=O)[C@@](C2=O)(C1(C)C)CC=C(C)C)C[C@H](CC=C(C)C)C(=C)C)C
• Description: Garcinol (78824-30-3) is a HAT (histone acetyltransferase) inhibitor (p300 IC50=7 μM and PCAF IC50=5 μM) both in vitro and in vivo.1 It potentiates TRAIL-induced apoptosis of cancer cells. In cancer cells garcinol, independent of the cell type, induces both of the TRAIL receptors, death receptor 4 (DR4) and DR5. Garcinol neither induces the receptors of normal cells nor sensitizes them to TRAIL.2
• Uses: Garcinol is an inhibitor of the histone acetyltransferases (HATs) p300 and PCAF (IC50 = 7 and 5 μM, respectively). It also inhibits the HAT GCN5 in Cryptococcus neoformans, inducing temperature sensitivity and impairing growth. A polyisoprenylated benzophenone isolated from Garcinia indica, garcinol promotes neurogenesis and ex vivo expansion of human hematopoietic stem cells. Moreover, it induces apoptosis in several types of cancer cells and has anti-inflammatory actions. Garcinol is a small molecule inhibitor of histone acetyltransferases. Used in cancer therapy. Garcinol, harvested from Garcinia indica.

Technology Process of CID 5281560

There total 4 articles about CID 5281560 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: 40.0%

4-(cyanocarbonyl)-1,2-phenylene diacetate (2214-15-5) + C31H46O3 → garcinol (147782-04-5,78824-30-3)

Guidance literature:

C₃₁H₄₆O₃; With samarium(III) chloride; triethylamine; In toluene; at 0 ℃; for 0.166667h; Inert atmosphere;

4-(cyanocarbonyl)-1,2-phenylene diacetate; In toluene; at 20 ℃; for 2h; Inert atmosphere;

With potassium carbonate; In methanol; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c01139

Reference yield:

C33H54O5 → garcinol (147782-04-5,78824-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethanethiol; trimethylaluminum / dichloromethane; n-heptane / 24 h / 50 °C / Inert atmosphere

2.1: samarium(III) chloride; triethylamine / toluene / 0.17 h / 0 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

2.3: 2 h / Inert atmosphere

With samarium(III) chloride; trimethylaluminum; triethylamine; ethanethiol; In n-heptane; dichloromethane; toluene;

DOI:10.1021/acs.orglett.1c01139

Reference yield:

C23H38O5 → garcinol (147782-04-5,78824-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.5 h / 0 - 50 °C / Inert atmosphere

1.2: 24 h / 40 °C / Inert atmosphere

2.1: ethanethiol; trimethylaluminum / dichloromethane; n-heptane / 24 h / 50 °C / Inert atmosphere

3.1: samarium(III) chloride; triethylamine / toluene / 0.17 h / 0 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

3.3: 2 h / Inert atmosphere

With samarium(III) chloride; trimethylaluminum; sodium hydride; triethylamine; ethanethiol; In n-heptane; dichloromethane; dimethyl sulfoxide; toluene; mineral oil;

DOI:10.1021/acs.orglett.1c01139

upstream raw materials:

4-(cyanocarbonyl)-1,2-phenylene diacetate

Downstream raw materials:

cambogin

GDPPH-1

Refernces