1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylate

Base Information

• Chemical Name: 1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylate
• CAS No.: 79410-20-1
• Molecular Formula: C12H18 O6
• Molecular Weight: 258.271
• Hs Code.: 2917209090
• DSSTox Substance ID: DTXSID001000457
• Nikkaji Number: J2.026.365B
• Mol file: 79410-20-1.mol

Synonyms:KEMPSTRIACID;1,3,5-trimethylcyclohexane-1,3,5-tricarboxylate;DTXSID001000457;1,3,5-Trimethylcyclohexane-1alpha,3alpha,5alpha-tricarboxylate

Chemical Property of 1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylate

Chemical Property:

• Appearance/Colour: WHITE POWDER, CRYSTALS, CRYSTALLINE POWDER AND/OR CHUNKS
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 241-243 °C(lit.)
• Boiling Point: 364 °C at 760 mmHg
• Flash Point: 188.1 °C
• PSA: 111.90000
• Density: 1.301 g/cm³
• LogP: 1.44300
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 255.08686319
• Heavy Atom Count: 18
• Complexity: 320

Purity/Quality:

98% ^*data from raw suppliers

cis,cis-1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylic acid 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CC(CC(C1)(C)C(=O)[O-])(C)C(=O)[O-])C(=O)[O-]
• General Description: Kemp's triacid (KTA) is a rigid, threefold-symmetric scaffold widely used in supramolecular chemistry and multivalent ligand design, particularly for constructing peptide-peptoid structures. Its inherent symmetry and stability make it ideal for assembling trivalent maleimides, as demonstrated in the synthesis of trivalent CD4-mimetic miniproteins for HIV-1 inhibition. KTA facilitates the precise spatial arrangement of functional groups, enhancing multivalent interactions critical for targeting the HIV-1 gp120 complex.

Technology Process of 1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylate

There total 5 articles about 1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylate 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: 95.0%

trimethyl-cis,cis-1,3,5-trimethyl-1,3,5-cyclohexane-tricarboxylate (79410-21-2) → Kemp's triacid (79410-20-1)

Guidance literature:

With sodium hydroxide; In methanol; at 65 ℃; for 12h;

DOI:10.1021/ja00242a029

Reference yield:

cis,cis-1,3,5-trimethyl-1-(hydroxymethyl)cyclohexane-3,5-dicarboxylic acid lactone (79410-25-6) → Kemp's triacid (79410-20-1)

Guidance literature:

With sodium hydroxide; periodic acid; ruthenium tetroxide; Yield given. Multistep reaction; 1) H₂O, 90 deg C, 30 min, 2) H₂O, 2.5 h;

DOI:10.1021/jo00338a014

Reference yield:

trimethyl cis,cis-cyclohexane-1,3,5-tricarboxylate (6998-83-0) + dimethyl sulfate (77-78-1) → Kemp's triacid (79410-20-1) + cis,cis-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid (118514-35-5)

Guidance literature:

Multistep reaction. Yields of byproduct given;

DOI:10.1021/ja00185a044

upstream raw materials:

trimethyl-cis,cis-1,3,5-trimethyl-1,3,5-cyclohexane-tricarboxylate

cis,cis-1,3,5-trimethyl-1-(hydroxymethyl)cyclohexane-3,5-dicarboxylic acid lactone

trimethyl cis,cis-cyclohexane-1,3,5-tricarboxylate

dimethyl sulfate

Downstream raw materials:

trimethyl-cis,cis-1,3,5-trimethyl-1,3,5-cyclohexane-tricarboxylate

C₃₃H₃₇N₃O₈S

1,3,5-Trimethyl-cyclohexane-1,3,5-tricarboxylic acid tripropyl ester

Refernces

Synthesis and anti-HIV activity of trivalent CD4-mimetic miniproteins

10.1016/j.bmc.2007.03.064

The research aimed to develop more potent HIV-1 entry inhibitors by synthesizing a series of trivalent CD4-mimetic miniproteins. These miniproteins were designed to target the CD4-binding sites on the trimeric gp120 complex of HIV-1, with the hypothesis that multivalent interactions would enhance their anti-HIV activity. The key chemicals used included CD4M9 miniprotein moieties, which were tethered to a threefold-symmetric scaffold via maleimide-thiol ligation. Kemp's triacid (KTA) is used as a core scaffold for constructing trivalent maleimides. It is chosen because it provides a rigid, threefold-symmetric framework that is ideal for assembling multivalent structures. The KTA scaffold is particularly useful in supramolecular chemistry for building peptide-peptoid structures due to its inherent symmetry and stability. In this study, mono-N-Boc-protected diamines with varying lengths are coupled to KTA using EDCI as a coupling agent, followed by deprotection and reaction with N-methoxycarbonylmaleimide to form the trivalent maleimides. These maleimides are then used to tether CD4M9 miniprotein moieties, creating trivalent CD4-mimetic miniproteins designed to target the CD4-binding sites on the HIV-1 gp120 complex. The use of Kemp's triacid allows for the precise arrangement of the CD4M9 moieties in a trivalent configuration, which is crucial for enhancing the anti-HIV activity through multivalent interactions.