(1R,3S,5s)-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid

• ChemBase ID: 150626
• Molecular Formular: C12H18O6
• Molecular Mass: 258.26772
• Monoisotopic Mass: 258.1103383
• SMILES: C[C@]1(C[C@@](C[C@@](C1)(C(=O)O)C)(C(=O)O)C)C(=O)O
• Canonical SMILES: OC(=O)[C@]1(C)C[C@@](C)(C[C@](C1)(C)C(=O)O)C(=O)O
• InChI: InChI=1S/C12H18O6/c1-10(7(13)14)4-11(2,8(15)16)6-12(3,5-10)9(17)18/h4-6H2,1-3H3,(H,13,14)(H,15,16)(H,17,18)/t10-,11+,12-
• InChIKey: AZWHPGZNOIYGFB-ZSBIGDGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5s)-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid
• IUPAC Traditional name: (1R,3S,5s)-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid
• Synonyms: Kemp’s triacid; cis,cis-1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylic acid; Kemp 三元酸; 顺,顺-1,3,5-三甲基环己烷-1,3,5-三羧酸

Database IDs

• CAS Number: 79410-20-1
• MDL Number: MFCD01545994
• Beilstein Number: 3557263
• PubChem SID: 24889657; 24861047; 162244787
• PubChem CID: 688137

CALCULATED PROPERTIES

• Acid pKa: 3.620689
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.9841865
• LogD (pH = 7.4): -7.045952
• Log P: 2.0036883
• Molar Refractivity: 59.8287 cm^3
• Polarizability: 23.841808 Å^3
• Polar Surface Area: 111.9 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 241-243 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (GC); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C12H18O6
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 342289

Packaging
1 g in glass bottle
Application
Versatile molecule for molecular recognition studies.1,2 Also used to prepare a chiral auxiliary for asymmetric radical addition, allylation, and annulation reactions.2,3

Sigma Aldrich - 92408

Other Notes
Properties1; Building block for the construction of synthetic molecular clefts, interesting as synthetic receptors2,3,4