7077-05-6

Basic information

• Product Name: trans-4-Isopropylcyclohexane carboxylic acid
• Synonyms: HEXAHYDROCUMIC ACID;TRANS-4-ISOPROPYLCYCLOHEXANECARBOXYLIC ACID;TRANS-4-(1-METHYLETHYL)CYCLOHEXANE CARBOXYLIC ACID;trans-4-Isopropyl Cyclohexyl Carboxylic Acid;(1α,4β)-4-(1-Methylethyl)cyclohexanecarboxylic acid;trans-p-Menthan-7-oic acid;trans-4-Isopropylcyclohexanecarboxylic;4-propan-2-ylcyclohexane-1-carboxylic acid
• CAS NO: 7077-05-6
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 230-375-8
• Product Categories: chiral;NATEGLINIDE;4-Substituted Cyclohexanecarboxylic Acids
• Mol File: 7077-05-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 95 °C
• Boiling Point: 263.8 °C at 760 mmHg
• Flash Point: 126.9 °C
• Appearance: White crystalline powder
• Density: 0.996 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.91±0.10(Predicted)
• CAS DataBase Reference: trans-4-Isopropylcyclohexane carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-Isopropylcyclohexane carboxylic acid(7077-05-6)
• EPA Substance Registry System: trans-4-Isopropylcyclohexane carboxylic acid(7077-05-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 7077-05-6(Hazardous Substances Data)

Usage

Description

Trans-4-Isopropylcyclohexane carboxylic acid is an organic compound that serves as an intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique molecular structure, which includes an isopropyl group and a cyclohexane ring, with a carboxylic acid functional group.

Uses

Used in Pharmaceutical Industry:
Trans-4-Isopropylcyclohexane carboxylic acid is used as an intermediate for the preparation of Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent. trans-4-Isopropylcyclohexane carboxylic acid plays a crucial role in the development of medications aimed at managing blood sugar levels in patients with diabetes.
Additionally, it is used in the preparation of Nateglinide USP Related Compound A, which is an essential component in the pharmaceutical formulation process. The use of trans-4-Isopropylcyclohexane carboxylic acid in these applications highlights its importance in the development of effective treatments for diabetes and related conditions.

InChI:InChI=1/C10H18O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h7-9H,3-6H2,1-2H3,(H,11,12)

Upstream product

• 536-66-3 p-isopropylbenzoic acid 
• 135355-08-7 (4S)-phellandric acid 
• 175284-00-1 p-menthan-7-oic acid methyl ester 
• 623-11-0 1-methyl-4-nitrosobenzene 

Downstream Products

• 25244-24-0 trans-p-menthanoic acid-⁽⁷⁾-ethyl ester 
• 13828-36-9 Methyl trans-4-isopropylcyclohexanecarboxylate 
• 107628-01-3 trans-p-menthanoic acid-⁽⁷⁾-(4-bromo-phenacyl ester) 
• 681448-30-6 trans-p-menthanoic acid-⁽⁷⁾-amide 
• 958230-63-2 N-[(trans-4-Isopropylcyclohexyl)carbonyl]-L-phenylalanine methyl ester 
• 105746-47-2 N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester 
• 321371-23-7 3-(4-hydroxy-phenyl)-2-[(4-isopropyl-cyclohexanecarbonyl)-amino]-propionic acid methyl ester 
• 21488-23-3 N-(ethoxycarbonyl)-(D)-phenylalanine 
• 105816-04-4 nateglinide 
• 944746-48-9 2-[2-[(trans-4-isopropylcyclohexanecarbonyl)amino]-3-phenylpropionylamino]-3-phenylpropionic acid 
• 84855-54-9 trans-4-iso-propylcyclohexylcarbonyl chloride 
• 105816-05-5 L-Nateglinide 
• 594837-85-1 C₁₉H₂₆NO₃^(1-)*Na⁽¹⁺⁾ 
• 183997-00-4 trans-4-isopropylcyclohexylcarboxylic acid N-hydroxysuccinimide ester 

Relevant articles and documents

Electrocatalytic hydrogenation of benzoic acids in a proton-exchange membrane reactor

The highly efficient chemoselective electrocatalytic hydrogenation of benzoic acids (BAs) to cyclohexanecarboxylic acids (CCAs) was carried out in a proton-exchange membrane reactor under mild conditions without hydrogenation of the carboxyl group. Among the investigated catalysts, the PtRu alloy catalyst was found to be the most suitable for achieving high current efficiencies for production of CCAs. An electrochemical spillover mechanism on the PtRu alloy catalyst was also proposed.

Epimerization of 2- or 4- substituted cyclohexanecarboxylic acids

The present invention relates to a new method for obtaining a purity of about 93% to 100% of the trans form of 2- or 4-substituted cyclohexanecarboxylic acid or reactive derivatives thereof from the cis form or a mixture of the cis and trans forms by a single step, particularly, to a method for obtaining a purity of substantially 100% of the trans form of 4-substituted cyclohexanecarboxylic acid.

N-(Cyclohexylcarbonyl)-D-phenylalanines and related compounds. A new class of oral hypoglycemic agents. 2

A series of analogues of N-(cyclohexylcarbonyl)-D-phenylalanine (5) have been synthesized and evaluated for their hypoglycemic activity. Relationships were studied between the activity and the three-dimensional structure of the acyl moiety, which was characterized by high-resolution 1H NMR spectroscopy and MNDO calculations. The role of the carboxyl group of the phenylalanine moiety was also studied by comparing the activities of the enantiomers, the decarboxyl derivative, the esters, and the amides of the phenylalanine derivatives. Thus, the structural requirements for possessing hypoglycemic activity was elucidated and a highly active compound, N-[(trans-4-isopropylcyclohexyl)carbonyl]-D-phenylalanine (13) was obtained, which showed a 20% blood glucose decrease at an oral dose of 1.6 mg/kg in fasted normal mice.