1412-97-1

Basic information

• Product Name: Phenol,3-methyl-2-(1-methylethenyl)-
• Synonyms: m-Cresol,2-isopropenyl- (6CI,7CI,8CI); Phenocarquejol
• CAS NO: 1412-97-1
• Molecular Formula: C10H12 O
• Molecular Weight: 148.205
• Mol File: 1412-97-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phenol,3-methyl-2-(1-methylethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol,3-methyl-2-(1-methylethenyl)-(1412-97-1)
• EPA Substance Registry System: Phenol,3-methyl-2-(1-methylethenyl)-(1412-97-1)

Safety Data

• Hazardous Substances Data: 1412-97-1(Hazardous Substances Data)

Upstream product

• 22061-78-5 2-bromo-3-methylphenol 
• 126726-62-3 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 54274-41-8 Carqueol 

Downstream Products

• 92847-71-7 (3-Methyl-2-isopropenyl-phenoxy)-essigsaeure 
• 98017-46-0 (3-Methyl-2-isopropenyl-phenoxy)-essigsaeure-methylester 
• 3228-01-1 3-methyl-2-isopropyl-phenol 

Relevant articles and documents

Synthesis, spectroscopic characterization and structural study of 2-isopropenyl-3-methylphenol, carquejiphenol, a carquejol derivative with potential medicinal use

In this work, 2-isopropenyl-3-methylphenol, hereafter referred to as carquejiphenol (CARP), a minor component of “carqueja” essential oil, was synthesized starting from carquejol and characterized by using Fourier Transform infrared (FT-IR) and Raman (FT-Raman) spectroscopies, Ultraviolet–Visible (UV–Visible) spectroscopy, Electron Impact Mass spectrometry (EI-MS), Hydrogen and Carbon Nuclear Magnetic Resonance (1H- and 13C-NMR) and 2D 1H–1H gCOSY, 1H–13C gHSQC, 1H–13C gHMBC experiments. A very good correlation between the predicted FTIR, FTRaman, UV–visible and 1H–13C-NMR spectra for monomer and dimer of CARP by using theoretical B3LYP/6-31G* and 6-311++G** calculations with the corresponding experimental ones was observed. The solvation energies for CARP were predicted by using both levels of calculations and considering the solvent effects with the polarised continuum and solvation models. The increase in volume in solution supports the H bonds formation due to the presence in its structure of an OH group, as revealed by atoms in molecules (AIM) analysis. A high stability for CARP was found by using natural bond orbital (NBO) and AIM studies, while the investigation of the frontier orbitals reveals that CARP is more reactive than carquejol and N-(3,4-dimethoxybenzyl)-hexadecanamide but less reactive than the sesquiterpene lactone cnicin. The proximity of both the electrophilicy and nucleophilicity index of CARP with those obtained respectively for carquejol and for N-(3,4-dimethoxybenzyl)-hexadecanamide, suggests that CARP could probably present pharmacological properties. The scaled quantum mechanical force field (SQMFF) methodology was used to compute the harmonic force fields and to perform the complete vibrational analysis. In this way, 63 normal modes of vibration were assigned and compared with other terpene substances.

Transformation of Terpene Piquerol A to Hydroquinone and Phenolic Derivatives. Effect of These Compounds on Weeds

Piquerol A (Ia), an allelopathic terpene from Piqueria trinervia (Asteraceae) was chemically transformed into its diacetate (Ib), benzylic alcohol (II), dialkyl hydroquinone derivative (IIIa and IIIb), and phenolics (IVa and V). The structures of these derivatives were determined by spectral analysis. Piquerol derivatives were found to act as powerful radicle growth inhibitors of the weed Amarantus hypochondriac us. Order of inhibition was Ib > IIIa > Ia > IVa > II. The first three compounds were also radicle growth inhibitors of the weed Echinocloa crusgalli.