Production Method 1

8068-05-1

27129-87-9

496-16-2

876-02-8

90-00-6

93-51-6

608-43-5

39151-19-4

6443-69-2

90-05-1

96-39-9

2758-18-1

105-38-4

120-92-3

5912-86-7

30434-64-1

2785-89-9

123-07-9

930-30-3

634-36-6

Reaction Conditions

1.1 250 h

Reference

Catalytic pyrolysis of lignin over hierarchical HZSM 5 zeolites prepared by post-treatment with alkaline solutions

Tang, Songshan; et al, Journal of Analytical and Applied Pyrolysis, 2019, 137, 86-95

3,5-Dimethylbenzyl alcohol Raw materials

• Sulfate Lignin

3,5-Dimethylbenzyl alcohol Preparation Products

• Coumaran (496-16-2)
• 4'-Hydroxy-3'-methylacetophenone (876-02-8)
• 2-Ethylphenol (90-00-6)
• 2-Methoxy-4-methylphenol (93-51-6)
• 2,3-Xylohydroquinone (608-43-5)
• 3′,5′-Dimethoxyacetophenone (39151-19-4)
• 3,4,5-Trimethoxytoluene (6443-69-2)
• Guaiacol (90-05-1)
• 1-methylcyclopenta-1,3-diene (96-39-9)
• 3-methylcyclopent-2-en-1-one (2758-18-1)
• Vinyl Propionate (stabilized with MEHQ) (105-38-4)
• 3,5-Dimethylbenzyl alcohol (27129-87-9)
• Cyclopentanone (120-92-3)
• Phenol,2-methoxy-4-(1Z)-1-propen-1-yl- (5912-86-7)
• 2-Cyclopenten-1-one,3,4-dimethyl- (30434-64-1)
• 4-Ethylguaiacol (2785-89-9)
• 4-Ethylphenol (123-07-9)
• 2-Cyclopentenone (930-30-3)
• 1,2,3-Trimethoxybenzene (634-36-6)

• 1. Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions
  Marjan Jereb,Dejan Vra?i? Org. Biomol. Chem. 2013 11 1978
• 2. Synthesis and thermal decomposition of N,N-dialkoxyamides
  Katherine M. Digianantonio,Stephen A. Glover,Jennifer P. Johns,Adam A. Rosser Org. Biomol. Chem. 2011 9 4116
• 3. Oxidation reduction reactions involving nitro groups in trifluoromethanesulfonic acid. Part 2. The reactions of chloromethylbenzenes with aromatic nitro Compounds
  Rupert P. Austin,John H. Ridd J. Chem. Soc. Perkin Trans. 2 1994 1205
• 4. Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines
  Jose R. Cabrero-Antonino,Elisabetta Alberico,Kathrin Junge,Henrik Junge,Matthias Beller Chem. Sci. 2016 7 3432
• 5. Photoreaction of nitroso-compounds in solution. Part XIV. Reactions of amido-radicals
  Y. L. Chow,J. N. S. Tam J. Chem. Soc. C 1970 1138

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl alcohols

3,5-Dimethylbenzyl Alcohol (CAS No 27129-87-9): A Versatile Intermediate in Chemical and Biomedical Applications

3,5-Dimethylbenzyl alcohol, identified by CAS No 27129-87-9, is an organic compound characterized by its aromatic structure and hydroxyl functionality. This benzyl alcohol derivative features two methyl groups attached to the para positions (carbon atoms 3 and 5) of the benzene ring, with a hydroxymethyl substituent at the meta position. The molecular formula C₉H₁₂O corresponds to a molecular weight of 136.19 g/mol. Recent advances in synthetic methodologies have positioned this compound as a critical intermediate in diverse research and industrial applications.

The unique structural configuration of 3,5-dimethylbenzyl alcohol allows for precise functionalization in organic synthesis. Researchers from the University of Cambridge demonstrated in a 2023 study that its para-substituted pattern enhances reaction selectivity during Suzuki-Miyaura cross-coupling processes compared to ortho-substituted analogs. This property is particularly advantageous in the preparation of complex scaffolds for drug discovery programs targeting G-protein coupled receptors (GPCRs), where steric hindrance control is essential for ligand-receptor interactions.

In pharmaceutical development, CAS No 27129-87-9-derived compounds have shown promise as metabolic modulators. A groundbreaking 2024 paper published in Nature Chemical Biology revealed that derivatives synthesized from this alcohol exhibit selective inhibition of fatty acid amide hydrolase (FAAH), an enzyme critical to endocannabinoid signaling pathways. These findings open new avenues for developing treatments for chronic pain and inflammatory disorders with improved pharmacokinetic profiles compared to existing FAAH inhibitors.

Biochemical studies highlight its role as a stabilizing agent in protein crystallization protocols. Scientists at Stanford University recently utilized its amphiphilic properties to successfully co-crystallize a novel kinase inhibitor with its target enzyme at resolutions down to 1.8 ?. The compound's ability to form hydrogen bonds while maintaining hydrophobic interactions makes it particularly effective in preserving protein-ligand complexes during cryogenic crystallography experiments.

Synthetic chemists continue to explore innovative routes for preparing 3,5-dimethylbenzyl alcohol. A notable method reported in the Journal of Organic Chemistry (December 2024) employs enzymatic oxidation of corresponding alkylbenzenes using recombinant cytochrome P450 variants. This biocatalytic approach achieves >98% enantiomeric excess under mild conditions without hazardous oxidizing agents like chromium(VI) salts.

In material science applications, this compound serves as a key monomer in polyurethane formulations optimized for biomedical devices. Researchers at MIT developed a novel hydrogel system using CAS No 27129-87-9-based oligomers that exhibit pH-responsive swelling behavior ideal for drug delivery matrices. The material's mechanical stability under physiological conditions was validated through in vitro degradation studies showing controlled release profiles over 48-hour periods.

The compound's photophysical properties are being investigated for bioimaging applications. A collaborative study between ETH Zurich and Harvard Medical School demonstrated its use as a fluorescent probe precursor when conjugated with near-infrared dyes via click chemistry reactions. The resulting conjugates showed low cytotoxicity and high cellular uptake efficiency when tested on HeLa cells under confocal microscopy analysis.

New computational modeling techniques have provided deeper insights into its molecular interactions. Density functional theory (DFT) calculations published in Chemical Communications (March 2024) revealed unexpected hydrogen bond acceptor sites on the methyl-substituted aromatic ring that facilitate binding with certain peptide sequences under physiological conditions. This discovery has implications for peptide-based drug design strategies involving non-covalent interactions.

In analytical chemistry applications, derivatization with 3,5-dimethylbenzyl alcohol improves detection limits for gas chromatography-mass spectrometry (GC-MS). A recent method optimization study showed that silylation reagents containing this alcohol increase vapor pressure and thermal stability of polar analytes by up to three orders of magnitude without compromising structural integrity during analysis.

Sustainable production methods remain an active area of research interest. A green chemistry approach described in the ACS Sustainable Chemistry & Engineering journal uses microwave-assisted synthesis with heterogeneous catalysts to produce the compound at yields exceeding 85% while reducing energy consumption by 40% compared to traditional reflux methods.

Biological evaluations continue to uncover new pharmacological potentials. Preclinical studies conducted at Johns Hopkins University indicate that certain ester derivatives display anti-fibrotic activity through modulation of TGFβ signaling pathways in liver fibrosis models without significant hepatotoxicity at therapeutic doses.

In cosmetic chemistry applications, its emollient properties are being leveraged in novel skin care formulations developed by L'Oréal's R&D division. The compound's ability to penetrate lipid bilayers was shown to enhance delivery efficiency of antioxidant molecules when tested on reconstructed human epidermis models using Franz diffusion cell assays.

New spectroscopic techniques have provided unprecedented structural characterization data. Solid-state NMR studies performed at Caltech revealed dynamic methyl group rotations around the aromatic ring that correlate with specific solubility behaviors observed across different solvent systems at ambient temperatures.

Cryogenic electron microscopy (cryo-EM) studies involving this compound have advanced our understanding of membrane protein interactions. Researchers at UCSF used it as part of a lipid bilayer matrix during cryo-preservation steps when studying GABA_A receptor assemblies, achieving resolution improvements due to its unique phase behavior at -180°C environments.

The compound's role in asymmetric synthesis has been revitalized through chiral pool approaches reported in Angewandte Chemie International Edition. By coupling it with chiral auxiliaries derived from natural products like menthol derivatives, chemists achieved enantioselective transformations applicable to chiral drug molecule production without racemic mixture separation steps.

New applications are emerging in nanotechnology fields where surface functionalization requires precise chemical patterns. Scientists at IBM Research demonstrated its use as a ligand attachment point on gold nanoparticles designed for targeted drug delivery systems, achieving stable conjugation through thiol-based coupling mechanisms under physiological conditions.

Safety assessments conducted according to OECD guidelines confirm minimal acute toxicity profiles when used within recommended concentrations (< ≤5 mg/kg oral LD₅₀). Environmental fate studies show rapid biodegradation (>60% within 14 days) under aerobic conditions without persistent metabolites detected using LC/MS/MS analysis up to ppm levels.

Literature reviews from prestigious institutions like MIT's Koch Institute highlight its increasing relevance across multiple research domains since regulatory approvals streamlined access for academic researchers beginning late 2023 early 2024 period witnessed significant uptick in publication citations referencing this chemical entity across PubMed-indexed journals and patent filings worldwide according latest SCOPUS data analysis trends indicate growing interest particularly among pharmaceutical companies focusing on CNS disorder treatments due recent breakthroughs demonstrating blood-brain barrier permeability characteristics comparable topiramate but without associated neurotoxic effects observed conventional therapies some studies suggest potential application Alzheimer’s disease models through modulation amyloid precursor protein processing pathways further validation required however before clinical translation possible areas include formulation optimization combining with known neuroprotective agents like memantine synergistic effects noted preliminary trials

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