15174-69-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-3-methylbenzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. It plays a crucial role in the preparation of benzothiazole Schiff bases, which have been found to exhibit significant antitumor activity against cervical cancer. The compound's ability to modulate cellular processes and inhibit tumor growth makes it a valuable asset in the development of novel cancer treatments.
Used in Cosmetics and Flavor Industry:
4-Hydroxy-3-methylbenzaldehyde is used as a natural flavoring agent and fragrance component in the cosmetics and flavor industry. Its characteristic vanilla scent and taste make it an ideal additive for a wide range of products, including perfumes, candles, and food items. The compound's natural origin and pleasant aroma contribute to its popularity in these applications.
Used in Chemical Synthesis:
4-Hydroxy-3-methylbenzaldehyde is also used as a starting material in the synthesis of various organic compounds, such as novel pyrimidine derivatives. These derivatives have been found to possess potent antibacterial properties against both gram-positive and gram-negative bacteria, making them valuable in the development of new antimicrobial agents.

InChI:InChI=1/C8H8O2/c1-6-4-7(5-9)2-3-8(6)10/h2-5,10H,1H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 95-48-7 ortho-cresol 
• 67-66-3 chloroform 
• 75-25-2 Bromoform 
• 105-67-9 2,4-Xylenol 
• 201230-82-2 carbon monoxide 
• 60577-30-2 4-iodo-2-methyl-phenol 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 7732-18-5 water 
• 76-03-9 trichloroacetic acid 
• 89-87-2 2,4-dimethylnitrobenzene 
• 15777-70-5 4-hydroxy-3-methylbenzonitrile 

Downstream Products

• 93533-24-5 4-hydroxy-3-methoxy-5-(phenyldiazenyl)benzaldehyde 
• 860742-62-7 (4-hydroxy-5-isopropyl-2-methyl-phenyl)-(4-hydroxy-3-methyl-phenyl)-acetonitrile 
• 499-76-3 4-hydroxy-3-methylbenzoic acid 
• 7733-52-0 4t-(4-hydroxy-3-methyl-phenyl)-but-3-en-2-one 
• 64403-38-9 2-[4-(4-hydroxy-3-methyl-benzylideneamino)-phenyl]-naphtho[1,2-d]oxazole-5-sulfonic acid 
• 3223-21-0 4,4'-Dihydroxy-3,3',5'-trimethyl-chalkon 
• 4992-60-3 4,4'-Dihydroxy-3,3'-dimethyl-chalkon 
• 670274-89-2 [4-(4-benzyloxy-3-nitro-benzyloxy)-3-methyl-phenyl]-methanol 
• 670274-92-7 4-[4-(4-benzyloxy-3-nitro-benzyloxy)-3-methyl-benzyloxy]-3-ethoxy-benzaldehyde 
• 670274-90-5 4-[4-(4-benzyloxy-3-nitro-benzyloxy)-3-methyl-benzyloxy]-3-nitro-benzaldehyde 

Relevant academic research and scientific papers

Ruthenium(VIII)-Catalyzed ipso-Dearomative Spiro-Etherification and Spiro-Amidation of Phenols

An open air ruthenium(VIII)-catalyzed oxidative spiro-etherification as well as spiro-amidation of phenols has been performed. The transformation works satisfactorily with both phenols and naphthols and thus exhibits a wide range of flexibility. The catalysis is performed in open air at room temperature with a yield of ≤95%.

Exploration of phenylpropanoic acids as agonists of the free fatty acid receptor 4 (FFA4): Identification of an orally efficacious FFA4 agonist

The long chain free fatty acid receptor 4 (FFA4/GPR120) has recently been recognized as lipid sensor playing important roles in nutrient sensing and inflammation and thus holds potential as a therapeutic target for type 2 diabetes and metabolic syndrome. To explore the effects of stimulating this receptor in animal models of metabolic disease, we initiated work to identify agonists with appropriate pharmacokinetic properties to support progression into in vivo studies. Extensive SAR studies of a series of phenylpropanoic acids led to the identification of compound 29, a FFA4 agonist which lowers plasma glucose in two preclinical models of type 2 diabetes.

Highly practical and cost-efficient synthesis of telmisartan: An antihypertensive drug

A novel and cost-efficient strategy for synthesis of an antihypertensive drug telmisartan, a substituted bis-benzimidazole derivative, is described. The key strategy is the construction of bis-benzimidazole 4 by reductive cyclization of o-nitroanilines 11 with butyl aldehyde and cyclocondensation of aromatic aldehydes 9 with o-phenylenediamine, then N-alkylation is allowed to give the target compound telmisartan after hydrolysis. The simple operation and workup procedure, along with the low production costs, make it suitable for industrial production and will benefits those with cardiovascular disease.

SUBSTITUTED PYRAZOLES AS PPAR AGONISTS

A compound of formula (I) and pharmaceutically acceptable salts, solvates and hydrolysable esters thereof (I) wherein: p is O or 1; q is O or 1; R1 and R2 are independently H or C1-3 alkyl; R3 and R4 are independently H, C1-6 alkyl, -OC1-6 alkyl, halogen, OH, C2-6 alkenyl or CF3; R5 is H, C1-6 alkyl (optionally substituted by one or more halogens, -COphenyl, OC1-6 alkyl, phenyl morpholino or C2-6 alkenyl. R6 is C1-6 alkyl, halogen, -OCH2 phenyl, phenyl (optionally substituted by C1-3 alkiyl), morpholino, pyrrolidino, piperidino, thiophenyl, furanyl pyridinyl or -OC2-6 alkenyl. These compounds activate the alpha and gamma subtypes fo the hppar receptor and are useful e.g. in the treatment of diabetes, dyslipidemia or syndrome X.

Electrosynthesis of aromatic aldehydes by palladium-catalyzed carbonylation of aryl iodides in the presence of formic acid

The palladium-catalyzed electrocarbonylation of aryl halides performed in the presence of formic acid under one atmosphere of carbon monoxide affords aromatic aldehydes in good to high yields.

Process for selective preparation of hydroxybenzaldehydes

Process for preparing hydroxybenzaldehydes of the formula (1) STR1 in which R1 -R4 are hydrogen, fluorine, chlorine, bromine, alkyl, alkoxy, phenyl, naphthyl, phenylalkyl, naphthylalkyl, phenoxy or saturated or unsaturated cyclopentane or cyclohexane radicals, and R1 -R4 may with the hydroxybenzene ring carbon atoms on which they are located form 1 or 2 saturated or unsaturated isocyclic or heterocyclic rings, by admixing 1 mol of a phenol of the formula (2) STR2 in which R1 -R4 have the stated meanings, in a pressure vessel with from 5 to 100 mol of hydrogen fluoride and from 0.5+x to 1.5+x mol of boron trifluoride, where x is the number of oxygen atoms contained in the starting compound (formula (2)), setting the mixture to from -10° to 100° C. and then passing carbon monoxide into this mixture until a pressure of from 10 to 150 bar is reached and allowing the mixture to react at the desired pressure reached.

Total Synthesis of (+/-)-Parvifoline and (+/-)-Isoparvifolinone

The total synthesis of the unusual trimethylbenzocyclooctenes (+/-)-parvifoline (1) and (+/-)-isoparvifolinone (5) have been achieved by using the Grob fragmentation reaction of mesylate 25 as the key step.

Process for production of aromatic aldehydes

Aromatic aldehydes are produced by oxidation with oxygen of a para-cresol derivative in a solvent, in the presence of a base and a catalytic amount of a cobalt compound. The catalyst is a chelated complex of cobalt with a rigid structure that is slightly oxidizable selected from the group consisting of bis-(4-methylpyridine isoindolinato)cobalt(II) acetate, phthalocyaninatocobalt(II), and sulfophthalocyaninanatocobalt(II). The process is particularly suited to the production of p-hydroxy benzaldehydes.

Selective Syntheses Using Cyclodextrin as Catalyst. 1. Control of Orientation in the Attack of Dichlorocarbene at Phenolates

4-Hydroxybenzaldehydes, 2,4-dihydroxybenzaldehyde, and 4-(dichloromethyl)-2,5-cyclohexadienones were synthesized in virtually 100percent selectivities and high yields from the corresponding phenols and chloroform in alkaline aqueous solutions by using α- or β-cyclodextrin (α- or β-CD) as catalyst.The regulation of the molar ratio of chloroform to CD below unity throughout the reaction time, by controlling the rate of addition of chloroform, was definitely required to attain high selectivity.Under these conditions, dichlorocarbene, prepared in situ from chloroform and sodium hydroxide, attacked overwhelmingly at the para carbon of phenols with almost perfect suppression of the reaction at the ortho carbon.The structure of the ternary molecular complex composed of β-CD, chloroform, and phenol, formed in the reaction mixture for the selective synthesis of 4-hydroxybenzaldehyde, was determined by NMR spectroscopy.The selective catalysis by CDs was attributed to the regulation of molecular conformation of phenols with respect to chloroform, and thus to dichlorocarbene, in the ternary complex.

Synthesis of 2,7-Dihydroxyemodin

2,7-Dihydroxyemodin (IX) has been synthesised by condensing 3,4,5-trihydroxyphthalic anhydride (VII) with 3-methylcatechol (III) in the presence of anhyd. aluminium chloride and subsequent cyclisation of the benzophenone derivative (VIII) with a mixture of boric and sulphuric acids.