57295-30-4

Basic information

• Product Name: 3-HYDROXY-4-METHYL-BENZALDEHYDE
• Synonyms: 3-HYDROXY-4-METHYL-BENZALDEHYDE;Benzaldehyde, 3-hydroxy-4-Methyl-
• CAS NO: 57295-30-4
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 57295-30-4.mol

Chemical Properties

• Melting Point: 73-74 °C
• Boiling Point: 252.4 °C at 760mmHg
• Flash Point: 104.1 °C
• Appearance: /
• Density: 1.175 g/cm³
• Vapor Pressure: 0.0121mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.59±0.10(Predicted)
• CAS DataBase Reference: 3-HYDROXY-4-METHYL-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-4-METHYL-BENZALDEHYDE(57295-30-4)
• EPA Substance Registry System: 3-HYDROXY-4-METHYL-BENZALDEHYDE(57295-30-4)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 57295-30-4(Hazardous Substances Data)

Usage

Purification Methods

Crystallise it from water or *C6H6 (m 71-71o). The O-methyl ether has m 45-46o (from Et2O/hexane). [Sedgwick & Allott J Chem Soc 2820 1923, Flitsch et al. Justus Liebigs Ann Chem 1413 1985, Beilstein 8 H 100, 8 II 103, 8 IV 368.]

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

Upstream product

• 31680-07-6 4-methyl-3-nitrobenzaldehyde 
• 92203-12-8 (3-Hydroxy-4-methyl-phenyl)-nitro-methan 
• 7218-22-6 6-acetoxy-3,6-dimethyl-cyclohexa-2,4-dienone 
• 50-00-0 formaldehyd 
• 90953-62-1 3-hydroxy-4-methylbenzyl alcohol 
• 586-30-1 3-hydroxy-4-methylbenzoic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 7577-74-4 6-acetoxy-6-methylcyclohexa-2,4-dienone 
• 24973-22-6 3-methoxy-4-methylbenzaldehyde 

Downstream Products

• 157143-21-0 3-Dodecyloxy-4-methylbenzaldehyd 
• 157143-22-1 3-Hexadecyloxy-4-methylbenzaldehyd 
• 157143-20-9 3-Ethoxy-4-methylbenzaldehyd 
• 138001-94-2 3-Hexyloxy-4-methylbenzaldehyde 
• 24973-22-6 3-methoxy-4-methylbenzaldehyde 
• 90843-49-5 3-hydroxy-4-methoxycinnamic acid 
• 359879-55-3 N-((3-hydroxy-4-methylphenyl)methyl)-4-amino-1-methylpiperidine 
• 883978-28-7 5-[(1Z)-1-hepten-1-yl]-2-methylphenol 

Relevant articles and documents

NOVEL BENZYLIDENEACETONE DERIVATIVE AND USE THEREOF

The present invention relates to novel benzylideneacetone derivatives or uses thereof, more specifically, the present invention relates to a pharmaceutical composition for preventing or treating, or food composition for ameliorating a cancer or a bone disease comprising a compound defined by Formula 1 or pharmaceutically acceptable salt thereof as an active ingredient. Since compounds according to the present invention exhibit strong inhibitory activity on proliferation and differentiation of osteoclast, and activity on proliferation and differentiation of osteoblast, it can be usefully used to develop safe and effective anti-cancer agents, and therapeutic agents for preventing and treating or foods for ameliorating bone diseases including osteoporosis, and the like.

SAR of non-hydrolysable analogs of pyridoxal 5′-phosphate against low molecular weight protein tyrosine phosphatase isoforms

Kinases and phosphatases are key enzymes in cell signal transduction pathways. Imbalances in these enzymes have been linked to numerous disease states ranging from cancer to diabetes to autoimmune disorders. The two isoforms (IFA and IFB) of Low Molecular Weight Protein Tyrosine Phosphatase (LMW-PTP) appear to play a role in these diseases. Pyridoxal 5′-phosphate (PLP) has been shown to act as a potent but, impractical micromolar inhibitor for both isoforms. In this study, a series of non-hydrolysable phosphonate analogs of PLP were designed, synthesized and tested against the two isoforms of LMW-PTP. Assay results demonstrated that the best inhibitor for both isoforms was compound 5 with a Kis of 1.84 μM (IFA) and 15.6 μM (IFB). The most selective inhibitor was compound 16, with a selectivity of roughly 370-fold for IFA over IFB.

Benzylideneacetone Derivatives Inhibit Osteoclastogenesis and Activate Osteoblastogenesis Independently Based on Specific Structure-Activity Relationship

(E)-3,4-Dihydroxybenzylideneacetone (compound 1) inhibited receptor activator of NF-κB ligand-induced osteoclastogenesis of C57BL/6 bone marrow monocyte/macrophages with IC50 of 7.8 μM (IC50 of alendronate, 3.7 μM) while stimulating the differentiation of MC3T3-E1 osteoblastic cells, accompanied by the induction of Runt-related transcription factor 2, alkaline phosphatase, and osteocalcin. (E)-4-(3-Hydroxy-4-methoxyphenyl)-3-buten-2-one (compound 2c) showed a dramatically increased osteoclast-inhibitory potency with IC50 of 0.11 μM while sustaining osteoblast-stimulatory activity. (E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one (compound 2g) stimulated alkaline phosphatase production 2-fold at 50 μM without changing osteoclast-inhibitory activity, compared with compound 1. Oral administration of compounds 1, 2c, and 2g prevented ovariectomy-induced osteoporosis in ddY mice to a degree proportional to their osteoclastogenesis-inhibitory potencies. The administration of 1 (mg/kg)/d compound 2c ameliorated histomorphometry of osteoporotic bone to a degree comparable with 10 (mg/kg)/d alendronate. Conclusively, the in vitro capacity of a few benzylideneacetone derivatives to inhibit osteoclastogenesis supported by independent osteoblastogenesis activation was convincingly reflected in in vivo management of osteoporosis, suggesting a potential novel therapeutics for osteopenic diseases.

Novel Compounds

The present invention provides compounds of formula (I): wherein Ra, Rb, Rc, R1, R2, R3, X1, Y1, Z1, A, n and m are as defined in the specification, and pharmaceutically acceptable salts thereof, as well as processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

Highly regioselective one-pot synthesis of 7-hydroxy-6-methylphthalide from 3-hydroxy-4-methylbenzylalcohol

7-Hydroxy-6-methylphthalide 2 was synthesized with high regioselectivity and moderate yield using a novel one-pot synthesis that employed 3-hydroxy-4-methylbenzylalcohol 1 and formaldehyde in the presence of tin(IV) chloride as catalyst and triethylamine

Cyclopropyl derivative lipoxygenase inhibitors

Certain carbocyclic aryl- and heterocyclic aryl- substituted cyclopropyl N-hydroxyureas, N-hydroxy-carboxamides, and N-acyl-N-hydroxyamines inhibit 5- and/or 12-lipoxygenase and are useful in the treatment of inflammatory disease states.

CYCLOPROPYL DERIVATIVE LIPOXYGENASE INHIBITORS

Certain carbocyclic aryl- and heterocyclic aryl-substituted cyclopropyl N-hydroxyureas, N-hydoroxycarboxamides, and N-acyl-N-hydroxyamides inhibit 5- and/or 12-lipoxygenase and are useful in the treatment of inflammatory disease states