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
• Article Data: 8

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

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

Downstream Products

• 138001-94-2 3-Hexyloxy-4-methylbenzaldehyde 
• 24973-22-6 3-methoxy-4-methylbenzaldehyde 
• 359879-55-3 N-((3-hydroxy-4-methylphenyl)methyl)-4-amino-1-methylpiperidine 
• 1600490-07-0 C₁₆H₁₆N₂O₂S 

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.

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.

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