61463-03-4

Basic information

• Product Name: CHAMUVARITIN
• Synonyms: 1-[4,6-Dihydroxy-3-[(2-hydroxyphenyl)methyl]-2-methoxyphenyl]-3-phenyl-1-propanone;Chamuvarin;Isouvaretin
• CAS NO: 61463-03-4
• Molecular Formula: C₂₃H₂₂O₅
• Molecular Weight: 378.42
• Mol File: 61463-03-4.mol

Chemical Properties

• Melting Point: 162 °C
• Boiling Point: 595°C at 760 mmHg
• Flash Point: 207.9°C
• Appearance: /
• Density: 1.274g/cm³
• Vapor Pressure: 9.45E-15mmHg at 25°C
• Refractive Index: 1.64
• PKA: 7.51±0.50(Predicted)
• CAS DataBase Reference: CHAMUVARITIN(CAS DataBase Reference)
• NIST Chemistry Reference: CHAMUVARITIN(61463-03-4)
• EPA Substance Registry System: CHAMUVARITIN(61463-03-4)

Safety Data

• Hazardous Substances Data: 61463-03-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H22O5/c1-28-23-17(13-16-9-5-6-10-18(16)24)20(26)14-21(27)22(23)19(25)12-11-15-7-3-2-4-8-15/h2-10,14,24,26-27H,11-13H2,1H3

Upstream product

• 100-52-7 benzaldehyde 
• 90-02-8 salicylaldehyde 
• 5896-17-3 2-(phenylmethoxy)benzaldehyde 
• 103633-34-7 3-C-(o-Benzyloxybenzyl)-4,6-dibenzyloxy-2-methoxyacetophenone 
• 103633-32-5 3-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone 
• 103633-30-3 2-bromomethylphenyl benzyl ether 
• 3381-87-1 2-benzyloxybenzyl alcohol 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 103633-35-8 3'-C-(o-Benzyloxybenzyl)-4',6'-dibenzyloxy-2'-methoxychalcone 

Downstream Products

• 61463-08-9 Chamuvarin-monomethylaether 
• 61463-11-4 4-(2-Hydroxy-benzyl)-5-methoxy-benzene-1,3-diol 

Relevant articles and documents

Aromatic Benzylation: Part III - Synthesis of Uvaretin, Isouvaretin and Related Nuclear Benzylated Dihydrochalcones

Reaction of 2-O-methylphloroacetophenone (5) with either o-benzyloxybenzyl alcohol (3) in the presence of boron trifluoride etherate and dioxan or with o-benzyloxybenzyl bromide (4) in the presence of methanolic potash affords 5-C-(o-benzyloxybenzyl) derivative (6) and its 3-C-isomer (7).Their orientation has been arrived at from a general behaviour of the chemical shift of chelated hydroxyl group in C-benzylated o-hydroxyacetophenones when C-benzyl group is present ortho or para to the chelated hydroxyl.Partial benzyl ether (9) of 6 and the complete benzyl ether (12) of 7 undergo facile condensation with benzaldehyde in the presence of alkali to give 10 and 13 respectively.These chalcones on hydrogenation in the presence of 10percent Pd-C afford uvaretin (11) and isouvaretin (14) respectively possessing physical characteristics identical with those of the natural samples.A parallel series of reactions starting from resacetophenone (15) provides C-benzylated dihydrochalcones 22 and 25 as analogues of uvaretin and isouvaretin respectively.