142628-53-3

Basic information

• Product Name: Macrocarpal C
• Synonyms: Macrocarpal C;Macrocarpal C/G
• CAS NO: 142628-53-3
• Molecular Formula: C₂₈H₃₈O₅
• Molecular Weight: 454.5983
• Product Categories: Sesquiterpenoids
• Mol File: 142628-53-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 509.6°Cat760mmHg
• Flash Point: 276.1°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 5.25E-11mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: Macrocarpal C(CAS DataBase Reference)
• NIST Chemistry Reference: Macrocarpal C(142628-53-3)
• EPA Substance Registry System: Macrocarpal C(142628-53-3)

Safety Data

• Hazardous Substances Data: 142628-53-3(Hazardous Substances Data)

Usage

General Description

Macrocarpal C is a chemical compound that primarily derived from the plant Eucalyptus globulus, which is a type of tree native to Australia. This chemical has shown promising anti-cancer properties, particularly in relation to leukemia, colon, and breast cancer cells in numerous scientific studies. In addition to its potential anti-cancer benefits, Macrocarpal C also exhibits antibacterial and anti-inflammatory capabilities. The isolation and extraction of Macrocarpal C from Eucalyptus globulus are done using varied organic solvents, allowing researchers to explore its numerous and powerful biological activities.

InChI:InChI=1/C28H38O5/c1-14(2)11-20(21-25(32)17(12-29)24(31)18(13-30)26(21)33)28(6)10-9-16-15(3)7-8-19-23(22(16)28)27(19,4)5/h12-14,16,19-20,22-23,31-33H,3,7-11H2,1-2,4-6H3/t16-,19+,20-,22+,23+,28+/m0/s1

Upstream product

• 142698-60-0 2,4,6-trihydroxy-5-((R)-1-((1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyldecahydro-1H-cyclopropa[e]azulen-7-yl)-3-methylbutyl)isophthalaldehyde 
• 201207-45-6 (+)-dimethyl 5-<(1'S)-1'-((1S,2R,4R,7S,11R)-7-<(tert-butyldimethylsiloxy)methyl>-3,3,11-trimethyl-10-oxotricyclo<6.3.0.0^2,4>undec-8-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 
• 201207-51-4 (+)-dimethyl 5-<(1'S)-1'-((1R,2R,4R,7S,8R,10S,11S)-10-hydroxy-7-(acetoxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 
• 219954-64-0 5-[(R)-1-((1aR,4S,4aR,7S,7aR,7bR)-4-Acetoxymethyl-1,1,7-trimethyl-1a,2,3,4,4a,7,7a,7b-octahydro-1H-cyclopropa[e]azulen-7-yl)-3-methyl-butyl]-2,4,6-trimethoxy-isophthalic acid dimethyl ester 
• 201207-49-0 (-)-dimethyl 5-<(1'S)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyl-10-oxotricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 
• 219954-67-3 (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-9-en-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 
• 201207-50-3 (+)-dimethyl 5-<(1'S)-1'-((1R,2R,4R,7S,8R,10S,11S)-10-hydroxy-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 
• 201207-52-5 (-)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,7S,8R,11S)-7-(hydroxymethyl)-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 
• 201207-53-6 (+)-dimethyl 5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalate 
• 201207-43-4 (-)-(1S,2R,4R,7S)-10-(tert-butyldimethylsiloxy)-7-<(tert-butyldimethylsiloxy)methyl>-3,3,11-trimethyltricyclo<6.3.0.0^2,4>undeca-8,10-diene 
• 175985-37-2 (1aR,4S,7R,7aR,7bR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-1,1,7-trimethyl-1a,3,4,7,7a,7b-hexahydro-1H,2H-cyclopropa[e]azulen-6-one 
• 201207-54-7 (+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxybenzene-1,3-dimethanol 
• 201207-55-8 (+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalaldehyde 

Downstream Products

• 142628-50-0 C₃₅H₅₂O₈ 
• 142628-50-0 C₃₅H₅₂O₈ 
• 142628-51-1 (1aR,4R,4aR,7S,7aS,7bR)-7-[(R)-1-(3,5-Bis-hydroxymethyl-2,4,6-trimethoxy-phenyl)-3-methyl-butyl]-1,1,4,7-tetramethyl-decahydro-cyclopropa[e]azulen-4-ol 
• 201207-54-7 (+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxybenzene-1,3-dimethanol 
• 201207-55-8 (+)-5-<(1'R)-1'-((1R,2R,4R,8R,11S)-3,3,11-trimethyl-7-methylenetricyclo<6.3.0.0^2,4>undec-11-yl)-3'-methylbutyl>-2,4,6-trimethoxyisophthalaldehyde 

Relevant articles and documents

Semisynthesis of macrocarpal c and analogues by selective dehydration of macrocarpal a or b

Macrocarpals A and C are structurally related compounds that have been extracted from different Eucalyptus species. Although macrocarpal C is of biological interest, its isolation in pure form is difficult to achieve. We report herein an efficient method for the semisynthesis of macrocarpal C by selective exo-dehydration of another member of the macrocarpal family, macrocarpal A. We also report the semisynthesis of three new macrocarpal structures derived from either macrocarpal A or B.

First stereoselective total synthesis of macrocarpal C: Structure elucidation of macrocarpal G

The first stereoselective total synthesis of macrocarpal C is achieved via a coupling reaction of a silyl dienol ether with a novel hexasubstituted benzene chromium tricarbonyl complex as an optically active benzyl cation equivalent, thereby clarifying the identity of macrocarpal C and G.