142628-53-3

Usage

Uses

Used in Pharmaceutical Industry:
Macrocarpal C is used as an anti-cancer agent for its potential to combat leukemia, colon, and breast cancer cells. It has shown promising results in scientific studies, indicating its effectiveness in inhibiting cancer cell growth and progression.
Used in Antibacterial Applications:
Macrocarpal C is used as an antibacterial agent, leveraging its ability to inhibit bacterial growth and prevent infections. This makes it a valuable component in the development of new antimicrobial treatments.
Used in Anti-inflammatory Applications:
Macrocarpal C is used as an anti-inflammatory agent, helping to reduce inflammation and alleviate pain associated with various conditions. Its anti-inflammatory properties make it a potential candidate for the treatment of inflammatory diseases.
Used in Drug Delivery Systems:
Macrocarpal C is used in the development of drug delivery systems to enhance its therapeutic efficacy and bioavailability. Researchers are exploring the use of various organic and metallic nanoparticles as carriers for Macrocarpal C, aiming to improve its delivery and overall effectiveness in treating cancer and other diseases.

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

• 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 
• 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 

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 academic research and scientific papers

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.

Total synthesis of (-)-macrocarpal C. Stereoselective coupling reaction with a novel hexasubstituted benzene Cr(CO)3 complex as a biomimetic chiral benzyl cation equivalent

The first total synthesis of (-)-macrocarpal C (3) is described. The synthesis features a highly stereoselective coupling reaction of silyldienol ether 6 with biomimetic benzyl cation species (R)- and (S)-B, which were generated from novel hexasubstituted benzene chromium tricarbonyl complexes (R)- and (S)-17. At the final step of the total synthesis, we developed the tris-O-demethylation of macrocarpal C trimethyl ether 34 under basic conditions using lithium p-thiocresolate. Moreover, spectroscopic evidence shows that the synthetic (-)-3 is identical to natural macrocarpal G (4).

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.