122540-27-6

Basic information

• Product Name: (3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one
• Synonyms: (3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one
• CAS NO: 122540-27-6
• Molecular Formula: C24H34O5
• Molecular Weight: 402.5238
• Mol File: 122540-27-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 650.5°Cat760mmHg
• Flash Point: 219.3°C
• Appearance: /
• Density: 1.048g/cm³
• Vapor Pressure: 1.13E-19mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: (3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one(122540-27-6)
• EPA Substance Registry System: (3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one(122540-27-6)

Safety Data

• Hazardous Substances Data: 122540-27-6(Hazardous Substances Data)

Usage

Description

(3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one is a complex organic molecule with a cyclohexanone ring and multiple double bonds. It contains three hydroxyl groups at positions 8, 14, and 16, as well as a methyl group at position 24. (3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one also has a combination of cis and trans double bond configurations at positions 3, 5, 9, 11, 17, and 19. Due to its complex structure and multiple functional groups, it likely has unique properties and potential applications in pharmaceuticals, organic synthesis, or materials science.

Uses

Used in Pharmaceutical Industry:
(3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one is used as a pharmaceutical compound for its potential therapeutic effects. Its complex structure and multiple functional groups may contribute to its bioactivity and interactions with biological targets, making it a promising candidate for drug development.
Used in Organic Synthesis:
(3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one is used as an intermediate in organic synthesis for the production of other complex organic molecules. Its unique structure and functional groups can be utilized in various synthetic routes to create novel compounds with potential applications in various industries.
Used in Materials Science:
(3Z,5E,8R,9E,11Z,14S,16S,17E,19E,24R)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one is used in materials science for the development of new materials with unique properties. Its complex structure and functional groups may contribute to the creation of materials with specific characteristics, such as improved mechanical strength, thermal stability, or chemical resistance, depending on the application.

InChI:InChI=1/C24H34O5/c1-20-13-7-3-2-4-8-16-22(26)19-23(27)17-11-5-9-14-21(25)15-10-6-12-18-24(28)29-20/h2,4-6,8-12,14,16,18,20-23,25-27H,3,7,13,15,17,19H2,1H3/b4-2+,10-6+,11-5-,14-9+,16-8+,18-12-/t20-,21+,22-,23+/m1/s1

Upstream product

• 185198-16-7 (2Z,4E,8E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-tributylstannanyl-nona-2,4,8-trienoic acid (5E,7E,13Z)-(1R,9R,11S)-9,11-bis-(tert-butyl-dimethyl-silanyloxy)-14-iodo-1-methyl-tetradeca-5,7,13-trienyl ester 
• 208336-91-8 (2Z,4E,8E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-tributylstannanyl-nona-2,4,8-trienoic acid (5E,7E,13Z)-(1R,9R,11S)-14-iodo-1-methyl-9,11-bis-triethylsilanyloxy-tetradeca-5,7,13-trienyl ester 
• 208336-94-1 (2Z,4E,8E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-iodo-nona-2,4,8-trienoic acid (5E,7E,13Z)-(1R,9R,11S)-9,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-14-trimethylstannanyl-tetradeca-5,7,13-trienyl ester 
• 208336-96-3 (2Z,4E,8E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-iodo-nona-2,4,8-trienoic acid (5E,7E,13Z)-(1R,9R,11S)-1-methyl-9,11-bis-triethylsilanyloxy-14-trimethylstannanyl-tetradeca-5,7,13-trienyl ester 
• 208336-92-9 (3Z,5E,9E,11Z,17E,19E)-(8S,14S,16R,24R)-8-(tert-Butyl-dimethyl-silanyloxy)-24-methyl-14,16-bis-triethylsilanyloxy-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one 
• 210293-75-7 (2E,4E,12Z,14E,18E,20Z)-(1R,9R,17S,23S)-17-(tert-Butyl-dimethyl-silanyloxy)-9,25,25-trimethyl-10,24,26-trioxa-bicyclo[21.3.1]heptacosa-2,4,12,14,18,20-hexaen-11-one 
• 210293-65-5 {(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid butyl ester 
• 210293-66-6 tert-Butyl-{(5E,7E)-(R)-8-[(4R,6S)-6-((Z)-3-iodo-allyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-methyl-octa-5,7-dienyloxy}-dimethyl-silane 
• 210293-73-5 {(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetaldehyde 
• 121785-59-9 (-)-(5R)-5-(tert-butyldimethylsilyloxy)-hexanal 
• 210293-64-4 6-[tert-Butyl(dimethyl)siloxy]-1-iod-1-hepten 
• 210293-69-9 (2E,4E,12Z,14E,18E,20Z)-(1R,9R,17S,23S)-17-Hydroxy-9,25,25-trimethyl-10,24,26-trioxa-bicyclo[21.3.1]heptacosa-2,4,12,14,18,20-hexaen-11-one 
• 185198-18-9 (3Z,5E,9E,11Z,17E,19E)-(8S,14S,16R,24R)-8,14,16-Tris-(tert-butyl-dimethyl-silanyloxy)-24-methyl-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one 
• 208336-93-0 (3Z,5E,9E,11Z,17E,19E)-(8S,14S,16R,24R)-8-(tert-Butyl-dimethyl-silanyloxy)-14,16-dihydroxy-24-methyl-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one 

Relevant articles and documents

Macrolactin W, a new antibacterial macrolide from a marine Bacillus sp.

Bioactivity-guided isolation for the new/novel metabolites from the EtOAc extract obtained from the culture broth of a marine Bacillus sp. 09ID194 followed by chromatographic fractionations and subsequently HPLC purifications led to the isolation of two known macrolides, macrolactins A (1) and Q (2), together with a new glycosylated marcrolide, macrolactin W (3). The chemical structures of compounds 1-3 were assigned based on extensive MS and NMR spectral data analysis and literature review. Compound 3 showed potent antibacterial activity against both Gram-positive and Gram-negative pathogenic bacteria.

Total syntheses of (-)-macrolactin a, (+)-macrolactin e, and (-)- macrolactinic acid: An exercise in stille cross-coupling chemistry

The total syntheses of the potent antiviral agent (-)-macrolactin A (1) and two related family members, (+)-macrolactin E (5) and (-)-macrolactinic acid (7), have been achieved, exploiting a unified, convergent, and highly stereocontrolled strategy. Extensive use of the palladium-catalyzed Stille cross-coupling reaction for the stereospecific construction of the three isolated dienes including macrocyclization formed the cornerstone of the successful strategy. The total syntheses of these natural products, no longer available via fermentation, confirm their relative and absolute stereochemistries and provide access to possible analogues for further biological study.