103576-44-9

Basic information

• Product Name: 5-OCTANOYL-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE
• Synonyms: 5-OCTANOYL-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE;2,2-dimethyl-5-(1-oxooctyl)-1,3-Dioxane-4,6-dione;2,2-diMethyl-5-octanoyl-1,3-dioxane-4,6-dione
• CAS NO: 103576-44-9
• Molecular Formula: C₁₄H₂₂O₅
• Molecular Weight: 270.32
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 103576-44-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 458.1°C at 760 mmHg
• Flash Point: 204.1°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 1.42E-08mmHg at 25°C
• Refractive Index: 1.457
• Solubility: Chloroform, Ethyl Acetate
• PKA: 8.88±0.40(Predicted)
• CAS DataBase Reference: 5-OCTANOYL-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-OCTANOYL-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE(103576-44-9)
• EPA Substance Registry System: 5-OCTANOYL-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE(103576-44-9)

Safety Data

• Hazardous Substances Data: 103576-44-9(Hazardous Substances Data)

Usage

Chemical Properties

Red Oil

Uses

5-Octanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione (cas# 103576-44-9) is a compound useful in organic synthesis.

InChI:InChI=1/C14H22O5/c1-4-5-6-7-8-9-10(15)11-12(16)18-14(2,3)19-13(11)17/h11H,4-9H2,1-3H3

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 111-64-8 n-octanoic acid chloride 
• 124-07-2 Octanoic acid 

Downstream Products

• 192883-12-8 N-(3-hydroxy-decanoyl)-L-homoserine lactone 
• 147795-40-2 N-(3-oxodecanoyl)-L-homoserine lactone 
• 66696-94-4 benzyl 3-oxodecanoate 
• 13195-66-9 ethyl 3-oxodecanoate 
• 40522-46-1 2-heptyl-quinolin-4(1H)-one 
• 19526-23-9 3-(S)-hydroxydecanoic acid 
• 206359-73-1 (S)-2-(Trityl-amino)-propionic acid (S)-1-((2S,3S)-3-decyl-4-oxo-oxetan-2-ylmethyl)-octyl ester 
• 56618-58-7 methyl (R)-3-hydroxydecanoate 
• 13283-92-6 β-ketodecanoic acid 
• 615265-14-0 3-Oxo-decanoic acid (3aS,6aS)-2-(4-methoxy-phenyl)-dihydro-furo[2,3-d][1,3]dioxol-3a-ylmethyl ester 
• 22348-96-5 methyl 3-oxodecanoate 

Relevant articles and documents

A structure activity-relationship study of the bacterial signal molecule HHQ reveals swarming motility inhibition in Bacillus atrophaeus

The sharp rise in antimicrobial resistance has been matched by a decline in the identification and clinical introduction of new classes of drugs to target microbial infections. Thus new approaches are being sought to counter the pending threat of a post-antibiotic era. In that context, the use of non-growth limiting small molecules, that target virulence behaviour in pathogens, has emerged as a solution with real clinical potential. We have previously shown that two signal molecules (HHQ and PQS) from the nosocomial pathogen Pseudomonas aeruginosa have modulatory activity towards other microorganisms. This current study involves the synthesis and evaluation of analogues of HHQ towards swarming and biofilm virulence behaviour in Bacillus atrophaeus, a soil bacterium and co-inhibitor with P. aeruginosa. Compounds with altered C6-C8 positions on the anthranilate-derived ring of HHQ, display a surprising degree of biological specificity, with certain candidates displaying complete motility inhibition. In contrast, anti-biofilm activity of the parent molecule was completely lost upon alteration at any position indicating a remarkable degree of specificity and delineation of phenotype.

Insights into the programmed ketoreduction of partially reducing polyketide synthases: Stereo- and substrate-specificity of the ketoreductase domain

One of the hallmarks of iterative polyketide synthases (PKSs) is the programming mechanism which is essential for the generation of structurally diverse polyketide products. In partially reducing iterative PKSs (PR-PKSs), the programming mechanism is mainly dictated by the ketoreductase (KR) domain. The KR domain contributes to the programming of PR-PKSs through selective reduction of polyketide intermediates. How the KR domain achieves the selective ketoreduction remains to be fully understood. In this study, we found that the KR domain of the (R)-mellein-synthesizing PR-PKS SACE5532 functions as a B-type KR domain to generate (R)-hydroxyl functionalities. Comparative studies of the KR domains of SACE5532 and NcsB suggested that the two KR domains have distinct substrate preferences towards simple N-acetylcysteamine thioester (SNAC) substrates. We further found that the substrate preference of KRSACE5532 can be switched by swapping several motifs with KRNcsB, and that swapping of the same motifs in the full length SACE5532 resulted in a reprogramming of the PKS. Together, the results advance our understanding of the programming of iterative PR-PKSs by providing new support to the hypothesis that the programmed ketoreduction is accomplished by differential recognition of polyketide intermediates. This journal is

Structure-activity relationships of rationally designed AMACR 1A inhibitors

α-Methylacyl-CoA racemase (AMACR; P504S) is a promising novel drug target for prostate and other cancers. Assaying enzyme activity is difficult due to the reversibility of the ‘racemisation’ reaction and the difficulties in the separation of epimeric prod

Structure-Activity Relationship Study of Majusculamides A and B and Their Analogues on Osteogenic Activity

We discovered that majusculamide A (1) and majusculamide B (2), isolated from a marine cyanobacterium collected in Okinawa, induced osteoblast differentiation in MC3T3-E1 cells. Although majusculamide A (1) has a different configuration only at the C-19 stereocenter, bearing a methyl group, compared to majusculamide B (2), the effect of 1 was stronger than that of 2. We synthesized some analogues of the majusculamides (3-15) and evaluated osteogenic activities of these analogues. The structure-activity relationship study of majusculamide analogues suggested that the number of methyls and configuration at C-19 and the nature of the substituent at C-20 of majusculamide A (1) may be important for the osteoblast differentiation-inducing effect of 1.