20291-40-1

Usage

Uses

Used in Food Industry:
Methyl hydrogen heptane-1,7-dioate serves as a flavoring agent, primarily in the creation of fruit and berry flavors. Its natural fruity scent enhances the taste and aroma of food products, making it a valuable ingredient in the formulation of a variety of edible items.
Used in Perfume and Cosmetics Industry:
Beyond its culinary applications, methyl hydrogen heptane-1,7-dioate also finds use as a fragrance component in perfumes and cosmetics. Its pleasant aroma adds to the sensory appeal of these products, contributing to their overall consumer experience.
Used in Pharmaceutical Industry:
Although not extensively detailed in the provided materials, methyl hydrogen heptane-1,7-dioate may have potential applications in the pharmaceutical industry. Its chemical structure could be harnessed for the development of new drugs or as an intermediate in the synthesis of medicinal compounds.
Used in Chemical Industry:
methyl hydrogen heptane-1,7-dioate's properties might also make it suitable for use in the chemical industry, where it could be employed as a reagent or precursor in various chemical processes or synthesis routes.
It is crucial to handle methyl hydrogen heptane-1,7-dioate with care due to its potential flammability and harmful effects if ingested or inhaled, ensuring safety in all applications where it is utilized.

InChI:InChI=1/C8H14O4/c1-12-8(11)6-4-2-3-5-7(9)10/h2-6H2,1H3,(H,9,10)

Upstream product

• 110-86-1 pyridine 
• 67-56-1 methanol 
• 3878-55-5 methyl hydrogen succinate 
• 54322-10-0 glutaric acid monobenzyl ester 
• 124-41-4 sodium methylate 
• 111-16-0 heptanedioic acid 
• 1732-08-7 dimethyl 1,7-heptanedioate 
• 186581-53-3 diazomethane 
• 14273-90-6 methyl 6-bromohexanoate 
• 124-38-9 carbon dioxide 
• 78019-66-6 Methyl 4-bromohexanoate 
• 41796-82-1 methyl 5-bromohexanoate 
• 16580-35-1 1-methoxy-1-hydroperoxycyclohexane 

Downstream Products

• 24330-31-2 2,2,3,3-²H-butane 
• 106-70-7 methyl hexanoate 
• 1731-79-9 dodecanedioic acid dimethyl ester 
• 6807-91-6 8-hydroxyoctadecanoic acid 
• 120167-89-7 8-(Acetyl-dodecyl-amino)-octanoic acid methyl ester 
• 120167-84-2 bis (N-dodecyl acetamido)-1,4 butane 
• 120181-43-3 8-(Acetyl-octadecyl-amino)-octanoic acid methyl ester 
• 120167-85-3 N-[4-(Acetyl-octadecyl-amino)-butyl]-N-octadecyl-acetamide 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 2396-80-7 methyl 5-hexenoate 
• 148114-12-9 Heptanedioic acid methyl ester 1-methyl-cyclohexyl ester 
• 148114-10-7 Heptanedioic acid 1,1-dimethyl-2-phenyl-ethyl ester methyl ester 
• 54527-03-6 methyl 7-oxomyristate 
• 78632-17-4 7-(2-<2-(Acetylamino)ethyl>-4,5-dimethoxyphenyl)-7-oxoheptansaeure-methylester 

Relevant academic research and scientific papers

Stereoselective Synthesis, Configurational Assignment and Biological Evaluations of the Lipid Mediator RvD2n-3 DPA

Herein we report the first total synthesis of RvD2n-3 DPA, an endogenously formed mediator biosynthesized from the omega-3 fatty acid n-3 docosapentaenoic acid. The key steps are the Midland Alpine borane reduction, Sonogashira cross-coupling reactions, and a Z-selective alkyne reduction protocol, yielding RvD2n-3 DPA methyl ester in 13 % yield over 12 steps (longest linear sequence). The physical property data (UV chromophore, chromatography and MS/MS fragmentation) of the synthetic lipid mediator matched those obtained from biologically produced material. Moreover, synthetic RvD2n-3 DPA also carried the potent biological activities of enhancing macrophage uptake of Staphylococcus aureus and zymosan A bioparticles.

First total syntheses of the pro-resolving lipid mediators 7(S),13(R),20(S)-Resolvin T1 and 7(S),13(R)-Resolvin T4

The first total syntheses of the pro-resolving lipid mediators 7(S),13(R),20(S)-Resolvin T1 [7(S),13(R),20(S)-RvT1] and 7(S),13(R)-Resolvin T4 [7(S),13(R)-RvT4], derived from n-3 docosapentaenoic acid (n-3 DPA), are described. 7(S),13(R),20(S)-RvT1 was prepared from 7(S),13(R)-RvT4 via an enzymatic lipoxidase reaction. 7(S),13(R)-RvT4 was obtained by total synthesis where the chiral centers at C7 and C13 where introduced by a Noyori transfer hydrogenation and a chiral pool strategy respectively. Wittig reactions, Sonogashira coupling and Boland Zn(Cu/Ag) reduction were the key steps in the synthesis.

CATALYTIC CARBOXYLATION OF ACTIVATED ALKANES AND/OR OLEFINS

The present invention relates to a method of reacting starting materials with an activating group, namely alkanes carrying a leaving group and/or olefins, with carbon dioxide under transition metal catalysis to give carboxyl group-containing products. It is a special feature of the method of the present invention that the carboxylation predominantly takes place at a preferred position of the molecule irrespective of the position of the activating group. The carboxylation position is either an aliphatic terminus of the molecule or it is a carbon atom adjacent to a carbon carrying an electron withdrawing group. The course of the reaction can be controlled by appropriately choosing the reaction conditions to yield the desired regioisomer.

Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide

Catalytic carbon-carbon bond formation has enabled the streamlining of synthetic routes when assembling complex molecules. It is particularly important when incorporating saturated hydrocarbons, which are common motifs in petrochemicals and biologically relevant molecules. However, cross-coupling methods that involve alkyl electrophiles result in catalytic bond formation only at specific and previously functionalized sites. Here we describe a catalytic method that is capable of promoting carboxylation reactions at remote and unfunctionalized aliphatic sites with carbon dioxide at atmospheric pressure. The reaction occurs via selective migration of the catalyst along the hydrocarbon side-chain with excellent regio- and chemoselectivity, representing a remarkable reactivity relay when compared with classical cross-coupling reactions. Our results demonstrate that site-selectivity can be switched and controlled, enabling the functionalization of less-reactive positions in the presence of a priori more reactive ones. Furthermore, we show that raw materials obtained in bulk from petroleum processing, such as alkanes and unrefined mixtures of olefins, can be used as substrates. This offers an opportunity to integrate a catalytic platform en route to valuable fatty acids by transforming petroleum-derived feedstocks directly.

A Fluorescence-Lifetime-Based Binding Assay for Class IIa Histone Deacetylases

Class IIa histone deacetylases (HDACs) show extremely low enzymatic activity and no commonly accepted endogenous substrate is known today. Increasing evidence suggests that these enzymes exert their effect rather through molecular recognition of acetylated proteins and recruiting other proteins like HDAC3 to the desired target location. Accordingly, class IIa HDACs like bromodomains have been suggested to act as “Readers” of acetyl marks, whereas enzymatically active HDACs of class I or IIb are called “Erasers” to highlight their capability to remove acetyl groups from acetylated histones or other proteins. Small-molecule ligands of class IIa histone deacetylases (HDACs) have gained tremendous attention during the last decade and have been suggested as pharmaceutical targets in several indication areas such as cancer, Huntington's disease and muscular atrophy. Up to now, only enzyme activity assays with artificial chemically activated trifluoroacetylated substrates are in use for the identification and characterization of new active compounds against class IIa HDACs. Here, we describe the first binding assay for this class of HDAC enzymes that involves a simple mix-and-measure procedure and an extraordinarily robust fluorescence lifetime readout based on [1,3]dioxolo[4,5-f]benzodioxole-based ligand probes. The principle of the assay is generic and can also be transferred to class I HDAC8.

Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif

A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA.

Design, synthesis and preliminary bioactivity studies of 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors

Histone deacetylase (HDAC) inhibitors have emerged as a new class of anticancer agents, targeting the biological processes including cell cycle, apoptosis and differentiation. In the present study, a series of 1,3,4-thiadiazole based hydroxamic acids were developed as potent HDAC inhibitors. Some of them showed good inhibitory activity in HDAC enzyme assay and potent growth inhibition in some tumor cell lines. Among them, compound 6i (IC50 = 0.089 μM), exhibited better inhibitory effect compared with SAHA (IC50 = 0.15 μM).

Synthesis and SAR requirements of adamantane-colchicine conjugates with both microtubule depolymerizing and tubulin clustering activities

A series of analogues of conjugate 1, combining an adamantane-based paclitaxel (taxol) mimetic with colchicine was synthesized and tested for cytotoxicity in a cell-based assay with the human lung carcinoma cell line A549. The most active compounds (10 EC50 2 ± 1.0 nM, 23 EC 50 6 ± 1.4 nM, 26 EC50 5 ± 1.8 nM, 28 EC50 11 ± 1.7 nM, 30 EC50 4.8 ± 0.5 nM) were found to interfere with the microtubule dynamics in an interesting manner. Treatment of the cells with these compounds promoted disassembly of microtubules followed by the formation of stable tubulin clusters. Structure-activity relationships for the analogues of 23 revealed the sensitivity of both cytotoxicity and tubulin clustering ability to the linker length. The presence of adamantane (or another bulky hydrophobic and non-aromatic moiety) in 23 was found to play an important role in the formation of tubulin clusters. Structural requirements for optimal activity have been partially explained by molecular modeling.

Chemical synthesis of exochelins

A process for the synthetic generation of high affinity, iron binding compounds known as Exochelins, and more particularly, to a synthetic process for making Exochelins and to modifications to these newly synthesized compounds to vary their physiological properties, including applications of these newly synthesized and utile compounds for diagnosing and treating disease in mammals.

Chemical synthesis of exochelins

A process for the synthetic generation of high affinity, iron binding compounds known as Exochelins, and more particularly, to a synthetic process for making Exochelins and to modifications to these newly synthesized compounds to vary their physiological properties, including applications of these newly synthesized and utile compounds for diagnosing and treating disease in mammals.