7735-42-4

Usage

Uses

Used in Pharmaceutical Industry:
1,16-Hexadecanediol is used as an activator for the Mps1 MAP kinase pathway, which plays a crucial role in regulating various cellular processes, including cell division and response to stress. Its activation can have potential therapeutic implications in the treatment of certain diseases.
Used in Chemical Industry:
1,16-Hexadecanediol is used as a precursor in the synthesis of various chemical compounds, such as BChl c monoesterified with the corresponding diols. This application is particularly relevant in the development of novel materials and products with specific properties and functions.

InChI:InChI=1/C16H34O2/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18/h17-18H,1-16H2

Upstream product

• 3788-56-5 9-hydroxynonanoic acid 
• 21964-51-2 hexadeca-1,15-diene 
• 421576-50-3 1-hexadecanol-15-one 
• 506-13-8 16-hydroxyhexadecanoic acid 
• 1120-10-1 9-chlorononanoic acid 
• 1561-48-4 1,1,1,9-tetrachloro-nonane 
• 2104-19-0 azelaic monomethyl ester 
• 109-29-5 15-hexadecanolide 
• 18451-85-9 15-(methoxycarbonyl)pentadecanoic acid 
• 505-54-4 thapsic acid 
• 1593-55-1 azelaic acid monoethyl ester 
• 30993-88-5 9-acetoxy nonanoic acid 
• 19102-90-0 dimethyl hexadecanedioate 
• 36575-67-4 16-hydroxyhexadecanoic acid methyl ester 

Downstream Products

• 505-54-4 thapsic acid 
• 214753-33-0 1,1'-di-O-hexadecamethylene-3,3'-O-dibenzyldi-rac-glycerol 
• 745073-18-1 16-triphenylmethoxy-1-hexadecanol 
• 141364-77-4 tyromycin A 
• 357627-22-6 1,16-bis[4-methyl-2,5-doxo-1-p-tolylpyrrol-3-yl]hexadecane 
• 259877-81-1 4-(16-hydroxy-hexadecyloxy)-benzaldehyde 
• 1218811-08-5 16-(tert-butyldiphenylsilyloxy)-1-hexadecanol 
• 73992-43-5 hexadecane-1,16-diyl bis(4-methylbenzenesulfonate) 
• 1621861-49-1 C₅₄H₈₉NO₁₁ 

Relevant academic research and scientific papers

Synthesis of 13C-labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO213C-(CH2)n-13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

13C-labeled dicarboxylic acids HO213C-(CH2)n-13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28) have been synthesized as internal standards for LC-MS and GC-MS analysis of cutin and suberin monomer degradation by soil-based microorganisms. Different synthetic strategies had to be applied depending on the chain length of the respective synthetic target and because of economic considerations. 13C-labels were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding dicarboxylic acids. All new compounds are characterized by GC/MS, IR, and NMR methods as well as by elemental analysis.

Inhibition of bacterial growth and galactosyltransferase activity of WbwC by α, ω-bis(3-alkyl-1H-imidazolium)alkane salts: Effect of varying carbon content

A series of compounds was designed and synthesized having two imidazolium rings separated by a polymethylene spacer and having alkyl substituents on each of the imidazolium rings. The compounds were assayed for their effects on the activity of galactosyltransferase WbwC, and also on the growth of Gram-negative and Gram-positive bacteria, as well as human cells. The inhibition observed on enzyme activities and cell growth was dependent on the total number of carbons in the spacer and the alkyl substituents on the imidazolium rings. These readily synthesized, achiral compounds have potential as antimicrobial and antiseptic agents.

At Long Last: Olefin Metathesis Macrocyclization at High Concentration

Macrocyclic lactones, ketones, and ethers can be obtained in the High-Concentration Ring-Closing Metathesis (HC-RCM) reaction in high yield and selectivity at concentrations 40 to 380 times higher than those typically used by organic chemists for similar macrocyclizations. The new method consists of using tailored ruthenium catalysts together with applying vacuum to distill off the macrocyclic product as it is formed by the metathetical backbiting of oligomers. Unlike classical RCM, no large quantities of organic solvents are used, but rather inexpensive nonvolatile diluents, such as natural or synthetic paraffin oils. Moreover, use of a protecting atmosphere or a glovebox is not needed, as the new catalysts are perfectly moisture and air stable. In addition, some other cyclic compounds previously reported as unobtainable by RCM in neat conditions, or in high dilutions even, can be formed with the help of the HC-RCM method.

METHOD OF CYCLIC COMPOUNDS PRODUCTION IN OLEFINE METATHESIS REACTION AND USE OF RUTHENIUM CATALYSTS IN PRODUCTION OF CYCLIC OLEFINS IN OLEFINE METATHESIS REACTION

The invention relates to a method for the preparation of cyclic compounds in the metathesis of olefins from acyclic dienes comprising terminal and/or non-terminal C=C double bonds; the invention also relates to the use of homogeneous ruthenium complexes and homogeneous ruthenium complexes deposited on a solid support as catalysts and/or pre-catalysts for the preparation of cyclic olefins in olefin metathesis reactions. Formula (I)

METHOD FOR MANUFACTURING ALCOHOL BY HYDROGENATION OF CARBOXYLIC ACID COMPOUND AND ESTER COMPOUND

PROBLEM TO BE SOLVED: To provide a method for obtaining alcohol by hydrogenation of carboxylic acid compound efficiently by using a homogeneous system catalyst, especially a method for obtaining alcohol by hydrogenation of various carboxylic acid compound and ester compound by the homogeneous system catalyst efficiently even under alleviation condition. SOLUTION: A carboxylic acid compound and/or an ester compound is hydrogenated in a presence of a rhenium complex represented by ReXmYnZp, where X is a halogen atom, Y is same or different and each a ligand containing one or more phosphorus atom, Z is a ligand other than X and Y, m is an integer of 1 to 6, p is an integer of 0 to 2 and the sum of m, n and p is an integer of 2 to 6, and a specific alkali metal salt. COPYRIGHT: (C)2015,JPOandINPIT

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

Total synthesis and absolute configuration of epicoccamide D, a naturally occurring mannosylated 3-acyltetramic acid

The endofungal metabolite epicoccamide D was synthesised in eighteen steps and 17 % yield as the first member of the family of natural glycotetramic acids. The modular character of the synthesis opens access also to analogues featuring different sugars and spacers. It comprises several high-yielding key steps. The β-D-mannosyl group was introduced by using an α-D-glucosyl imidate donor with subsequent oxidative-reductive epimerisation at C-2′. The pyrrolidine ring was closed quantitatively by a Lacey-Dieckmann condensation of an N-(β-ketoacyl)-N-methyl alaninate. The resulting 3-[ω-(β-D- mannosyl)octadec-2-enoyl]tetramic acid was hydrogenated in the presence of the rhodium catalyst (R,R)-[Rh(Et-DUPHOS)][BF4] to establish the (7S)-stereocentre. This was possible only after blocking the acyltetramic acid as a BF2-chelate to prevent capture of the metal catalyst. We also assigned the hitherto unknown configuration of the natural product as being 5S,7S by comparison of its 13C NMR spectroscopic and optical rotation data with those of our two synthetic 5S,7R/S-diasteromers. Copyright

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

The anti-malarial activity of bivalent imidazolium salts

A series of compounds containing bivalent imidazolium rings and one triazolium analog were synthesized and evaluated for their ability to inhibit the replication of Plasmodium falciparum cultures. The activity and selectivity of the compounds for P. falciparum cultures were found to depend on the presence of electron-deficient rings that were spaced an appropriate distance apart. The activity of the compounds was not critically dependent on the nature of the linker between the electron-deficient rings, an observation that suggests that the rings were responsible for the primary interaction with the molecular target of the compounds in the parasite. The bivalent imidazolium and triazolium compounds disrupted the process whereby merozoites gain entry into erythrocytes, however, they did not appear to prevent merozoites from forming. The compounds were also found to be active in a murine Plasmodium berghei infection, a result consistent with the compounds specifically interacting with a parasite component that is required for replication and is conserved between two Plasmodium species.

Solid-phase synthesis of quinol fatty alcohols, design of N/O-substituted quinol fatty alcohols and comparative activities on axonal growth

Following the promising activity of Q2FA15 on axonal growth, two new series of N/O-substituted QFAs were synthesized, based on a SN2-type reaction. O-alkylated QFA bearing 14 carbon atoms on the side chain (n = 14) shows a very potent activity on axonal growth though lowered when compared to Q2FA15. While O-alkylation allows good retention of the biological activity, N-alkylation abolishes it nonetheless. A solid-phase-supported synthesis of Q2FA15 allowing the conception of new hybrid compounds is also described.