21668-03-1

Basic information

• Product Name: monolauryl succinate
• Synonyms: monolauryl succinate;Succinic acid hydrogen 1-dodecyl ester;Succinic acid monododecyl ester
• CAS NO: 21668-03-1
• Molecular Formula: C16H30 O4
• Molecular Weight: 286.41
• Mol File: 21668-03-1.mol

Chemical Properties

• Boiling Point: 404.8°Cat760mmHg
• Flash Point: 136.6°C
• Appearance: /
• Density: 0.985g/cm³
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: monolauryl succinate(CAS DataBase Reference)
• NIST Chemistry Reference: monolauryl succinate(21668-03-1)
• EPA Substance Registry System: monolauryl succinate(21668-03-1)

Safety Data

• Hazardous Substances Data: 21668-03-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H30O4/c1-2-3-4-5-6-7-8-9-10-11-14-20-16(19)13-12-15(17)18/h2-14H2,1H3,(H,17,18)

Upstream product

• 108-30-5 succinic acid anhydride 
• 112-53-8 1-dodecyl alcohol 

Relevant articles and documents

Interfacial properties of novel surfactants based on maleic and succinic acid for potential application in personal care

Hemiesters and Hemiamides of maleic and succinic acid viz. sodium lauryl succinate (C12SE), sodium lauryl maleate (C12ME), sodium lauryl succinamide (C12SA), sodium lauryl maleamide (C12MA), sodium hexadecyl succinate (C16SE) and sodium hexadecyl maleate (C16ME) were synthesized and investigated as surfactants in the pure water and aqueous hydrotrope [sodium p-toluene sulfonate (NaPTs)] solution. The chemical structures of the prepared surfactants were established by FTIR and 1H NMR spectroscopy. The surface tension measurements depicted low CMC and a high adsorption efficiency (pC20) which is highly beneficial for creating personal care formulations. The dynamic light scattering (DLS) technique indicated the formation of larger micelles which was important for skin care as larger micelles cannot penetrate the skin layer. Moreover, these surfactants depicted good foamability and stability attributed to faster monomer adsorption and small bubble size which was preferred for cleansing application. Additionally, low protein/lipid solubilization by these surfactants indicated its mild behaviour on skin as compared to other commonly used conventional anionic [sodium lauryl sulfate (SLS)], zwitterionic [cocamidopropyl betaine (CAPB)] and nonionic [decyl glucoside (DG)] surfactants. Viscosity measurements suggested decent thickening ability of surfactants in the presence of co-surfactant like lauramine oxide. Basis of all the properties discussed, these novel hemiesters and hemiamides seem promising as surfactants for improving various characteristics in potential personal care formulations.

A comparative study of the thermal properties of homologous series of crystallisable n-alkyl maleate and itaconate monoesters

Homologous series of crystallisable C8-C22 even-numbered alkane oligomers with either maleate or itaconate monoesters end-groups were synthesized. Their total phase change enthalpy (ΔHtpce) and entropy (ΔStpce) on melting, determined by DSC, show a linear dependence with the number of carbons of the alkyl chain. A comparison was performed with corresponding succinate derivatives. The influence of the end functions on ΔStpce was examined in view of ΔStpce values estimated by the group additivity approach. A fair agreement between the experimental and the estimated entropy values could be demonstrated. Thermogravimetric analysis (TGA) has shown that the maleate oligomers are less stable than the corresponding succinate and itaconate derivatives. This behaviour could be confirmed by the activation energies of the degradation process.

Method for overcoming drug resistance of EGFR mutation and cancerous stemness of human non-small cell lung carcinoma

EGFR mutation (T790M) and cancerous stemness have shown drug resistances in human non-small-cell lung cancer (NSCLC), thus development of novel drugs in overcoming drug resistances in the NSCLC therapy is highly desired. SP101 is a novel gefitinib derivative, which can bind the ATP-binding pocket of EGFR to inhibit its EGFR kinase activity. SP101 can reduce the drug resistances of EGFR mutation (T790M) and cancerous stemness in NSCLC. SP101 induced cancer cell death and apoptosis in the gefitinib-resistant EGFR mutation (T790M) H1975 cells. SP101 inhibited phosphorylated EGFR and its downstream Survivin proteins but conversely induced Caspase 3 activation for apoptosis induction. Moreover, SP101 could decrease Oct4 protein level and reduce Survivin proteins but conversely elicited active Caspase 3 in the xenograft human H1975 lung tumors in nude mice.

Optimization of gefitinib analogues with potent anticancer activity

The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.

PHOSPHOLIPID-DETERGENT CONJUGATES AND USES THEREOF

The invention relates to novel compounds, in particular novel O-substituted phospholipids that are useful for the in vitro and in vivo delivery of drugs as well as nucleic acids into cells. The invention also relates to pharmaceutical compositions and supramolecular complexes comprising said compounds and the use of these compounds in therapeutic treatment, in particular in gene therapy.

Bioresponsive deciduous-charge amphiphiles for liposomal delivery of DNA and siRNA

Purpose: Biolabile cationic lipids were developed for efficient intracellular delivery of DNA and siRNA. Methods: The compounds have been designed starting from the membrane lipid DOPC in a way they may loose their cationic charge when exposed to an acidic and/or enzymatic stimulus, such as those met during the journey of a lipoplex in biological media. Results: They demonstrated remarkable efficiency to deliver DNA in various cell lines (BHK-21, Calu-3, NCI-H292, and A549), with no significant cytotoxicity. Furthermore, two of the compounds (carbonate-based DOPC derivatives) revealed able to deliver small interfering RNA in U87Luc and A549Luc cancer cells and to mediate a selective 70-80% knockdown of the stably transfected luciferase gene. Conclusions: The results show that the described bioresponsive cationic lipids have high DNA and siARN delivery activity which is encouraging in view of delivering a therapeutic nucleic acid to pulmonary tissues in vivo.

Dicarboxylic acid esters as transdermal permeation enhancers: Effects of chain number and geometric isomers

A series of transdermal permeation enhancers based on dicarboxylic acid esters was studied. Single-chain amphiphiles were markedly more effective than the double-chain ones. Monododecyl maleate, that is a cis derivative, was a more potent enhancer than its trans isomer, while the activity of succinates strongly depended on the donor vehicle. No difference between diastereoisomeric tartaric and meso-tartaric acid derivatives was found.

Acetazolamide-related compounds, process for their preparation, and pharmaceutical composition containing the same

Compounds related to acetazolamide and to its N-methyl derivatives, of the formulae: STR1 wherein Y is one of the following groups: STR2 R1 being a straight or branched alkylene or arylalkylene, or a phenylene, and the processes for their preparation; the compounds so obtained are inhibitors of carbonic anhydrase like acetazolamide but, in addition, they are well absorbed topically so that they can be used as drugs for treating glaucoma.

Acetazolamide-related compounds, process for their preparation, and pharmaceutical composition containing the same

Compounds related to acetazolamide and to its N--methyl derivatives, of the formulae: wherein Y is one of the following groups: R1 being a straight or branched alkylene or arylalkylene, or a phenylene, and the processes for their preparation; the compounds so obtained are inhibitors of carbonic anhydrase like acetazolamide but, in addition, they are well absorbed topically so that they can be used as drugs for treating glaucoma.