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CAPRYLIC ACID N-SUCCINIMIDYL ESTER is a chemical compound derived from caprylic acid and N-succinimide. It is a versatile reagent used in various chemical and pharmaceutical applications due to its unique properties and reactivity.

14464-30-3

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14464-30-3 Usage

Uses

Used in Pharmaceutical Industry:
CAPRYLIC ACID N-SUCCINIMIDYL ESTER is used as an intermediate for the synthesis of various pharmaceutical compounds. Its ability to react with different functional groups makes it a valuable building block in the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, CAPRYLIC ACID N-SUCCINIMIDYL ESTER is used as a reagent for the preparation of various organic compounds. Its high reactivity and specificity in reactions contribute to the synthesis of complex molecules with desired properties.
Used in Eliglustat Preparation:
CAPRYLIC ACID N-SUCCINIMIDYL ESTER is used as a key intermediate in the preparation of eliglustat and its tartrate form. Eliglustat is a drug used for the treatment of Gaucher disease, a genetic disorder that affects the body's ability to break down a certain type of fat.

Check Digit Verification of cas no

The CAS Registry Mumber 14464-30-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,4,6 and 4 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 14464-30:
(7*1)+(6*4)+(5*4)+(4*6)+(3*4)+(2*3)+(1*0)=93
93 % 10 = 3
So 14464-30-3 is a valid CAS Registry Number.

14464-30-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(Octanoyloxy)-2,5-pyrrolidinedione

1.2 Other means of identification

Product number -
Other names octanoic acid N-hydroxysuccinimide ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14464-30-3 SDS

14464-30-3Relevant articles and documents

Expeditious synthesis and assembly of sub-100 nm hollow spherical gold nanoparticle superstructures

Song, Chengyi,Zhao, Gongpu,Zhang, Peijun,Rosi, Nathaniel L.

, p. 14033 - 14035 (2010)

Sub-100 nm hollow gold nanoparticle superstructures were prepared in a direct one-pot reaction. A gold-binding peptide conjugate, C6-AA- PEPAu (PEPAu = AYSSGAPPMPPF), was constructed and used to direct the simultaneous synthesis and assembly of gold nanoparticles. Transmission electron microscopy and electron tomography revealed that the superstructures are uniform and consist of monodisperse gold nanoparticles arranged into a spherical monolayer shell.

Isolation and synthesis of N-acyladenine and adenosine alkaloids from a southern Australian marine sponge, Phoriospongia sp.

Farrugia, Michelle,Trotter, Nicholas,Vijayasarathy, Soumini,Salim, Angela A.,Khalil, Zeinab G.,Lacey, Ernest,Capon, Robert J.

, p. 5902 - 5904 (2014)

Chemical fractionation of the southern Australian marine sponge Phoriospongia sp. (CMB-03107) yielded phorioadenine A (1) as a nematocidal agent and the first reported example of a 6-N-acyladenine natural product. The structure of 1 was confirmed by spectroscopic analysis and the chemical synthesis of racemic (1a) and enantiomeric (1b) analogues. HPLC-ESIMS analysis of the crude sponge extract with comparisons to the synthetic 6-N-acyladenosine 2a provided evidence that the biosynthetically related adenosine, phorioadenosine A (2), was present as a trace co-metabolite. The rare starfish metabolite asterubine (3) was also isolated as a co-metabolite, and its structure confirmed by spectroscopic analysis and chemical synthesis. Biological investigations confirmed that natural products 1-3 and synthetic analogues 1a-e and 2a were not cytotoxic to multiple mammalian cancer cell lines, or Gram-positive or -negative bacteria. Nematocidal activity (inhibition of larval development of Haemonchus contortus) detected in the Phoriospongia sp. extract was attributed to 1 (LD9931 μg/mL), with preliminary structure-activity relationship investigations confirming the importance of the N-acyl side chain.

N-hydroxysuccinimide-promoted oxidation of primary alcohols and aldehydes to form active esters with hypervalent(III) iodine

Wang, Naiwei,Liu, Renhua,Xu, Qing,Liang, Xinmiao

, p. 566 - 567 (2006)

A simple, mild, and efficient method for the conversion of primary alcohols and aldehydes to N-hydroxysuccinimide esters with (diacetoxyiodo)benzene in high yield is developed. N-Hydroxysuccinimide acts not only as an esterification partner but also as an activator of PhI(OAc)2 in this reaction. Copyright

Synthesis and Characterization of Fatty Acid Grafted Chitosan Polymer and Their Nanomicelles for Nonviral Gene Delivery Applications

Sharma, Divya,Singh, Jagdish

, p. 2772 - 2783 (2017)

The aim of this study was to synthesize and characterize fatty acid-grafted-chitosan (fatty acid-g-CS) polymer and their nanomicelles for use as carriers for gene delivery. CS was hydrophobically modified using saturated fatty acids of increasing fatty acyl chain length. Carbodiimide along with N-hydroxysuccinimide was used for coupling carboxyl group of fatty acids with amine groups of CS. Proton nuclear magnetic resonance and Fourier transform infrared spectroscopy were used to quantify fatty acyl substitution onto CS backbone. The molecular weight distribution of the synthesized polymers was determined using size exclusion high performance liquid chromatography and was found to be in range of the parent CS polymer (~50 kDa). The critical micelle concentration (cmc) of the polymers was determined using pyrene as a fluorescent probe. The cmc was found to decrease with an increase in fatty acyl chain length. The amphiphilic fatty acid-g-CS polymers self-assembled in an aqueous environment to form nanomicelles of ~200 nm particle size and slightly positive net charge due to the cationic nature of free primary amino groups on CS molecule. These polymeric nanomicelles exhibited excellent hemo- and cytocompatibility, as evaluated by in vitro hemolysis and MTT cell viability assay, respectively, and showed superior transfection efficiency compared to unmodified chitosan and naked DNA. The surface of these nanomicelles can be further modified with ligands allowing for selective targeting, enhanced cell binding, and internalization. These nanomicelles can thus be exploited as potential nonviral gene delivery vectors for safe and efficient gene therapy.

SYNTHESIS AND BIOLOGICAL ACTIVITIES OF SOME PEPTIDOGLYCAN MONOMER DERIVATIVES

Suskovic, B.,Vajtner, Z.,Naumski, R.

, p. 8407 - 8416 (1991)

N-acyl derivatives and N-acetyl-glucosaminyl-β-(1->4)-N-acetyl-muramoyl-L-alanyl-D-isoglutaminyl-L-meso-diaminopimelyl-(D-amide)-(L)-D-alanyl-D-alanine (peptidoglycan monomer, PGM) complexes with some bivalent metals were prepared and their immunomodulatory activities examined.

Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis

Aldrich, Courtney C.,Baran, Marzena,Boshoff, Helena I. M.,Fu, Peng,Grimes, Kimberly D.,Sibbald, Paul A.,Wilson, Daniel J.

, (2020/06/29)

Lipid metabolism in Mycobacterium tuberculosis (Mtb) relies on 34 fatty acid adenylating enzymes (FadDs) that can be grouped into two classes: fatty acyl-CoA ligases (FACLs) involved in lipid and cholesterol catabolism and long chain fatty acyl-AMP ligases (FAALs) involved in biosynthesis of the numerous essential and virulence-conferring lipids found in Mtb. The precise biochemical roles of many FACLs remain poorly characterized while the functionally non-redundant FAALs are much better understood. Here we describe the systematic investigation of 5′-O-[N-(alkanoyl)sulfamoyl]adenosine (alkanoyl adenosine monosulfamate, alkanoyl-AMS) analogs as potential multitarget FadD inhibitors for their antitubercular activity and biochemical selectivity towards representative FAAL and FACL enzymes. We identified several potent compounds including 12-azidododecanoyl-AMS 28, 11-phenoxyundecanoyl-AMS 32, and nonyloxyacetyl-AMS 36 with minimum inhibitory concentrations (MICs) against M. tuberculosis ranging from 0.098 to 3.13 μM. Compound 32 was notable for its impressive biochemical selectivity against FAAL28 (apparent Ki = 0.7 μM) versus FACL19 (Ki > 100 μM), and uniform activity against a panel of multidrug and extensively drug-resistant TB strains with MICs ranging from 3.13 to 12.5 μM in minimal (GAST) and rich (7H9) media. The SAR analysis provided valuable insights for further optimization of 32 and also identified limitations to overcome.

Deuterated eliglustat racemate synthetic process

-

Paragraph 0038; 0072; 0073; 0074, (2019/01/16)

The invention belongs to the technical field of pharmaceutical synthesis, and in particular relates to a deuterated eleustat racemate synthetic process. The process includes a synthetic method of a key intermediate 2,3-dihydro-1,4-benzdioxan2,2,3,3-d4-6-a

Synthesis of UDP-glucose: N-acylsphingosine glucosyl transferase inhibitors

-

Page/Page column 24, (2017/02/09)

Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

Method for preparing tartrate EGS

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Paragraph 0096; 0097; 0098; 0099; 0100, (2017/07/31)

The invention discloses a method for preparing tartrate EGS. The method comprises the following steps: (1) subjecting EGS-A4 represented by a formula shown in the description and trifluoroacetic acid to a reduction reaction in an inert atmosphere in the presence of a catalyst, so as to obtain EGS-SMA represented by a formula shown in the description after the reaction is complete, wherein the catalyst is Pd/C or the like; (2) preparing EGS-SMB represented by a formula shown in the description from EGS-B0 represented by a formula shown in the description, an acid binding agent and EGS-B0' represented by a formula shown in the description, then, subjecting the EGS-SMB to a reaction with the EGS-SMA so as to obtain EGS-API represented by a formula shown in the description, and then, subjecting the EGS-API to a reaction with L-tartaric acid, thereby obtaining the final product. The method can adapt to large-scale production processes and has the process characteristics of wide source, low cost and stable yield, and the yield of the obtained tartrate EGS is remarkably higher than that of the existing methods and can reach 95%, so that the method has an important application value.

SURFACE FUNCTIONALIZED, HOST-GUEST POLYMER NANO-ASSEMBLIES AND METHODS THEREOF

-

Paragraph 00118; 00122, (2015/09/28)

The invention generally relates to polymer-based nano-structures. More particularly, the invention relates to novel, surface-functionalized, guest-host polymer nano-assemblies and nano-delivery vehicles useful in diverse fields including drug delivery, diagnostics and specialty materials. The nano-assemblies and nano-delivery vehicles of the invention are afforded via simplify and reliable approaches.

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