10251-17-9

Basic information

• Product Name: 2-NAPHTHYL CAPRYLATE
• Synonyms: OCTANOIC ACID 2-NAPHTHYL ESTER;OCTANOIC ACID BETA-NAPHTHYL ESTER;Octanoic acid, 2-naphthalenyl ester;2-NAPHTHYL OCTANOATE;2-NAPHTHYL CAPRYLATE;BETA-NAP-CAPRYLATE;BETA-NAPHTHYL CAPRYLATE;2-NAPHTHYL OCTANOATE 98%
• CAS NO: 10251-17-9
• Molecular Formula: C₁₈H₂₂O₂
• Molecular Weight: 270.37
• EINECS: 233-591-0
• Product Categories: Substrates
• Mol File: 10251-17-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 394.2 °C at 760 mmHg
• Flash Point: 130.3 °C
• Appearance: White to off-white crystalline powder
• Density: 1.039 g/cm³
• Vapor Pressure: 2.01E-06mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-NAPHTHYL CAPRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NAPHTHYL CAPRYLATE(10251-17-9)
• EPA Substance Registry System: 2-NAPHTHYL CAPRYLATE(10251-17-9)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37/39
• Hazardous Substances Data: 10251-17-9(Hazardous Substances Data)

Usage

Uses

2-Naphthyl caprylate is a chromogenic substrate. 2-Naphthyl caprylateis a chromogenic substrate for CES (carboxylesterase) and lipase. 2-naphthol is released upon hydrolyzation. By simultaneous coupling with a diazonium salt, the corresponding azo-dye is formed. Naphthols can also be detected by fluorescence analysis. Used in an colorimetric assay for the extracellular lipase of Pseudomonas fluorescens B52.

Definition

ChEBI: A octanoate ester obtained by formal condensation of the carboxy group of octanoic acid with the hydroxy group of 2-naphthol.

InChI:InChI=1/C18H22O2/c1-2-3-4-5-6-11-18(19)20-17-13-12-15-9-7-8-10-16(15)14-17/h7-10,12-14H,2-6,11H2,1H3

Synthetic route

Octanoic acid (124-07-2) + β-naphthol (135-19-3) → naphthalen-2-yl octanoate (10251-17-9)

Conditions	Yield
Stage #1: Octanoic acid With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Stage #2: β-naphthol In dichloromethane at 25℃; for 3h;	91%

naphthalen-2-yl octanoate (10251-17-9) → 1-(2-hydroxy-[1]naphthyl)-octan-1-one (95455-13-3)

Conditions	Yield
With aluminium trichloride

Upstream product

• 124-07-2 Octanoic acid 
• 135-19-3 β-naphthol 

Relevant articles and documents

Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o -NosylOXY): A recyclable coupling reagent for racemization-free synthesis of peptide, amide, hydroxamate, and ester

Ubiquitousness of amide and ester functionality makes coupling reactions extremely important. Although numerous coupling reagents are available, methods of preparation of the common and efficient reagents are cumbersome. Those reagents generate a substantial amount of chemical waste and lack recyclability. Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY), the first member of a new generation of coupling reagents, produces byproducts that can be easily recovered and reused for the synthesis of the same reagent, making the method more environmentally friendly and cost-effective. The synthesis of amides, hydroxamates, peptides, and esters using this reagent is described. The synthesis of the difficult sequences, for example, the islet amyloid polypeptide (22-27) fragment (with a C-terminal Gly, H-Asn-Phe-Gly-Ala-Ile-Leu-Gly-NH 2) and acyl carrier protein (65-74) fragment (H-Val-Gln-Ala-Ala-Ile- Asp-Tyr-Ile-Asn-Gly-OH), following the solid-phase peptide synthesis (SPPS) protocol and Amyloid β (39-42) peptide (Boc-Val-Val-IIe-Ala-OMe), following solution-phase strategy is demonstrated. Remarkable improvement is noticed with respect to reaction time, yield, and retention of stereochemistry. A mechanistic investigation and recyclability are also described.