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ETHYL 6-HYDROXYHEXANOATE is an ethyl ester with a variety of applications in different industries. It is known for its role in the synthesis of cross-reactive carbohydrate determinants (CCDs) and other compounds, making it a versatile chemical intermediate.

5299-60-5

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5299-60-5 Usage

Chemical Description

Ethyl 6-hydroxyhexanoate is an ester with the formula C10H20O3.

Uses

Used in Allergy Diagnosis:
ETHYL 6-HYDROXYHEXANOATE is used as a reagent for the synthesis of cross-reactive carbohydrate determinants (CCDs) as tools for in vitro allergy diagnosis. This application aids in the detection and analysis of allergens, contributing to the field of medical diagnostics.
Used in Pharmaceutical Synthesis:
ETHYL 6-HYDROXYHEXANOATE is used in the preparation of N-5-Carboxypentyl-1-deoxymannojirimycin (C181150), a ligand used for the preparation of an affinity resin specific for Man9 mannosidase. This application is crucial in the development of pharmaceuticals and drug targeting.
Used in the Chemical Industry:
ETHYL 6-HYDROXYHEXANOATE is suitable for use in the synthesis of a series of model phenol carbonate ester prodrugs having fatty acid-like structures. It may also be used in the preparation of alkyl triflates and in the synthesis of ethyl 6-(trifluoromethylsulfonyloxy)hexanoate. These applications highlight its importance in the development of new chemical compounds and materials.
General Description:
ETHYL 6-HYDROXYHEXANOATE has been evaluated for its concentration in Bordeaux red wines, and a two-step preparation method via hydrolysis of e-caprolactone has been reported. This information underscores its relevance in the chemical and food industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 2786, 1973 DOI: 10.1021/jo00956a011Synthetic Communications, 11, p. 599, 1981 DOI: 10.1080/00397918108063631

Check Digit Verification of cas no

The CAS Registry Mumber 5299-60-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,2,9 and 9 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5299-60:
(6*5)+(5*2)+(4*9)+(3*9)+(2*6)+(1*0)=115
115 % 10 = 5
So 5299-60-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O3/c1-2-11-8(10)6-4-3-5-7-9/h9H,2-7H2,1H3

5299-60-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 6-hydroxyhexanoate

1.2 Other means of identification

Product number -
Other names ETHYL 6-HYDROXYHEXANOATE

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:5299-60-5 SDS

5299-60-5Relevant articles and documents

Method for preparing epsilon-caprolactone, 6-hydroxyhexanoic acid and esters thereof from tetrahydrofuranacetic acid and esters thereof

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Paragraph 0005; 0017; 0025, (2021/05/29)

The invention provides a method for preparing epsilon-caprolactone and 6-hydroxyhexanoic acid and esters thereof from tetrahydrofuranacetic acid and esters thereof, which comprises the following steps: in a solvent, in a reducing atmosphere and under the action of a catalyst, carrying out reduction reaction on tetrahydrofuranacetic acid and ester compounds thereof under the conditions that the pressure is 0.1-10MPa and the temperature is 20-200 DEG C for 0.5-48 hours, separating the catalyst, and distilling out the solvent, so that the target products epsilon-caprolactone, 6-hydroxyhexanoic acid and ester compounds of 6-hydroxyhexanoic acid are obtained. According to the method, efficient conversion of bio-based tetrahydrofuranacetic acid and esters thereof is realized under relatively mild conditions, the produced epsilon-caprolactone and 6-hydroxycaproic acid and ester compounds thereof are polymer monomers and are wide in application, and the application range of biomass is expanded; and meanwhile, the dilemma that the preparation of [epsilon]-caprolactone, 6-hydroxycaproic acid and ester thereof must depend on fossil resources is solved.

Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

Luo, Jie,Rauch, Michael,Avram, Liat,Ben-David, Yehoshoa,Milstein, David

supporting information, p. 21628 - 21633 (2021/01/11)

Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.

CYCLOHEXANE OXIDATION PROCESS BYPRODUCT DERIVATIVES AND METHODS FOR USING THE SAME

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Page/Page column 48-50, (2010/08/05)

Disclosed are ester compositions, solvents, cleaning formulations, curing agents, reactive diluent solvents, controlled acid function release agents, polyol monomers, drilling mud and methods of making and using the same. Disclosed compositions include: a) about 10 to 60 weight percent methyl hydroxycaproate; b) about 20 to 80 weight percent dimethyl adipate; c) about 1 to 15 wt % of dimethyl glutarate; d) about 0.1 to 5 wt % of dimethyl succinate; e) about 0.1 to 7 wt % of at least one cyclohexanediol; and f) less than about 20 wt% oligomeric esters.

Sunlight oxidation of alkyl aryl tellurides to the corresponding carbonyl compounds: A new carbonyl precursor

Ouchi, Akihiko,Hyugano, Takeshi,Liu, Chuanxiang

supporting information; experimental part, p. 4870 - 4873 (2010/01/06)

Alkyl aryl tellurides were efficiently transformed to the corresponding carbonyl compounds by photo-oxidation with sunlight without affecting various functional groups in the alkyl moiety. The tellurides can be used as a new carbonyl precursor, and the photolysis can be conducted without special equipment for light sources.

Facile photochemical transformation of alkyl aryl selenides to the corresponding carbonyl compounds by molecular oxygen: Use of selenides as masked carbonyl groups

Hyugano, Takeshi,Liu, Suyou,Ouchi, Akihiko

supporting information; scheme or table, p. 8861 - 8866 (2009/04/05)

(Chemical Equation Presented) Alkyl aryl selenides with and without functional groups on the alkyl group were transformed efficiently into the corresponding carbonyl compounds, particulary primary alkyl aryl selenides in good yields, by a simple photolysis in the presence of air or oxygen. This transformation can be conducted without protection of functional groups. The yield of carbonyl compounds was much affected by the solvent viscosity, reaction temperature, concentration of dissolved oxygen in the solvents, wavelength of light, and structure of the aryl substituents. The present study indicates that aryl selenides can be considered as a masked carbonyl group that can be easily converted to a carbonyl group by very mild reaction conditions even in the presence of various unprotected functional groups. Therefore, this functional group transformation can be used as an important tool in organic synthesis due to its simplicity and mild reaction condition.

Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer-Villiger reaction. Synthesis of dicarboxylic acid esters

Terent'ev, Alexander O.,Platonov, Maxim M.,Kashin, Alexey S.,Nikishin, Gennady I.

, p. 7944 - 7948 (2008/12/21)

The acid-catalyzed oxidation of cycloalkanones C5-C8 and C12 with hydrogen peroxide in alcohols was performed, and dicarboxylic acid esters were obtained as the major products in 53-70% yields. In the first step, geminal bishydroperoxides are generated from five-to-seven-membered cyclic ketones. The Baeyer-Villiger reaction is a side process accompanied by the formation of ω-hydroxycarboxylic acid esters.

A Simple and Mild Esterification Method for Carboxylic Acids Using Mixed Carboxylic-Carbonic Anhydrides

Kim, Sunggak,Lee, Jae In,Kim, Youn Chul

, p. 560 - 565 (2007/10/02)

A simple and mild esterification method using mixed carboxylic-carbonic anhydrides has been developed.Simple aliphatic carboxylic esters are prepared in high yields by the reaction of acids with equimolar amounts of chloroformates (2,2,2-trichloroethyl chloroformate is an exception) and triethylamine in the presence of a catalytic amount of 4-(dimethylamino)pyridine.Although aromatic acids give a mixture of the ester, the acid anhydride, and the carbonate under normal conditions utilized in this study, it is found that increasing the amount of 4-(dimethylamino)pyridine drastically decreases the formation of the acid anhydride and the carbonate, affording a satisfactory yield of the ester.This method reaches a limit with sterically hindered acids and the formation of the acid anhydride and the carbonate is favored.

An Oxidative Ether Cleavage with p-Nitroperbenzoic Acid

Schneider, Hans-Joerg,Ahlhelm, Alfred,Mueller, Walter

, p. 3297 - 3302 (2007/10/02)

The reaction of p-nitroperbenzoic acid in chloroform with alkyl ethers (1a, 2a) leads by selective attack at C - H bonds in α-position to the ether oxygen to hemiacetals, which decompose to aldehydes and alcohols, yielding carboxylic acids.Secondary alkoxy groups as in 3a, 4a furnish Baeyer-Villiger oxidation products of initially formed ketones. Kinetic measurements with substituted benzyl methyl ethers show a Hammett reaction constant ρ = -0.9, which is in accordance with the observed relatively small discrimination between secondary and tertiary C - H bonds.The results are compared with similar hydroxylations of alkanes and with monooxygenase reactions and point to oxenoid transition states.Radical reactions as found with some alkanes are not observed, which is shown by the small amounts of nitrobenzene ( 10percent) formed during the reaction. 13C-NMR shifts of several ethers and oxidation products are reported.

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