10038-16-1

Basic information

• Product Name: METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE
• Synonyms: METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE;METHYL ESTER OF FURAN FATTY ACID
• CAS NO: 10038-16-1
• Molecular Formula: C19H32O3
• Molecular Weight: 308.45558
• Product Categories: methyl 8-(5-hexylfuran-2-yl)octanoate
• Mol File: 10038-16-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE(10038-16-1)
• EPA Substance Registry System: METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE(10038-16-1)

Safety Data

• Hazardous Substances Data: 10038-16-1(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE is used as a flavoring agent for its fruity, sweet, and slightly floral aroma, enhancing the taste and smell of various food products.
Used in Cosmetics Industry:
In cosmetics, METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE is used as a fragrance ingredient to provide a pleasant and distinctive scent to products such as perfumes, lotions, and creams.
Used in Perfumery:
METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE is used as a base note in perfumes for its long-lasting and complex aroma, contributing to the overall scent profile of the fragrance.
Used in Pharmaceutical Industry:
METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE is used as an ingredient in medications and therapeutic products, potentially benefiting from its aromatic qualities for various applications in healthcare.
Overall, METHYL 8-(5-HEXYL-2-FURYL)-OCTANOATE is a versatile chemical compound that is highly valued for its aromatic properties and is extensively utilized in the production of scented consumer goods across different industries.

Upstream product

• 4179-48-0 9,12-Dioxo-octadecanoic acid 
• 2500-56-3 methyl 8-(3-((3-pentyloxiran-2-yl)methyl)oxiran-2-yl)octanoate 
• 79760-41-1 (E)-12-Methanesulfonyloxy-octadec-9-enoic acid methyl ester 
• 67529-83-3 (E)-methyl 12-hydroxy-9-octadecenoate 
• 822-10-6 octadeca-9,11-dienoic acid methyl ester 
• 112-63-0 Methyl linoleate 
• 88919-64-6 13-Iodo-9,12-epoxyoctadecanoic acid 
• 105182-18-1 9-hydroxyoctadec-cis-12-enoic acid 
• 41989-07-5 methyl ricinoleate 
• 141-24-2 methyl ricinoleate 
• 34724-40-8 Methyl 9,10-cis-epoxy-12-oxooctadecanoate 
• 95336-35-9 6-hexyl-3-(7-methoxycarbonylheptyl)-3,6-dihydro-1,2-dioxine 
• 3047-65-2 methyl (9Z)-12-oxo-9-octadecenoate 
• 34724-40-8 methyl 12-oxo-9,10-epoxyoctadecanoate 

Downstream Products

• 3884-92-2 methyl 8-oxooctanoate 
• 50717-73-2 methyl 13-oxo-9,12-epoxytrideca-9,11-dienoate 

Relevant articles and documents

Novel Synthesis of a 1,4-Dioxo Derivative by the Reaction of a γ-Hydroxyolefinic Acid with the Silver Chromate-Iodine Complex followed by m-Chloroperbenzoic Acid Oxidation

Reaction of the complex of silver chromate and iodine with a γ-hydroxyolefinic acid (isoricinoleic) yielded 13-iodo-9,12-epoxyoctadecanoic acid, which on treatment with m-chloroperbenzoic acid gave a quantitative yield of 9,12-dioxo-octadecanoic acid.

Selective oxidations of methyl ricinoleate: Diastereoselective epoxidation with titaniumIV catalysts

Conditions were developed for the selective epoxidation of the double bond of methyl ricinoleate (1) with ethylmethyldioxirane (EMDO) to give the homoallylic epoxyalcohol, methyl (Z)-9,10-oxido-12-hydroxyoctadecanoate (2) in high yields but in poor enantiomeric excess. The diastereomeric ratio for epoxyalcohol 2 was improved modestly when t-butyl-hydroperoxide, coupled with a titanium catalyst and a D-tartrate ligand, was used as oxidizing agent. Reaction of 1 with excess EMDO resulted in the concomitant epoxidation of the double bond and oxidation of the hydroxy group of 1 to give methyl (Z)-9,10-oxido-12-oxo-octadecanoate (4), along with methyl 8-(5-hexylfuran-2-yl)octanoate (5). Alternatively, ketoepoxide 4 was prepared by dioxirane oxidation of methyl 12-oxo-(Z)-9-octadecene (3) or by treating epoxyalcohol 2 with sodium hypochlorite. The ketoepoxide 4 is acid-labile and rearranges with loss of water to give furan 5 in high yield.

Synthesis of fatty ketoesters by tandem epoxidation-rearrangement with heterogeneous catalysis

Unsaturated fatty esters can be easily transformed into ketoesters through a two-step process. The highly efficient epoxidation is carried out with tert-butyl hydroperoxide (TBHP) in α,α,α-trifluorotoluene (TFT) using a Ti-silica heterogeneous catalyst. The formed epoxide is easily rearranged by a heterogeneous Br?nsted acid, with Nafion-silica SAC13 as the most efficient one. Both reactions can be combined in a tandem process, with separation of the Ti-silica catalyst by filtration from the reaction medium and addition of the second acid catalyst to perform the second reaction. Each catalyst is separated individually and can be reused, with or without re-activation, under the same conditions to maximize the productivity.

A Convenient Route to a Linear C18 Carboxylic Acid Derivative Containing a Thiophene Ring in the Chain via a 9,10-Epithio-12-oxo Intermediate

Methyl ricinoleate (1) is oxidized to methyl 12-oxo-cis-9-octadecenoate (2) with chromic acid; epoxidation then affords methyl cis-9,10-epoxy-12-oxooctadecanoate (3).Treatment of 3 with dimethylthioformamide in presence of trifluoroacetic acid gives a mixture of methyl cis-9,10-epithio-12-oxooctadecanoate (4, 27percent), methyl 5-hexylthiophene-2-octanoate (5, 15percent), and methyl 5-hexylfuran-2-octanoate (6, 9percent).Compound 4 can be conveniently converted to 5 (83percent) by refluxing with trifluoroacetic acid in 1,2-dichloroethane.

Ricinoleic Acid to Prostaglandins-I: Synthesis of Methyl 2-(6'-Methoxycarbonylhexyl)-cyclopent-2-en-1-one-3-carboxylate and PGE1

Ricinoleic acid (1) has been converted into methyl 9,13-bisacetoxy-12-oxooctadecanoate (17), an envisaged key intermediate for the synthesis of prostanoids.As a preliminary, 17 has been transformed into the title compound (14) which has been earlier conve

Ultrasound in Lipids. Furan Formation under Ultrasonic assisted Simmons-Smith Reaction and the Effect of Cadmium and Copper as Zinc Replacers

Methyl 12-oxo-octadec-9-cis-enoate gave methyl 9,12-epoxyoctadeca-9,11-dienoate when treated with zinc or cadmium in the presence of di-iodomethane and 1,2-dimethoxyethane under concomitant ultrasonic irradiation, while under similar conditions copper caused cyclopropanation across the ethylenic bond in methyl oleate and ricinoleate.

Synthesis, Characterisation, and Transformations of a Lipid Cyclic Peroxide

Photosensitised oxidation of (9E,11E)-methyl octadeca-9,11-dienoate gave an unsaturated cyclic peroxide (epidioxide) in high yield.This was characterised spectroscopically.The peroxide underwent facile rearrangement to a furanoid ester under a variety of reaction conditions.Catalytic reduction of the unsaturated peroxide cleaved the O-O bond.Bromination and epoxidation gave dibromo and epoxy esters respectively with the peroxide group still intact.

Conversion of Linoleic and Latex Furanoid Acid to Fish C18 Dimethyl Furanoid Isomers

Methyl 9(10),12(13)-dioxo-octadecanoate (derived from methyl linoleate) and 10,13-dioxo-11-methyloctadecanoate (derived from the latex of the rubber plant) were methylated at the methylene carbons located between the two oxo-groups (using MeI, KOH in DMSO) and cyclodehydration furnished a mixture of methyl 9(10),12(13)-epoxy-10(11),11(12)-dimethyloctadeca-9(10),11(12)-dienoates and methyl 10,13-epoxy-11,12-dimethyloctadeca-10,12-dienoate respectively.