1207204-70-3

Basic information

• Product Name: (S)-1-(furan-3-yl)ethan-1-ol
• Synonyms: (S)-1-(furan-3-yl)ethan-1-ol
• CAS NO: 1207204-70-3
• Molecular Weight: 112.128
• Mol File: 1207204-70-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-1-(furan-3-yl)ethan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(furan-3-yl)ethan-1-ol(1207204-70-3)
• EPA Substance Registry System: (S)-1-(furan-3-yl)ethan-1-ol(1207204-70-3)

Safety Data

• Hazardous Substances Data: 1207204-70-3(Hazardous Substances Data)

Usage

Description

(S)-1-(furan-3-yl)ethan-1-ol, commonly known as sotolone, is an organic compound classified under the furan derivatives. It exists as a colorless liquid with a distinct sweet, caramel-like aroma. (S)-1-(furan-3-yl)ethan-1-ol is naturally present in a variety of foods and beverages, such as coffee, bread, beer, and certain types of honey, contributing to their unique flavors and scents. Beyond its natural occurrence, sotolone is also synthetically produced and utilized as a flavoring agent in the food industry. Its potential therapeutic effects have been a subject of interest, with studies exploring its ability to inhibit advanced glycation end-products and its anti-inflammatory properties. Furthermore, research has investigated sotolone's potential to enhance cognitive function and memory.

Uses

Used in Flavor and Fragrance Industry:
(S)-1-(furan-3-yl)ethan-1-ol is used as a flavoring agent for its sweet, caramel-like odor, adding depth and complexity to the taste and aroma profiles of various foods and beverages. Its natural occurrence in coffee, bread, beer, and honey makes it a suitable additive to mimic or enhance these familiar flavors.
Used in Pharmaceutical Applications:
Sotolone is investigated for its potential therapeutic uses, particularly in inhibiting the formation of advanced glycation end-products, which are associated with aging and chronic diseases like diabetes. This application type is significant for developing treatments that could slow down or prevent the progression of these conditions.
Used in Anti-Inflammatory Applications:
Due to its anti-inflammatory properties, (S)-1-(furan-3-yl)ethan-1-ol is studied for its potential use in reducing inflammation, which could be beneficial in treating a range of inflammatory diseases and conditions.
Used in Cognitive Function and Memory Enhancement:
Sotolone's potential to improve cognitive function and memory is being explored, making it a candidate for applications in the development of treatments for cognitive decline and related disorders.

Upstream product

• 498-60-2 furan-3-carboxaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 13129-26-5 1-(3'-furyl)-ethanol 
• 14313-09-8 3-acetylfuran 

Downstream Products

• 85828-09-7 (-)-α-(2-Furyl)ethyl acetate 

Relevant articles and documents

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.

Enantioselective addition of dialkylzincs to aldehydes catalyzed by (-)-MITH

An effective catalytic system that imparts high enantioselectivity has been disclosed for the synthesis of optically active alcohols, which may undergo further chemical transformations. The enantioselective alkylation of aldehydes with dialkylzincs to afford the corresponding optically active alcohols with excellent enantioselectvities has been achieved in the presence of 0.1-0.5 mol % of the camphor-derived chiral ligand (-)-2-exo-morpholinoisobornane-10-thiol (MITH) (1) at room temperature or at 0 °C. I zinc so too: The enantioselective alkylation of aldehydes with dialkylzincs yielded the desired alcohol products with up to 99 % ee in the presence of 0.1-0.5 mol % of ligand (-)-2-exo-morpholinoisoborne-10-thiol (1) at room temperature or at 0°C. Copyright

The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications

The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.