131651-38-2

Basic information

• Product Name: (6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one
• Synonyms: (6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one;Turmeronol B
• CAS NO: 131651-38-2
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32
• Mol File: 131651-38-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one(131651-38-2)
• EPA Substance Registry System: (6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one(131651-38-2)

Safety Data

• Hazardous Substances Data: 131651-38-2(Hazardous Substances Data)

Usage

Description

(6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one is a chiral chemical compound with the molecular formula C15H20O2. It features a six-carbon chain with a methyl group at the 2nd position and a 2-hydroxy-4-methylphenyl group attached to the 6th position, which includes a ketone functional group. (6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one is known for its distinct stereochemistry, indicated by the (6S) designation, and is characterized by its sweet, floral, and fruity aroma.

Uses

Used in Flavoring Agents:
(6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one is used as a flavoring agent in the food and beverage industry to impart a sweet, floral, and fruity aroma to various products, enhancing their overall taste and appeal.
Used in Perfume and Fragrance Production:
In the perfumery and fragrance industry, (6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one is utilized for its pleasant scent, contributing to the creation of long-lasting and stable odors in consumer products.
Trade Name:
(6S)-2-Methyl-6-(2-hydroxy-4-methylphenyl)-2-hepten-4-one is also known by the trade name Sylkolide, which highlights its value in the market for its ability to provide enduring and stable fragrances in a wide range of applications.

Upstream product

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Relevant articles and documents

Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/ Z-Isomerization, Regioselectivity, and Synthetic Applications

The chiral bisphosphine dioxide-catalyzed asymmetric conjugate reduction of acyclic β,β-disubstituted α,β-unsaturated ketones with trichlorosilane affords saturated ketones having a stereogenic carbon center at the carbonyl β-position with high enantioselectivities. Because the E/Z-isomerizations of enone substrates occur concomitantly, reduction products with the same absolute configurations are obtained from either (E)- or (Z)-enones. Conjugate reduction is accelerated in the presence of an electron-rich aryl group at the β-position of the enone owing to its carbocation-stabilizing ability. Computational studies were also conducted in order to elucidate the origin of the observed enantioselectivity. The regio- and enantioselective reductions of dienones were realized and applied to the syntheses of ar-turmerone, turmeronol A, mutisianthol, and jungianol, which are optically active sesquiterpenes.

Use of 1,1'-binaphthalene-8,8'-diol as a chiral auxiliary for asymmetric Michael addition. Application to the syntheses of turmeronol A and B

Highly diastereoselective Michael addition of lithium diorganocuprates to the half-ester of 1,1'-binaphthalene-8,8'-diol gave β-substituted esters with high enantiomeric excess after methanolysis. The optically active phenolic sesquiterpenes turmeronol A (1) and B (2) have been synthesized using this reaction as a key step.