15456-69-6

Usage

Uses

Used in the Food Industry:
(Z)-6-dodecen-γ-lactone is used as a flavoring agent for its creamy, coconut-like aroma, making it a popular choice for enhancing the taste of dairy products and baked goods.
Dihydro-5-(2-octenyl)-2(3H)-furanone, commonly known as maltol, is used as a flavoring agent for its sweet, caramel-like scent, adding depth and complexity to the taste of various foods.
4-Hydroxy-γ-lactone-6-dodecenoic acid is used as a flavoring agent for its sweet, creamy aroma, which is often found naturally in fruits and dairy products, and is used to enhance the taste of food products.
Used in the Fragrance Industry:
(Z)-6-dodecen-γ-lactone, dihydro-5-(2-octenyl)-2(3H)-furanone, and 4-hydroxy-γ-lactone-6-dodecenoic acid are also used in the fragrance industry for their distinct and pleasant aromas, contributing to the creation of various scents in perfumes and other scented products.

InChI:InChI=1S/C12H20O2/c1-2-3-4-5-6-7-8-11-9-10-12(13)14-11/h6-7,11H,2-5,8-10H2,1H3/b7-6+

Upstream product

• 4762-26-9 hexyltriphenylphosphonium bromide 
• 134359-16-3 γ-(prop-2-enyl)-γ-butyrolactone 
• 5711-29-5 <9,10-2H2>-oleic acid 
• 73697-60-6 ethyl 3-(oxiran-2-yl)propanoate 
• 1968-40-7 ethyl 4-pentenoate 

Relevant academic research and scientific papers

Biosynthesis of (R)-γ-decanolactone in the yeast Sporobolomyces odorus

Addition of [9,10-2H2]oleic acid to cultures of the yeast Sporobolomyces odorus led to the formation of labeled (R)-γ-decanolactone and both enantiomers of (Z)-6-γ-dodecenolactone and γ-dodecanolactone. The labeling patterns of these lactones were estimated by a quantitative gas chromatography/mass spectrometry method, suitable for ring-labeled lactones. For the first time, there is strong evidence of oleic acid being a genuine precursor of the important aroma compound (R)-γ-decanolactone. On the basis of the presented and former results, a new biosynthetic pathway of this compound is proposed. Starting with a strict enantioselective (R)-12-hydroxylation of oleic acid as an initial step, the following β-oxidation led to the lactone. In addition, biosynthetic aspects of the formation of (Z)-6-γ-dodecenolactone and γ-dodecanolactone in S. odorus are discussed.

Identification and Synthesis of New γ-Lactones from Tuberose Absolute (Polianthes tuberosa)

Six unsaturated γ-lactones, (Z)-5-octen-4-olide (1), (Z)-5-decen-4-olide (2), (Z)-6-nonen-4-olide (3), (Z)-6-dodecen-4-olide (4), (Z,Z)-6,9-dodecadien-4-olide (5), and tuberolide (6) have been identified for the first time in tuberose absolute (from Polianthes tuberosa L.).All structures were corroborated by synthesis and all, except 3 and 4, are new.An improved method for the stereoselective synthesis of (+/-)-cis-bicyclo-non-3-en-7-one (23) by an AlCl3-catalyzed Diels-Alder reaction is reported.

Vinyl-copper derivatives-XI1 1 Part X: A. Alexakis, G. Cahiez and J.F. Normant, Synthesis, 826 (1979). Reactivity of Z-alkenyl cuprates towards various electrophiles. Application to the synthesis of some natural products

Z-Alkenylcuprates 1 and 2, prepared in situ by addition of acetylene to alkylcuprates, react with a variety of electrophiles (epoxides, carbon dioxide, aldehydes) and give conjugate addition products with α,β-unsaturated aldehydes, ketones and esters, and with activated cyclopropanes. They also add across the triple bond of some alkynes. The synthesis of natural products (7,9,22) is described.