85551-39-9

Usage

Uses

Used in Fragrance Industry:
(-)-(5R,6S)-6-Acetoxy-5-hexadecanolide is used as a fragrance ingredient for its sweet, floral, and fruity scent. It is valued in the industry for adding complex and pleasant aromas to various products.
Used in Perfume Production:
In the perfume industry, (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide is used as a fixative agent to enhance the longevity and stability of perfumes. Its unique aroma contributes to the overall scent profile, providing a rich and appealing fragrance.
Used as a Flavoring Agent in Food Products:
(-)-(5R,6S)-6-Acetoxy-5-hexadecanolide is utilized in the food industry as a flavoring agent to impart its distinctive sweet, floral, and fruity taste to various food items, enhancing the overall flavor experience for consumers.
Used in Pharmaceutical Applications:
Due to its pleasant scent and potential bioactive properties, (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide may find use in the pharmaceutical industry for developing scent-based therapies or as an additive in medication formulations to improve patient compliance through a more appealing aroma.
Used in Cosmetics:
In the cosmetics industry, (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide can be employed for its scent to create appealing products such as lotions, creams, and other personal care items. Its potential bioactive properties may also contribute to the development of cosmetic products with added benefits for the skin.

InChI:InChI=1/C18H32O4/c1-3-4-5-6-7-8-9-10-12-16(21-15(2)19)17-13-11-14-18(20)22-17/h16-17H,3-14H2,1-2H3/t16-,17+/m0/s1

Upstream product

• 108-05-4 vinyl acetate 
• 89102-35-2 (5R*,6S*)-6-hydroxyhexadecan-5-olide 
• 108044-63-9 Acetic acid (R)-(S)-1-(3,4-dihydro-2H-pyran-2-yl)-undecyl ester 
• 693-67-4 bromoundecane 
• 108044-63-9 Acetic acid (S)-(S)-1-(3,4-dihydro-2H-pyran-2-yl)-undecyl ester 
• 108044-61-7 (R)-(S)-1-(3,4-Dihydro-2H-pyran-2-yl)-undecan-1-ol 
• 17049-50-2 n-decyl magnesium bromide 
• 100-73-2 acrolein dimer 
• 108-24-7 acetic anhydride 
• 382136-74-5 (Z)-1-benzyl-hexadecan-5-ene 
• 60669-22-9 n-undecyltriphenylphosphonium bromide 
• 7056-84-0 (E)-5-Hexadecenoic acid 
• 99142-09-3 (1S,2R,3R)-2-Decyl-3-tributylstannanyl-cyclohexanol 
• 99142-09-3 (1R,2R,3R)-2-Decyl-3-tributylstannanyl-cyclohexanol 

Downstream Products

• 89102-35-2 (5R*,6S*)-6-hydroxyhexadecan-5-olide 

Relevant academic research and scientific papers

Syntheses of 5-hexadecanolide, 6-acetoxy-5-hexadecanolide and tanikolide

Total syntheses of 5-hexadecanolide (1), 6-acetoxy-5-hexadecanolide (2) and tanikolide (3) are described. 1-Bromoundecane (4) and 5-benzyl-1-pentanal (5) were chosen as starting materials. Wittig olefination and Grignard addition 4 and 5 afforded the 16-carbon skeleton, which underwent a series of functional group transformations to give δ-lactone derivatives 1, 2 and 3.

Enzymes in organic synthesis. 27: Lipase-catalyzed synthesis of (5R,6S)-6-acetoxyalkan-5-olides - Homologues of the mosquito oviposition attractant pheromone

Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac-5 and their acetoxy derivatives rac-6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac-4 and hydrolysi

Enzymes in Organic Synthesis, 23. - Chemo-Enzymatic Synthesis of (5R,6S)-6-Acetoxyhexadecan-5-olide - The Major Component of The Mosquito Oviposition Attractant Pheromone

The methyl ester rac-4a of (5R*,6S*)-5,6-dihydroxyhexadecanoic acid was prepared by a Wittig reaction of (4-carboxybutyl)triphenylphosphonium bromide (2) with undecanal (1) followed by esterification with methanol and cis dihydroxylation with osmium(VIII) oxide / N-methylmorpholine N-oxide.After conversion of the dihydroxy ester rac-4a into (5R*,6S*)-6-hydroxyhexadecan-5-olide (rac-5) by lactonization (5R,6S)-6-acetoxyhexadecan-5-olide (6), the mosquito oviposition attractant pheromone, was obtained by an enantioselective lipase-catalyzed acetylation with vinyl acetate.In an alternative route the dihydroxy ester rac-4a was subjected to a lipase-catalyzed lactonization, which afforded as the main product (5S,6R)-6-hydroxyhexadecan-5-olide (ent-5), the enantiomer of the deacetylated pheromone. - Key Words: 5,6-Dihydroxyhexadecanoic acid derivatives / δ-Lactones / Resolution, kinetic / Lipases / Mosquito pheromone / Pheromones

Oxidative Grob Fragmentation of γ-Tributylstannyl Alcohols with a Combination of Iodosylbenzene, Dicyclohexylcarbodiimide, and Boron Trifluoride

Exposure of cyclic γ-stannyl alcohols, prepared from cyclic vinyl ketones, to a combination of iodosylbenzene, dicyclohexylcarbodiimide, and boron trifluoride-diethyl ether in dichlorometane undergoes an oxidative Grob fragmentation to give unsaturated carbonyl compounds.The dicyclohexylcarbodiimide in this reaction apparently activates iodosylbenzene and decreases Lewis acidity of boron trifluoride.The fact that the iodine(III)-mediated Grob fragmentation proceeds stereospecifically suggests the fragmentation is concerted.The fragmentation, combined with conjugate addition of (tributylstannyl)lithium and reduction or alkylation, offers an efficient procedure for the reductive and alkylative ring opening of cyclic vinyl ketones.Since cis-benzyl ether 36, after quenching of the reaction mixture with aqueous NH4Cl, afforded the chlorostannane 37, the reaction mechanism involving the formation of iodine(III) species 32 with two oxygen ligands at iodine proposed.

A SHORT, STEREODIVERGENT SYNTHESIS OF THE RACEMIC ERYTHRO AND THREO DIASTEREOMERS OF 6-ACETOXY-5-HEXADECANOLIDE, A MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE

A versatile 3-step synthesis of the title lactones has been accomplished by the stereocontrolled addition of n-decylmetallic reagents to acrolein dimer.

erythro-6-Acetoxy-5-hexadecanolide, the Major Component of a Mosquito Oviposition Attractant Pheromone

The major component of the oviposition attractant pheromone from the apical droplet of eggs of the mosquito Culex pipiens fatigans is shown by g.l.c.-mass spectrometry, microchemical methods, and synthesis to be erythro-6-acetoxy-5-hexadecanolide (1); laboratory tests have demonstrated the activity of synthetic (1).