81792-36-1

Basic information

• Product Name: 6-Acetoxy-5-Hexadecanolide
• Synonyms: 6-Acetoxy-5-Hexadecanolide;MOSQUITOOVIPOSITIONPHEROMONE;(6S)-6-[(1R)-1-(Acetyloxy)undecyl]tetrahydro-2H-pyran-2-one
• CAS NO: 81792-36-1
• Molecular Formula: C₁₈H₃₂O₄
• Molecular Weight: 312.44428
• Product Categories: insect pheromone
• Mol File: 81792-36-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 0.992±0.06 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: 6-Acetoxy-5-Hexadecanolide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Acetoxy-5-Hexadecanolide(81792-36-1)
• EPA Substance Registry System: 6-Acetoxy-5-Hexadecanolide(81792-36-1)

Safety Data

• Hazardous Substances Data: 81792-36-1(Hazardous Substances Data)

Usage

General Description

6-Acetoxy-5-Hexadecanolide, also known as alpha-Hexadecalactone, is a white crystalline solid with a sweet, creamy, and coconut-like odor. It is commonly used as a fragrance ingredient in a variety of cosmetic and personal care products, as well as in perfumes, soaps, and detergents. This chemical compound is also found in nature as a component of essential oils and is known for its long-lasting and pleasant aroma. Additionally, it is used as a flavor additive in food products and has been studied for its potential insecticidal properties. Overall, 6-Acetoxy-5-Hexadecanolide has a wide range of applications in the fragrance, cosmetic, and food industries due to its unique odor and flavor characteristics.

Upstream product

• 108-24-7 acetic anhydride 
• 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 
• 60669-22-9 n-undecyltriphenylphosphonium bromide 
• 382136-74-5 (Z)-1-benzyl-hexadecan-5-ene 
• 7056-90-8 (Z)-Hexadec-5-enoic Acid 
• 100-73-2 acrolein dimer 
• 17049-50-2 n-decyl magnesium bromide 
• 108044-61-7 (R)-(S)-1-(3,4-Dihydro-2H-pyran-2-yl)-undecan-1-ol 
• 7056-84-0 (E)-5-Hexadecenoic acid 
• 99142-11-7 (E)-Hexadec-5-enal 
• 96720-18-2 4-((2S,3S)-3-Decyl-oxiranyl)-butyric acid 
• 99142-09-3 (1R,2R,3R)-2-Decyl-3-tributylstannanyl-cyclohexanol 

Downstream Products

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

Relevant articles and documents

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.

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.

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).