85551-39-9

Basic information

• Product Name: (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide
• Synonyms: (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide;(5S,6R)-6-Acetoxy-5-hydroxyhexadecanoic acid lactone;(6S)-Tetrahydro-6-[(R)-1-(acetyloxy)undecyl]-2H-pyran-2-one;(S)-6-[(R)-1-Acetoxyundecyl]tetrahydro-2H-pyran-2-one
• CAS NO: 85551-39-9
• Molecular Formula: C₁₈H₃₂O₄
• Molecular Weight: 312.44
• Mol File: 85551-39-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 426.2°C at 760 mmHg
• Flash Point: 205.9°C
• Appearance: /
• Density: 0.992g/cm³
• Vapor Pressure: 1.8E-07mmHg at 25°C
• Refractive Index: 1.463
• CAS DataBase Reference: (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide(85551-39-9)
• EPA Substance Registry System: (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide(85551-39-9)

Safety Data

• Hazardous Substances Data: 85551-39-9(Hazardous Substances Data)

Usage

Description

(-)-(5R,6S)-6-Acetoxy-5-hexadecanolide is a 16-carbon lactone compound that belongs to the category of cyclic esters of hydroxy acids. It features an acetoxy group and a specific stereochemistry with the R configuration at the fifth carbon and the S configuration at the sixth carbon. (-)-(5R,6S)-6-Acetoxy-5-hexadecanolide is known for its natural occurrence in floral scents and is characterized by a sweet, floral, and fruity aroma.

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 
• 108-24-7 acetic anhydride 
• 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 

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.

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

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.