16509-46-9

Basic information

• Product Name: (R)-linalyl acetate
• Synonyms: (R)-linalyl acetate;1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate, (3R)-;1,6-Octadien-3-ol, 3,7-dimethyl-, acetate, (3R)-;Einecs 240-575-7;laevo-linalyl acetate
• CAS NO: 16509-46-9
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.286
• EINECS: 240-575-7
• Mol File: 16509-46-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 220°C (estimate)
• Flash Point: 200.3°C
• Appearance: /
• Density: 0.8951
• Refractive Index: 1.4544 (estimate)
• CAS DataBase Reference: (R)-linalyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-linalyl acetate(16509-46-9)
• EPA Substance Registry System: (R)-linalyl acetate(16509-46-9)

Safety Data

• Hazardous Substances Data: 16509-46-9(Hazardous Substances Data)

Usage

Description

(R)-linalyl acetate, a chemical compound predominantly found in essential oils such as lavender, clary sage, and bergamot, is renowned for its delightful floral and fruity aroma. It is characterized by its potential therapeutic properties, which include anti-inflammatory, antimicrobial, calming, and sedative effects, making it a valuable compound for various applications.

Uses

Used in Perfumery and Cosmetics Industry:
(R)-linalyl acetate is used as a fragrance ingredient for its pleasant floral and fruity scent, enhancing the appeal of perfumes, soaps, and other cosmetic products.
Used in Aromatherapy:
(R)-linalyl acetate is used as a therapeutic agent for its calming and sedative properties, promoting relaxation and stress relief in aromatherapy practices.
Used in Pharmaceutical Industry:
(R)-linalyl acetate is used as a potential therapeutic compound for its anti-inflammatory and antimicrobial effects, offering health benefits in the development of medicinal products.
Used in Flavor and Food Industry:
(R)-linalyl acetate is used as a flavoring agent for its distinctive scent, adding a unique taste and aroma to the food and beverage industry.

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

Upstream product

• 108-24-7 acetic anhydride 
• 126-90-9 (S)-(+)-linalool 
• 82188-73-6 (2S,3S)-2,3-epoxygeraniol 
• 91423-25-5 (2S,3R)-3-Iodomethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 72-89-9 acetylcoenzyme A 
• 115-95-7 linalool acetate 
• 75-36-5 acetyl chloride 
• 126-91-0 linalool 

Downstream Products

• 106-25-2 Nerol 
• 106-24-1 Geraniol 
• 252857-45-7 (2RS,3R,6R)-tetrahydro-3-(N-1-naphthyl)carbamoyloxy-6-ethenyl-2-phenylselenylmethyl-2,6-dimethyl-2H-pyuran 
• 1036407-06-3 C₂₀H₃₀O₂S 
• 1036407-04-1 1-acetoxy-7-(phenylthio)iridane 
• 1036407-07-4 C₁₈H₂₅NO₄S 

Relevant articles and documents

Biogenetic studies in Syringa vulgaris L.: Synthesis and bioconversion of deuterium-labeled precursors into lilac aldehydes and lilac alcohols

Syringa vulgaris L. inflorescences were fed with aqueous solutions of regioselectively deuterated compounds assumed to be precursors of lilac aldehyde and lilac alcohol, respectively. Volatiles were extracted by stir bar sorptive extraction (SBSE) and analyzed using enantioselective multidimensional gas chromatography/mass spectrometry (enantio-MDGC/MS); deuterium-labeled lilac aldehydes and lilac alcohols were separated from unlabeled stereoisomers on a fused silica capillary column, coated with heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin (DIME-β-CD) (30%) in SE 52 (70%), as the chiral stationary phase. Feeding experiments with [5,5-2H2]mevalonic acid lactone 22 and [5,5-2H2]deoxy-D-xylose 23 indicate that the novel mevalonate independent 1-deoxy-D-xylose 5-phosphate/2C-methyl-D-erythritol 4-phosphate pathway is the dominant metabolic route for biosynthesis in lilac flowers. Additionally, bioconversion of deuterium-labeled d5-(R/S)-linalool 3, d6-(R)-linalool 21, d5-(R/S)-8-hydroxylinalool 6, d5-(R/S)-8-oxolinalool 7, d5-lilac aldehydes 8-11 and d5-lilac alcohols 12-15 into lilac during in vivo feeding experiments was investigated and the metabolic pathway is discussed. Incubation of petals with an aqueous solution of deuterated d5-(R/S)-linalool 3 indicates an autonomic terpene biosynthesis of lilac flavor compounds in the flower petals of lilac.

Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis

A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35°C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis.

Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: The linalool route

Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-α or AD-mix-β, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol.