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Linalyl acetate

Basic information Description Reference Safety Related Supplier

Linalyl acetate Basic information

Product Name:
Linalyl acetate
CAS:
115-95-7
MF:
C12H20O2
MW:
196.29
EINECS:
204-116-4
Mol File:
115-95-7.mol
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Linalyl acetate Chemical Properties

Melting point:
85°C
Boiling point:
220 °C(lit.)
Density 
0.901 g/mL at 25 °C(lit.)
vapor density 
6.8 (vs air)
vapor pressure 
0.1 mm Hg ( 20 °C)
refractive index 
n20/D 1.453(lit.)
FEMA 
2636 | LINALYL ACETATE
Flash point:
194 °F
storage temp. 
2-8°C
form 
Liquid
color 
Clear colorless
Water Solubility 
499.8mg/L(25 ºC)
JECFA Number
359
Merck 
14,5496
BRN 
1724500
InChIKey
UWKAYLJWKGQEPM-LBPRGKRZSA-N
CAS DataBase Reference
115-95-7(CAS DataBase Reference)
NIST Chemistry Reference
1,6-Octadien-3-ol, 3,7-dimethyl-, acetate(115-95-7)
EPA Substance Registry System
Linalyl acetate (115-95-7)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38-38
Safety Statements 
26-36-37-24/25
RIDADR 
NA 1993 / PGIII
WGK Germany 
1
RTECS 
RG5910000
HS Code 
29153900
Hazardous Substances Data
115-95-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 13934 mg/kg

MSDS

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Linalyl acetate Usage And Synthesis

Description

Linalyl acetate belongs to monoterpene compound. It is a naturally occurring phytochemical found in many flowers and spice plants. It is the one of the principle components of essential oils of bergamont and lavender.1 It is a clear, colorless liquid with a boiling point of 220°C. Chemically, it is the acetate ester of linalool, and the two often occur in conjunction in the essential oils of Lavender and Lavandin.2
Linalyl acetate is an approved flavoring food additive. It is the most important fragrance ingredient for bergamot, lilac, lavender, linden, neroli, ylang-ylang, and fantasy nots. It is used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents.3,4

Reference

  1. https://pubchem.ncbi.nlm.nih.gov/compound/linalyl_acetate#section=Top
  2. A. Martin, V. Silva, L. Perez, J. Garcia-Serna, M. J. Cocero, Direct Synthesis of Linalyl Acetate from Linalool in Supercritical Carbon Dioxide: A Thermodynamic Study, Chemical Engineering & Technology, 2007, vol. 30, pp. 726-731
  3. H. Surbung, J. Panten, Common Fragrance and Flavor Materials: Preparation, Properties und Uses, 2006, ISBN 978-3-527-31315-0
  4. C. S. Letizia, J. Cocchiara, J. Lalko, A. M. Api, Fragrance material review on linalyl acetate, Food and Chemical Toxicology, 2003, vol. 41, pp. 965-976

Chemical Properties

Linalyl Acetate occurs as its isomer as the main component of lavender oil (30–60%, depending on the origin of the oil), of lavandin oil (25–50%, depending on the species), and of bergamot oil (30–45%). It has also been found in clary sage oil (up to 75%) and in a small amount in many other essential oils. Racemic linalyl acetate is a colorless liquid with a distinct bergamot–lavender odor.
Linalyl acetate
Linalyl acetate is used extensively in perfumery. It is an excellent fragrance material for, among others, bergamot, lilac, lavender, linden, neroli, ylang-ylang, and fantasy notes (particularly chypre). Smaller amounts are used in other citrus products. Since linalyl acetate is fairly stable toward alkali, it can also be employed in soaps and detergents.

Chemical Properties

Linalyl acetate has a characteristic bergamot–lavender odor and persistent sweet, acrid taste.

Occurrence

Reported found in the essential oils of bergamot, lavender, clary sage and lavandin; also identified among the constituents of the essential oils of Salvia officinalis, petitgrain, sassafras, neroli, lemon, Italian lime, jasmine, Mentha citrata, Mentha aquatica, Thymus mastichina, etc; also reported in abundant quantities in the essential oil from flowers, leaves and stems of Tagetes patula, in the distillate from leaves of Citrus aurantifolia from India, and in the essential oil of Mentha arvensis. Also reported found in citrus peel oils and juices, berries, peach, celery, tomato, cinnamon, clove, nutmeg, pepper, thymus, grape wines, avocado, mushroom, marjoram, mango, cardamom, coriander, gin, origanum, lovage, laurel, myrtle leaf, rosemary, sage and mastic gum oil.

Uses

In perfumery.

Preparation

Linalyl acetate is synthesized by two methods:
1) Esterification of linalool requires special reaction conditions since it tends to undergo dehydration and cyclization as it is an unsaturated tertiary alcohol. These reactions can be avoided as follows: esterification with ketene in the presence of an acidic esterification catalyst below 30 °C results in the formation of linalyl acetate without any by-products. Esterification can be achieved in good yield, with boiling acetic anhydride, whereby the acetic acid is distilled off as it is formed; a large excess of acetic anhydride must be maintained by continuous addition of anhydride to the still vessel. Highly pure linalyl acetate can be obtained by transesterification of tert-butyl acetate with linalool in the presence of sodium methylate and by continuous removal of the tert-butanol formed in the process.
2) Dehydrolinalool, obtained by ethynylation of 6-methyl-5-hepten-2-one, can be converted into dehydrolinalyl acetatewith acetic anhydride in the presence of an acidic esterification catalyst. Partial hydrogenation of the triple bond to linalyl acetate can be carried out with, for example, palladium catalysts deactivated with lead.

Aroma threshold values

Detection: 1 ppm

Taste threshold values

Taste characteristics at 5 ppm: floral, green, waxy, terpy, citrus, herbal and spicy nuances.

Contact allergens

Structurally close to linalool, linalyl acetate is the main component of lavender oil and is commonly used in fragrances and toiletries, and in household cleaners and detergents as well. By autoxidation, it leads mainly to hydroperoxides, with a high sensitizing potent.

Chemical Synthesis

Normally prepared by direct acetylation of linalool; another method starts from myrcene hydrochloride, anhydrous sodium acetate and acetate anhydride in the presence of a catalyst; all synthetic methods tend to avoid the simultaneous formation (because of isomerization) of terpenyl and geranyl acetate.

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Jiangxi Zhonghuan New Material Co., Ltd. Gold
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J & K SCIENTIFIC LTD.
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801
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TCI (Shanghai) Development Co., Ltd.
Tel:
021-67121386 / 800-988-0390
Email:
Sales-CN@TCIchemicals.com
Basic information Description Reference Safety Related Supplier