| Identification | More | [Name]
Linalyl acetate | [CAS]
115-95-7 | [Synonyms]
1,5-DIMETHYL-1-VINYL-4-HEXENYLACETATE
3,7-DIMETHYL-1,6-OCTADIEN-3-OL ACETATE
3,7-DIMETHYL-1,6-OCTADIEN-3-YL ACETATE
3-ACETOXY-3,7-DIMETHYL-1,6-OCTADIENE
ACETIC ACID-LINALYL ESTER
FEMA 2636
LAVANDEX(R)
LICAREOL ACETATE
LINALOOL ACETATE
LINALYL ACETATE
LINALYL ACETATE EX-BOIS DE ROSE
1,6-Octadien-3-ol,3,7-dimethyl-,acetate
6-octadien-3-ol,3,7-dimethyl-acetate
Acetic acid linalool ester
aceticacidlinaloolester
Bergamiol
Bergamol
Bergamot mint oil
bergamotmintoil
exboisderose(synthetic) | [EINECS(EC#)]
204-116-4 | [Molecular Formula]
C12H20O2 | [MDL Number]
MFCD00008907 | [Molecular Weight]
196.29 | [MOL File]
115-95-7.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS LIQUID | [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)
| [FEMA ]
2636 | [refractive index ]
n20/D 1.453(lit.)
| [Fp ]
194 °F
| [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [color ]
Clear colorless | [Odor]
at 100.00 %. sweet green citrus bergamot lavender woody | [Odor Type]
herbal | [Water Solubility ]
499.8mg/L(25 ºC) | [JECFA Number]
359 | [Merck ]
5496 | [BRN ]
1724500 | [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.
| [InChIKey]
UWKAYLJWKGQEPM-LBPRGKRZSA-N | [LogP]
3.9 at 25℃ | [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]
115-95-7(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLOURLESS LIQUID | [Uses]
In perfumery. | [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. | [Definition]
ChEBI: 3,7-dimethylocta-1,6-dien-3-yl acetate is a monoterpenoid that is the acetate ester of linalool. It forms a principal component of the essential oils from bergamot and lavender. It is an acetate ester and a monoterpenoid. It is functionally related to a linalool. | [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. | [General Description]
Linalyl acetate is a monoterpene ester mainly found in lavandula essential oil. It is used as a flavoring agent in food industries, as well as a preservative additive in cosmetics and fragrances such as soaps, colognes, perfumes, and skin lotions. | [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. | [storage]
Store at -20°C |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R38:Irritating to the skin. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37:Wear suitable gloves . | [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 |
| Questions And Answer | Back Directory | [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]
- https://pubchem.ncbi.nlm.nih.gov/compound/linalyl_acetate#section=Top
- 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
- H. Surbung, J. Panten, Common Fragrance and Flavor Materials: Preparation, Properties und Uses, 2006, ISBN 978-3-527-31315-0
- 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
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