115-95-7 Usage
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
Chemical Properties
Different sources of media describe the Chemical Properties of 115-95-7 differently. You can refer to the following data:
1. 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 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.
2. 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
Different sources of media describe the Uses of 115-95-7 differently. You can refer to the following data:
1. Linalyl Acetate ermentative production of medium or short chain length alcohol, esters and/or glucosides by metabolically engineered microorganism.
2. 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.
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 115-95-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 5 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 115-95:
(5*1)+(4*1)+(3*5)+(2*9)+(1*5)=47
47 % 10 = 7
So 115-95-7 is a valid CAS Registry Number.
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/t12-/m1/s1
115-95-7Relevant articles and documents
Acylation of linalool in the presence of polymeric pyrrolidinopyridines
Alieva,Truhmanova,Plate
, p. 1226 - 1229 (1996)
The effect of a number of factors on the efficiency of polymers containing immobilized pyrrolidinopyridine groups as polymeric activating reagents for the acylation of weakly reactive sterically hindered alcohols was studied. The conditions of the acylation of linalool with acetic anhydride in the presence of polymeric pyrrolidinopyridines were selected in such a way that the activity of polymeric systems under study was close to that of their low-molecular-weight analog, pyrrolidinopyridine (in a homogeneous medium).
Synthesis of dimeric terpenoyl glycoside side chains from cytotoxic saponins
Reicheneder, Sabine,Unverzagt, Carlo
, p. 4353 - 4357 (2004)
A bottleneck in the synthesis of the model compound 1, which bears a dimeric terpenoyl glycoside side chain from cytotoxic saponins, was overcome by the stepwise construction of the terpene part by regioselective acylation of the sugar with a functionalized phosphonate followed by a Horner-Wadsworth-Emmons olefination.
Kogami,Kumanotani
, p. 226 (1974)
Scalable green approach toward fragrant acetates
Puchl'Ová, Eva,Szolcsányi, Peter
, (2020/08/07)
The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70percent yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68percent yield from the equimolar mixture of 1-pentanol and 3-pentanol.
Unravelling transition metal-catalyzed terpenic alcohol esterification: A straightforward process for the synthesis of fragrances
Da Silva,Ayala
, p. 3197 - 3207 (2016/05/24)
Iron nitrate is a simple and commercially available Lewis acid and is demonstrated to be able to catalyze β-citronellol esterification with acetic acid, achieving high conversion and ester selectivity (ca. 80 and 70%, respectively), within shorter reaction times than those reported in the literature. To the best of our knowledge, this is the first report of a terpenic alcohol esterification reaction catalyzed by Fe(NO3)3. This process is an attractive alternative to the slow and expensive enzymatic processes commonly used in terpenic alcohol esterification. Moreover, it avoids the undesirable steps of neutralizing the products, which are always required in mineral acid-catalyzed reactions. We have performed a study of the activity of different metal Lewis acid catalysts, and found that their efficiency is directly linked to the ability of the metal cation to generate H+ ions from acetic acid ionization. The measurement of pH as well as the conversions achieved in the reactions allowed us to obtain the following trend: Fe(NO3)3 > Al(NO3)3 > Cu(NO3)2 > Ni(NO3)2 > Zn(NO3)2 > Mn(NO3)2 > Co(NO3)2 > LiNO3. The first three are recognized as stronger Lewis acids and they generate more acidic solutions. When we carried out reactions with different iron salts, it was possible to conclude that the type of anion affects the solubility of the catalyst, as well as the conversion and selectivity of the process. Fe2(SO4)3 and FeSO4 were insoluble and less active. Conversely, though they were equally soluble, Fe(NO3)3 was more selective for the formation of β-citronellyl acetate than FeCl3. We assessed the effects of the main reaction variables such as reactant stoichiometry, temperature, and catalyst concentration. In addition to citronellol, we investigated the efficiency of the iron(iii) catalyst in the solvent free esterification of several terpenic alcohols (geraniol, nerol, linalool, α-terpineol) as well as other carboxylic acids.
