ScenTree, la nouvelle encyclopédie des ingrédients de parfum.

Exploring the branches of scent

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Crédits photo: ScenTree SAS

CAS number :

78-70-6

EINECS number :

201-134-4

FEMA number :

2635

JECFA number :

356

FLAVIS number :

02.013

Volatility :

Head/Heart

Appearance :

Colorless liquid

Price Range :

€

Stability :

Terpenes tend to polymerize by oxydation.

Density :

0.862

Molecular formula :

C₁₀H₁₈O

Molecular Weight :

154.25 g/mol

Flash Point :

177.8°F (81°C)

Log P :

2.7

Fusion Point :

177.8°F (81°C)

Boiling Point :

390.2°F (199°C)

Detection Threshold :

6 ppb (0.0000006% !)

Crédits photo: ScenTree SAS

Year of discovery :

synthesized for the first time in 1919. Levorotatory Linalool extracted from rosewood was anyway used for the first time in 1889 in Jicky, by Guerlain.

Synthesis route :

Linalool can be produced in many different ways. A first synthetic route starts from alpha-Pinene, hydrogenated in pinane catalytically. Pinane is then catalytically re-oxygenated to give a mixture of cis and trans Pinane hydroperoxides. A new catalytic hydrogenation allows to synthesize cis and trans-pinanol, separated by fractional distillation. A pyrolysis of the two separated compounds allows to obtain the two isomers of Linalool separately. Laevorotatory alpha-Pinene synthesizes dextrorotatory Linalool and dextrorotatory alpha-Pinene synthesizes laevorotatory linalool. Another synthetic route uses Myrcene, synthesized from beta-Pinene. A hydrohalogenation of Myrcene leads to the formation of geranyl, neryl and linalyl chlorides. A reaction of this mixture with copper (I) chloride gives Linalyl Acetate with a yield of about 80%. Then, Linalool is obtained by saponification. Finally, 6-methyl-5-hepten-2-one, produced in several possible ways, is converted to Linalool by reaction with ethylene, synthesizing dehydrolinalool, followed by a catalysed hydrogenation by a Lindlar palladium catalyst.

Synthesis precursor :

Linalool is the precursor to the synthesis of many compounds of olfactory interest. In an acid medium, Linalool isomerizes in Geraniol, Nerol and alpha-Terpineol. The presence of chromic acid with Linalool oxides it into Citral. Linalool Oxide is obtained by its oxidation in the presence of peracetic acid. A catalytic hydrogenation of Linalool allows to synthesize Tetrahydrolinalool. Finally, several Linalool esters exist: Linalyl Acetate remains the most widely used and renowned of all.

Isomerism :

The difference in smell between the two enantiomers of Linalool is quite small. Laevorotatory Linalool (Licareol) is woodier. In most cases, the racemic mixture of the two enantiomers (dextrorotatory Linalool is called Coriandrol) is used in perfumery. Several constitutional isomers of Linalool exist: Geraniol, Nerol, Eucalyptol and Rose Oxide are among them, but they all have very different smells.

Natural availability :

Linalool can be extracted from many natural compounds, as it is very often present in nature. The laevorotatory Linalool is present up to 85% in Camphor Wood EO and about 80% in Rosewood EO. Dextrorotatory Linalool is present up to 70% in Coriander Seed EO.

Allergens :

Linalool may provoke an allergic reaction on skin contact (redness, heat, scraching, prickling) for some people.

For more information on allergens used in perfumery, please consult our article about allergens

IFRA :

This ingredient is not restricted

Annexe I :

Maximum usage according to the product category :
Ingredients containing
Ingredient Name	CAS N°	Estimated Concentration
Geraniol	106-24-1	0,3
1-Octen-3-yl acetate	2442-10-6	0,06
l-Carvone	6485-40-1	67
Carvone	99-49-0	0,1
l-Carvone	6485-40-1	0,25
Benzyl benzoate	120-51-4	0,45
Geraniol	106-24-1	1,5
Geraniol	106-24-1	0,4

Restriction type :

SPECIFICATIONS

Cause of restriction :

SENSITIZATION

Amendment :

Comments :

Linalool and natural products known to be rich in linalool, such as bois de rose, coriander or ho wood oil, should only be used when the level of peroxides is kept to the lowest practical level. It is recommended to add antioxidants at the time of production of the raw material. The addition of 0.1% BHT or alpha-tocopherol for example has shown great efficiency. The maximum peroxide level for products in use should be 20 millimoles per liter. The (hydro)peroxide content can be determined by using the FMA method.

Quantitative usage limits :

Cat.1	Cat.2	Cat.3	Cat.4	Cat.5	Cat.6	Cat.7	Cat.8	Cat.9	Cat.10	Cat.11

Skin contact products		Non skin contact products
Leave on products	Rinse off products	Non skin contact products

Annexe I :

Some regulated synthetic ingredients are found in nature and in certain proportions in natural ingredients. This presence in nature has to be taken into account when calculating limits of use recommended by the IFRA. In case you do not know these concentrations, you can use the ones estimated by the IFRA. Here They are :

List of natural ingredients containing the material presented here
Ingredient Name	Botanical Name	CAS N°	Estimated Concentration

Annexe I :

Maximum usage according to the product category :
Ingredients containing
Ingredient Name	CAS N°	Estimated Concentration
Geraniol	106-24-1	0,3
d,l-Carvone	99-49-0	0,4
Safrole	94-59-7	80
beta-Thujone	471-15-8	8
alpha-Thujone	546-80-5	25
Thujone	76231-76-0; 1125-12-8	33
1-Octen-3-yl acetate	2442-10-6	0,06
l-Carvone	6485-40-1	67
d,l-Carvone	99-49-0	0,1
l-Carvone	6485-40-1	0,25
Geraniol	106-24-1	0,8
Benzyl benzoate	120-51-4	1,2
Geraniol	106-24-1	0,4

Restriction type :

SPECIFICATION

Cause of restriction :

DERMAL SENSITIZATION

Amendment :

38

Comments :

Oxidation products of Linalool, especially hydroperoxides, have been demonstrated to be potent sensitizers. d-, l- and dl-Linalool and natural products containing substantial amounts of it, should only be used when the level of (hydro)peroxides is kept to the lowest practical level, for instance by adding antioxidants at the time of production. The addition of 0.1% BHT or α-Tocopherol for example has shown great efficiency. Such products should have a peroxide value of less than 20 millimoles per liter, determined according to the IFRA analytical method for the determination of the peroxide value, which can be downloaded from the IFRA website (www.ifrafragrance.org). Natural products known to be rich in Linalool include bois de rose, coriander or ho wood oil.

Quantitative limit on the use :

Cat.1	Cat.2	Cat.3	Cat.4	Cat.5A	Cat.5B	Cat.5C	Cat.5D	Cat.6

Cat.7A	Cat.7B	Cat.8	Cat.9	Cat.10A	Cat.10B	Cat.11A	Cat.11B	Cat.12

Annexe I :

Some regulated synthetic ingredients are found in nature and in certain proportions in natural ingredients. This presence in nature has to be taken into account when calculating limits of use recommended by the IFRA. In case you do not know these concentrations, you can use the ones estimated by the IFRA. Here They are :

List of natural ingredients containing the material presented here
Ingredient Name	Botanical Name	CAS N°	Estimated Concentration

To learn more about IFRA's standards : https://ifrafragrance.org/safe-use/library
To find out the specificities of each category and the ingredients prohibited by IFRA, click article about l'IFRA
ScenTree is solely responsible for the information provided here.

Uses in perfumery :

Linalool gives richness and naturalness to floral notes. Used in several floral reconstructions for a fresh and floral character. Linalool is one of the most widely used molecules in perfumery.

Other names :

Coriandrol, Licareol, 3,7-dimethylocta-1,6-dien-3-ol, coriander oil terpeneless, linalol, linalyl alcohol

Other comments :

Linalool is one of the 26 allergens in perfumery. Most of the production of Linalool is made for the synthesis of vitamin E on an industrial scale.