ScenTree, la nouvelle encyclopédie des ingrédients de parfum.

Exploring the branches of scent

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Crédits photo: ScenTree SAS

CAS number :

2216-51-5

EINECS number :

218-690-9

FEMA number :

2665

JECFA number :

Data not available.

FLAVIS number :

Data not available.

Volatility :

Head

Appearance :

White solid

Price Range :

€€

Stability :

Stable in perfumes and diverse functional bases

Density :

0.89

Molecular formula :

C₁₀H₂₀O

Molecular Weight :

156.27 g/mol

Flash Point :

201.2°F (94°C)

Log P :

3.15

Fusion Point :

107.6°F (42°C)

Boiling Point :

426.2°F (219°C)

Detection Threshold :

Data not available.

Crédits photo: ScenTree SAS

Year of discovery :

Data not available.

Synthesis route :

L-Menthol can be synthesized in several ways. The first one is the result of dextrorotatory Citronellal cyclization (obtained naturally or from Myrcene), by reaction with a Lewis acid such as zinc chloride. The product obtained is a mixture of Isopulegol isomers (the laevorotatory isomer being obtained in majority). Then, the isomers of Isopulegol can be separated to recover the laevorotatory component and synthesize L-Menthol by a catalytic hydrogenation. This hydrogenation can also take place before the separation of the L-Menthol (which then, would have to be esterified). A second route of synthesis starts from laevorotatory piperitone which is hydrogenated in the presence of a Raney nickel catalyst. A mixture of L-Menthol isomers is obtained. The isomers are separated by saponification and crystallization, through an esterification reaction of the L-Menthol. A third process starts from the dextrorotatory Delta-3-Carene, present in Turpentine EO. It is isomerized into dextrorotatory 2-Carene and pyrolyzed to trans-2,8-p-Menthadiene. Isomerizing the latter synthesizes dextrorotatory Isoterpinolene. A catalytic hydrogenation gives dextrorotatory 3-para-Menthene. A final step of epoxidation, followed by a rearrangement and a catalytic hydrogenation of the compound obtained forms a mixture of Menthol, separable by fractional distillation. There is a last rather complex process starting from Thymol. This process is not detailed here.

Synthesis precursor :

Like its isomers, L-Menthol is a precursor to the synthesis of several compounds of olfactory interest. A catalytic hydrogenation of the molecule leads to the formation of para-Menthan. An oxidation by chromic acid or dehydrogenation leads to the synthesis of Menthone®. A dehydrogenation without catalyst leads to the formation of 3-para-Menthene. Finally, in the presence of an acid catalyst, an esterification with carboxylic acids synthesizes menthyl esters. An esterification with benzoic acid is used on an industrial scale for the resolution of a racemic L-Menthol.

Isomerism :

Menthol has four pairs of isomers (laevorotatory and dextrorotatory), derived from the presence of three asymmetric carbons in the molecule. Menthol, NeoMenthol, IsoMenthol and IsoneoMenthol are part of the isomers mixture. Only L-Menthol causes a sensation of cold during olfaction and is the most often used in perfumery. Citronellol, Dihydromyrcenol and Patchone® are among the L-Menthol isomers. These have very different smells from L-Menthol, as they are more floral or earthy and woody.

Natural availability :

L-Menthol is mostly produced naturally from Corn Mint EO at more than 15 000 tonnes per year. The essential oil contains up to 80% L-Menthol and can be glazed to crystallize L-Menthol, separated from the oil by centrifugation. A recrystallization is necessary to obtain a greater purity. Then, the essential oil contains 30 to 50% of Menthone® that can be mobilized again to produce hemi-synthetic L-Menthol. A catalytic hydrogenation of the oil forms L-Menthol and D-Neomenthol. The present menthyl esters are saponified and a new crystallization of L-Menthol takes place. Peppermint EO can also be used to extract natural L-Menthol.

Allergens :

This ingredient does not contain any allergen.

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

IFRA :

This ingredient is not restricted

Maximum usage according to the product category :
Ingredients containing
Ingredient Name	CAS N°	Estimated Concentration
1-Octen-3-yl acetate	2442-10-6	0,9
Geraniol	106-24-1	0,2
1-Octen-3-yl acetate	2442-10-6	0,7
Geraniol	106-24-1	0,15
Estragole	140-67-0	0,3
p-Methoxybenzaldehyde	123-11-5	0,03
Citral	5392-40-5	0,8
Citronellol	106-22-9	11
Eugenol	97-53-0	0,9
Geraniol	106-24-1	22

Cat.1	Cat.2	Cat.3	Cat.4	Cat.5	Cat.6	Cat.7	Cat.8	Cat.9	Cat.10	Cat.11
0,08 %	0,1 %	0,4 %	1,2 %	0,6 %	1,9 %	0,2 %	2 %	5 %	2,5 %	Not restricted

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

List of natural ingredients containing the material presented here
Ingredient Name	Botanical Name	CAS N°	Estimated Concentration
Mentha arvensis oil	Mentha arvenis L.	68917-18-0	0,25
Spearmint oil	Mentha spicata L.	8008-79-5	67
Spearmint oil, 60%	Mentha x gracilis Sole	91770-24-0	60,2
Spearmint oil, 80%	Mentha x gracilis Sole	91770-24-0	80
Spearmint oil, terpene-free	Mentha spicata L.	68917-46-4	85
Spearmint, Mentha spicata crispa, extract	Mentha spicata L. spicata	98561-44-5	67

Maximum usage according to the product category :
Ingredients containing
Ingredient Name	CAS N°	Estimated Concentration
p-Isopropylbenzyl alcohol	536-60-7	0,1
1-Octen-3-yl acetate	2442-10-6	0,9
Geraniol	106-24-1	0,2
7-Methoxycoumarin	531-59-9	0,01
1-Octen-3-yl acetate	2442-10-6	0,7
Geraniol	106-24-1	0,9
7-Methoxycoumarin	531-59-9	5
p-Methoxybenzaldehyde	123-11-5	1
Estragole	140-67-0	0,3
d,l-Citronellol	106-22-9	11
Citronellal	106-23-0	36
Geraniol	106-24-1	22
Farnesal	19317-11-4	0,01
Citral	5392-40-5	0,8
Eugenol	97-53-0	0,9

Cat.1	Cat.2	Cat.3	Cat.4	Cat.5A	Cat.5B	Cat.5C	Cat.5D	Cat.6
0,2 %	0,06 %	0,02 %	0,59 %	0,2 %	0,039 %	0,059 %	0,013 %	0,66 %
Cat.7A	Cat.7B	Cat.8	Cat.9	Cat.10A	Cat.10B	Cat.11A	Cat.11B	Cat.12
0,039 %	0,039 %	0,013 %	0,18 %	0,18 %	0,43 %	0,013 %	0,013 %	17 %

List of natural ingredients containing the material presented here
Ingredient Name	Botanical Name	CAS N°	Estimated Concentration
Basil oil, chemotype estragole	Ocimum basilicum L.	8015-73-4	0,5
Cistus oil	Cistus ladaniferus L.	8016-26-0	0,6
Mentha arvensis oil	Mentha arvenis L.	68917-18-0	0,25
Myrtle oil	Myrtus communis L.	8008-46-6	0,2
Origanum oil (extractive)	Thymus capitatus L. Hoffmanns & Link	8007-11-2	0,2
Parsley herb oil	Petroselinum crispum (Mill.) Nyman ex A.W.Hill	8000-68-8	0,2
Spearmint oil	Mentha spicata L.	8008-79-5	67
Spearmint oil, 60%	Mentha gracilis, Sole	91770-24-0	60
Spearmint oil, 80%	Mentha gracilis, Sole	91770-24-0	80
Spearmint oil, terpeneless	Mentha spicata L.	68917-46-4	86,5
Spearmint, Mentha spicata crispa, extract	Mentha spicata L. spicata	8008-79-5	67
Yarrow oil	Achillea millefolium L.	8022-07-9	0,2

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 :

L-Menthol is used in mint reconstitutions, in men perfumes, to boost top note.

Other names :

(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol, L-hexahydrothymol, levomenthol, L-menthacamphor, trans-para-menthan-cis-ol, (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexanol, L-peppermint camphor, 1-isopropyl-4-methyl cyclohexan-2-ol

Other comments :

L-Menthol is the most widely encountered isomer of Menthol in nature. L-Menthol is a 'trigeminal' raw material. This means that it involves the trigeminal nerve, responsible for a motor and sensitive function for humans. In the case of L-Menthol, smelling it gives the nose a sensation of cold.

Exploring the branches of scent

Year of discovery :

Data not available.

Synthesis route :

Synthesis precursor :

Isomerism :

Natural availability :

Allergens :

This ingredient does not contain any allergen.

Annexe I :

Restriction type :

RESTRICTION QRA

Cause of restriction :

SENSITIZATION

Amendment :

43

Comments :

Quantitative usage limits :

Annexe I :

Annexe I :

Restriction type :

Cause of restriction :

DERMAL SENSITIZATION AND SYSTEMIC TOXICITY

Amendment :

49

Comments :

The natural contribution of Carvone is determined by the sum of the natural contributions of each of its isomers.

Quantitative limit on the use :

Annexe I :