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CAS number :

31906-04-4

EINECS number :

250-863-4

FEMA number :

Data not available.

JECFA number :

Data not available.

FLAVIS number :

Data not available.

Volatility :

Heart

Aspect :

Colorless liquid that crystallizes at room temperature

Price :

€€

Stability :

Aldehydes may form diethylacetals in alcoholic perfumes, with no real impact on their smell.

Density :

0,995

Molecular formula :

C₁₃H₂₂O₂

Molecular Weight :

210.32 g/mol

Flash Point :

221°F (105°C)

Log P :

2,08

Fusion Point :

-4°F (-20°C)

Boiling Point :

249.8°F (121°C)

Detection Threshold :

0.1 ng/L air

Crédits photo: ScenTree SAS

Discovery :

Discovered in 1958.

Synthesis route :

Lyral® is synthesized by a Diels-Alder reaction between Myrcenol and Acrolein (or Propenal) in the presence of a Lewis catalyst such as zinc chloride. When this reaction is performed without a catalyst and at a high temperature, it results in the formation of a mixture of two positional isomers of Lyral®, although Lyral® is still predominant (70%).

Synthesis precursor :

Lyral® forms Schiff bases in the presence of amino compounds such as Methyl Anthranilate or Indole.

Isomerism :

The positional isomer that is formed during the synthesis of Lyral® has no great olfactory difference with Lyral® used in perfumery. Geranyl Propionate is a constitutional isomer of Lyral®. Their smell is very different as Geranyl Propionate is much rosier.

Natural availability :

Lyral® is not available in its natural state.

Crédits photo: ScenTree SAS

Allergens :

Lyral® 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
Benzyl alcohol	100-51-6	0,5
Benzyl benzoate	120-51-4	7
Benzyl salicylate	118-58-1	3
Eugenol	97-53-0	0,5
Farnesol	4602-84-0	1,5
Geraniol	106-24-1	1,4
Isoeugenol	97-54-1	0,5
Benzyl alcohol	100-51-6	0,5
Benzyl benzoate	120-51-4	6
Benzyl salicylate	118-58-1	3
Eugenol	97-53-0	0,5
Farnesol	4602-84-0	1,5
Geraniol	106-24-1	1
Isoeugenol	97-54-1	0,5
Methyl eugenol	93-15-2	2,8

Restriction type :

RESTRICTION QRA

Cause of restriction :

SENSITIZATION

Amendment :

47

Comments :

The restrictions as given for the individual categories are not based on the Quantitative Risk Assessment (QRA) methodology but solely represent a pragmatic approach to address the specific situation for 3 and 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde (HMPCC). This ingredient is part of the Schiff base (Lyral-methyl anthranilate (or Lyrantion) - N°CAS :67634-12-2) and induces the application of IFRA regulations for 61,3% of the Schiff base usage. Please also refer to the IFRA Annex II for more information

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
0,02 %	0,02 %	0,2 %	0,2 %	0,2 %	0,2 %	0,02 %	0,2 %	0,2 %	0,2 %	Not restricted

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
Benzyl alcohol	100-51-6	0,1
Cinnamyl acetate	103-54-8	4,2
Geraniol	106-24-1	0,3
Benzyl salicylate	118-58-1	3
Benzyl benzoate	120-51-4	4,5
Benzyl cyanide	140-29-4	0,05
Farnesal	19317-11-4	0,02
Farnesol	4602-84-0	1,4
Eugenol	97-53-0	0,5
Isoeugenol	97-54-1	0,5
Benzyl alcohol	100-51-6	0,5
Cinnamyl acetate	103-54-8	3
Geraniol	106-24-1	1
Benzyl salicylate	118-58-1	3
Benzyl benzoate	120-51-4	6
Benzyl cyanide	140-29-4	0,03
Farnesal	19317-11-4	0,02
Farnesol	4602-84-0	1,5
Eugenol	97-53-0	0,5
Isoeugenol	97-54-1	0,5
Geraniol	106-24-1	0,4
Methyl eugenol	93-15-2	2,8

Restriction type :

RESTRICTION

Cause of restriction :

DERMAL SENSITIZATION AND SYSTEMIC TOXICITY

Amendment :

49

Comments :

The restrictions as given for the individual categories are not based on the Quantitative Risk Assessment (QRA) methodology but solely represent a pragmatic approach to address the specific situation for 3 and 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde (HMPCC). This ingredient is part of the Schiff base (Lyral-methyl anthranilate (or Lyrantion) - N°CAS :67634-12-2) and induces the application of IFRA regulations for 61,3% of the Schiff base usage. Please also refer to the IFRA Annex II for more information

Quantitative limit on the use :

Cat.1	Cat.2	Cat.3	Cat.4	Cat.5A	Cat.5B	Cat.5C	Cat.5D	Cat.6
0,02 %	0,02 %	0,1 %	0,2 %	0,2 %	0,2 %	0,2 %	0,067 %	0,2 %
Cat.7A	Cat.7B	Cat.8	Cat.9	Cat.10A	Cat.10B	Cat.11A	Cat.11B	Cat.12
0,02 %	0,02 %	0,067 %	0,2 %	0,2 %	0,2 %	0,067 %	0,067 %	91 %

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/understanding-the-ifra-standards
To find out the specificities of each category and the ingredients prohibited by IFRA, click article about l'IFRA

Uses in perfumery :

Lyral® is used in floral notes such as white flowers, lily of the valley, lilac or lily.

Other names :

Kovanol®, Leerall®, 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde, cyclohexal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, kovyral, landolal, lanyral, lydoucal, lysinal, mugonal

Other comments :

Lyral® was subject to a recall procedure in 2019, and its use will be banned in 2021. It is one of the 26 allergens in perfumery.