ScenTree, la nouvelle encyclopédie des ingrédients de parfum.

Exploring the branches of scent

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Crédits photo: ScenTree SAS

CAS number :

97-54-1

EINECS number :

202-590-7

FEMA number :

2468

JECFA number :

1260

FLAVIS number :

04.004

Volatility :

Heart

Appearance :

Pinkish liquid

Price Range :

€€

Stability :

Becomes red under the effect of light. This raw material is not convenient in every functional base : can't be used in a candle or shower gel base.

Density :

1.087

Molecular formula :

C₁₀H₁₂O₂

Molecular Weight :

164.2 g/mol

Flash Point :

233.6°F (112°C)

Log P :

2.65

Fusion Point :

Data not available.

Boiling Point :

518°F (270°C)

Detection Threshold :

100 ppb (0.00001%).

Crédits photo: ScenTree SAS

Year of discovery :

Data not available.

Synthesis route :

Isoeugenol can be produced from Eugenol. Forming sodium or potassium salts from Eugenol allows to isomerize the molecule by heating it in order to obtain Isoeugenol by an acid treatment. This isomerization can also be obtained directly by a ruthenium or rhodium catalysis.

Synthesis precursor :

Isoeugenol is a precursor to the synthesis of several compounds of olfactory interest. Catalytic hydrogenation of the molecule allows to obtain Dihydoeugenol. In the past, Vanillin was produced by an oxidation reaction on Isoeugenol. The alcohol function of the molecule can finally be used for several esterification reactions, to obtain Isoeugenyl Acetate for example.

Isomerism :

Isoeugenol has two diastereomers with a similar smell. It is the mixture of these two isomers that is the most used in perfumery. The trans isomer is nevertheless the most present in this mixture, as it is thermodynamically more stable. Eugenol is an isomer of Isoeugenol, as the double bond present in the two molecules is simply relocated from one molecule to another. Its smell is less fruity but more woody and vanillic. Styrallyl Acetate and Frambinone® are examples of constitutional isomers of Isoeugenol. Their smell is however very different.

Natural availability :

In many cases, naturally present Isoeugenol is accompanied by Eugenol, which is present in greater quantities in the following raw materials. Isoeugenol can be extracted from Clove Bud EO (1%), betel leaf (about 10%) or Ylang-Ylang Extra EO, or other fractions (up to 0.5% depending on the fractions).

Allergens :

Isoeugenol 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 benzoate	120-51-4	0,6
Benzyl cinnamate	103-41-3	0,8
Benzaldehyde	100-52-7	0,05
Benzyl alcohol	100-51-6	0,2
Benzyl benzoate	120-51-4	10,4
Benzyl cinnamate	103-41-3	2,6
Cinnamic alcohol	104-54-1	0,03
Cinnamic aldehyde	104-55-2	0,5
Eugenol	97-53-0	0,12
Isoeugenol	97-54-1	0,08
Coumarin	91-64-5	25
Dihydrocoumarin	119-84-6	2
Cuminaldehyde	122-03-2	21
Benzaldehyde	100-52-7	0,16
Benzyl benzoate	120-51-4	3,5
Cinnamic aldehyde	104-55-2	2
Coumarin	91-64-5	0,3
Eugenol	97-53-0	70
Farnesol	4602-84-0	0,12
Isoeugenol	97-54-1	0,13
Methyl eugenol	93-15-2	0,01
Estragole	140-67-0	1
Eugenol	97-53-0	58
Methyl eugenol	93-15-2	2
Eugenol	97-53-0	85,3

Restriction type :

RESTRICTION QRA

Cause of restriction :

SENSITIZATION

Amendment :

43

Comments :

The limit only applies to applications on skin exposed to sunshine, excluding rinse-off products (please refer to Table 4 of the QRA booklet for more detailed information). If combinations of phototoxic fragrance ingredients are used, the use levels have to be reduced accordingly. The sum of the concentrations of all phototoxic ingredients, expressed in % of their recommended maximum level in the consumer product shall not exceed 100. Note: See remark on phototoxic ingredients in the Introduction to the IFRA Standards (Appendix 8 to the IFRA Code of Practice) and the Standard on Citrus oil and other furocoumarins-containing essential oils.

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
0,01 %	0,01 %	0,02 %	0,02 %	0,02 %	0,2 %	0,02 %	0,02 %	0,02 %	0,02 %	Not restricted

Skin contact products		Non skin contact products
Leave on products	Rinse off products	Non skin contact products
0,4 %	X	X

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
Balsam oil, Peru	Myroxylon balsamum (L.) Harms var. pereirae (Royle) Harms	8007-00-9	15,2
Benzoin extract, Siam	Styrax tonkinensis Craib	9000-72-0	0,8
Benzoin extract, Sumatra	Styrax benzoin Dryand.	9000-05-9	0,8
Tolu, balsam, extract	Myroxylon balsamum (L.) Harms.	8024-03-1	2,6
Tolu, balsam, gum	Myroxylon balsamum (L.) Harms.	8024-03-1	0,6
Cumin seed oil	Cuminum cyminum L.	8014-13-9	21
Balsam oil, Peru	Myroxylon balsamum (L.) Harms var. pereirae (Royle) Harms	8007-00-9	0,03
Cinnamon bark extract	Cinnamomum spp.	8015-91-6	0,01
Cinnamon bark oil	Cinnamomum spp.	8015-91-6	0,02
Cinnamon leaf oil	Cinnamomum zeylanicum Blume	8015-91-6	0,13
Tolu, balsam, extract	Myroxylon balsamum (L.) Harms.	8024-03-1	0,08
Tolu, balsam, gum	Myroxylon balsamum (L.) Harms.	8024-03-1	0,02
Tuberose absolute	Poliantes tuberosa L.	8024-05-3	0,5
Tuberose concrete	Poliantes tuberosa L.	8024-05-3	0,5
Ylang ylang oil I	Cananga odorata (Lam.) Hook.f. & Thomson	8006-81-3	0,5
Ylang ylang oil II	Cananga odorata (Lam.) Hook.f. & Thomson	8006-81-3	0,5
Ylang ylang oil III	Cananga odorata (Lam.) Hook.f. & Thomson	8006-81-3	0,5
Ylang, Ylang oil extra	Cananga odorata (Lam.) Hook.f. & Thomson	8006-81-3	0,5
Ylang, Ylang oil, terpene-free	Cananga odorata (Lam.) Hook.f. & Thomson	68952-44-3	0,5

Annexe I :

Maximum usage according to the product category :
Ingredients containing
Ingredient Name	CAS N°	Estimated Concentration
Benzyl cinnamate	103-41-3	0,8
Benzyl benzoate	120-51-4	0,6
Benzyl alcohol	100-51-6	0,2
Benzaldehyde	100-52-7	0,05
Benzyl cinnamate	103-41-3	2,6
Cinnamic alcohol	104-54-1	0,04
Cinnamic aldehyde	104-55-2	0,5
Benzyl benzoate	120-51-4	10,4
Eugenol	97-53-0	0,12
Isoeugenol	97-54-1	0,08
Dihydrocoumarin	119-84-6	2
Coumarin	91-64-5	25
Cuminaldehyde	122-03-2	21
p-Isopropylbenzyl alcohol	536-60-7	0,2
Benzyl alcohol	100-51-6	0,1
Benzaldehyde	100-52-7	0,16
Cinnamyl acetate	103-54-8	1,7
Benzyl benzoate	120-51-4	3,5
Farnesol	4602-84-0	0,12
Coumarin	91-64-5	0,3
Methyl eugenol	93-15-2	0,01
Safrole	94-59-7	1,2
Eugenol	97-53-0	74
Isoeugenol	97-54-1	0,13
1-Octen-3-yl acetate	2442-10-6	0,3
Estragole	140-67-0	0,1
Methyl eugenol	93-15-2	2
Eugenol	97-53-0	51
Eugenol	97-53-0	85,3

Restriction type :

RESTRICTION

Cause of restriction :

DERMAL SENSITIZATION AND SYSTEMIC TOXICITY

Amendment :

49

Comments :

The Standard is set due to the phototoxic effects of Cumin oil. For more detailed information on the application of this Standard, please refer to the note on phototoxic ingredients in chapter 1 of the Guidance for the use of IFRA Standards. If the level of furocoumarins is unknown, the restriction level specified in this IFRA Standard applies. Combination effects of phototoxic ingredients are only taken into consideration for the furocoumarin-containing fragrance ingredients (extracts) listed in the IFRA Standard of Citrus oils and other furocoumarins containing essential oils. If combinations of furocoumarin-containing phototoxic fragrance ingredients (extracts) are used, the use levels must be reduced accordingly. The sum of the concentrations of all furocoumarin-containing phototoxic fragrance ingredients (extracts), expressed in of their recommended upper concentration level in the consumer product shall not exceed 100.

Quantitative limit on the use :

Cat.1	Cat.2	Cat.3	Cat.4	Cat.5A	Cat.5B	Cat.5C	Cat.5D	Cat.6
0,019 %	0,0057 %	0,12 %	0,11 %	0,027 %	0,027 %	0,027 %	0,009 %	0,063 %
Cat.7A	Cat.7B	Cat.8	Cat.9	Cat.10A	Cat.10B	Cat.11A	Cat.11B	Cat.12
0,22 %	0,22 %	0,009 %	0,21 %	0,21 %	0,75 %	0,009 %	0,009 %	Not restricted

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
Balsam oil, Peru	Myroxylon balsamum (L.) Harms var. pereirae (Royle) Harms	8007-00-9	15,2
Benzoin extract, Siam	Styrax tonkinensis Craib	9000-72-0	0,8
Benzoin extract, Sumatra	Styrax benzoin Dryand.	9000-05-9	0,8
Styrax extract	Liquidambar styraciflua L.	8046-19-3	1
Styrax oil, Honduras	Liquidambar styraciflua L.	8046-19-3	2,1
Tolu, balsam, extract	Myroxylon balsamum (L.) Harms.	8024-03-1	2,6
Tolu, balsam, gum	Myroxylon balsamum (L.) Harms.	8024-03-1	0,6
Cubeb oil	Piper cubeba L. f.	8007-87-2	0,1
Cumin seed oil	Cuminum cyminum L.	8014-13-9	21
Birch tar oil, rectified	Betula spp.	8001-88-5	0,9
Cade oil, rectified	Juniperus oxycedrus L.	8013-10-3	0,5
Balsam oil, Peru	Myroxylon balsamum (L.) Harms var. pereirae (Royle) Harms	8007-00-9	0,03
Cassia oil	Cinnamomum aromaticum Nees	8007-80-5	0,1
Cinnamon bark extract	Cinnamomum zeylanicum Blume	8015-91-6	0,01
Cinnamon bark oil	Cinnamomum zeylanicum Blume	8015-91-6	0,02
Cinnamon leaf oil	Cinnamomum zeylanicum Blume	8015-91-6	0,13
Jasmine officinale absolute	Jasminum officinale L.	8024-43-9	0,1
Lemongrass oil, East Indian	Cymbopogon flexuosus (Nees ex Steudel) Will. Watson	8007-02-1	0,5
Lemongrass oil, West Indian	Cymbopogon citratus (DC) Stapf.	8007-02-1	0,5
Nutmeg oil	Myristica fragrans Houtt.	8008-45-5	0,5
Tolu, balsam, extract	Myroxylon balsamum (L.) Harms.	8024-03-1	0,08
Tolu, balsam, gum	Myroxylon balsamum (L.) Harms.	8024-03-1	0,02
Tuberose absolute	Poliantes tuberosa L.	8024-05-3	1,5
Tuberose concrete	Poliantes tuberosa L.	8024-05-3	1,5
Ylang ylang oil I	Cananga odorata (Lam.) Hook. f. &Thomson oil (forma genuine Steenis)	8006-81-3	0,5
Ylang ylang oil II	Cananga odorata (Lam.) Hook. f. &Thomson oil (forma genuine Steenis)	8006-81-3	0,5
Ylang ylang oil III	Cananga odorata (Lam.) Hook. f. &Thomson oil (forma genuine Steenis)	8006-81-3	0,5
Ylang, Ylang oil extra	Cananga odorata (Lam.) Hook. f. &Thomson oil (forma genuine Steenis)	8006-81-3	0,5
Ylang, Ylang oil, terpene-free	Cananga odorata (Lam.) Hook. f. &Thomson oil (forma genuine Steenis)	68952-44-3	0,5

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 :

Isoeugenol is used in carnation, spicy and ambery notes, often combined with Eugenol. Often replaced by Acetyl-Isoeugenol, unregulated.

Other names :

2-methoxy-4-prop-1-en-2-ylphenol, 4-hydroxy-3-methoxy-1-propen-1-yl benzene, 4- hydroxy-3-methoxy-1-propenyl benzene, 4- hydroxy-3-methoxypropenyl benzene, 2-methoxy-4-(1-methylethenyl)phenol, 2-methoxy-4-(1-methylvinyl)phenol, 2-methoxy-4-(1-propenyl)phenol, 3-methoxy-4-hydroxy-1-propen-1-yl benzene, 2-methoxy-4-propenyl phenol, 4-propenyl guaiacol

Other comments :

Isoeugenol is one of the 26 allergens in perfumery. Smokier and more rounded than Eugenol, but less floral and metallic. Slightly more expensive than Eugenol.