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Eugenol

RESTRICTION
CAS
97-53-0
EC
Material type
other
Canonical source
document derived
Reverse-composition

Contained in

Other ingredients whose composition declares this material as a constituent. The percentage shown is the supplier-declared concentration in that parent.

Ingredient%Range
SANDALWOOD FRAGRANCE0.1–1%
chemicals · No. 1369

Arctander monograph

Perfume and Flavor Chemicals, page 559.

BASEtenacity · highpower · strongsteam distillationG.R.A.S.FEMA 2467
warmspicydrysharp
MW
164.21
BP
253°C
MP
Sp.Gr.
1.07
Refractive n
Rotation
Appearance

Colorless or very pale straw-colored oily liquid.

Solubility

Very slightly soluble in water, miscible with alcohol and oils, soluble in propylene glycol and in dilute aqueous alkali.

Odor

Powerful, warm-spicy, rather dry and almost sharp odor, drier and harder than that of Clove bud oil, less peppery-woody than that of Clove leaf oil.

Flavor

Warm-spicy taste, somewhat burning unless highly diluted. The taste is usually followed by a warm mouthfeel, then a burning sensation, delay and sequence depending upon the acidity or alkalinity of the saliva. Pungency depends upon the concentration of Eugenol.

Uses in perfumery

Extensively used in perfume compositions, conventionally in Carnation, for which purpose the author would recommend iso-Eugenol in spite of the almost unanimous use of Eugenol in published formulations. For incense, Oriental fragrances, Rose bases, certain types of Fougére, 'Blue-Grass' type fragrances, etc. and in all variations of modern Spice types, Eugenol is commonly used in large amounts.

Uses in flavor

For flavors, this phenol is used not only in spice complexes, but also as a modifier in Mint flavors, Nut flavors, various fruit complexes, and rare flavors such as date, etc. Eugenol is in no way a substitute for Clove bud oil in flavors, but it may add to the strength and give a clove-like note to combination-spice flavors.

Production

Produced by isolation from Clove leaf oil, or Clove stem oil, or Cinnamon leaf oil, occasionally from Bay leaf oil or from Clove bud oil. Synthesis: One method uses Guaiacol as a starting material. Although Guaiacol is present in wood tar, it is most conveniently prepared from Catechol (Pyrocatechol) by Monomethylation. Catechol is obtained from Phenol which is a coal tar derivative. When Guaiacol is reacted with Allyl chloride the Guaiacol allylether can be rearranged to Eugenol.

Document-derived

IFRA restrictions

CategoryKindMax %NotesSource
Category 1Max %0.45%
DOC
Category 2Max %0.14%
DOC
Category 3Max %1.4%
DOC
Category 4Max %2.5%
DOC
Category 5AMax %0.64%
DOC
Category 5BMax %0.64%
DOC
Category 5CMax %0.64%
DOC
Category 5DMax %0.21%
DOC
Category 6Max %0.64%
DOC
Category 7AMax %1.4%
DOC
Category 7BMax %1.4%
DOC
Category 8Max %0.21%
DOC
Category 9Max %4.9%
DOC
Category 10AMax %4.9%
DOC
Category 10BMax %18%
DOC
Category 11AMax %0.21%
DOC
Category 11BMax %0.21%
DOC
Category 12No restrictionNo Restriction
DOC

Compliance-support only. Values resolved from the current IFRA corpus; each row cites the document excerpt it came from. Not a substitute for a qualified safety assessor.

IFRA Annex I

Found naturally in

Natural complex substances (NCSs) in which this material typically occurs.

NCSBotanicalTypical %
Clove bud extractSyzygium aromaticum L.82%
Bay Leaf Oil, TerpenelessPimenta acris Kostel73%
Allspice oilPimenta officinalis Lindl.69%
Bay leaf, West Indian, oilPimenta acris Kostel40%
Carnation AbsoluteDianthus caryophyllus L.18%
Rose absoluteRosa x damascena Mill.2.3%
Jasmine officinale absoluteJasminum officinale L.2%
Rose oilRosa x damascena Mill.1.2%
Lavandin Absolute from Distillation WaterLaurus nobilis L1.1%
Armoise vulgaris oilArtemisia vulgaris L.1%
Jasmine absolute (grandiflorum)Jasminum grandiflorum L.1%
Cinnamon bark extractCinnamomum zeylanicum Blume1%
Snakeroot oilAsarum canadense L.1%
Flouve OilAnthoxanthum odorantum L.1%
Turmeric oilCurcuma longa L.1%
Artemisia arborescens extractArtemisia arborescens L.0.9%
Mace oilMyristica fragrans Houtt.0.7%
Tarragon oilArtemisia dracunculus L.0.6%
Verbena oil and absolute (Lippia citriodora Kunth.)Lippia citriodora (L.) Kunth0.55%
Basil oil, chemotype linaloolOcimum basilicum L.0.5%
Tuberose AbsolutePoliantes tuberosa L.0.5%
Cascarilla bark oilCroton eleuteria (L.) W.Wright0.4%
Cananga OilCananga odorata (Lam.) Hook. f. & Thomson (forma macrophylla Steenis)0.4%
Cistus absoluteCistus ladaniferus L.0.4%
Calamus OilAcorus calamus L.0.2%
Citronella oil, Ceylon typeCymbopogon nardus (L.) Rendle0.2%
Nutmeg ExtractMyristica fragrans Houtt.0.2%
Origanum oil (extractive)Thymus capitatus L. Hoffmanns & Link0.2%
Hyacinth AbsoluteHyacinthus orientalis L.0.2%
Lemongrass oil, East IndianCymbopogon flexuosus (Nees ex Steudel) Will. Watson0.2%
Tolu, balsam, extractMyroxylon balsamum (L.) Harms.0.12%
Osmanthus absoluteOsmanthus fragrans Lour.0.07%
Cassie absoluteVachellia farnesiana (L.) Willd.0.06%
Thyme oil, wildThymus vulgaris L.0.05%
Cassia bark extractCinnamomum cassia Blume0.03%
Peru BalsamMyroxylon balsamum (L.) Harms var. pereirae (Royle) Harms0.03%
Genet absoluteSpartium junceum L.0.02%
Identity
Aliases · 23
97-53-0Eugenol1-Allyl-4-hydroxy-3-methoxybenzene1-Hydroxy-2-methoxy-4-allylbenzene1-Hydroxy-2-methoxy-4-propenylbenzene2-Methoxy-4-allyl phenol2-Hydroxy-5-allylanisole2-Methoxy-4-(2-propenyl)phenol2-Methoxy-4-allylphenol4-Allyl-2-methoxyphenol4-Allylcatechol-2-methylether4-Allylguaiacol4-Hydroxy-3-methoxy-allylbenzene4-Allyl-2-methoxyphenol4-Allylcatechol-2-methyl ether4-Allylguaiacol4-Hydroxy-3-methoxy-1-allylbenzeneAllylguaiacolCarygenolCaryophyllic acidEugenic acidPhenol, 2-methoxy-4-(2-propenyl)-Phyllol (trade name, confusing)
Compliance note. Restriction data is sourced directly from IFRA publications and preserved with its document excerpt. Perfume Foundry is a compliance-support tool — not a substitute for a qualified safety assessor (CPSR / PIF).