Eugenol acetate

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  • Identifiers

    CAS number
    93-28-7

    Molecular formula
    C12H14O3

    SMILES
    CC(=O)OC1=C(C=C(C=C1)CC=C)OC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1535.0
    • Carbowax: 2263.0

  • Odor profile

    Sweet 79.73%
    Spicy 75.27%
    Woody 72.78%
    Fruity 67.4%
    Floral 66.96%
    Clove 56.12%
    Balsamic 50.69%
    Warm 42.48%
    Powdery 41.45%
    Dry 38.56%

    Scent© AI

  • Properties

    XLogP3-AA
    2.3

    Molecular weight
    206.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    277°C

    Melting point expt.

    • 30 - 31 °C

    Flash point est.
    120.91 ˚C

    Solubility expt.

    • Insoluble in water; Soluble in ether, fixed oils
    • Soluble (in ethanol)

  • Synonyms

    • Eugenol acetate
    • EUGENYL ACETATE
    • Acetyleugenol
    • 93-28-7
    • Aceteugenol
    • 4-Allyl-2-methoxyphenyl acetate
    • Acetyl eugenol
    • 4-Allyl-2-methoxyphenol acetate
    • 1,3,4-Eugenol acetate
    • Aceto eugenol
    • Phenol, 2-methoxy-4-(2-propenyl)-, acetate
    • Phenol, 4-allyl-2-methoxy-, acetate
    • FEMA No. 2469
    • 1-Acetoxy-2-methoxy-4-allylbenzene
    • 2-Methoxy-4-(2-propenyl)phenyl acetate
    • NSC 1242
    • EINECS 202-235-6
    • 2-Methoxy-4-(2-propen-1-yl)phenyl acetate
    • (2-methoxy-4-prop-2-enylphenyl) acetate
    • UNII-V9OSB376X8
    • BRN 1964745
    • V9OSB376X8
    • 1,4-Eugenol acetate
    • AI3-01780
    • NSC-1242
    • Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-acetate
    • CHEMBL108299
    • DTXSID5052624
    • CHEBI:34522
    • 3-06-00-05029 (Beilstein Handbook Reference)
    • Acetic acid 4-allyl-2-methoxy-phenyl ester
    • Acetat
    • acetate phenol
    • acet eugenol
    • MFCD00026191
    • 4-allyl-2-methoxy-
    • acetyl eugenol fg 25
    • 2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
    • bmse010055
    • Eugenol acetate (Standard)
    • 1-acetate AI3-01780
    • BRN 1964745 Phenol
    • BIDD:ER0670
    • EUGENYL ACETATE [FCC]
    • SCHEMBL112232
    • 2-methoxy-4-(2-propenyl)-
    • EUGENOL ACETATE [FHFI]
    • DTXCID9031197
    • FEMA 2469
    • WLN: 1VOR BO1 D2U1
    • 2-Methoxy-4-(prop-2-enyl)phenyl Acetate (Acetyleugenol)
    • Eugenyl acetate, >=98%, FCC
    • NSC1242
    • Acetyleugenol, analytical standard
    • 2-methoxy-4-(2-propen-1-yl)-
    • HY-W014612R
    • 11EUA7501
    • BDBM50240728
    • s9377
    • 3-(4-acetoxy-3-methoxyphenyl)propene
    • AKOS015837940
    • Eugenyl acetate, >=98%, FCC, FG
    • CCG-266622
    • CS-W015328
    • FA11965
    • HY-W014612
    • CHEMBL108299 V9OSB376X8
    • AS-56614
    • 1-(3-methoxy-4-acetoxyphenyl)-2-propene
    • 1-Acetoxy-2-methoxy-4-allylbenzene Phenol
    • acetate NSC 1242 UNII-V9OSB376X8
    • E0210
    • NS00012476
    • Eugenol acetate 1000 microg/mL in Acetonitrile
    • acetate 2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
    • Q27116129
    • Z28076598
    • CHEBI:34522 SCCDQYPEOIRVGX-UHFFFAOYSA-N (2-methoxy-4-prop-2-enylphenyl)
    • 202-235-6
    • InChI=1/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H

  • Applications

    Eugenyl acetate (CAS 93-28-7) is the naturally occurring ester of eugenol and acetic acid, present in clove, cinnamon and basil oils; it is widely employed as a key fragrance ingredient in fine perfumes, soaps, detergents, personal-care products and cosmetics because of its warm spicy-sweet odour and excellent substantivity; in the food industry it serves as a flavour additive in confectionery, chewing gum, baked goods, spices, alcoholic and non-alcoholic beverages, while its antioxidant capacity helps stabilize formulations; thanks to its inherent antibacterial and antifungal activities, eugenyl acetate is incorporated into toothpastes, mouthwashes, oral-care preparations and household deodorizing cleaners; in pharmaceuticals it is investigated as a topical analgesic and anti-inflammatory excipient, particularly in dental cements and sore-throat remedies; the compound is also an important intermediate for the synthesis of vanillin, iso-eugenol and other fine chemicals, and has demonstrated potential as an eco-friendly insect repellent and biopesticide.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 200.22
    methanol 295.89
    isopropanol 135.06
    water 0.31
    ethyl acetate 205.49
    n-propanol 149.78
    acetone 351.96
    n-butanol 139.79
    acetonitrile 183.65
    DMF 578.54
    toluene 89.63
    isobutanol 104.89
    1,4-dioxane 337.74
    methyl acetate 228.77
    THF 477.03
    2-butanone 230.11
    n-pentanol 109.67
    sec-butanol 117.62
    n-hexane 9.96
    ethylene glycol 94.92
    NMP 397.29
    cyclohexane 17.7
    DMSO 701.55
    n-butyl acetate 150.55
    n-octanol 53.66
    chloroform 527.99
    n-propyl acetate 123.69
    acetic acid 235.31
    dichloromethane 574.36
    cyclohexanone 281.53
    propylene glycol 96.62
    isopropyl acetate 105.86
    DMAc 515.77
    2-ethoxyethanol 222.85
    isopentanol 125.16
    n-heptane 6.24
    ethyl formate 141.87
    1,2-dichloroethane 396.7
    n-hexanol 110.88
    2-methoxyethanol 359.92
    isobutyl acetate 87.58
    tetrachloromethane 49.84
    n-pentyl acetate 74.93
    transcutol 487.56
    n-heptanol 46.86
    ethylbenzene 65.56
    MIBK 108.84
    2-propoxyethanol 207.72
    tert-butanol 233.0
    MTBE 167.93
    2-butoxyethanol 99.56
    propionic acid 139.62
    o-xylene 73.19
    formic acid 89.47
    diethyl ether 153.36
    m-xylene 75.07
    p-xylene 78.13
    chlorobenzene 150.95
    dimethyl carbonate 114.03
    n-octane 4.35
    formamide 145.61
    cyclopentanone 356.58
    2-pentanone 172.43
    anisole 156.94
    cyclopentyl methyl ether 189.06
    gamma-butyrolactone 385.79
    1-methoxy-2-propanol 228.98
    pyridine 223.71
    3-pentanone 144.01
    furfural 336.87
    n-dodecane 5.85
    diethylene glycol 216.57
    diisopropyl ether 41.97
    tert-amyl alcohol 165.33
    acetylacetone 218.35
    n-hexadecane 6.71
    acetophenone 147.64
    methyl propionate 186.35
    isopentyl acetate 129.78
    trichloroethylene 637.87
    n-nonanol 48.48
    cyclohexanol 135.73
    benzyl alcohol 133.09
    2-ethylhexanol 70.74
    isooctanol 41.03
    dipropyl ether 65.32
    1,2-dichlorobenzene 145.96
    ethyl lactate 83.83
    propylene carbonate 212.79
    n-methylformamide 197.88
    2-pentanol 84.23
    n-pentane 7.56
    1-propoxy-2-propanol 129.36
    1-methoxy-2-propyl acetate 145.37
    2-(2-methoxypropoxy) propanol 136.38
    mesitylene 47.03
    ε-caprolactone 225.0
    p-cymene 42.6
    epichlorohydrin 464.86
    1,1,1-trichloroethane 265.56
    2-aminoethanol 122.53
    morpholine-4-carbaldehyde 356.71
    sulfolane 463.71
    2,2,4-trimethylpentane 10.05
    2-methyltetrahydrofuran 288.33
    n-hexyl acetate 119.27
    isooctane 7.03
    2-(2-butoxyethoxy)ethanol 165.77
    sec-butyl acetate 88.34
    tert-butyl acetate 131.99
    decalin 17.64
    glycerin 153.43
    diglyme 312.57
    acrylic acid 138.55
    isopropyl myristate 52.42
    n-butyric acid 166.57
    acetyl acetate 142.0
    di(2-ethylhexyl) phthalate 60.38
    ethyl propionate 112.33
    nitromethane 385.33
    1,2-diethoxyethane 153.32
    benzonitrile 137.66
    trioctyl phosphate 42.41
    1-bromopropane 173.51
    gamma-valerolactone 362.17
    n-decanol 39.18
    triethyl phosphate 69.21
    4-methyl-2-pentanol 55.88
    propionitrile 135.07
    vinylene carbonate 195.42
    1,1,2-trichlorotrifluoroethane 287.41
    DMS 139.45
    cumene 48.92
    2-octanol 34.17
    2-hexanone 123.88
    octyl acetate 66.56
    limonene 60.06
    1,2-dimethoxyethane 344.39
    ethyl orthosilicate 64.27
    tributyl phosphate 55.74
    diacetone alcohol 160.24
    N,N-dimethylaniline 108.39
    acrylonitrile 178.39
    aniline 129.69
    1,3-propanediol 159.04
    bromobenzene 160.82
    dibromomethane 370.85
    1,1,2,2-tetrachloroethane 497.51
    2-methyl-cyclohexyl acetate 98.36
    tetrabutyl urea 74.4
    diisobutyl methanol 43.58
    2-phenylethanol 121.58
    styrene 81.83
    dioctyl adipate 82.56
    dimethyl sulfate 203.03
    ethyl butyrate 102.27
    methyl lactate 111.75
    butyl lactate 72.34
    diethyl carbonate 88.89
    propanediol butyl ether 107.23
    triethyl orthoformate 76.22
    p-tert-butyltoluene 42.16
    methyl 4-tert-butylbenzoate 112.28
    morpholine 373.39
    tert-butylamine 108.94
    n-dodecanol 32.73
    dimethoxymethane 310.53
    ethylene carbonate 161.44
    cyrene 145.21
    2-ethoxyethyl acetate 119.69
    2-ethylhexyl acetate 102.6
    1,2,4-trichlorobenzene 176.07
    4-methylpyridine 231.95
    dibutyl ether 70.54
    2,6-dimethyl-4-heptanol 43.58
    DEF 202.67
    dimethyl isosorbide 206.43
    tetrachloroethylene 279.09
    eugenol 120.36
    triacetin 127.7
    span 80 96.95
    1,4-butanediol 79.01
    1,1-dichloroethane 305.71
    2-methyl-1-pentanol 108.05
    methyl formate 199.56
    2-methyl-1-butanol 116.25
    n-decane 8.17
    butyronitrile 143.41
    3,7-dimethyl-1-octanol 58.95
    1-chlorooctane 41.27
    1-chlorotetradecane 20.61
    n-nonane 7.4
    undecane 6.79
    tert-butylcyclohexane 16.28
    cyclooctane 5.82
    cyclopentanol 137.2
    tetrahydropyran 261.18
    tert-amyl methyl ether 125.54
    2,5,8-trioxanonane 221.43
    1-hexene 49.21
    2-isopropoxyethanol 147.18
    2,2,2-trifluoroethanol 89.69
    methyl butyrate 152.33

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Basil (India), herb 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.23%
Basil (India), flower 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.16%
Basil (India), whole plant 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.86%
Cassia, branch & leaf (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.09%
Cassia, bark (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.04%
Cassia, leaf (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 1.12%
Cinnamon bark 2a 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 1.8%
Cinnamon bark 3 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.17%
Cinnamon bark 2b 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 1.34%
Cinnamon leaf 1 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 1.0%
Clove bud 2 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 7.05%
Clove bud (Malagasy) 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 22.07%
Clove stem 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 2.25%
Laurel leaf (France) 1 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.14%
Laurel leaf (Morocco) 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.01%
Laurel leaf (Spain) 2 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.2%
Laurel leaf (Spain) 3 8006-78-8 Laurus nobilis L., fam. Lauraceae 1.0%
Laurel leaf (Spain) 1 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.01%
Laurel leaf (Yugoslavia) 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.01%
Laurel leaf (Turkey) 1 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.9%
Lavender (France) 2a 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.05%
Myrtle leaf, cultivated (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.1%
Ocimum canum (camphor-type) 2 Ocimum canum Sims., fam. Lamiaceae (Labiatae) 14.56%
Ocimum canum (camphor-type) 1 Ocimum canum Sims., fam. Lamiaceae (Labiatae) 4.97%
Santolina canescens Santolina rosmarinifolia (L.) ssp. canescens (Lag.) Nyman, fam. Asteraceae 0.4%
Santolina pectina Santolina pectina Lag., fam. Asteraceae (Compositae) 1.3%
Santolina rosmarinifolia Santolina rosmarinifolia L.ssp.rosmarinifolia, fam.Asteraceae (Compositae) 1.3%
Santolina semidentata Santolina semidentata Hoffmanns. & Link, fam. Asteraceae (Compositae) 1.2%
Tejpat leaf (eugenol-type) 1 Cinnamomum tamala (Ham.) Nees et Eberm., fam. Lauraceae 1.2%
Myrtle flower (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.06%
Laurel leaf (Pakistan) 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.36%
Basil (India) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Clove stem (Madagascar) 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison, fam. Myrtaceae 4.79%
Clove bud (Madagascar) 1 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison, fam. Myrtaceae 7.63%
Galangal root (Malaysia) 8023-91-4 Alpinia galanga (L.) Willd., fam. Zingiberaceae 1.5%
Cinnamon bark 1 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.05%
Cinnamomum impressinervium Cinnamomum impressinervium Meissn., fam. Lauraceae 1.1%
Clove bud 1 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 0.3%
Tagetes filifolia (Argentina) 1 Tagetes filifolia Lag., fam. Asteraceae (Compositae) 0.05%
Cassia, bark (China) 2 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.15%
Cinnamon leaf (China) 1 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 1.56%
Cinnamon leaf 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 4.5%
Laurel leaf (Russia) 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Laurel leaf (Albania) 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Betel leaf Bangla (India) Piper betle L. var. Bangla, fam. Piperaceae 18.68%
Myrtle leaf (Morocco) 3 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.03%
Tagetes (Argentina) 2a 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.01%
Tagetes (Argentina) 2b 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.01%
Tagetes filifolia (Argentina) 2 Tagetes filifolia Lag., fam. Asteraceae (Compositae) 0.01%
Genet headspace 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.01%