Isoeugenol

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  • Identifiers

    CAS number
    97-54-1

    Molecular formula
    C10H12O2

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

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1460.0
    • Carbowax: 2293.0

  • Odor profile

    Spicy 89.07%
    Sweet 88.81%
    Clove 70.08%
    Phenolic 65.95%
    Woody 62.89%
    Vanilla 59.18%
    Floral 56.07%
    Smoky 55.33%
    Balsamic 52.46%
    Powdery 46.24%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    Molecular weight
    164.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Melting point expt.

    • 14 °F (NTP, 1992)
    • -10 °C

    Boiling point

    • 511 °F at 760 mmHg (NTP, 1992)
    • 266 °C
    • 125.00 to 126.00 °C. @ 14.00 mm Hg

    Flash point est.
    115.58 ˚C

    Flash point expt.

    • 235 °F (NTP, 1992)
    • 235 °F
    • >212 °F(>100 °C)(closed cup)

    Solubility expt.

    • Slightly soluble (NTP, 1992)
    • In water, 810 mg/L at 25 °C
    • Miscible with alcohol and ether
    • Soluble in alcohol, ether and other organic solvents
    • Soluble in most fixed oils
    • soluble (in ethanol)

  • Synonyms

    • Isoeugenol
    • 97-54-1
    • (E)-Isoeugenol
    • trans-Isoeugenol
    • 2-Methoxy-4-propenylphenol
    • 4-Propenylguaiacol
    • 2-methoxy-4-(prop-1-en-1-yl)phenol
    • 5932-68-3
    • 4-Hydroxy-3-methoxy-1-propenylbenzene
    • Isoeugenol trans-form
    • trans-p-Propenylquaiacol
    • 4-Hydroxy-3-methoxypropenylbenzene
    • 2-METHOXY-4-(1-PROPENYL)PHENOL
    • Phenol, 2-methoxy-4-propenyl-
    • Phenol, 2-methoxy-4-(1-propenyl)-
    • 1-Hydroxy-2-methoxy-4-propenylbenzene
    • trans-2-Methoxy-4-propenylphenol
    • 2-methoxy-4-[(E)-prop-1-enyl]phenol
    • (E)-2-Methoxy-4-(prop-1-enyl)phenol
    • Propenylguaiacol
    • Isoeugenol (I)
    • 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
    • 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene
    • Propenylgualacol
    • Iso-eugenol
    • NCI-C60979
    • 3-Methoxy-4-hydroxypropenylbenzene
    • 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene
    • NSC 6769
    • (E)-2-Methoxy-4-(prop-1-en-1-yl)phenol
    • Phenol, 2-methoxy-4-propenyl-, (E)-
    • Isoeugenol and isomers
    • CHEBI:50545
    • 1-(3-Methoxy-4-hydroxyphenyl)-1-propene
    • 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene
    • Phenol, 2-methoxy-4-(1-propenyl)-, (E)-
    • trans-4-Propenylgualacol
    • 28FSR1NAY4
    • CHEMBL193598
    • Isoeugenol,c&t
    • NSC-209522
    • 2-Methoxy-4-[(1E)-1-propenyl]phenol
    • NCGC00091470-02
    • Phenol, 2-methoxy-4-(1-propen-1-yl)-
    • Isoeugenol,predominantly trans
    • DTXCID502413
    • 2-Methoxy-4-[1-propenyl]phenol
    • UIL135434
    • 3-Methoxy-4-hydroxy-1-propenylbenzene
    • CAS-97-54-1
    • CCRIS 744
    • FEMA No. 2468
    • 2-methoxy-4-propenyl-Phenol
    • EINECS 202-590-7
    • EINECS 227-678-2
    • UNII-28FSR1NAY4
    • DTXSID7022413
    • NSC 209522
    • BRN 1909602
    • BRN 2046156
    • isougenol
    • UNII-5M0MWY797U
    • isoeugenol fcc
    • isoeugenol tech
    • e-isoeugenol
    • 1-(3-Methoxy-4-hydroxyphenyl)-1-propane
    • Iso eugenol
    • AI3-15356
    • Isoeugenol E
    • Isoeugenol Z
    • HSDB 8044
    • iso-Eugenol 2
    • isoeugenol 916
    • MFCD00009285
    • CHISOEUG
    • iso eugenol 88%+
    • Isoeugenol (Standard)
    • isoeugenol extra nat us
    • Phenol, (E)-
    • Phenol, 2-methoxy-4-(1E)-1-propenyl-
    • ISOEUGENOL, E-
    • Isoeugenol, cis + trans
    • ISOEUGENOL, TRANS-
    • bmse010052
    • ISOEUGENOL, (E)-
    • IE TRANS 92
    • SCHEMBL57986
    • 3-06-00-04993 (Beilstein Handbook Reference)
    • MLS001065576
    • BIDD:ER0697
    • WLN: 2U1R DQ CO1
    • Isoeugenol, analytical standard
    • Isoeugenol, predominantly trans
    • 5M0MWY797U
    • (E)-4-PROPENYLGUAIACOL
    • HY-N1952R
    • Isoeugenol, natural, 99%, FG
    • DTXSID50872350
    • NSC6769
    • HMS2268O09
    • WLN: 2U1R DQ CO1 -E
    • (E)-2-methoxy-4-propenyl-Phenol
    • 2-methoxy-4-(1-propenyl)-Phenol
    • ISOEUGENOL TRANS-FORM [MI]
    • HY-N1952
    • NSC-6769
    • Tox21_111138
    • Tox21_202433
    • Tox21_300303
    • BDBM50548724
    • NSC209522
    • s5757
    • STL264281
    • AKOS000120575
    • Tox21_111138_1
    • DB14188
    • trans-2-methoxy-4-(1-propenyl)phenol
    • (E)-2-methoxy-4-(1-propenyl)-Phenol
    • 2-Methoxy-4-propenylphenol (isoeugenol)
    • NCGC00091470-01
    • NCGC00091470-03
    • NCGC00091470-04
    • NCGC00091470-05
    • NCGC00254142-01
    • NCGC00259982-01
    • (E)-2-methoxy-4- (1-propenyl)-Phenol
    • AC-34996
    • AS-61702

  • Applications

    Isoeugenol (CAS 97-54-1) is an aromatic phenylpropanoid found in clove oil and balsam resins whose warm, sweet-spicy scent underpins wide-ranging applications: in fragrance manufacturing it is a key note in perfumes, soaps, detergents, scented candles and personal-care items; in foods it serves as a flavour additive for confectionery, beverages and spice blends; in chemical synthesis it is an economical precursor for vanillin, isovanillin and other aldehydes, and an intermediate for anti-inflammatory, antimicrobial and local-anesthetic drugs; in dentistry zinc-oxide–isoeugenol mixtures are used as temporary cements and root-canal sealers; it also functions as an antioxidant stabiliser for plastics and rubbers, a semiochemical attractant for agricultural pest control, and a versatile scaffold in the search for natural preservatives, although it is listed as a potential skin allergen requiring concentration limits in cosmetics.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1294.94
    methanol 1411.37
    isopropanol 904.23
    water 1.08
    ethyl acetate 1562.66
    n-propanol 1152.57
    acetone 2257.19
    n-butanol 799.05
    acetonitrile 1890.28
    DMF 1846.13
    toluene 331.34
    isobutanol 681.1
    1,4-dioxane 1982.92
    methyl acetate 1486.87
    THF 2120.88
    2-butanone 1380.19
    n-pentanol 454.96
    sec-butanol 763.93
    n-hexane 66.5
    ethylene glycol 353.32
    NMP 954.96
    cyclohexane 136.18
    DMSO 2671.34
    n-butyl acetate 651.61
    n-octanol 170.84
    chloroform 1789.09
    n-propyl acetate 694.14
    acetic acid 1135.24
    dichloromethane 2073.57
    cyclohexanone 1240.23
    propylene glycol 368.96
    isopropyl acetate 542.94
    DMAc 728.79
    2-ethoxyethanol 900.89
    isopentanol 584.82
    n-heptane 37.38
    ethyl formate 766.94
    1,2-dichloroethane 1813.96
    n-hexanol 455.1
    2-methoxyethanol 1681.33
    isobutyl acetate 319.28
    tetrachloromethane 282.61
    n-pentyl acetate 261.54
    transcutol 1964.88
    n-heptanol 166.9
    ethylbenzene 166.41
    MIBK 459.67
    2-propoxyethanol 743.53
    tert-butanol 1299.55
    MTBE 1147.3
    2-butoxyethanol 334.98
    propionic acid 877.71
    o-xylene 171.7
    formic acid 421.2
    diethyl ether 1651.68
    m-xylene 200.89
    p-xylene 179.75
    chlorobenzene 536.2
    dimethyl carbonate 490.45
    n-octane 17.13
    formamide 1064.97
    cyclopentanone 1682.22
    2-pentanone 1073.23
    anisole 470.05
    cyclopentyl methyl ether 823.8
    gamma-butyrolactone 1919.7
    1-methoxy-2-propanol 934.06
    pyridine 1135.32
    3-pentanone 780.87
    furfural 1134.29
    n-dodecane 14.34
    diethylene glycol 624.89
    diisopropyl ether 255.19
    tert-amyl alcohol 884.28
    acetylacetone 943.2
    n-hexadecane 16.99
    acetophenone 359.58
    methyl propionate 1111.23
    isopentyl acetate 454.16
    trichloroethylene 2491.5
    n-nonanol 144.66
    cyclohexanol 581.05
    benzyl alcohol 335.09
    2-ethylhexanol 219.76
    isooctanol 135.02
    dipropyl ether 294.64
    1,2-dichlorobenzene 406.45
    ethyl lactate 221.22
    propylene carbonate 755.7
    n-methylformamide 1265.61
    2-pentanol 529.15
    n-pentane 77.62
    1-propoxy-2-propanol 430.46
    1-methoxy-2-propyl acetate 452.51
    2-(2-methoxypropoxy) propanol 291.85
    mesitylene 130.6
    ε-caprolactone 947.91
    p-cymene 92.03
    epichlorohydrin 2226.91
    1,1,1-trichloroethane 1267.26
    2-aminoethanol 595.07
    morpholine-4-carbaldehyde 988.26
    sulfolane 1726.16
    2,2,4-trimethylpentane 44.01
    2-methyltetrahydrofuran 1402.04
    n-hexyl acetate 366.92
    isooctane 37.5
    2-(2-butoxyethoxy)ethanol 445.21
    sec-butyl acetate 347.62
    tert-butyl acetate 548.91
    decalin 54.3
    glycerin 473.69
    diglyme 896.1
    acrylic acid 742.17
    isopropyl myristate 127.77
    n-butyric acid 954.21
    acetyl acetate 594.26
    di(2-ethylhexyl) phthalate 107.33
    ethyl propionate 527.27
    nitromethane 2407.04
    1,2-diethoxyethane 613.32
    benzonitrile 429.14
    trioctyl phosphate 92.09
    1-bromopropane 849.1
    gamma-valerolactone 1487.81
    n-decanol 106.78
    triethyl phosphate 146.74
    4-methyl-2-pentanol 236.23
    propionitrile 1068.85
    vinylene carbonate 691.6
    1,1,2-trichlorotrifluoroethane 1065.8
    DMS 365.28
    cumene 107.65
    2-octanol 115.73
    2-hexanone 563.62
    octyl acetate 164.39
    limonene 142.14
    1,2-dimethoxyethane 1212.26
    ethyl orthosilicate 144.14
    tributyl phosphate 120.24
    diacetone alcohol 573.09
    N,N-dimethylaniline 217.43
    acrylonitrile 1249.44
    aniline 554.54
    1,3-propanediol 806.98
    bromobenzene 530.59
    dibromomethane 1380.72
    1,1,2,2-tetrachloroethane 1733.06
    2-methyl-cyclohexyl acetate 222.58
    tetrabutyl urea 139.56
    diisobutyl methanol 127.42
    2-phenylethanol 277.15
    styrene 247.29
    dioctyl adipate 178.65
    dimethyl sulfate 627.54
    ethyl butyrate 356.21
    methyl lactate 365.29
    butyl lactate 191.78
    diethyl carbonate 245.15
    propanediol butyl ether 327.98
    triethyl orthoformate 213.9
    p-tert-butyltoluene 93.42
    methyl 4-tert-butylbenzoate 229.2
    morpholine 2103.25
    tert-butylamine 677.3
    n-dodecanol 80.84
    dimethoxymethane 1281.2
    ethylene carbonate 612.2
    cyrene 284.41
    2-ethoxyethyl acetate 410.82
    2-ethylhexyl acetate 340.62
    1,2,4-trichlorobenzene 480.35
    4-methylpyridine 851.32
    dibutyl ether 242.31
    2,6-dimethyl-4-heptanol 127.42
    DEF 883.24
    dimethyl isosorbide 452.32
    tetrachloroethylene 1089.89
    eugenol 241.96
    triacetin 326.38
    span 80 227.51
    1,4-butanediol 278.64
    1,1-dichloroethane 1540.18
    2-methyl-1-pentanol 373.71
    methyl formate 1066.77
    2-methyl-1-butanol 568.85
    n-decane 23.67
    butyronitrile 839.74
    3,7-dimethyl-1-octanol 163.5
    1-chlorooctane 122.44
    1-chlorotetradecane 46.09
    n-nonane 23.88
    undecane 17.88
    tert-butylcyclohexane 50.04
    cyclooctane 42.04
    cyclopentanol 646.23
    tetrahydropyran 1763.72
    tert-amyl methyl ether 583.94
    2,5,8-trioxanonane 517.52
    1-hexene 252.11
    2-isopropoxyethanol 515.86
    2,2,2-trifluoroethanol 370.53
    methyl butyrate 684.29

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.019 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0.22 %
Category 2
Products applied to the axillae
 0.0057 % Category 7B
Leave-on products applied to the hair with some hand contact
 0.22 %
Category 3
Products applied to the face/body using fingertips
 0.12 % Category 8
Products with significant anogenital exposure
 0.009 %
Category 4
Products related to fine fragrance
 0.11 % Category 9
Products with body and hand exposure, primarily rinse off
 0.21 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0.027 % Category 10A
Household care products with mostly hand contact
 0.21 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0.027 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0.75 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.027 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0.009 %
Category 5D
Baby Creams, baby Oils and baby talc
 0.009 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0.009 %
Category 6
Products with oral and lip exposure
 0.063 % 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) 3.38%
Basil (India), flower 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.24%
Cassia, branch & leaf (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.01%
Cassia, bark (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.01%
Cassia, leaf (Australia) 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 1.83%
Mace 1 8007-12-3 Myristica fragrans Houtt., fam. Myristicaceae 0.1%
Nutmeg (Sri Lanka) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.05%
Nutmeg 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.2%
Ocimum canum (camphor-type) 2 Ocimum canum Sims., fam. Lamiaceae (Labiatae) 9.19%
Ocimum canum (camphor-type) 1 Ocimum canum Sims., fam. Lamiaceae (Labiatae) 1.87%
Ocimum micranthum (Brazil) Ocimum micranthum (common name: Alfavaca de campo), fam. Lamiaceae (Lab.) 15.93%
Annual wormwood, leaf (U.S.A., Indiana) 1 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.04%
Annual wormwood, leaf (U.S.A., Indiana) 2 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.11%
Annual wormwood, flower (U.S.A., Indiana) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.03%
Daphne genkwa Daphne genkwa Sieb. et Zucc., fam. Thymelaeaceae 0.7%
Narcissus poeticus absolute 8023-75-4 Narcissus poeticus L., fam. Amaryllidaceae 0.6%
Nutmeg 4 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.27%
Nutmeg (Indonesia) 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.1%
Nutmeg 2 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.04%
Thyme 5 8007-46-3 Thymus vulgaris L., fam. Lamiaceae (Labiatae) 0.01%
Basil (Turkey) 1 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 2.04%
Basil (India) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.24%
Clove stem (Madagascar) 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison, fam. Myrtaceae 0.17%
Clove bud (Madagascar) 1 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison, fam. Myrtaceae 0.19%
Cinnamon leaf (Sri Lanka) 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 1.1%
Betel leaf Kapoori (India) 2 Piper betle L. var. Kapoori, fam. Piperaceae 10.59%
Betel leaf Bangla (India) Piper betle L. var. Bangla, fam. Piperaceae 5.2%
Ylang Ylang 2a 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.2%
Ylang Ylang 5a 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.5%
Ylang Ylang 5b 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonacaea 0.5%
Ylang Ylang 5c 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.29%
Ylang Ylang 5d 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.36%
Bay, West Indian (Benin) 8015-73-4 Pimenta racemosa var. racemosa (P. Miller) J.W. Moore, fam. Myrtaceae 0.3%
Sudachi peel (Japan) Citrus sudachi Hort. ex Shirai, fam. Rutaceae 0.01%
Mochiyuzu peel (Japan) Citrus inflata Hort. ex Tanaka, fam. Rutaceae 0.01%
Clove bud 4 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 0.9%
Clove bud 5 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 0.6%
Tamarind 3 fruit Tamarindus indica L., fam. Leguminosae 0.01%
Canella winterana (Cuba) 2 Canella winterana (L.) Gaertn., fam. Canellaceae 0.1%
Nutmeg 7 8008-45-5 Myristica fragrans Houtt., fam. Myrsticaceae 4.5%
Nutmeg 5a 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.05%
Nutmeg 5b 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.06%
Tejpat leaf (cinnamaldehyde-type) 2 Cinnamomum tamala (Ham.) Nees et Eberm., fam. Lauraceae 4.9%
Yuzu (Japana) 6 Citrus junos Sieb. ex Tanaka, fam. Rutaceae 0.01%
Cassie absolute 1a extract 8023-82-3 Acacia farnesiana (L.) Willd., fam. Mimosaceae (Leguminosae) 0.5%
Asafoetida (Pakistan) 2 9000-04-8 Ferula assafoetida L., fam. Apiaceae (Umbelliferae) 0.27%