Isoeugenol

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  • Identifiers

    CAS number
    5932-68-3

    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: 2286.5

  • 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 5932-68-3) is an aromatic phenylpropanoid with a clove–vanilla note, widely used as a fragrance ingredient in perfumes, soaps, detergents, candles and personal care to add warmth to floral, oriental and woody accords; as a low-level flavoring in confectionery, baked goods and beverages; as a key intermediate for manufacturing vanillin and other aroma chemicals, and as a synthetic building block for pharmaceuticals, agrochemicals and materials (e.g., conversion to glycidyl ether or acrylate for epoxy and UV-curable systems); in aquaculture, isoeugenol also serves as a fish anesthetic/sedative in certain jurisdictions; it exhibits antioxidant/antimicrobial activity exploited in research and formulations, but is a known skin sensitizer and therefore subject to concentration limits under regulations (e.g., IFRA, EU).

  • 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
Wistaria sinensis headspace Wistaria sinensis DC., fam. Leguminosae (Papilionaceae) 1.0%
Hedychium coronarium flower (Japan) Hedychium coronarium Koenig, fam. Zingiberaceae 1.63%
Osmanthus concentrate 2 (Sukhumi-Abkhasia) 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 0.02%
Mandrake fruit (Israel) Mandragora officinarum L., fam. Solanaceae 1.63%
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.05%
Aerangis brachycarpa flower headspace Aerangis brachycarpa Rchb. f., fam. Orchidaceae 0.05%
Jasmine (China) 1 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 28.94%
Jasmine rose absolute (India) Gardenia jasminoides Ellis, fam. Rubiaceae 0.48%
Ylang Ylang (China) 4 68606-83-7 Cananga odorata (Lamk.) Hook. f. et Thomson, fam. Annonaceae 1.54%
Jasmine (China) 2b (absolute) 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 1.02%
Nutmeg (India) 5a leaf 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.2%
Nutmeg (India) 5b flower 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.56%
Nutmeg (India) 6 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.05%
Lemongrass (Bangladesh) 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 0.3%
Psidium cattleianum fruit (R‚union Island) Psidium cattleianum Sabine, fam. Myrtaceae 0.1%
Acinos alpinus oil (Greece) Acinos alpinus (L.) Moench., fam. Lamiaceae (Labiatae) 0.2%
Nutmeg (West Indies) 4 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.01%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.2%
Thymus x oblongifolius (Lithuania) Thymus x oblongifolius Opiz, fam. Lamiaceae (Labiatae) 0.2%