Isosafrole

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  • Identifiers

    CAS number
    120-58-1

    Molecular formula
    C10H10O2

    SMILES
    C/C=C/C1=CC2=C(C=C1)OCO2

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Retention indicies (RI)

    • DB5: 1373.0
    • Carbowax: 2029.0

  • Odor profile

    Spicy 84.42%
    Sweet 81.94%
    Floral 55.11%
    Warm 47.23%
    Cinnamon 44.36%
    Clove 44.06%
    Balsamic 41.95%
    Powdery 37.88%
    Woody 36.48%
    Anisic 32.77%

    Scent© AI

  • Properties

    XLogP3-AA
    3.1

    Molecular weight
    162.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 8.2 °C
    • MP: 6.7-6.8 °C

    Boiling point

    • 487 °F at 760 mmHg (NTP, 1992)
    • 253 °C

    Flash point est.
    109.66 ˚C

    Solubility expt.

    • Practically insoluble in water
    • Soluble in organic solvents; practically insoluble in water
    • Soluble in ether, benzene, alcohol

  • Synonyms

    • ISOSAFROLE
    • Izosafrol
    • beta-Isosafrole
    • 120-58-1
    • Isosafrol
    • (E)-Isosafrole
    • RCRA waste number U141
    • trans-Isosafrole
    • 5-(1-Propenyl)-1,3-benzodioxole
    • 4-Propenyl-1,2-methylenedioxybenzene
    • 1,3-Benzodioxole, 5-(1-propenyl)-
    • 4-Propenylcatechol methylene ether
    • Isosafrole (TGMX)
    • NSC 4884
    • 5-[(E)-prop-1-enyl]-1,3-benzodioxole
    • 6-(1-Propenyl)-1,3-benzodioxole
    • CCRIS 353
    • 1,2-Methylenedioxy-4-propenylbenzene
    • Benzene, 1,2-(methylenedioxy)-4-propenyl-
    • 4043-71-4
    • 3,4-(Methylenedioxy)-1-propenylbenzene
    • HSDB 2862
    • EINECS 204-410-2
    • .beta.-Isosafrole
    • 1,3-Benzodioxole, 5-(1-propenyl)-, (E)-
    • 3,4-Methylenedioxy-1-propenyl benzene
    • BRN 0082640
    • Benzene, 1,2-(methylenedioxy)-4-propenyl-, (E)-
    • 5-[(E)-prop-1-enyl]benzo[1,3]dioxole
    • AI3-02068
    • trans-1,2-(Methylenedioxy)-4-propenylbenzene
    • DTXCID00767
    • 1,3-Benzodioxole, 5-(1-propen-1-yl)-
    • MLS001055464
    • 94BY31ALL6
    • CHEBI:6054
    • DTXSID2020767
    • 5-[(1E)-prop-1-en-1-yl]-1,3-benzodioxole
    • 5-19-01-00552 (Beilstein Handbook Reference)
    • W6337429LF
    • 5-Prop-1-enyl-1,3-benzodioxole
    • SMR001227197
    • ISOSAFROLE (IARC)
    • ISOSAFROLE [IARC]
    • 1,2-(Methylenedioxy)-4-propenylbenzene
    • 5-[(1E)-prop-1-en-1-yl]-2H-1,3-benzodioxole
    • CAS-120-58-1
    • 5-((E)-prop-1-enyl)-1,3-benzodioxole
    • 5-((1E)-prop-1-en-1-yl)-2H-1,3-benzodioxole
    • RCRA waste no. U141
    • UNII-94BY31ALL6
    • NSC-4884
    • UNII-W6337429LF
    • 5-(1-Propen-1-yl)-1,3-benzodioxole
    • 5-((1E)-1-propenyl)-1,3-benzodioxole
    • ISOSAFROLE [MI]
    • Spectrum5_000388
    • ISOSAFROLE [HSDB]
    • ISOSAFROLE, TRANS-
    • 1,3-Benzodioxole, 5-(1E)-1-propen-1-yl-
    • BSPBio_002813
    • SPECTRUM300533
    • 5(1Propenyl)1,3benzodioxole
    • 6(1Propenyl)1,3benzodioxole
    • SCHEMBL266169
    • ISOSAFROLE (PROHIBITED)
    • CHEMBL487603
    • cid_637796
    • 1,3Benzodioxole, 5(1propenyl)
    • 4Propenylcatechol methylene ether
    • BDBM74206
    • 1,2Methylenedioxy4propenylbenzene
    • 4Propenyl1,2methylenedioxybenzene
    • 3,4Methylenedioxy1propenyl benzene
    • DTXSID201316597
    • HMS1373B16
    • ISOSAFROLE TRANS-FORM [MI]
    • 3,4(Methylenedioxy)1propenylbenzene
    • 3,4-(Methylenedioxy)propenylbenzene
    • Tox21_201783
    • Tox21_302946
    • 5-trans-propenyl-benzo-1,3-dioxole
    • BBL027540
    • CCG-38570
    • STK801280
    • AKOS001684145
    • ISOSAFROLE (PROHIBITED) [FHFI]
    • SDCCGMLS-0066561.P001
    • 4-PROPENYLCATECHOLMETHYLENE ETHER
    • NCGC00090700-01
    • NCGC00090700-02
    • NCGC00090700-03
    • NCGC00090700-04
    • NCGC00090700-05
    • NCGC00090700-06
    • NCGC00256538-01
    • NCGC00259332-01
    • 1,3-BENZODIOXOLE,5-(1-PROPENYL)-
    • 3,4-METHYLENEDIOXY-1-PROPENYLBENZENE
    • 5-(PROPEN-1-YL)-1,3-BENZODIOXOLE
    • 5-[(1E)-1-Propenyl]-1,3-benzodioxole #
    • BENZENE,1,2-(METHYLENEDIOXY)-4-PROPENYL
    • SR-05000002391
    • Q1088741
    • SR-05000002391-1
    • BRD-K44005821-001-07-4
    • InChI=1/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2

  • Applications

    Isosafrole (CAS 120-58-1) is a methylenedioxy-substituted organic intermediate used mainly in fragrance, flavor, and specialty-chemical synthesis: it serves as a key starting material for oxidation to piperonal (heliotropin) and other piperonyl derivatives, enabling manufacture of piperonyl butoxide (PBO) as a pesticide synergist and providing access to aroma ingredients with floral–vanillic notes and intermediates for agrochemical and pharmaceutical research; in laboratories it is employed as a reference standard and as a model substrate for epoxidation, hydrogenation, and oxidative cleavage to probe catalysts and mechanisms for allylbenzene transformations; because it can be misused as a controlled precursor, its sale and handling are regulated in many jurisdictions, requiring compliance with legal, safety, and occupational health controls.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 200.35
    methanol 187.52
    isopropanol 137.67
    water 0.59
    ethyl acetate 390.78
    n-propanol 174.26
    acetone 485.9
    n-butanol 155.03
    acetonitrile 416.31
    DMF 581.46
    toluene 190.01
    isobutanol 131.4
    1,4-dioxane 684.36
    methyl acetate 374.56
    THF 644.68
    2-butanone 355.22
    n-pentanol 125.61
    sec-butanol 145.22
    n-hexane 16.76
    ethylene glycol 141.26
    NMP 429.1
    cyclohexane 31.99
    DMSO 717.47
    n-butyl acetate 180.72
    n-octanol 65.07
    chloroform 833.3
    n-propyl acetate 193.88
    acetic acid 264.35
    dichloromethane 911.05
    cyclohexanone 354.91
    propylene glycol 132.94
    isopropyl acetate 210.03
    DMAc 410.46
    2-ethoxyethanol 313.77
    isopentanol 162.89
    n-heptane 12.75
    ethyl formate 175.96
    1,2-dichloroethane 709.9
    n-hexanol 118.68
    2-methoxyethanol 471.35
    isobutyl acetate 132.37
    tetrachloromethane 110.67
    n-pentyl acetate 103.44
    transcutol 1485.84
    n-heptanol 55.98
    ethylbenzene 93.54
    MIBK 191.93
    2-propoxyethanol 272.17
    tert-butanol 226.97
    MTBE 268.04
    2-butoxyethanol 144.42
    propionic acid 192.36
    o-xylene 105.45
    formic acid 138.72
    diethyl ether 398.57
    m-xylene 120.54
    p-xylene 104.62
    chlorobenzene 263.24
    dimethyl carbonate 229.46
    n-octane 6.65
    formamide 304.87
    cyclopentanone 511.27
    2-pentanone 286.33
    anisole 278.04
    cyclopentyl methyl ether 293.53
    gamma-butyrolactone 527.96
    1-methoxy-2-propanol 340.32
    pyridine 477.32
    3-pentanone 246.63
    furfural 447.89
    n-dodecane 7.94
    diethylene glycol 335.96
    diisopropyl ether 103.53
    tert-amyl alcohol 188.75
    acetylacetone 398.65
    n-hexadecane 9.29
    acetophenone 206.07
    methyl propionate 312.06
    isopentyl acetate 167.86
    trichloroethylene 1082.95
    n-nonanol 60.84
    cyclohexanol 149.66
    benzyl alcohol 169.4
    2-ethylhexanol 80.47
    isooctanol 54.71
    dipropyl ether 105.83
    1,2-dichlorobenzene 232.77
    ethyl lactate 113.07
    propylene carbonate 267.89
    n-methylformamide 295.58
    2-pentanol 122.43
    n-pentane 17.3
    1-propoxy-2-propanol 167.81
    1-methoxy-2-propyl acetate 227.14
    2-(2-methoxypropoxy) propanol 225.63
    mesitylene 77.87
    ε-caprolactone 288.85
    p-cymene 54.91
    epichlorohydrin 788.04
    1,1,1-trichloroethane 450.58
    2-aminoethanol 177.04
    morpholine-4-carbaldehyde 504.16
    sulfolane 555.43
    2,2,4-trimethylpentane 15.85
    2-methyltetrahydrofuran 432.64
    n-hexyl acetate 168.83
    isooctane 14.49
    2-(2-butoxyethoxy)ethanol 302.47
    sec-butyl acetate 149.62
    tert-butyl acetate 238.85
    decalin 24.96
    glycerin 224.45
    diglyme 563.87
    acrylic acid 209.94
    isopropyl myristate 75.96
    n-butyric acid 218.93
    acetyl acetate 246.26
    di(2-ethylhexyl) phthalate 79.13
    ethyl propionate 192.95
    nitromethane 656.3
    1,2-diethoxyethane 327.61
    benzonitrile 206.78
    trioctyl phosphate 53.82
    1-bromopropane 290.34
    gamma-valerolactone 506.74
    n-decanol 48.76
    triethyl phosphate 92.84
    4-methyl-2-pentanol 90.57
    propionitrile 247.17
    vinylene carbonate 266.25
    1,1,2-trichlorotrifluoroethane 461.88
    DMS 234.55
    cumene 65.24
    2-octanol 42.66
    2-hexanone 175.55
    octyl acetate 88.91
    limonene 70.53
    1,2-dimethoxyethane 455.18
    ethyl orthosilicate 87.44
    tributyl phosphate 77.27
    diacetone alcohol 245.9
    N,N-dimethylaniline 147.13
    acrylonitrile 346.78
    aniline 230.23
    1,3-propanediol 216.57
    bromobenzene 309.37
    dibromomethane 546.04
    1,1,2,2-tetrachloroethane 749.47
    2-methyl-cyclohexyl acetate 124.66
    tetrabutyl urea 90.81
    diisobutyl methanol 59.5
    2-phenylethanol 144.09
    styrene 135.01
    dioctyl adipate 113.02
    dimethyl sulfate 311.93
    ethyl butyrate 136.16
    methyl lactate 172.28
    butyl lactate 93.38
    diethyl carbonate 122.34
    propanediol butyl ether 160.85
    triethyl orthoformate 112.15
    p-tert-butyltoluene 56.06
    methyl 4-tert-butylbenzoate 150.54
    morpholine 644.46
    tert-butylamine 141.59
    n-dodecanol 41.08
    dimethoxymethane 479.3
    ethylene carbonate 228.02
    cyrene 186.45
    2-ethoxyethyl acetate 215.53
    2-ethylhexyl acetate 136.91
    1,2,4-trichlorobenzene 275.46
    4-methylpyridine 349.35
    dibutyl ether 112.33
    2,6-dimethyl-4-heptanol 59.5
    DEF 302.41
    dimethyl isosorbide 306.98
    tetrachloroethylene 452.02
    eugenol 159.18
    triacetin 204.6
    span 80 143.85
    1,4-butanediol 101.55
    1,1-dichloroethane 506.1
    2-methyl-1-pentanol 133.24
    methyl formate 258.41
    2-methyl-1-butanol 148.15
    n-decane 11.34
    butyronitrile 195.02
    3,7-dimethyl-1-octanol 86.07
    1-chlorooctane 54.43
    1-chlorotetradecane 27.8
    n-nonane 10.35
    undecane 9.29
    tert-butylcyclohexane 21.48
    cyclooctane 13.46
    cyclopentanol 149.75
    tetrahydropyran 433.02
    tert-amyl methyl ether 191.51
    2,5,8-trioxanonane 386.5
    1-hexene 67.26
    2-isopropoxyethanol 221.03
    2,2,2-trifluoroethanol 142.04
    methyl butyrate 207.69

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition / Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 See notebox Category 7A
Rinse-off products applied to the hair with some hand contact
 See notebox
Category 2
Products applied to the axillae
 See notebox Category 7B
Leave-on products applied to the hair with some hand contact
 See notebox
Category 3
Products applied to the face/body using fingertips
 See notebox Category 8
Products with significant anogenital exposure
 See notebox
Category 4
Products related to fine fragrance
 See notebox Category 9
Products with body and hand exposure, primarily rinse off
 See notebox
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 See notebox Category 10A
Household care products with mostly hand contact
 See notebox
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 See notebox Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 See notebox
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 See notebox Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 See notebox
Category 5D
Baby Creams, baby Oils and baby talc
 See notebox Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 See notebox
Category 6
Products with oral and lip exposure
 See notebox Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 See notebox

Prohibition
Safrole, Isosafrole and/or Dihydrosafrole as such should not be used as fragrance ingredients.
The natural extracts containing Safrole, Isosafrole and/or Dihydrosafrole should not be used as substitutes for these ingredients.

Restriction
On the basis of established maximum concentration levels of this substance in commercially available natural sources (like essential oils, extracts and absolutes), exposure to this substance from the use of these oils and extracts is regarded acceptable as long as the total concentration of Safrole, Isosafrole and Dihydrosafrole in the finished consumer product does not exceed 0.01%.

Botanical

Name CAS Botanical Proportion
Cinnamomum parthenoxylon (Vietnam) 1b Cinnamomum parthenoxylon (Jack) Nees, fam. Lauraceae 0.05%
Tagetes filifolia (Peru) Tagetes filifolia Lag., fam. Asteraceae (Compositae) 0.1%
Tagetes (Italy) 1b 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.32%
Lantana camara (India) 1b flower 90046-17-6 Lantana camara L., fam. Verbenaceae 0.1%