Apiole (dill)

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    484-31-1

    Molecular formula
    C12H14O4

    SMILES
    COC1=C(C2=C(C=C1CC=C)OCO2)OC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1622.5
    • Carbowax: 2354.67

  • Odor profile

    Spicy 84.26%
    Woody 56.08%
    Phenolic 44.74%
    Herbal 40.45%
    Smoky 38.41%
    Warm 38.33%
    Clove 35.33%
    Balsamic 27.64%
    Dry 24.9%
    Floral 24.42%

    Scent© AI

  • Properties

    XLogP3-AA
    2.7

    Molecular weight
    222.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 29.5 °C

    Boiling point

    • 285.00 to 292.00 °C. @ 760.00 mm Hg

    Flash point est.
    119.06 ˚C

  • Synonyms

    • Dillapiole
    • Dillapiol
    • Dill apiole
    • 484-31-1
    • Dill apiol
    • Apiole (dill)
    • Apiol, liquid
    • 4,5-dimethoxy-6-prop-2-enyl-1,3-benzodioxole
    • Parsley fruit oleoresin
    • Resins, oleo-, parsley
    • 4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole
    • BRN 0196037
    • 6-Allyl-4,5-dimethoxy-1,3-benzodioxole
    • 1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)-
    • APIOLE, DILL
    • BENZENE, 1-ALLYL-2,3-DIMETHOXY-4,5-(METHYLENEDIOXY)-
    • APIOLE (DILL) [MI]
    • CHEMBL470874
    • 8025-95-4
    • CHEBI:70453
    • DTXSID80862007
    • 438CJQ562D
    • 4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
    • 1-Allyl-2,3-dimethoxy-4,5-methylenedioxybenzene
    • UNII-438CJQ562D
    • Parsley oleoresin
    • MFCD00210045
    • SCHEMBL310992
    • 1-allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene
    • Dillapiole, analytical standard
    • DTXCID00810843
    • LIKYNOPXHGPMIH-UHFFFAOYSA-N
    • DTXSID101061335
    • BDBM50242106
    • STK689576
    • AKOS005602275
    • HY-W320276
    • 5-Allyl 6,7-dimethoxy 1,3-benzodioxole
    • 6-Allyl-4,5-dimethoxy-1,3-benzodioxole #
    • 6-allyl-4,5-dimethoxybenzo[d][1,3]dioxole
    • CS-0360943
    • NS00123152
    • Q419537
    • 1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)-Benzene
    • 4,5-dimethoxy-6-(prop-2-en-1-yl)-1,3-benzodioxole
    • 4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole, 9CI
    • 1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- (9CI)
    • 1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)-(9CI)
    • 621-020-1

  • Applications

    Apiole (dill), CAS 484-31-1, is a natural phenylpropanoid occurring in dill and other Apiaceae essential oils; in flavor and fragrance it is used at trace levels to impart warm, herbal, spicy nuances to seasonings, beverages, and baked goods and to adjust green–herbal facets in perfumes/personal care; historically, apiole-rich preparations were used as antispasmodic, carminative, and emmenagogue agents, but modern therapeutic use is curtailed by safety concerns (hepato‑/nephrotoxicity, neurostimulation, and reproductive toxicity at high doses), so it is mainly confined to regulated flavor use and analytical standards; in research, apiole and derivatives are investigated for antioxidant, antimicrobial/antifungal, antiparasitic, anti-inflammatory, neuroprotective, and insecticidal/repellent activities (e.g., mosquito larvae), and serve as chemotaxonomic markers and reference compounds in GC–MS/HPLC profiling of essential oils; overall, apiole’s value lies in trace-level flavor–fragrance functionality, analytical applications, and as a scaffold for derivative synthesis, under strict quality control and regulatory limits.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 91.56
    methanol 125.4
    isopropanol 61.83
    water 1.04
    ethyl acetate 132.05
    n-propanol 70.65
    acetone 186.65
    n-butanol 66.7
    acetonitrile 152.4
    DMF 275.98
    toluene 44.48
    isobutanol 52.65
    1,4-dioxane 239.34
    methyl acetate 157.72
    THF 259.63
    2-butanone 112.71
    n-pentanol 56.53
    sec-butanol 55.59
    n-hexane 2.9
    ethylene glycol 118.75
    NMP 218.21
    cyclohexane 12.24
    DMSO 279.5
    n-butyl acetate 85.41
    n-octanol 48.17
    chloroform 427.81
    n-propyl acetate 91.58
    acetic acid 208.87
    dichloromethane 428.03
    cyclohexanone 186.43
    propylene glycol 66.83
    isopropyl acetate 72.94
    DMAc 176.05
    2-ethoxyethanol 162.21
    isopentanol 57.21
    n-heptane 5.85
    ethyl formate 162.17
    1,2-dichloroethane 267.76
    n-hexanol 64.42
    2-methoxyethanol 263.44
    isobutyl acetate 61.39
    tetrachloromethane 77.05
    n-pentyl acetate 71.59
    transcutol 187.19
    n-heptanol 48.65
    ethylbenzene 33.37
    MIBK 59.97
    2-propoxyethanol 151.58
    tert-butanol 74.47
    MTBE 49.83
    2-butoxyethanol 109.47
    propionic acid 108.93
    o-xylene 41.12
    formic acid 117.95
    diethyl ether 57.12
    m-xylene 36.57
    p-xylene 48.32
    chlorobenzene 139.75
    dimethyl carbonate 119.82
    n-octane 5.16
    formamide 180.11
    cyclopentanone 238.85
    2-pentanone 88.91
    anisole 92.24
    cyclopentyl methyl ether 95.07
    gamma-butyrolactone 315.5
    1-methoxy-2-propanol 148.58
    pyridine 200.98
    3-pentanone 73.2
    furfural 345.71
    n-dodecane 6.91
    diethylene glycol 219.64
    diisopropyl ether 19.94
    tert-amyl alcohol 60.24
    acetylacetone 156.79
    n-hexadecane 7.86
    acetophenone 112.27
    methyl propionate 126.2
    isopentyl acetate 79.05
    trichloroethylene 496.74
    n-nonanol 44.38
    cyclohexanol 84.72
    benzyl alcohol 109.56
    2-ethylhexanol 47.62
    isooctanol 42.4
    dipropyl ether 35.21
    1,2-dichlorobenzene 148.66
    ethyl lactate 81.94
    propylene carbonate 206.68
    n-methylformamide 190.76
    2-pentanol 40.11
    n-pentane 3.7
    1-propoxy-2-propanol 87.08
    1-methoxy-2-propyl acetate 100.7
    2-(2-methoxypropoxy) propanol 90.47
    mesitylene 25.72
    ε-caprolactone 178.86
    p-cymene 32.55
    epichlorohydrin 351.9
    1,1,1-trichloroethane 205.04
    2-aminoethanol 103.45
    morpholine-4-carbaldehyde 252.34
    sulfolane 320.66
    2,2,4-trimethylpentane 4.61
    2-methyltetrahydrofuran 142.21
    n-hexyl acetate 89.35
    isooctane 3.7
    2-(2-butoxyethoxy)ethanol 111.86
    sec-butyl acetate 54.82
    tert-butyl acetate 73.22
    decalin 9.52
    glycerin 148.26
    diglyme 222.42
    acrylic acid 146.92
    isopropyl myristate 40.83
    n-butyric acid 133.87
    acetyl acetate 124.64
    di(2-ethylhexyl) phthalate 58.99
    ethyl propionate 80.7
    nitromethane 322.07
    1,2-diethoxyethane 73.6
    benzonitrile 150.8
    trioctyl phosphate 44.59
    1-bromopropane 82.39
    gamma-valerolactone 292.62
    n-decanol 36.01
    triethyl phosphate 57.21
    4-methyl-2-pentanol 29.38
    propionitrile 102.99
    vinylene carbonate 218.8
    1,1,2-trichlorotrifluoroethane 307.36
    DMS 104.6
    cumene 29.22
    2-octanol 33.67
    2-hexanone 75.56
    octyl acetate 54.6
    limonene 39.55
    1,2-dimethoxyethane 215.14
    ethyl orthosilicate 50.27
    tributyl phosphate 49.71
    diacetone alcohol 98.38
    N,N-dimethylaniline 61.85
    acrylonitrile 172.76
    aniline 92.81
    1,3-propanediol 140.56
    bromobenzene 137.44
    dibromomethane 247.66
    1,1,2,2-tetrachloroethane 348.33
    2-methyl-cyclohexyl acetate 73.81
    tetrabutyl urea 61.59
    diisobutyl methanol 30.0
    2-phenylethanol 104.19
    styrene 42.71
    dioctyl adipate 67.5
    dimethyl sulfate 169.8
    ethyl butyrate 72.12
    methyl lactate 111.82
    butyl lactate 67.96
    diethyl carbonate 68.56
    propanediol butyl ether 94.55
    triethyl orthoformate 57.4
    p-tert-butyltoluene 29.94
    methyl 4-tert-butylbenzoate 97.83
    morpholine 211.93
    tert-butylamine 40.6
    n-dodecanol 30.27
    dimethoxymethane 213.89
    ethylene carbonate 180.36
    cyrene 126.77
    2-ethoxyethyl acetate 98.79
    2-ethylhexyl acetate 64.74
    1,2,4-trichlorobenzene 165.91
    4-methylpyridine 147.3
    dibutyl ether 38.74
    2,6-dimethyl-4-heptanol 30.0
    DEF 114.3
    dimethyl isosorbide 149.16
    tetrachloroethylene 270.95
    eugenol 107.98
    triacetin 103.75
    span 80 75.05
    1,4-butanediol 80.22
    1,1-dichloroethane 183.35
    2-methyl-1-pentanol 53.09
    methyl formate 224.22
    2-methyl-1-butanol 53.76
    n-decane 9.03
    butyronitrile 98.52
    3,7-dimethyl-1-octanol 44.07
    1-chlorooctane 37.31
    1-chlorotetradecane 19.69
    n-nonane 7.69
    undecane 7.75
    tert-butylcyclohexane 7.46
    cyclooctane 5.21
    cyclopentanol 99.62
    tetrahydropyran 132.14
    tert-amyl methyl ether 40.92
    2,5,8-trioxanonane 151.25
    1-hexene 13.0
    2-isopropoxyethanol 102.96
    2,2,2-trifluoroethanol 138.47
    methyl butyrate 109.33

    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
Artemisia scoparia (India) 1 Artemisia scoparia Waldst. & Kit., fam. Asteraceae (Compositae) 0.05%
Bunium cylidricum seed Bunium cylindricum Boiss & Hoh and Drude, fam. Apiaceae (Umbelliferae) 0.05%
Carrot seed (France) 1 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.1%
Indian dill Anethum sowa Roxb., fam. Apiaceae (Umbelliferae) 20.7%
Parsley absolute (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.08%
Parsley 1c seed 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 18.76%
Parsley 1a herb 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 1.24%
Dill herb (Europa) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.05%
Dill seed 3 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.5%
Peucedanum zenkeri (Cameroon) 1a Peucedanum zenkeri Engl., fam. Apiaceae (Umbelliferae) 3.3%
Peucedanum zenkeri (Cameroon) 1b Peucedanum zenkeri Engl., fam. Apiaceae (Umbelliferae) 19.1%
Dill herb (Cuba) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.31%
Geum montanum root Geum montanum L., fam. Rosaceae 7.71%
Fennel, bitter, seedling (France) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 55.75%
Protium heptaphyllum 1a leaf Protium heptaphyllum (Aubl.) March., fam. Burseraceae 0.35%
Protium heptaphyllum 1b stem Protium heptaphyllum (Aubl.) March., fam. Burseraceae 2.31%
Minthostachys spicata Minthostachys spicata (Benth.) Epl., fam Lamiaceae (Labiatae) 0.1%
Coriander fruit (Cuba) 8008-32-4 Coriandrum sativum L., fam. Apiaceae (Umbelliferae) 0.45%
Dill herb (U.S.A.) 1 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.5%
Perilla frutescens (China) 2a herb 90082-61-4 Perilla frutescens (L.) Brit., fam. Lamiaceae (Labiatae) 0.14%
Ajowan (India) 2 seed Trachyspermum copticum (L.) Link., fam. Apiaceae (Umbelliferae) 8.9%
Parsley herb (Egypt) 3 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 4.03%
Cubeb 2 8007-87-2 Piper cubeba L., fam. Piperaceae 0.05%
Cubeb (India) 8007-87-2 Piper cubeba L., fam. Piperaceae 0.16%
Dill seed (Egypt) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 26.8%
Seafennel (Greece) 89997-98-8 Crithmum maritimum L., fam. Apiaceae (Umbelliferae) 0.2%
Seafennel (Turkey) 1b Mersin 89997-98-8 Crithmum maritimum L., fam. Apiaceae (Umbelliferae) 20.6%
Bunium persicum fruit (Iran) Bunium persicum (Boiss.) B. Fedtsch., fam. Apiaceae (Umbelliferae) 1.7%
Seafennel (Turkey) 2 89997-98-8 Crithmum maritimum L., fam. Apiaceae (Umbelliferae) 0.01%
Astronium urundeuva (Brazil) Astronium urundeuva (Allemao) Engl., fam. Anacardiaceae 0.1%
Petiveria alliaceae (Brazil) flower Petiveria alliaceae L., fam. Phytolaccaceae 0.1%
Ridolfia segetum (Spain) 1d fruit Ridolfia segetum (L.) Moris, fam. Apiaceae (Umbelliferae) 22.0%
Cymbopogon validus (Zimbabwe) Cymbopogon validus (Stapf) Stapf ex Burtt Davy, fam. Poaceae (Gramineae) 0.95%