Ascaridole

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  • Identifiers

    CAS number
    512-85-6

    Molecular formula
    C10H16O2

    SMILES
    CC(C)C12CCC(C=C1)(OO2)C

    Retention indicies (RI)

    • DB5: 1237.0

  • Odor profile

    Mint 42.95%
    Green 38.35%
    Fruity 38.17%
    Herbal 36.39%
    Woody 34.52%
    Fresh 31.52%
    Sweet 28.12%
    Earthy 26.93%
    Spicy 25.57%
    Citrus 25.22%

    Scent© AI

  • Properties

    XLogP3-AA
    2.3

    Molecular weight
    168.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Melting point expt.

    • 3.3 °C

    Boiling point

    • 112.00 to 115.00 °C. @ 20.00 mm Hg

    Flash point est.
    62.04 ˚C

  • Synonyms

    • ASCARIDOLE
    • 512-85-6
    • Ascaridol
    • 1,4-Peroxido-p-menthene-2
    • Ascaridiol
    • 1,4-Peroxy-p-menth-2-ene
    • 1,4-Epidioxy-p-menth-2-ene
    • Ascaricum
    • Ascarisin
    • Askaridol
    • cis-Ascaridole
    • 2,3-Dioxabicyclo[2.2.2]oct-5-ene, 1-methyl-4-(1-methylethyl)-
    • NSC 406266
    • CHEBI:2866
    • 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-ene
    • 1-methyl-4-propan-2-yl-2,3-dioxabicyclo[2.2.2]oct-5-ene
    • 2,3-Dioxabicyclo(2.2.2)oct-5-ene, 1-isopropyl-4-methyl-
    • 2,3-Dioxabicyclo(2.2.2)oct-5-ene, 1-methyl-4-(1-methylethyl)-
    • 1,4-Epidioxy-2-p-menthene
    • NSC-406266
    • NSC-406924
    • p-Menth-2-ene, 1,4-epidioxy-
    • 1-methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
    • EINECS 208-147-4
    • UNII-1718D0GEVJ
    • 2, 1-isopropyl-4-methyl-
    • p-Menth-2-ene,4-epidioxy-
    • AI3-11049
    • 1-Isopropyl-4-methyl-2,3-Dioxabicyclo(2.2.2)oct-5-ene
    • 1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene
    • 4-methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
    • 2, 1-methyl-4-(1-methylethyl)-
    • WLN: T66 A B AO BO DUTJ CY F
    • Ascaridole (organic peroxide) [Forbidden]
    • Uncinacina
    • Ascapurin
    • 4-methyl-1-(propan-2-yl)-2,3-dioxabicyclo(2.2.2)oct-5-ene
    • 1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
    • Kebal II
    • SCHEMBL156673
    • 1, 4-Peroxy-p-menth-2-ene
    • CHEMBL467614
    • 1, 4-Epidioxy-p-menth-2-ene
    • NSC406266
    • NSC406924
    • AKOS004910035
    • FA179595
    • TS-08412
    • HY-118494
    • CS-0066135
    • NS00010548
    • C09836
    • G86204
    • Q419442
    • 1-isopropyl-4-methyl-7-oxabicyclo[2.2.1]hept-2-ene
    • 1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene #
    • 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9CI
    • 208-147-4

  • Applications

    Ascaridole (CAS 512-85-6) is a natural monoterpene endoperoxide abundant in epazote oil with applications and research uses that include: historical human and veterinary anthelmintic use from chenopodium oil (now largely obsolete due to toxicity); a bioactive component in plant-based insecticidal, acaricidal and larvicidal formulations, and in antifungal/antiprotozoal strategies for crop protection and stored-product preservation; a reference/marker analyte in GC-MS/HPLC to authenticate epazote essential oil, quantify content and monitor peroxide stability/oxidative degradation; a mechanistic endoperoxide model in medicinal chemistry to study artemisinin-like Fe(II)-triggered peroxide cleavage and ROS generation; an oxygen-transfer and radical-initiating reagent in photooxidations, thiol-ene processes and other monoterpene transformations, as well as a building block for terpene derivatives; and a candidate natural preservative or active antimicrobial in food-packaging systems at low doses under strict regulatory limits; because it is a strong oxidant, photosensitive and irritating/toxic, direct uses are limited and require rigorous safety controls.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 54.31
    methanol 56.4
    isopropanol 43.25
    water 0.68
    ethyl acetate 135.78
    n-propanol 51.71
    acetone 115.72
    n-butanol 50.33
    acetonitrile 135.62
    DMF 156.83
    toluene 201.95
    isobutanol 46.11
    1,4-dioxane 278.0
    methyl acetate 166.88
    THF 263.39
    2-butanone 150.55
    n-pentanol 48.88
    sec-butanol 53.02
    n-hexane 16.41
    ethylene glycol 12.73
    NMP 245.75
    cyclohexane 46.49
    DMSO 98.31
    n-butyl acetate 171.68
    n-octanol 84.18
    chloroform 773.97
    n-propyl acetate 114.33
    acetic acid 83.56
    dichloromethane 623.99
    cyclohexanone 257.28
    propylene glycol 17.2
    isopropyl acetate 94.28
    DMAc 215.27
    2-ethoxyethanol 75.73
    isopentanol 55.71
    n-heptane 18.99
    ethyl formate 103.26
    1,2-dichloroethane 241.83
    n-hexanol 87.45
    2-methoxyethanol 94.19
    isobutyl acetate 94.14
    tetrachloromethane 128.29
    n-pentyl acetate 120.82
    transcutol 417.28
    n-heptanol 59.86
    ethylbenzene 135.83
    MIBK 86.47
    2-propoxyethanol 132.8
    tert-butanol 63.29
    MTBE 88.16
    2-butoxyethanol 97.35
    propionic acid 74.28
    o-xylene 161.56
    formic acid 30.56
    diethyl ether 83.35
    m-xylene 148.8
    p-xylene 194.28
    chlorobenzene 261.2
    dimethyl carbonate 64.44
    n-octane 12.38
    formamide 57.75
    cyclopentanone 242.2
    2-pentanone 100.63
    anisole 199.37
    cyclopentyl methyl ether 131.3
    gamma-butyrolactone 274.98
    1-methoxy-2-propanol 75.16
    pyridine 315.65
    3-pentanone 107.32
    furfural 332.38
    n-dodecane 14.9
    diethylene glycol 82.38
    diisopropyl ether 44.71
    tert-amyl alcohol 66.07
    acetylacetone 159.1
    n-hexadecane 17.68
    acetophenone 204.93
    methyl propionate 108.01
    isopentyl acetate 165.91
    trichloroethylene 573.84
    n-nonanol 79.24
    cyclohexanol 83.49
    benzyl alcohol 123.17
    2-ethylhexanol 79.08
    isooctanol 55.52
    dipropyl ether 76.93
    1,2-dichlorobenzene 282.39
    ethyl lactate 63.35
    propylene carbonate 206.11
    n-methylformamide 76.82
    2-pentanol 41.46
    n-pentane 14.84
    1-propoxy-2-propanol 103.48
    1-methoxy-2-propyl acetate 169.05
    2-(2-methoxypropoxy) propanol 159.77
    mesitylene 105.09
    ε-caprolactone 242.85
    p-cymene 101.86
    epichlorohydrin 283.79
    1,1,1-trichloroethane 301.01
    2-aminoethanol 26.42
    morpholine-4-carbaldehyde 292.28
    sulfolane 238.96
    2,2,4-trimethylpentane 15.62
    2-methyltetrahydrofuran 209.27
    n-hexyl acetate 192.9
    isooctane 12.03
    2-(2-butoxyethoxy)ethanol 176.94
    sec-butyl acetate 95.94
    tert-butyl acetate 112.13
    decalin 37.66
    glycerin 26.86
    diglyme 310.16
    acrylic acid 73.28
    isopropyl myristate 98.49
    n-butyric acid 92.63
    acetyl acetate 134.86
    di(2-ethylhexyl) phthalate 104.48
    ethyl propionate 109.32
    nitromethane 173.75
    1,2-diethoxyethane 176.98
    benzonitrile 253.39
    trioctyl phosphate 69.16
    1-bromopropane 146.63
    gamma-valerolactone 329.26
    n-decanol 60.19
    triethyl phosphate 91.96
    4-methyl-2-pentanol 39.01
    propionitrile 110.79
    vinylene carbonate 246.99
    1,1,2-trichlorotrifluoroethane 188.19
    DMS 189.02
    cumene 105.03
    2-octanol 50.43
    2-hexanone 116.6
    octyl acetate 115.71
    limonene 115.75
    1,2-dimethoxyethane 178.56
    ethyl orthosilicate 86.0
    tributyl phosphate 93.44
    diacetone alcohol 91.51
    N,N-dimethylaniline 140.84
    acrylonitrile 146.19
    aniline 142.8
    1,3-propanediol 42.44
    bromobenzene 322.6
    dibromomethane 373.24
    1,1,2,2-tetrachloroethane 422.95
    2-methyl-cyclohexyl acetate 154.63
    tetrabutyl urea 106.26
    diisobutyl methanol 53.66
    2-phenylethanol 150.59
    styrene 160.01
    dioctyl adipate 138.84
    dimethyl sulfate 91.25
    ethyl butyrate 138.97
    methyl lactate 55.02
    butyl lactate 95.79
    diethyl carbonate 124.57
    propanediol butyl ether 92.45
    triethyl orthoformate 113.17
    p-tert-butyltoluene 95.23
    methyl 4-tert-butylbenzoate 174.23
    morpholine 219.43
    tert-butylamine 49.71
    n-dodecanol 48.52
    dimethoxymethane 111.6
    ethylene carbonate 175.57
    cyrene 133.89
    2-ethoxyethyl acetate 177.84
    2-ethylhexyl acetate 155.07
    1,2,4-trichlorobenzene 331.41
    4-methylpyridine 308.25
    dibutyl ether 100.45
    2,6-dimethyl-4-heptanol 53.66
    DEF 126.31
    dimethyl isosorbide 294.95
    tetrachloroethylene 297.36
    eugenol 163.38
    triacetin 218.17
    span 80 138.32
    1,4-butanediol 22.64
    1,1-dichloroethane 257.92
    2-methyl-1-pentanol 63.39
    methyl formate 75.49
    2-methyl-1-butanol 54.85
    n-decane 22.01
    butyronitrile 108.24
    3,7-dimethyl-1-octanol 88.37
    1-chlorooctane 77.79
    1-chlorotetradecane 40.57
    n-nonane 19.05
    undecane 17.52
    tert-butylcyclohexane 32.12
    cyclooctane 21.3
    cyclopentanol 78.82
    tetrahydropyran 201.17
    tert-amyl methyl ether 79.26
    2,5,8-trioxanonane 245.2
    1-hexene 54.09
    2-isopropoxyethanol 69.31
    2,2,2-trifluoroethanol 48.18
    methyl butyrate 132.11

    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
Erichtites hieracifolia (Brazil) Erichtites hieracifolia (L.) Raf. ex DC, fam. Asteraceae (Compositae) 10.2%