trans-Piperitone epoxide

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  • Identifiers

    CAS number
    4713-37-5

    Molecular formula
    C10H16O2

    SMILES
    CC(C)[C@H]1CC[C@@]2([C@H](C1=O)O2)C

    Retention indicies (RI)

    • DB5: 1261.0
    • Carbowax: 1727.0

  • Odor profile

    Mint 68.28%
    Herbal 63.92%
    Woody 54.46%
    Camphoreous 54.38%
    Cooling 50.16%
    Fresh 44.8%
    Spicy 34.47%
    Sweet 31.53%
    Pine 30.99%
    Earthy 28.55%

    Scent© AI

  • Properties

    XLogP3-AA
    1.8

    Molecular weight
    168.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    231°C

    Flash point est.
    102.13 ˚C

  • Synonyms

    • trans-Piperitone epoxide
    • Piperitone oxide, trans-
    • Y4ZF10N3DK
    • Piperitone oxide, (1R,2R,4R)-
    • UNII-Y4ZF10N3DK
    • (+)-(1R,2R,4R)-trans-Piperitone oxide
    • p-Menthan-3-one, 1,2-epoxy-, (1R,2R,4R)-
    • 4713-37-5
    • 7-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethyl)-, (1R,3R,6R)-
    • 7-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethyl)-, (1R-(1alpha,3beta,6alpha))-
    • X83LW7ZZB5
    • PIPERITONE OXIDE, TRANS-(+/-)-
    • PIPERITONE OXIDE, (1S,2R,4R)-REL-
    • Q67880140
    • 7-OXABICYCLO(4.1.0)HEPTAN-2-ONE, 6-METHYL-3-(1-METHYLETHYL)-, (1R,3R,6R)-REL-
    • 7-OXABICYCLO(4.1.0)HEPTAN-2-ONE, 6-METHYL-3-(1-METHYLETHYL)-, (1.ALPHA.,3.BETA.,6.ALPHA.)-
    • 7-OXABICYCLO(4.1.0)HEPTAN-2-ONE, 6-METHYL-3-(1-METHYLETHYL)-, (1R-(1.ALPHA.,3.BETA.,6.ALPHA.))-

  • Applications

    trans-Piperitone epoxide (CAS 4713-37-5) is a monoterpene epoxide used primarily as a reactive intermediate and terpenoid building block: its strained epoxide ring undergoes selective ring-opening with amines, alcohols, thiols, and heteroatom nucleophiles to give amino alcohols, diols, and further functionalized derivatives; accordingly it serves in the synthesis of flavor and fragrance chemicals (e.g., menthone/menthol derivatives and oxidized terpenes), pharmaceutical intermediates, and natural-product-like scaffolds; it is also a convenient substrate for catalytic transformations (asymmetric ring-opening, hydrogenation, rearrangement) and for biocatalysis/biotransformations (epoxide hydrolases) to access enantioenriched monoterpenes; in analysis it is used as a reference/quality-control standard and method-development compound for GC–MS/LC–MS when monitoring monoterpene epoxides, as well as a model molecule for mechanistic and kinetic studies of epoxide reactivity; in industrial practice it is seldom used directly but is typically converted further to deliver desired odor stability, safety, and performance in formulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 127.49
    methanol 165.08
    isopropanol 94.13
    water 2.22
    ethyl acetate 73.02
    n-propanol 96.73
    acetone 84.81
    n-butanol 86.67
    acetonitrile 107.11
    DMF 94.13
    toluene 60.37
    isobutanol 67.88
    1,4-dioxane 194.52
    methyl acetate 86.95
    THF 189.64
    2-butanone 82.99
    n-pentanol 64.25
    sec-butanol 72.85
    n-hexane 4.45
    ethylene glycol 46.47
    NMP 101.24
    cyclohexane 14.33
    DMSO 69.07
    n-butyl acetate 77.87
    n-octanol 47.09
    chloroform 339.59
    n-propyl acetate 56.59
    acetic acid 126.72
    dichloromethane 234.32
    cyclohexanone 130.06
    propylene glycol 53.3
    isopropyl acetate 52.08
    DMAc 87.18
    2-ethoxyethanol 100.36
    isopentanol 68.62
    n-heptane 5.31
    ethyl formate 83.95
    1,2-dichloroethane 105.32
    n-hexanol 81.36
    2-methoxyethanol 149.55
    isobutyl acetate 46.93
    tetrachloromethane 50.27
    n-pentyl acetate 53.59
    transcutol 236.93
    n-heptanol 45.12
    ethylbenzene 38.21
    MIBK 50.19
    2-propoxyethanol 132.92
    tert-butanol 86.76
    MTBE 54.0
    2-butoxyethanol 81.13
    propionic acid 79.17
    o-xylene 41.7
    formic acid 68.49
    diethyl ether 52.93
    m-xylene 42.03
    p-xylene 56.95
    chlorobenzene 88.74
    dimethyl carbonate 31.09
    n-octane 3.47
    formamide 86.08
    cyclopentanone 129.21
    2-pentanone 60.75
    anisole 69.83
    cyclopentyl methyl ether 60.51
    gamma-butyrolactone 148.93
    1-methoxy-2-propanol 100.12
    pyridine 153.91
    3-pentanone 45.57
    furfural 166.25
    n-dodecane 4.52
    diethylene glycol 137.68
    diisopropyl ether 20.25
    tert-amyl alcohol 66.35
    acetylacetone 73.15
    n-hexadecane 5.16
    acetophenone 72.35
    methyl propionate 55.78
    isopentyl acetate 78.0
    trichloroethylene 215.05
    n-nonanol 43.11
    cyclohexanol 75.68
    benzyl alcohol 76.94
    2-ethylhexanol 48.53
    isooctanol 36.37
    dipropyl ether 31.61
    1,2-dichlorobenzene 82.32
    ethyl lactate 46.83
    propylene carbonate 104.41
    n-methylformamide 77.45
    2-pentanol 49.98
    n-pentane 6.17
    1-propoxy-2-propanol 90.42
    1-methoxy-2-propyl acetate 80.96
    2-(2-methoxypropoxy) propanol 83.66
    mesitylene 27.03
    ε-caprolactone 120.86
    p-cymene 30.3
    epichlorohydrin 160.34
    1,1,1-trichloroethane 112.35
    2-aminoethanol 74.88
    morpholine-4-carbaldehyde 138.44
    sulfolane 114.71
    2,2,4-trimethylpentane 5.68
    2-methyltetrahydrofuran 116.45
    n-hexyl acetate 75.38
    isooctane 4.75
    2-(2-butoxyethoxy)ethanol 113.71
    sec-butyl acetate 43.91
    tert-butyl acetate 52.72
    decalin 8.97
    glycerin 77.33
    diglyme 160.2
    acrylic acid 76.39
    isopropyl myristate 33.95
    n-butyric acid 101.3
    acetyl acetate 62.95
    di(2-ethylhexyl) phthalate 44.09
    ethyl propionate 47.84
    nitromethane 137.11
    1,2-diethoxyethane 72.86
    benzonitrile 109.88
    trioctyl phosphate 31.02
    1-bromopropane 62.43
    gamma-valerolactone 174.09
    n-decanol 33.27
    triethyl phosphate 36.25
    4-methyl-2-pentanol 37.83
    propionitrile 86.05
    vinylene carbonate 114.71
    1,1,2-trichlorotrifluoroethane 121.43
    DMS 64.65
    cumene 28.66
    2-octanol 32.88
    2-hexanone 58.09
    octyl acetate 41.87
    limonene 35.2
    1,2-dimethoxyethane 130.36
    ethyl orthosilicate 34.48
    tributyl phosphate 34.22
    diacetone alcohol 69.14
    N,N-dimethylaniline 44.17
    acrylonitrile 104.17
    aniline 75.77
    1,3-propanediol 104.57
    bromobenzene 87.01
    dibromomethane 151.48
    1,1,2,2-tetrachloroethane 160.07
    2-methyl-cyclohexyl acetate 61.51
    tetrabutyl urea 41.36
    diisobutyl methanol 29.92
    2-phenylethanol 90.82
    styrene 42.85
    dioctyl adipate 47.08
    dimethyl sulfate 40.26
    ethyl butyrate 56.39
    methyl lactate 45.95
    butyl lactate 56.27
    diethyl carbonate 49.37
    propanediol butyl ether 81.14
    triethyl orthoformate 47.11
    p-tert-butyltoluene 27.35
    methyl 4-tert-butylbenzoate 63.29
    morpholine 175.98
    tert-butylamine 54.13
    n-dodecanol 25.77
    dimethoxymethane 72.98
    ethylene carbonate 95.8
    cyrene 81.18
    2-ethoxyethyl acetate 74.62
    2-ethylhexyl acetate 62.74
    1,2,4-trichlorobenzene 99.33
    4-methylpyridine 128.44
    dibutyl ether 35.59
    2,6-dimethyl-4-heptanol 29.92
    DEF 58.61
    dimethyl isosorbide 113.2
    tetrachloroethylene 120.91
    eugenol 69.91
    triacetin 73.63
    span 80 73.83
    1,4-butanediol 51.53
    1,1-dichloroethane 119.13
    2-methyl-1-pentanol 58.22
    methyl formate 68.7
    2-methyl-1-butanol 58.56
    n-decane 6.55
    butyronitrile 95.94
    3,7-dimethyl-1-octanol 46.94
    1-chlorooctane 25.98
    1-chlorotetradecane 12.86
    n-nonane 5.4
    undecane 5.36
    tert-butylcyclohexane 7.85
    cyclooctane 4.8
    cyclopentanol 81.92
    tetrahydropyran 126.57
    tert-amyl methyl ether 39.21
    2,5,8-trioxanonane 118.92
    1-hexene 20.15
    2-isopropoxyethanol 74.45
    2,2,2-trifluoroethanol 56.71
    methyl butyrate 62.87

    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
Mentha longifolia ssp. himalaiensis 90063-99-3 Mentha longifolia (L.) Hudson, ssp. himalaiensis Briq., fam. Lamiaceae 0.8%
Mentha longifolia ssp. petiolata (Greece) 2 90063-99-3 Mentha longifolia (L.) ssp. petiolata (Chemotype II), fam. Lamiaceae 0.01%
Mentha rotundifolia (Japan) Mentha rotundifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 2.0%
Mentha spicata (Greece) Chemotype I Mentha spicata L. (Chemotype I), fam. Lamiaceae (Labiatae) 0.01%
Mentha spicata (Greece) Chemotype II Mentha spicata L. (Chemotype II), fam. Lamiaceae (Labiatae) 0.02%
Calamintha nepeta (Greece) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 6.1%
Calamintha nepeta (Turkey) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 25.23%
Micromeria congesta (Turkey) Micromeria congesta Boiss. et Hausskn. ex Boiss., fam. Lamiaceae (Labiat. 4.95%
Mentha grandiflora (Australia) Mentha grandiflora Benth., fam. Lamiaceae (Labiatae) 21.4%
Plectranthus glandulosus (Cameroon) 2 Plectranthus glandulosus Hook f., fam. Lamiaceae (Labiatae) 0.5%
Oregano, greek (Greece) 2 84012-24-8 Origanum vulgare L. ssp. hirtum (Link) Ietsw., fam. Lamiaceae (Labiatae) 0.6%