Carvone-5,6-oxide, cis-(-)-

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  • Identifiers

    CAS number
    18383-49-8

    Molecular formula
    C10H14O2

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

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1277.0
    • Carbowax: 1805.0

  • Odor profile

    Sweet 70.93%
    Mint 59.8%
    Spicy 47.72%
    Herbal 43.82%
    Woody 36.9%
    Camphoreous 36.29%
    Citrus 32.42%
    Caramellic 32.37%
    Tobacco 29.93%
    Hay 28.76%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    Molecular weight
    166.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    236°C

    Flash point est.
    99.05 ˚C

    Solubility expt.

    • Insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • 18383-49-8
    • Carvone oxide
    • Carvone-5,6-oxide, cis-(-)-
    • cis-Carvone oxide
    • Carvone oxide, cis-
    • (1S,4R,6S)-1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one
    • TV5341W478
    • (1S,4R,6S)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-one
    • DTXSID60171487
    • L-(-)-CARVONE CIS-EPOXIDE
    • 1,6-Epoxy-p-menth-8-en-2-one, (1S,4R,6S)-
    • P-Menth-8-en-2-one, 1,6-epoxy-, (1S,4R6S)-
    • FEMA NO. 4084, CIS-(-)-
    • 1-Methyl-4-(1-methylethenyl)-7-oxabicyclo(4.1.0)heptan-2-one, (1S-(1alpha,4beta,6alpha))-
    • 7-Oxabicyclo(4.1.0)heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1S-(1alpha,4beta,6alpha))-
    • P-MENTH-8-EN-2-ONE, 1,6-EPOXY-, (1S,4R,6S)-
    • 7-OXABICYCLO(4.1.0)HEPTAN-2-ONE, 1-METHYL-4-(1-METHYLETHENYL)-, (1S,4R,6S)-
    • trans-carvone oxide
    • 7-OXABICYCLO(4.1.0)HEPTAN-2-ONE, 1-METHYL-4-(1-METHYLETHENYL)-, (1S-(1.ALPHA.,4.BETA.,6.ALPHA.))-
    • UNII-TV5341W478
    • DTXSID70865668
    • (1S,4R,6S)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo(4.1.0)heptan-2-one
    • (1S,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo(4.1.0)heptan-2-one
    • cis-(-)-carvone-5,6-oxide
    • DTXCID0093978
    • DTXCID20217850
    • NS00127656
    • G39938
    • EN300-1608166
    • Q27290410
    • Z1513601121
    • 641-405-8

  • Applications

    Carvone-5,6-oxide, cis-(-)- (CAS 18383-49-8) is a chiral terpene epoxide derived from carvone and widely used as an asymmetric building block in organic synthesis: its epoxide ring undergoes selective ring openings to afford 1,2-diols, amino alcohols, ethers, and lactones with configuration transfer, serving as an intermediate to carveol/dihydrocarvone derivatives and for tuning minty–green notes in fragrance R&D; in pharma and agrochemicals it offers a renewable terpene scaffold for SAR libraries and bioactive precursors; in materials it is exploited as a bio-based epoxide monomer for optically active networks, a surface modifier, and a supramolecular motif; it also functions as a chiral standard/resolution aid in analysis and as a teaching model for stereocontrolled epoxide chemistry.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 172.57
    methanol 240.16
    isopropanol 146.2
    water 2.49
    ethyl acetate 117.3
    n-propanol 130.42
    acetone 121.32
    n-butanol 111.88
    acetonitrile 146.27
    DMF 131.5
    toluene 75.97
    isobutanol 87.04
    1,4-dioxane 311.55
    methyl acetate 146.43
    THF 182.82
    2-butanone 125.87
    n-pentanol 79.75
    sec-butanol 103.18
    n-hexane 1.65
    ethylene glycol 65.91
    NMP 54.62
    cyclohexane 5.79
    DMSO 105.51
    n-butyl acetate 72.72
    n-octanol 41.86
    chloroform 264.72
    n-propyl acetate 67.01
    acetic acid 109.15
    dichloromethane 193.9
    cyclohexanone 115.37
    propylene glycol 74.63
    isopropyl acetate 67.08
    DMAc 143.63
    2-ethoxyethanol 198.19
    isopentanol 98.18
    n-heptane 2.42
    ethyl formate 101.89
    1,2-dichloroethane 87.18
    n-hexanol 80.27
    2-methoxyethanol 307.98
    isobutyl acetate 47.89
    tetrachloromethane 34.49
    n-pentyl acetate 47.33
    transcutol 400.91
    n-heptanol 41.24
    ethylbenzene 40.17
    MIBK 60.93
    2-propoxyethanol 190.94
    tert-butanol 133.04
    MTBE 72.92
    2-butoxyethanol 106.58
    propionic acid 87.51
    o-xylene 44.82
    formic acid 88.57
    diethyl ether 68.88
    m-xylene 44.23
    p-xylene 61.06
    chlorobenzene 76.41
    dimethyl carbonate 46.75
    n-octane 1.58
    formamide 152.03
    cyclopentanone 96.87
    2-pentanone 80.98
    anisole 104.47
    cyclopentyl methyl ether 53.71
    gamma-butyrolactone 101.71
    1-methoxy-2-propanol 189.04
    pyridine 211.17
    3-pentanone 54.37
    furfural 154.45
    n-dodecane 2.29
    diethylene glycol 198.24
    diisopropyl ether 19.36
    tert-amyl alcohol 87.08
    acetylacetone 99.26
    n-hexadecane 2.66
    acetophenone 89.75
    methyl propionate 80.72
    isopentyl acetate 71.52
    trichloroethylene 189.21
    n-nonanol 39.88
    cyclohexanol 72.3
    benzyl alcohol 117.71
    2-ethylhexanol 41.03
    isooctanol 33.97
    dipropyl ether 27.93
    1,2-dichlorobenzene 63.92
    ethyl lactate 47.25
    propylene carbonate 71.6
    n-methylformamide 116.47
    2-pentanol 63.21
    n-pentane 2.72
    1-propoxy-2-propanol 109.57
    1-methoxy-2-propyl acetate 93.02
    2-(2-methoxypropoxy) propanol 100.3
    mesitylene 24.66
    ε-caprolactone 106.83
    p-cymene 23.79
    epichlorohydrin 165.21
    1,1,1-trichloroethane 94.87
    2-aminoethanol 107.72
    morpholine-4-carbaldehyde 169.55
    sulfolane 64.77
    2,2,4-trimethylpentane 2.65
    2-methyltetrahydrofuran 104.97
    n-hexyl acetate 63.46
    isooctane 2.51
    2-(2-butoxyethoxy)ethanol 146.45
    sec-butyl acetate 49.09
    tert-butyl acetate 61.2
    decalin 4.68
    glycerin 102.78
    diglyme 250.65
    acrylic acid 72.52
    isopropyl myristate 27.68
    n-butyric acid 106.94
    acetyl acetate 79.77
    di(2-ethylhexyl) phthalate 33.78
    ethyl propionate 53.35
    nitromethane 182.84
    1,2-diethoxyethane 107.5
    benzonitrile 121.25
    trioctyl phosphate 21.32
    1-bromopropane 46.1
    gamma-valerolactone 198.65
    n-decanol 29.01
    triethyl phosphate 29.22
    4-methyl-2-pentanol 46.06
    propionitrile 114.34
    vinylene carbonate 93.42
    1,1,2-trichlorotrifluoroethane 125.8
    DMS 64.08
    cumene 27.36
    2-octanol 28.24
    2-hexanone 63.11
    octyl acetate 34.0
    limonene 24.17
    1,2-dimethoxyethane 233.64
    ethyl orthosilicate 28.91
    tributyl phosphate 26.89
    diacetone alcohol 93.53
    N,N-dimethylaniline 59.47
    acrylonitrile 148.55
    aniline 103.06
    1,3-propanediol 174.68
    bromobenzene 73.37
    dibromomethane 111.24
    1,1,2,2-tetrachloroethane 137.61
    2-methyl-cyclohexyl acetate 48.54
    tetrabutyl urea 34.86
    diisobutyl methanol 28.01
    2-phenylethanol 104.78
    styrene 47.68
    dioctyl adipate 37.94
    dimethyl sulfate 43.38
    ethyl butyrate 51.75
    methyl lactate 59.22
    butyl lactate 49.62
    diethyl carbonate 44.31
    propanediol butyl ether 100.87
    triethyl orthoformate 39.77
    p-tert-butyltoluene 21.94
    methyl 4-tert-butylbenzoate 59.4
    morpholine 281.64
    tert-butylamine 62.5
    n-dodecanol 21.35
    dimethoxymethane 140.38
    ethylene carbonate 75.84
    cyrene 76.67
    2-ethoxyethyl acetate 89.13
    2-ethylhexyl acetate 50.79
    1,2,4-trichlorobenzene 76.67
    4-methylpyridine 179.33
    dibutyl ether 35.41
    2,6-dimethyl-4-heptanol 28.01
    DEF 72.86
    dimethyl isosorbide 115.05
    tetrachloroethylene 93.97
    eugenol 76.18
    triacetin 69.9
    span 80 67.67
    1,4-butanediol 72.39
    1,1-dichloroethane 107.81
    2-methyl-1-pentanol 70.09
    methyl formate 86.04
    2-methyl-1-butanol 76.33
    n-decane 3.33
    butyronitrile 108.89
    3,7-dimethyl-1-octanol 47.0
    1-chlorooctane 15.68
    1-chlorotetradecane 7.63
    n-nonane 2.45
    undecane 2.7
    tert-butylcyclohexane 4.21
    cyclooctane 2.13
    cyclopentanol 66.27
    tetrahydropyran 143.44
    tert-amyl methyl ether 44.4
    2,5,8-trioxanonane 173.01
    1-hexene 11.11
    2-isopropoxyethanol 120.83
    2,2,2-trifluoroethanol 53.35
    methyl butyrate 69.6

    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
Lippia alba (Peru) leaf Lippia alba (Mill.) N.E. Brown, fam. Verbenaceae 0.6%
Balsamite/Costmary (Lithuania) 1a Chrysanthemum balsamita L., fam. Asteraceae (Compositae) 0.37%
Balsamite/Costmary (Lithuania) 1b Chrysanthemum balsamita L., fam. Asteraceae (Compositae) 0.19%
Balsamite/Costmary (Iran) Chrysanthemum balsamita L., fam. Asteraceae (Compositae) 0.3%
Mentha longifolia (Iran) 2 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.1%
Pepper, black (India) 6b free volatiles 8006-82-4 Piper nigrum L., fam. Piperaceae 0.1%