(1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

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  • Identifiers

    CAS number
    4680-24-4

    Molecular formula
    C10H16O

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

    Retention indicies (RI)

    • DB5: 1137.5
    • Carbowax: 1448.83

  • Odor profile

    Herbal 83.07%
    Sweet 71.58%
    Mint 71.39%
    Green 71.12%
    Fresh 69.56%
    Citrus 63.5%
    Fruity 59.45%
    Spicy 56.04%
    Woody 53.78%
    Cooling 53.52%

    Scent© AI

  • Properties

    XLogP3-AA
    2.5

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    189°C

    Flash point est.
    72.61 ˚C

  • Synonyms

    • (1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
    • 4680-24-4
    • cis-(+)-Limonene oxide
    • 13837-75-7
    • (+)-cis-Limonene oxide
    • KBX06MQJ5Y
    • (4R)-limonene 1beta,2beta-epoxide
    • rel-(1R,4R,6S)-1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
    • 1beta,2beta-epoxy-4betaH-p-menth-8-ene
    • (1R,4R,6S)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
    • (1R,4R,6S)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane
    • +(-)-limonene oxide
    • cis-limonene-1,2-oxide
    • UNII-KBX06MQJ5Y
    • (R)-cis-Limonene epoxide
    • SCHEMBL2747593
    • (+)-cis-limonene-1,2-epoxide
    • CHEBI:35669
    • DTXSID10196943
    • LIMONENE OXIDE, CIS-(+)-
    • AKOS006302844
    • AT23318
    • DB02924
    • (+)-(1R,4R)-limonene-1,2- epoxide
    • BS-46525
    • FEMA NO. 4655, CIS-(+)-
    • NS00069039
    • (+)-(1R,2S,4R)-1,2-epoxy-8-p-menthene
    • (+)-(1R,2S,4R)-LIMONENE 1,2-EPOXIDE
    • Q27093910
    • 1-Methyl-4-(1-methylethenyl)-7-oxabicyclo(4.1.0)heptane (1alpha,4alpha,6alpha)-(+)-
    • 7-Oxabicyclo(4.1.0)heptane, 1-methyl-4-(1-methylethenyl)-, (1alpha,4alpha,6alpha)-(+)-
    • 7-OXABICYCLO(4.1.0)HEPTANE, 1-METHYL-4-(1-METHYLETHENYL)-, (1R,4R,6S)-

  • Applications

    (1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane (commonly known as limonene 1,2-epoxide) is a renewable monoterpene epoxide derived from limonene in citrus essential oils, used in flavor and fragrance to impart fresh citrus, green, terpenic top notes and to fine-tune diffusion and stability of compositions. In organic synthesis it serves as a versatile, stereodefined intermediate for ring-opening to diols, amino alcohols, carbonates, and other p-menthane derivatives, enabling routes toward pharmaceuticals and advanced agrochemicals. In materials science it is a key bio-based monomer for epoxide–CO2 copolymerization to poly(limonene carbonate) and participates in cationic and thiol–epoxy curing to produce sustainable coatings, adhesives, and resins. It is also employed as a GC/LC reference standard, a substrate for epoxide hydrolases, and a probe for mechanistic and enantioselective studies, with distinct stereoisomers allowing tailored odor profiles and reaction outcomes.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 936.79
    methanol 805.31
    isopropanol 752.52
    water 2.0
    ethyl acetate 510.33
    n-propanol 660.75
    acetone 349.61
    n-butanol 600.33
    acetonitrile 587.36
    DMF 231.96
    toluene 296.77
    isobutanol 411.09
    1,4-dioxane 1466.74
    methyl acetate 447.41
    THF 956.83
    2-butanone 388.43
    n-pentanol 361.54
    sec-butanol 459.71
    n-hexane 33.15
    ethylene glycol 161.45
    NMP 117.57
    cyclohexane 84.84
    DMSO 190.13
    n-butyl acetate 331.41
    n-octanol 185.28
    chloroform 1139.69
    n-propyl acetate 218.13
    acetic acid 370.09
    dichloromethane 781.61
    cyclohexanone 327.59
    propylene glycol 262.48
    isopropyl acetate 281.33
    DMAc 246.18
    2-ethoxyethanol 571.46
    isopentanol 415.75
    n-heptane 40.2
    ethyl formate 284.12
    1,2-dichloroethane 323.0
    n-hexanol 470.2
    2-methoxyethanol 868.59
    isobutyl acetate 148.34
    tetrachloromethane 164.12
    n-pentyl acetate 164.45
    transcutol 1484.14
    n-heptanol 182.46
    ethylbenzene 127.32
    MIBK 179.0
    2-propoxyethanol 780.11
    tert-butanol 555.92
    MTBE 385.5
    2-butoxyethanol 338.2
    propionic acid 292.12
    o-xylene 135.01
    formic acid 179.09
    diethyl ether 561.91
    m-xylene 159.79
    p-xylene 159.28
    chlorobenzene 236.14
    dimethyl carbonate 110.09
    n-octane 15.38
    formamide 263.55
    cyclopentanone 279.25
    2-pentanone 287.1
    anisole 282.14
    cyclopentyl methyl ether 282.6
    gamma-butyrolactone 283.34
    1-methoxy-2-propanol 632.5
    pyridine 674.19
    3-pentanone 187.62
    furfural 326.37
    n-dodecane 14.53
    diethylene glycol 528.24
    diisopropyl ether 135.37
    tert-amyl alcohol 343.37
    acetylacetone 256.46
    n-hexadecane 16.59
    acetophenone 188.44
    methyl propionate 276.32
    isopentyl acetate 277.08
    trichloroethylene 565.52
    n-nonanol 165.02
    cyclohexanol 328.3
    benzyl alcohol 265.01
    2-ethylhexanol 198.54
    isooctanol 125.97
    dipropyl ether 248.54
    1,2-dichlorobenzene 174.11
    ethyl lactate 113.24
    propylene carbonate 198.6
    n-methylformamide 244.58
    2-pentanol 344.27
    n-pentane 51.38
    1-propoxy-2-propanol 482.17
    1-methoxy-2-propyl acetate 382.16
    2-(2-methoxypropoxy) propanol 277.72
    mesitylene 88.32
    ε-caprolactone 336.53
    p-cymene 87.68
    epichlorohydrin 494.03
    1,1,1-trichloroethane 322.6
    2-aminoethanol 356.81
    morpholine-4-carbaldehyde 403.38
    sulfolane 150.0
    2,2,4-trimethylpentane 22.58
    2-methyltetrahydrofuran 546.02
    n-hexyl acetate 240.3
    isooctane 21.32
    2-(2-butoxyethoxy)ethanol 442.41
    sec-butyl acetate 168.69
    tert-butyl acetate 213.83
    decalin 31.65
    glycerin 248.5
    diglyme 722.45
    acrylic acid 196.74
    isopropyl myristate 97.65
    n-butyric acid 436.45
    acetyl acetate 271.86
    di(2-ethylhexyl) phthalate 94.92
    ethyl propionate 188.3
    nitromethane 393.83
    1,2-diethoxyethane 530.27
    benzonitrile 306.55
    trioctyl phosphate 62.5
    1-bromopropane 278.98
    gamma-valerolactone 532.48
    n-decanol 114.75
    triethyl phosphate 88.8
    4-methyl-2-pentanol 196.48
    propionitrile 500.34
    vinylene carbonate 222.83
    1,1,2-trichlorotrifluoroethane 307.1
    DMS 180.76
    cumene 82.46
    2-octanol 110.34
    2-hexanone 200.02
    octyl acetate 118.99
    limonene 108.71
    1,2-dimethoxyethane 646.37
    ethyl orthosilicate 95.6
    tributyl phosphate 81.16
    diacetone alcohol 227.48
    N,N-dimethylaniline 150.55
    acrylonitrile 439.72
    aniline 334.76
    1,3-propanediol 543.97
    bromobenzene 246.9
    dibromomethane 533.65
    1,1,2,2-tetrachloroethane 434.76
    2-methyl-cyclohexyl acetate 150.47
    tetrabutyl urea 89.94
    diisobutyl methanol 118.61
    2-phenylethanol 314.3
    styrene 161.74
    dioctyl adipate 118.73
    dimethyl sulfate 75.97
    ethyl butyrate 208.51
    methyl lactate 147.31
    butyl lactate 133.53
    diethyl carbonate 153.78
    propanediol butyl ether 284.67
    triethyl orthoformate 168.43
    p-tert-butyltoluene 84.53
    methyl 4-tert-butylbenzoate 138.87
    morpholine 1365.79
    tert-butylamine 363.89
    n-dodecanol 83.84
    dimethoxymethane 394.56
    ethylene carbonate 212.86
    cyrene 144.19
    2-ethoxyethyl acetate 309.63
    2-ethylhexyl acetate 205.56
    1,2,4-trichlorobenzene 209.49
    4-methylpyridine 491.16
    dibutyl ether 184.64
    2,6-dimethyl-4-heptanol 118.61
    DEF 219.89
    dimethyl isosorbide 316.58
    tetrachloroethylene 291.78
    eugenol 162.31
    triacetin 226.07
    span 80 220.06
    1,4-butanediol 200.56
    1,1-dichloroethane 434.92
    2-methyl-1-pentanol 246.95
    methyl formate 157.79
    2-methyl-1-butanol 332.42
    n-decane 24.34
    butyronitrile 510.28
    3,7-dimethyl-1-octanol 181.28
    1-chlorooctane 82.27
    1-chlorotetradecane 35.33
    n-nonane 21.68
    undecane 18.01
    tert-butylcyclohexane 28.82
    cyclooctane 27.06
    cyclopentanol 282.73
    tetrahydropyran 930.48
    tert-amyl methyl ether 213.23
    2,5,8-trioxanonane 467.14
    1-hexene 130.4
    2-isopropoxyethanol 372.08
    2,2,2-trifluoroethanol 103.37
    methyl butyrate 204.69

    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
Bergamot (Italy) 1 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Bergamot (Italy) 3 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Myrtle leaf, cultivated (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.02%
Myrtle leaf, wildgrowing (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.05%
Lemon (USA-California) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Lemon (Italy-Sicily) 8 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 0.2%
Caraway seed (The Netherlands) 2 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.05%
Caraway seed (Yugoslavia) 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.77%
Mandarin (Italy) 5 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%
Myrtle leaf (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.05%
Laser tribolum (Turkey) Laser tribolum (L.) Borkh. (Laserpitium t.L., Siler t.Crantz),fam.Apiaceae 0.17%
Orange, sweet (Italy) 5 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.01%
Orange, bitter (Italy) 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.01%
Orange, sweet (USA) (hydrocarbon-free) 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.23%
Yuzu (Japan) 3 Citrus junos Sieb. ex Tanaka, fam. Rutaceae 0.01%
Lemon (Japan) 4 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.07%
Shima-mikan peel 1b Citrus kinokuni Hort. ex Tanaka, fam. Rutaceae 0.05%
Myrtle leaf (Morocco) 3 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.02%
Myrtle leaf (Albania) 1 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.01%
Orange, sweet (Vietnam) 1 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.7%
Lemon (Vietnam) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.08%
Fennel, sweet (Italy) 1 8006-84-6 Foeniculum vulgare Miller, var. dulce DC, fam. Apiaceae (Umbelliferae) 0.1%
Mentha longifolia (Lithuania) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.04%
Citron (Vietnam) peel 1a Citrus medica L., cultivar sarcodactylis (Noot.) Swingle, fam. Rutaceae 0.6%
Citron (Vietnam) peel 1b Citrus medica L., cultivar sarcodactylis (Noot.) Swingle, fam. Rutaceae 0.1%
Lemon leaf (petitgrain) (Italy) 4 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.03%
Tagetes (USA) 2 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.4%
Sudachi peel (Japan) Citrus sudachi Hort. ex Shirai, fam. Rutaceae 0.01%
Mochiyuzu peel (Japan) Citrus inflata Hort. ex Tanaka, fam. Rutaceae 0.01%
Valeriana javanica root (Indonesia) Valeriana javanica Blume, fam. Valerianaceae 0.05%
Lemon verbena (Turkey) Aloysia triphylla (L'Herit.) Britton, fam. Verbenaceae 0.2%
Bergamot (Italy) 4 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Lemon (Italy-Sicily) 11 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Clementine (Italy) 3a Citrus clementina Hort. ex Tan., cultivar Oroval, fam. Rutaceae 0.01%
Clementine (Italy) 3b Citrus clementina Hort. ex Tan., cultivar Monreal, fam. Rutaceae 0.01%
Clementine (Italy) 3c Citrus clementina Hort. ex Tan., cultivar Comune, fam. Rutaceae 0.02%
Lemon (Uruguay) 8a 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Lemon (Uruguay) 8b 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Eremocharis triradiata Eremocharis triradiata (Wolff.) Johnston, fam. Apiaceae (Umbelliferae) 0.01%
Lime (Mexican, West Indian, Key) (Ivory Coast) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.01%
Lime (Mexican, West Indian, Key) 7 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.02%
Clementine (Uruguay) 1a Citrus clementina Hort. ex Tan., cultivar Nules, fam. Rutaceae 0.01%
Clementine (Uruguay) 1b Citrus clementina Hort. ex Tan., cultivar Comune, fam. Rutaceae 0.01%
Laurel leaf 1 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Helichrysum stoechas (France) 8023-85-8 Helichrysum stoechas L., fam. Asteraceae (Compositae) 0.01%
Lemon (Italy-Sicily) 12b Lo Porto 84929-31-7 Citrus limon (L.) Burm. f., cultivar Lo Porto, fam. Rutaceae 0.01%
Grapefruit (Cuba), distilled 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.1%
Grapefruit (Cuba), cold-pressed 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.1%
Pummelo (Shaddock) (India) peel 84696-38-8 Citrus maxima (J. Burman) Merrill. (C. grandis (L.) Osbeck), fam. Rutaceae 0.01%