(5R,6S)-5,6-Epoxy-7-megastigmen-9-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    23267-57-4

    Molecular formula
    C13H20O2

    SMILES
    CC(=O)/C=C/C12C(CCCC1(O2)C)(C)C

    Retention indicies (RI)

    • DB5: 1491.0
    • Carbowax: 1959.5

  • Odor profile

    Woody 88.13%
    Floral 86.27%
    Fruity 79.92%
    Berry 64.73%
    Sweet 62.56%
    Raspberry 54.29%
    Powdery 51.2%
    Violet 50.93%
    Orris 50.82%
    Tobacco 44.75%

    Scent© AI

  • Properties

    XLogP3-AA
    2.0

    Molecular weight
    208.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    266°C

    Melting point expt.

    • 48.5 - 49.5 °C

    Flash point est.
    120.84 ˚C

    Solubility expt.

    • Insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • beta-Ionone epoxide
    • 23267-57-4
    • 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-3-en-2-one
    • (E)-4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-3-en-2-one
    • .beta.-Ionon-5,6-epoxide
    • (5R,6S)-5,6-Epoxy-7-megastigmen-9-one
    • .beta.-Ionone epoxide
    • beta-ionone 5,6-epoxide
    • Epoxy-.beta.-ionone
    • 5,6-Epoxy-.beta.-ionone
    • .beta.-Ionone-5,6-epoxide
    • .beta.-Ionone-5,6-epoxyde
    • 5,6-.beta.-Ionone epoxide
    • SCHEMBL1774698
    • CHEMBL3355912
    • SCHEMBL17627686
    • CHEBI:87546
    • CHEBI:208937
    • 7-Oxabicyclo[4.1.0]heptane, 3-buten-2-one deriv.
    • (e)-4-(2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]heptan-1-yl)but-3-en-2-one
    • 4-(1',2'-epoxy-2',6',6'-trimethyl-2'-cyclohex-1'-yl)-3-buten-2-one
    • (3E)-4-{2,2,6-TRIMETHYL-7-OXABICYCLO[4.1.0]HEPTAN-1-YL}BUT-3-EN-2-ONE

  • Applications

    (5R,6S)-5,6-Epoxy-7-megastigmen-9-one (CAS 23267-57-4) is a carotenoid-derived norisoprenoid used across flavor–fragrance applications and analytical research. At trace levels (ppb–ppm) it functions as a flavor ingredient or modulator for black/oolong teas, tobacco, wines, fruit beverages, and confectionery, reinforcing tea-like, woody, osmanthus, stone-fruit, and dried-fruit nuances. The enantiopure (5R,6S) form enables accurate sensory formulation and development of enantioselective GC-O/GC-MS methods, calibration, and aroma recombination/omission tests. In food science it serves as a marker of carotenoid degradation, fermentation/aging, and storage conditions, supporting provenance tracing, authenticity, and process optimization. In laboratories it is employed as a reference standard, metabolomics tracer, and a synthetic intermediate/model compound for studies on the megastigmane family, stereochemistry, and chiral separations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 136.94
    methanol 191.69
    isopropanol 94.51
    water 2.97
    ethyl acetate 146.11
    n-propanol 102.05
    acetone 158.04
    n-butanol 95.03
    acetonitrile 212.95
    DMF 252.2
    toluene 127.09
    isobutanol 78.42
    1,4-dioxane 353.44
    methyl acetate 169.86
    THF 443.49
    2-butanone 142.62
    n-pentanol 71.56
    sec-butanol 79.19
    n-hexane 11.11
    ethylene glycol 53.64
    NMP 274.51
    cyclohexane 26.1
    DMSO 149.58
    n-butyl acetate 106.86
    n-octanol 51.4
    chloroform 519.11
    n-propyl acetate 100.88
    acetic acid 143.9
    dichloromethane 458.19
    cyclohexanone 203.44
    propylene glycol 57.3
    isopropyl acetate 100.92
    DMAc 234.36
    2-ethoxyethanol 128.11
    isopentanol 84.88
    n-heptane 10.5
    ethyl formate 108.48
    1,2-dichloroethane 179.11
    n-hexanol 90.68
    2-methoxyethanol 201.97
    isobutyl acetate 79.71
    tetrachloromethane 79.04
    n-pentyl acetate 80.3
    transcutol 327.19
    n-heptanol 55.24
    ethylbenzene 74.01
    MIBK 88.66
    2-propoxyethanol 186.46
    tert-butanol 108.38
    MTBE 114.95
    2-butoxyethanol 113.08
    propionic acid 105.36
    o-xylene 81.13
    formic acid 104.98
    diethyl ether 113.95
    m-xylene 89.94
    p-xylene 106.94
    chlorobenzene 165.81
    dimethyl carbonate 93.83
    n-octane 4.95
    formamide 170.74
    cyclopentanone 270.28
    2-pentanone 110.73
    anisole 157.0
    cyclopentyl methyl ether 146.43
    gamma-butyrolactone 297.82
    1-methoxy-2-propanol 138.36
    pyridine 266.95
    3-pentanone 99.59
    furfural 289.88
    n-dodecane 5.57
    diethylene glycol 164.26
    diisopropyl ether 43.56
    tert-amyl alcohol 86.42
    acetylacetone 153.47
    n-hexadecane 6.41
    acetophenone 143.33
    methyl propionate 125.94
    isopentyl acetate 108.95
    trichloroethylene 381.0
    n-nonanol 49.76
    cyclohexanol 91.33
    benzyl alcohol 112.51
    2-ethylhexanol 58.82
    isooctanol 47.6
    dipropyl ether 64.65
    1,2-dichlorobenzene 156.38
    ethyl lactate 63.79
    propylene carbonate 184.55
    n-methylformamide 149.01
    2-pentanol 62.13
    n-pentane 12.66
    1-propoxy-2-propanol 114.62
    1-methoxy-2-propyl acetate 138.88
    2-(2-methoxypropoxy) propanol 120.6
    mesitylene 54.36
    ε-caprolactone 198.29
    p-cymene 45.25
    epichlorohydrin 329.93
    1,1,1-trichloroethane 199.13
    2-aminoethanol 87.28
    morpholine-4-carbaldehyde 316.98
    sulfolane 227.03
    2,2,4-trimethylpentane 10.43
    2-methyltetrahydrofuran 236.4
    n-hexyl acetate 113.36
    isooctane 8.25
    2-(2-butoxyethoxy)ethanol 138.52
    sec-butyl acetate 80.0
    tert-butyl acetate 103.59
    decalin 19.19
    glycerin 80.54
    diglyme 243.0
    acrylic acid 105.22
    isopropyl myristate 51.8
    n-butyric acid 111.33
    acetyl acetate 141.49
    di(2-ethylhexyl) phthalate 62.63
    ethyl propionate 98.15
    nitromethane 252.05
    1,2-diethoxyethane 121.04
    benzonitrile 155.4
    trioctyl phosphate 42.61
    1-bromopropane 103.24
    gamma-valerolactone 336.86
    n-decanol 37.41
    triethyl phosphate 60.04
    4-methyl-2-pentanol 49.07
    propionitrile 135.42
    vinylene carbonate 199.63
    1,1,2-trichlorotrifluoroethane 201.5
    DMS 125.16
    cumene 52.94
    2-octanol 36.76
    2-hexanone 98.23
    octyl acetate 62.39
    limonene 53.7
    1,2-dimethoxyethane 236.68
    ethyl orthosilicate 58.27
    tributyl phosphate 49.89
    diacetone alcohol 101.89
    N,N-dimethylaniline 103.44
    acrylonitrile 168.03
    aniline 125.59
    1,3-propanediol 105.76
    bromobenzene 179.7
    dibromomethane 252.32
    1,1,2,2-tetrachloroethane 266.3
    2-methyl-cyclohexyl acetate 97.3
    tetrabutyl urea 60.84
    diisobutyl methanol 39.1
    2-phenylethanol 128.38
    styrene 89.18
    dioctyl adipate 73.3
    dimethyl sulfate 117.83
    ethyl butyrate 88.33
    methyl lactate 80.39
    butyl lactate 67.77
    diethyl carbonate 78.35
    propanediol butyl ether 94.9
    triethyl orthoformate 72.1
    p-tert-butyltoluene 43.85
    methyl 4-tert-butylbenzoate 108.24
    morpholine 327.36
    tert-butylamine 79.86
    n-dodecanol 29.21
    dimethoxymethane 202.83
    ethylene carbonate 163.86
    cyrene 138.25
    2-ethoxyethyl acetate 126.76
    2-ethylhexyl acetate 90.51
    1,2,4-trichlorobenzene 184.76
    4-methylpyridine 236.98
    dibutyl ether 52.3
    2,6-dimethyl-4-heptanol 39.1
    DEF 131.75
    dimethyl isosorbide 210.17
    tetrachloroethylene 187.63
    eugenol 113.1
    triacetin 124.84
    span 80 91.94
    1,4-butanediol 52.21
    1,1-dichloroethane 194.26
    2-methyl-1-pentanol 70.48
    methyl formate 124.25
    2-methyl-1-butanol 76.94
    n-decane 8.81
    butyronitrile 125.64
    3,7-dimethyl-1-octanol 55.71
    1-chlorooctane 35.18
    1-chlorotetradecane 16.66
    n-nonane 7.45
    undecane 6.76
    tert-butylcyclohexane 15.93
    cyclooctane 10.06
    cyclopentanol 109.71
    tetrahydropyran 215.82
    tert-amyl methyl ether 84.11
    2,5,8-trioxanonane 179.69
    1-hexene 37.64
    2-isopropoxyethanol 98.47
    2,2,2-trifluoroethanol 78.15
    methyl butyrate 114.92

    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
Lemon balm (Germany) 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Boronia megastigma 91771-36-7 Boronia megastigma Nees., fam. Rutaceae 0.5%
Anthoxanthum odoratum (Italy) 1b hay Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 0.1%
Catharanthus roseus leaf Catharanthus roseus (L.) G. Don, fam. Apocynaceae 0.3%
Catharanthus roseus marcs Catharanthus roseus (L.) G. Don, fam. Apocynaceae 1.0%