(+)-Methysticin

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  • Identifiers

    CAS number
    495-85-2

    Molecular formula
    C15H14O5

    SMILES
    COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3

    Safety labels

  • Odor profile

    Fragrance
    Spicy 68.28%
    Sweet 61.78%
    Coumarinic 38.98%
    Cinnamon 38.11%
    Vanilla 34.3%
    Coconut 34.15%
    Warm 33.92%
    Balsamic 31.82%
    Floral 30.39%
    Herbal 30.12%

     

    Flavor
    Bitter 65.45%
    Lovage 20.33%
    Parsley 19.26%
    Cedarleaf 18.55%
    Ethyl benzoate 18.23%
    Ripe apricot 18.2%
    Red fruit 17.99%
    Basil 17.93%
    Seedy 17.87%
    Fenugreek 17.85%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    5.96 (weak acid)

    Molecular weight
    274.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    677°C

    Flash point

    • 180.37 ˚C est.

  • Synonyms

    • Methysticin
    • Kavatin
    • 495-85-2
    • Kavahin
    • (+)-Methysticin
    • DTXSID5033674
    • M832AIJ6HX
    • (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
    • NSC-112158
    • DTXCID3013674
    • (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-4-methoxy-2,3-dihydropyran-6-one
    • (2R)-2-((E)-2-(1,3-benzodioxol-5-yl)ethenyl)-4-methoxy-2,3-dihydropyran-6-one
    • (2R)-2-((E)-2-(1,3-benzodioxol-5-yl)vinyl)-4-methoxy-2,3-dihydropyran-6-one
    • RefChem:42736
    • GlyTouCan:G64494CY
    • G64494CY
    • Methylsticin
    • NSC 112158
    • C15H14O5
    • (R,E)-6-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one
    • 20697-20-5
    • UNII-M832AIJ6HX
    • BRN 0091701
    • CCRIS 9370
    • 2H-Pyran-2-one,6-[(1E)-2-(1,3-benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-, (6R)-
    • (R)-5,6-Dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-2H-pyran-2-one
    • (R-(E))-6-(2-(1,3-Benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one
    • R-(+)-Methysticin
    • Methylsticin (Standard)
    • METHYSTICIN [MI]
    • 4-Methoxy-6-(beta-(3',4'-methylenedioxyphenyl)vinyl)-5,6-dihydro-alpha-pyrone
    • 5-Hydroxy-3-methoxy-7-(3,4-(methylenedioxy)phenyl)-2,6-heptadienoic acid gamma-lactone
    • 5-19-10-00456 (Beilstein Handbook Reference)
    • CHEBI:6895
    • CHEMBL579224
    • SCHEMBL1393508
    • SCHEMBL30148105
    • HY-N2465R
    • WLZ4678
    • Tox21_200901
    • MFCD21364778
    • NSC112158
    • AKOS030573530
    • FM69761
    • 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-, (R)-
    • 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-, (R)- (VAN)
    • 2H-Pyran-2-one, 6-(2-(1,3-benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-, (R-(E))-
    • NCGC00091903-01
    • NCGC00091903-02
    • NCGC00258455-01
    • AC-34499
    • CAS-495-85-2
    • DA-55436
    • DA-75502
    • C09952
    • A827756
    • Q3333720
    • 2H-Pyran-2-one,3-benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-, [R-(E)]-
    • 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)styryl]-, (+)-
    • 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)styryl]-, (R)-
    • 6-(3',4'-METHYLENEDIOXYSTYRYL)-4-METHOXY-5,6-DIHYDRO-2H-PYRAN-2-ONE
    • (6R)-6-((1E)-2-(1,3-BENZODIOXOL-5-YL)ETHENYL)-5,6-DIHYDRO-4-METHOXY-2H-PYRAN-2-ONE
    • (6R)-6-[(E)-2-(2H-1,3-Benzodioxol-5-yl)ethen-1-yl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
    • 495-85-2

  • Applications

    (+)-Methysticin (CAS 495-85-2) is a natural kavalactone component of Piper methysticum (kava) root. In industry, it appears mainly in kava extracts used for herbal dietary supplements and related traditional beverages, where it contributes to the product's phytochemical profile. It is commonly used as a marker compound for quality control and standardization of kava-derived products, supporting chromatographic analysis and batch-to-batch consistency. In research settings, (+)-Methysticin is studied as part of phytochemical and pharmacology investigations on kavalactones, including preclinical studies to explore its activity and mechanism of action. Regulatory and formulation considerations mean its use is typically subject to local rules and limits in kava-containing products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.43
    methanol 19.21
    isopropanol 21.14
    water 0.08
    ethyl acetate 46.31
    n-propanol 17.0
    acetone 91.65
    n-butanol 13.7
    acetonitrile 90.53
    DMF 111.44
    toluene 8.13
    isobutanol 13.01
    1,4-dioxane 117.56
    methyl acetate 62.5
    THF 173.8
    2-butanone 68.74
    n-pentanol 12.27
    sec-butanol 16.64
    n-hexane 0.2
    ethylene glycol 19.87
    NMP 55.85
    cyclohexane 0.6
    DMSO 403.82
    n-butyl acetate 21.04
    n-octanol 5.41
    chloroform 119.04
    n-propyl acetate 26.41
    acetic acid 49.88
    dichloromethane 119.0
    cyclohexanone 55.52
    propylene glycol 22.46
    isopropyl acetate 23.52
    DMAc 218.51
    2-ethoxyethanol 89.89
    isopentanol 13.46
    n-heptane 0.37
    ethyl formate 30.47
    1,2-dichloroethane 66.01
    n-hexanol 8.71
    2-methoxyethanol 127.62
    isobutyl acetate 15.88
    tetrachloromethane 5.0
    n-pentyl acetate 8.97
    transcutol 189.34
    n-heptanol 4.6
    ethylbenzene 4.92
    MIBK 20.63
    2-propoxyethanol 62.01
    tert-butanol 24.92
    MTBE 12.86
    2-butoxyethanol 24.46
    propionic acid 24.82
    o-xylene 5.84
    formic acid 30.13
    diethyl ether 18.85
    m-xylene 5.0
    p-xylene 7.61
    chlorobenzene 16.41
    dimethyl carbonate 37.01
    n-octane 0.27
    formamide 74.48
    cyclopentanone 79.38
    2-pentanone 37.31
    anisole 31.42
    cyclopentyl methyl ether 26.17
    gamma-butyrolactone 85.17
    1-methoxy-2-propanol 84.17
    pyridine 66.98
    3-pentanone 32.09
    furfural 87.25
    n-dodecane 0.49
    diethylene glycol 85.45
    diisopropyl ether 4.24
    tert-amyl alcohol 17.56
    acetylacetone 65.42
    n-hexadecane 0.58
    acetophenone 31.08
    methyl propionate 46.57
    isopentyl acetate 20.57
    trichloroethylene 141.33
    n-nonanol 6.28
    cyclohexanol 16.2
    benzyl alcohol 30.4
    2-ethylhexanol 6.88
    isooctanol 4.96
    dipropyl ether 10.63
    1,2-dichlorobenzene 16.22
    ethyl lactate 24.16
    propylene carbonate 33.92
    n-methylformamide 54.25
    2-pentanol 9.86
    n-pentane 0.15
    1-propoxy-2-propanol 39.0
    1-methoxy-2-propyl acetate 42.21
    2-(2-methoxypropoxy) propanol 48.42
    mesitylene 3.17
    ε-caprolactone 44.98
    p-cymene 4.39
    epichlorohydrin 150.12
    1,1,1-trichloroethane 34.6
    2-aminoethanol 25.97
    morpholine-4-carbaldehyde 111.97
    sulfolane 100.35
    2,2,4-trimethylpentane 0.29
    2-methyltetrahydrofuran 54.28
    n-hexyl acetate 14.1
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 55.63
    sec-butyl acetate 17.01
    tert-butyl acetate 22.2
    decalin 0.67
    glycerin 57.78
    diglyme 116.28
    acrylic acid 28.77
    isopropyl myristate 9.51
    n-butyric acid 30.03
    acetyl acetate 33.68
    di(2-ethylhexyl) phthalate 12.52
    ethyl propionate 26.94
    nitromethane 181.48
    1,2-diethoxyethane 44.0
    benzonitrile 34.8
    trioctyl phosphate 7.16
    1-bromopropane 17.14
    gamma-valerolactone 117.19
    n-decanol 5.4
    triethyl phosphate 16.08
    4-methyl-2-pentanol 6.59
    propionitrile 45.81
    vinylene carbonate 36.98
    1,1,2-trichlorotrifluoroethane 101.11
    DMS 27.13
    cumene 3.82
    2-octanol 3.43
    2-hexanone 25.45
    octyl acetate 11.01
    limonene 4.88
    1,2-dimethoxyethane 130.04
    ethyl orthosilicate 13.99
    tributyl phosphate 11.12
    diacetone alcohol 37.59
    N,N-dimethylaniline 17.09
    acrylonitrile 70.21
    aniline 26.61
    1,3-propanediol 43.57
    bromobenzene 16.22
    dibromomethane 53.64
    1,1,2,2-tetrachloroethane 101.88
    2-methyl-cyclohexyl acetate 18.92
    tetrabutyl urea 16.53
    diisobutyl methanol 5.24
    2-phenylethanol 21.18
    styrene 7.27
    dioctyl adipate 18.37
    dimethyl sulfate 62.57
    ethyl butyrate 21.43
    methyl lactate 43.72
    butyl lactate 13.51
    diethyl carbonate 19.62
    propanediol butyl ether 23.56
    triethyl orthoformate 19.92
    p-tert-butyltoluene 3.84
    methyl 4-tert-butylbenzoate 22.59
    morpholine 120.22
    tert-butylamine 7.39
    n-dodecanol 4.68
    dimethoxymethane 98.75
    ethylene carbonate 32.29
    cyrene 40.32
    2-ethoxyethyl acetate 24.92
    2-ethylhexyl acetate 15.41
    1,2,4-trichlorobenzene 25.15
    4-methylpyridine 49.23
    dibutyl ether 10.55
    2,6-dimethyl-4-heptanol 5.24
    DEF 44.14
    dimethyl isosorbide 67.73
    tetrachloroethylene 41.58
    eugenol 27.81
    triacetin 30.49
    span 80 22.61
    1,4-butanediol 21.92
    1,1-dichloroethane 47.0
    2-methyl-1-pentanol 11.75
    methyl formate 47.22
    2-methyl-1-butanol 11.95
    n-decane 0.66
    butyronitrile 29.61
    3,7-dimethyl-1-octanol 8.06
    1-chlorooctane 3.56
    1-chlorotetradecane 2.13
    n-nonane 0.5
    undecane 0.56
    tert-butylcyclohexane 0.49
    cyclooctane 0.25
    cyclopentanol 20.48
    tetrahydropyran 49.21
    tert-amyl methyl ether 11.72
    2,5,8-trioxanonane 97.51
    1-hexene 1.46
    2-isopropoxyethanol 48.92
    2,2,2-trifluoroethanol 29.16
    methyl butyrate 30.86

    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