(+)-Kavain

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  • Identifiers

    CAS number
    500-64-1

    Molecular formula
    C14H14O3

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

    Safety labels

  • Odor profile

    Fragrance
    Sweet 80.6%
    Spicy 75.46%
    Cinnamon 60.64%
    Balsamic 52.5%
    Coumarinic 43.06%
    Warm 40.14%
    Herbal 38.9%
    Vanilla 33.03%
    Floral 32.36%
    Coconut 31.73%

     

    Flavor
    Floral 37.1%
    Balsam 33.82%
    Spice 32.25%
    Bitter 30.87%
    Sweet 29.1%
    Herbal 27.55%
    Cinnamon 27.29%
    Spicy 22.54%
    Minty 22.29%
    Warm 20.77%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    6.87 (neutral)

    Molecular weight
    230.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    512°C

    Flash point

    • 166.1 ˚C est.

  • Synonyms

    • Kawain
    • kavain
    • 500-64-1
    • (+)-Kavain
    • DTXSID5033595
    • W1ES06373M
    • NSC-112162
    • DTXCID3013595
    • Cavain
    • (2R)-4-methoxy-2-[(E)-styryl]-2,3-dihydropyran-6-one
    • kavaine
    • (2R)-4-methoxy-2-((E)-styryl)-2,3-dihydropyran-6-one
    • RefChem:40431
    • GlyTouCan:G36625OI
    • (2R)-4-methoxy-2-((E)-2-phenylethenyl)-2,3-dihydropyran-6-one
    • G36625OI
    • 207-907-2
    • Gonosan
    • L-KAWAIN
    • (R)-(+)-Kavain
    • C14H14O3
    • NSC 112162
    • (R,E)-4-methoxy-6-styryl-5,6-dihydro-2H-pyran-2-one
    • 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-, (+)-
    • Kavain, dl-
    • (R)-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one
    • 2H-PYRAN-2-ONE, 5,6-DIHYDRO-4-METHOXY-6-STYRYL-, (R)-
    • (R)-Kavain
    • Kawaih
    • UNII-W1ES06373M
    • 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethenyl)-, (R-(E))-
    • D-Kawain
    • Kavaform (TN)
    • CAS-500-64-1
    • EINECS 207-907-2
    • MFCD00467093
    • KAWAIN [USP-RS]
    • KAWAIN [WHO-DD]
    • Prestwick2_000207
    • Prestwick3_000207
    • KAWAIN [MI]
    • (+)-Kavain (Standard)
    • (+)-KAWAIN
    • BSPBio_000193
    • MLS002154236
    • SCHEMBL515202
    • BPBio1_000213
    • CHEBI:6117
    • CHEMBL578607
    • orb1302730
    • 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethenyl)-, [R-(E)]-
    • CHEBI:92164
    • HY-B1671R
    • 4-Methoxy-6-(beta-phenylvinyl)-5,6-dihydro-alpha-pyrone
    • WLZ4683
    • HMS1568J15
    • HMS2095J15
    • HMS2230N15
    • HMS3887G03
    • 5-Hydroxy-3-methoxy-7-phenyl-2,6-heptadienoic acid gamma-lactone
    • HY-B1671
    • Tox21_200907
    • NSC112162
    • s9409
    • (6R)-4-methoxy-6-[(1E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one
    • AKOS030631732
    • CCG-266792
    • EBC-616716
    • FK65505
    • NCGC00091905-01
    • NCGC00091905-02
    • NCGC00091905-03
    • NCGC00091905-05
    • NCGC00258461-01
    • AC-35093
    • DA-74729
    • MS-23309
    • SMR001233508
    • SY231863
    • AB00513818
    • CS-0013634
    • NS00080159
    • C09947
    • D08096
    • Q3194310
    • BRD-K09497549-001-03-6
    • 2H-Pyran-2-one,6-dihydro-4-methoxy-6-styryl-, (+)-
    • 2H-Pyran-2-one,6-dihydro-4-methoxy-6-styryl-, (R)-
    • (R-(E))-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one
    • (6R)-4-Methoxy-6-[(E)-2-phenylethen-1-yl]-5,6-dihydro-2H-pyran-2-one
    • 2H-Pyran-2-one,6-dihydro-4-methoxy-6-(2-phenylethenyl)-, [R-(E)]-
    • 2H-PYRAN-2-ONE, 5,6-DIHYDRO-4-METHOXY-6-((1E)-2-PHENYLETHENYL)-, (6R)-
    • 500-64-1

  • Applications

    (+)-Kavain is a major kavalactone derived from Piper methysticum (kava) and is commonly encountered as a constituent of kava extracts used in herbal and plant-based dietary supplement formulations. In pharmaceutical research and related chemical synthesis, it is often evaluated as a natural product scaffold or a chiral building block for synthetic chemistry. Its distinctive aroma characteristics have spurred exploratory work in fragrance research, and it may be studied for cosmetic and personal-care applications as a natural extract ingredient, subject to regulatory constraints. Accordingly, kavain serves as a reference compound in kavalactone chemistry and natural-product-based research, with use limited by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 49.81
    methanol 52.63
    isopropanol 27.89
    water 0.04
    ethyl acetate 75.64
    n-propanol 35.68
    acetone 132.92
    n-butanol 25.59
    acetonitrile 98.32
    DMF 181.85
    toluene 40.99
    isobutanol 20.67
    1,4-dioxane 178.89
    methyl acetate 97.3
    THF 270.21
    2-butanone 105.57
    n-pentanol 21.18
    sec-butanol 21.98
    n-hexane 0.57
    ethylene glycol 30.48
    NMP 105.36
    cyclohexane 1.46
    DMSO 612.68
    n-butyl acetate 34.14
    n-octanol 6.27
    chloroform 355.13
    n-propyl acetate 33.42
    acetic acid 58.2
    dichloromethane 374.11
    cyclohexanone 89.44
    propylene glycol 57.19
    isopropyl acetate 33.59
    DMAc 294.91
    2-ethoxyethanol 99.71
    isopentanol 21.85
    n-heptane 0.73
    ethyl formate 37.08
    1,2-dichloroethane 233.33
    n-hexanol 17.63
    2-methoxyethanol 181.15
    isobutyl acetate 22.17
    tetrachloromethane 10.75
    n-pentyl acetate 12.21
    transcutol 410.14
    n-heptanol 6.56
    ethylbenzene 17.82
    MIBK 34.25
    2-propoxyethanol 78.98
    tert-butanol 32.1
    MTBE 25.01
    2-butoxyethanol 31.09
    propionic acid 45.86
    o-xylene 19.69
    formic acid 28.64
    diethyl ether 38.0
    m-xylene 19.74
    p-xylene 19.5
    chlorobenzene 59.98
    dimethyl carbonate 53.53
    n-octane 0.37
    formamide 64.94
    cyclopentanone 149.22
    2-pentanone 57.0
    anisole 67.2
    cyclopentyl methyl ether 56.49
    gamma-butyrolactone 152.77
    1-methoxy-2-propanol 116.42
    pyridine 159.23
    3-pentanone 53.35
    furfural 152.95
    n-dodecane 0.6
    diethylene glycol 97.53
    diisopropyl ether 7.63
    tert-amyl alcohol 22.08
    acetylacetone 104.32
    n-hexadecane 0.72
    acetophenone 54.86
    methyl propionate 86.68
    isopentyl acetate 33.34
    trichloroethylene 384.35
    n-nonanol 6.93
    cyclohexanol 23.49
    benzyl alcohol 50.82
    2-ethylhexanol 12.18
    isooctanol 6.79
    dipropyl ether 19.68
    1,2-dichlorobenzene 52.21
    ethyl lactate 29.16
    propylene carbonate 61.69
    n-methylformamide 81.4
    2-pentanol 13.48
    n-pentane 0.43
    1-propoxy-2-propanol 49.34
    1-methoxy-2-propyl acetate 68.53
    2-(2-methoxypropoxy) propanol 64.69
    mesitylene 10.21
    ε-caprolactone 66.4
    p-cymene 10.43
    epichlorohydrin 313.2
    1,1,1-trichloroethane 87.28
    2-aminoethanol 50.01
    morpholine-4-carbaldehyde 152.17
    sulfolane 190.53
    2,2,4-trimethylpentane 0.85
    2-methyltetrahydrofuran 94.08
    n-hexyl acetate 20.79
    isooctane 0.67
    2-(2-butoxyethoxy)ethanol 79.51
    sec-butyl acetate 23.94
    tert-butyl acetate 38.52
    decalin 2.12
    glycerin 88.12
    diglyme 174.02
    acrylic acid 48.59
    isopropyl myristate 11.7
    n-butyric acid 45.39
    acetyl acetate 48.66
    di(2-ethylhexyl) phthalate 17.75
    ethyl propionate 37.23
    nitromethane 190.43
    1,2-diethoxyethane 70.23
    benzonitrile 52.51
    trioctyl phosphate 9.02
    1-bromopropane 59.76
    gamma-valerolactone 168.83
    n-decanol 5.91
    triethyl phosphate 23.62
    4-methyl-2-pentanol 10.19
    propionitrile 52.02
    vinylene carbonate 61.38
    1,1,2-trichlorotrifluoroethane 170.58
    DMS 48.35
    cumene 11.66
    2-octanol 3.76
    2-hexanone 34.21
    octyl acetate 14.0
    limonene 12.63
    1,2-dimethoxyethane 134.61
    ethyl orthosilicate 20.98
    tributyl phosphate 15.0
    diacetone alcohol 57.63
    N,N-dimethylaniline 37.55
    acrylonitrile 82.31
    aniline 68.03
    1,3-propanediol 64.77
    bromobenzene 65.28
    dibromomethane 188.25
    1,1,2,2-tetrachloroethane 291.77
    2-methyl-cyclohexyl acetate 30.37
    tetrabutyl urea 22.23
    diisobutyl methanol 9.19
    2-phenylethanol 37.5
    styrene 27.35
    dioctyl adipate 25.91
    dimethyl sulfate 100.04
    ethyl butyrate 31.98
    methyl lactate 54.54
    butyl lactate 18.78
    diethyl carbonate 29.91
    propanediol butyl ether 34.11
    triethyl orthoformate 28.24
    p-tert-butyltoluene 9.65
    methyl 4-tert-butylbenzoate 37.02
    morpholine 205.53
    tert-butylamine 13.32
    n-dodecanol 5.13
    dimethoxymethane 159.37
    ethylene carbonate 46.46
    cyrene 53.95
    2-ethoxyethyl acetate 39.26
    2-ethylhexyl acetate 24.65
    1,2,4-trichlorobenzene 72.03
    4-methylpyridine 99.66
    dibutyl ether 14.53
    2,6-dimethyl-4-heptanol 9.19
    DEF 68.1
    dimethyl isosorbide 105.2
    tetrachloroethylene 117.21
    eugenol 41.01
    triacetin 45.24
    span 80 32.5
    1,4-butanediol 24.27
    1,1-dichloroethane 130.85
    2-methyl-1-pentanol 19.96
    methyl formate 61.0
    2-methyl-1-butanol 18.63
    n-decane 0.81
    butyronitrile 39.31
    3,7-dimethyl-1-octanol 10.45
    1-chlorooctane 5.1
    1-chlorotetradecane 2.9
    n-nonane 0.64
    undecane 0.68
    tert-butylcyclohexane 1.78
    cyclooctane 0.57
    cyclopentanol 28.2
    tetrahydropyran 90.61
    tert-amyl methyl ether 20.87
    2,5,8-trioxanonane 134.25
    1-hexene 5.11
    2-isopropoxyethanol 53.09
    2,2,2-trifluoroethanol 25.89
    methyl butyrate 41.6

    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