Yangonin

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  • Identifiers

    CAS number
    500-62-9

    Molecular formula
    C15H14O4

    SMILES
    COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=O)O2)OC

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 73.17%
    Spicy 55.08%
    Fruity 45.95%
    Balsamic 45.59%
    Floral 43.7%
    Vanilla 41.53%
    Powdery 40.49%
    Cinnamon 35.89%
    Coumarinic 34.23%
    Warm 29.96%

     

    Flavor
    Bitter 46.21%
    Balsam 40.97%
    Sweet 37.15%
    Floral 34.73%
    Spice 24.64%
    Balsamic 23.23%
    Spicy 22.47%
    Flower 21.62%
    Warm 21.49%
    Anise 21.48%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    6.64 (neutral)

    Molecular weight
    258.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    536°C

    Melting point expt.

    • 153 - 154 °C

    Flash point

    • 172.32 ˚C est.

  • Synonyms

    • Yangonin
    • 500-62-9
    • 4-Methoxy-6-(p-methoxystyryl)-2H-pyran-2-one
    • DTXSID4034102
    • 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
    • R970U49V3C
    • 2H-PYRAN-2-ONE, 4-METHOXY-6-(p-METHOXYSTYRYL)-
    • NSC-212502
    • 2H-Pyran-2-one, 4-methoxy-6-(2-(4-methoxyphenyl)ethenyl)-, (E)-
    • DTXCID2014102
    • 4-METHOXY-6-((E)-2-(4-METHOXYPHENYL)ETHENYL)PYRAN-2-ONE
    • 4-methoxy-6-((E)-2-(4-methoxyphenyl)ethenyl)-2H-pyran-2-one
    • 2H-Pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)-
    • 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
    • RefChem:52493
    • (E)-4-Methoxy-6-(4-methoxystyryl)-2H-pyran-2-one
    • 4-Methoxy-6-(beta-(p-anisyl)vinyl)-alpha-pyrone
    • C15H14O4
    • MFCD00221733
    • NSC212502
    • 4-Methoxy-6-[(1E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
    • 4-methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]pyran-2-one
    • 2H-Pyran-2-one, 4-methoxy-6-[(1E)-2-(4-methoxyphenyl)ethenyl]-
    • NSC 212502
    • Methoxyxerin
    • UNII-R970U49V3C
    • CCRIS 9372
    • 2H-PYRAN-2-ONE, 4-METHOXY-6-((1E)-2-(4-METHOXYPHENYL)ETHENYL)-
    • XLHIYUYCSMZCCC-VMPITWQZSA-N
    • Yangonin (Standard)
    • YANGONIN [MI]
    • UPCMLD-DP034
    • 5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid gamma-lactone
    • Yangonin, analytical standard
    • orb1303412
    • SCHEMBL1393965
    • CHEMBL1098658
    • UPCMLD-DP034:001
    • UPCMLD-DP034:002
    • CHEBI:10089
    • HY-N0919R
    • WLZ4682
    • HMS3887I03
    • HMS5086L03
    • HY-N0919
    • Tox21_202547
    • NSC112160
    • s9413
    • AKOS022184639
    • CCG-208617
    • EBC-615522
    • NSC-112160
    • NCGC00091909-01
    • NCGC00091909-03
    • NCGC00260096-01
    • 4-Methoxy-6-(4-methoxystyryl)-a-pyrone
    • AC-34333
    • CAS-500-62-9
    • DA-79028
    • FY137901
    • MS-23639
    • NS00017751
    • C09980
    • 500Y629
    • SR-05000002174
    • Q8048635
    • SR-05000002174-2
    • 4-Methoxy-6-(.beta.-(p-anisyl)vinyl)-.alpha.-pyrone
    • 4-methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one
    • 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethen-1-yl]-2H-pyran-2-one
    • 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one #
    • 4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one, 9CI
    • 5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid .gamma.-lactone
    • 500-62-9

  • Applications

    Yangonin (CAS 500-62-9) is a kavalactone isolated from Piper methysticum and is primarily encountered as a constituent of traditional kava beverages; in industry, it is used as a chemical marker for quality control of kava products in the food and beverage sector. It is also studied in pharmaceutical research for CNS activity and may contribute to investigations of anxiolytic-like effects. In cosmetic/personal care contexts that rely on kava extracts, yangonin may be present as part of the natural phytochemical profile. As a natural product, its use as a standalone chemical is limited, but it can serve as a reference standard or analytical target in research and quality-control workflows.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 28.13
    methanol 28.77
    isopropanol 21.01
    water 0.01
    ethyl acetate 71.7
    n-propanol 22.53
    acetone 104.18
    n-butanol 12.6
    acetonitrile 68.86
    DMF 113.3
    toluene 30.01
    isobutanol 12.55
    1,4-dioxane 186.04
    methyl acetate 99.4
    THF 450.34
    2-butanone 89.21
    n-pentanol 11.71
    sec-butanol 16.82
    n-hexane 0.51
    ethylene glycol 15.5
    NMP 70.58
    cyclohexane 1.39
    DMSO 661.52
    n-butyl acetate 23.31
    n-octanol 3.82
    chloroform 197.32
    n-propyl acetate 26.34
    acetic acid 45.27
    dichloromethane 238.82
    cyclohexanone 67.52
    propylene glycol 35.23
    isopropyl acetate 29.57
    DMAc 272.53
    2-ethoxyethanol 75.55
    isopentanol 10.86
    n-heptane 0.83
    ethyl formate 28.9
    1,2-dichloroethane 155.75
    n-hexanol 8.46
    2-methoxyethanol 148.05
    isobutyl acetate 16.76
    tetrachloromethane 7.29
    n-pentyl acetate 8.85
    transcutol 187.58
    n-heptanol 4.03
    ethylbenzene 11.5
    MIBK 22.43
    2-propoxyethanol 57.05
    tert-butanol 30.36
    MTBE 29.32
    2-butoxyethanol 19.66
    propionic acid 32.69
    o-xylene 14.04
    formic acid 17.58
    diethyl ether 36.31
    m-xylene 11.99
    p-xylene 14.36
    chlorobenzene 35.56
    dimethyl carbonate 46.51
    n-octane 0.38
    formamide 55.12
    cyclopentanone 129.22
    2-pentanone 38.36
    anisole 49.44
    cyclopentyl methyl ether 55.64
    gamma-butyrolactone 146.7
    1-methoxy-2-propanol 87.67
    pyridine 128.47
    3-pentanone 43.37
    furfural 117.46
    n-dodecane 0.54
    diethylene glycol 64.56
    diisopropyl ether 7.2
    tert-amyl alcohol 21.2
    acetylacetone 89.73
    n-hexadecane 0.65
    acetophenone 39.52
    methyl propionate 75.44
    isopentyl acetate 23.85
    trichloroethylene 263.42
    n-nonanol 4.61
    cyclohexanol 16.44
    benzyl alcohol 33.61
    2-ethylhexanol 7.46
    isooctanol 4.33
    dipropyl ether 16.9
    1,2-dichlorobenzene 30.62
    ethyl lactate 20.4
    propylene carbonate 43.39
    n-methylformamide 53.26
    2-pentanol 8.07
    n-pentane 0.39
    1-propoxy-2-propanol 33.42
    1-methoxy-2-propyl acetate 52.04
    2-(2-methoxypropoxy) propanol 39.07
    mesitylene 6.82
    ε-caprolactone 53.15
    p-cymene 7.39
    epichlorohydrin 284.94
    1,1,1-trichloroethane 71.36
    2-aminoethanol 28.6
    morpholine-4-carbaldehyde 122.08
    sulfolane 173.76
    2,2,4-trimethylpentane 0.72
    2-methyltetrahydrofuran 117.74
    n-hexyl acetate 13.17
    isooctane 0.46
    2-(2-butoxyethoxy)ethanol 43.75
    sec-butyl acetate 19.15
    tert-butyl acetate 33.96
    decalin 1.6
    glycerin 53.64
    diglyme 110.62
    acrylic acid 32.88
    isopropyl myristate 8.82
    n-butyric acid 30.39
    acetyl acetate 45.84
    di(2-ethylhexyl) phthalate 10.79
    ethyl propionate 31.01
    nitromethane 172.35
    1,2-diethoxyethane 52.49
    benzonitrile 31.45
    trioctyl phosphate 5.64
    1-bromopropane 39.51
    gamma-valerolactone 137.4
    n-decanol 3.96
    triethyl phosphate 20.11
    4-methyl-2-pentanol 5.54
    propionitrile 40.29
    vinylene carbonate 40.92
    1,1,2-trichlorotrifluoroethane 131.48
    DMS 36.84
    cumene 7.76
    2-octanol 2.67
    2-hexanone 26.17
    octyl acetate 9.54
    limonene 9.08
    1,2-dimethoxyethane 120.71
    ethyl orthosilicate 18.32
    tributyl phosphate 9.59
    diacetone alcohol 40.87
    N,N-dimethylaniline 26.66
    acrylonitrile 56.81
    aniline 47.37
    1,3-propanediol 38.95
    bromobenzene 39.71
    dibromomethane 115.86
    1,1,2,2-tetrachloroethane 194.54
    2-methyl-cyclohexyl acetate 24.15
    tetrabutyl urea 14.27
    diisobutyl methanol 6.42
    2-phenylethanol 24.3
    styrene 16.15
    dioctyl adipate 18.4
    dimethyl sulfate 88.31
    ethyl butyrate 25.34
    methyl lactate 40.42
    butyl lactate 11.42
    diethyl carbonate 23.55
    propanediol butyl ether 17.0
    triethyl orthoformate 24.09
    p-tert-butyltoluene 7.04
    methyl 4-tert-butylbenzoate 26.85
    morpholine 205.27
    tert-butylamine 10.76
    n-dodecanol 3.58
    dimethoxymethane 149.4
    ethylene carbonate 32.32
    cyrene 38.02
    2-ethoxyethyl acetate 27.2
    2-ethylhexyl acetate 18.74
    1,2,4-trichlorobenzene 45.76
    4-methylpyridine 73.43
    dibutyl ether 10.83
    2,6-dimethyl-4-heptanol 6.42
    DEF 49.01
    dimethyl isosorbide 80.32
    tetrachloroethylene 75.88
    eugenol 27.36
    triacetin 28.86
    span 80 19.39
    1,4-butanediol 12.92
    1,1-dichloroethane 91.88
    2-methyl-1-pentanol 10.85
    methyl formate 44.48
    2-methyl-1-butanol 10.32
    n-decane 0.72
    butyronitrile 23.38
    3,7-dimethyl-1-octanol 6.49
    1-chlorooctane 3.82
    1-chlorotetradecane 2.34
    n-nonane 0.59
    undecane 0.62
    tert-butylcyclohexane 1.36
    cyclooctane 0.51
    cyclopentanol 25.45
    tetrahydropyran 100.03
    tert-amyl methyl ether 21.79
    2,5,8-trioxanonane 89.36
    1-hexene 3.56
    2-isopropoxyethanol 38.74
    2,2,2-trifluoroethanol 19.93
    methyl butyrate 32.31

    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