Piperlongumine

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  • Identifiers

    CAS number
    20069-09-4

    Molecular formula
    C17H19NO5

    SMILES
    COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Spicy 34.53%
    Roasted 29.05%
    Odorless 27.42%
    Savory 25.66%
    Caramellic 24.96%
    Burnt 23.03%
    Sweet 22.87%
    Fruity 22.76%
    Warm 21.6%
    Mint 20.71%

     

    Flavor
    Bitter 70.08%
    Odorless 26.21%
    Bland 20.84%
    Lovage 19.45%
    Parsley 19.15%
    Cedarleaf 18.72%
    Sweet-like 18.48%
    Taco 18.25%
    Ethyl benzoate 18.22%
    Broom 18.16%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    6.99 (neutral)

    Molecular weight
    317.34 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    569°C

    Melting point expt.

    • 124 °C

    Flash point

    • 184.53 ˚C est.

  • Synonyms

    • Piperlongumine
    • Piplartine
    • 20069-09-4
    • SGD66V4SVJ
    • 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
    • 2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
    • 1-((E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl)-2,3-dihydropyridin-6-one
    • RefChem:45515
    • 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-2(1H)pyridinone
    • (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
    • MFCD00075706
    • Piplartin
    • 2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-
    • 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one
    • CHEBI:8241
    • ST079382
    • BRD2293
    • BRD-2293
    • (E)-1-[3-(3,4,5-Trimethoxyphenyl)acryloyl]-5,6-dihydropyridin-2(1H)-one
    • UNII-SGD66V4SVJ
    • Piperlongumine?
    • Prestwick_399
    • PPLGM
    • Prestwick2_000604
    • Prestwick3_000604
    • Piperlongumine; Piplartine
    • PIPERLONGUMINE [MI]
    • BSPBio_000508
    • MLS002153903
    • SCHEMBL173092
    • SPECTRUM1505135
    • BPBio1_000560
    • CHEMBL465843
    • orb1300321
    • 1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one
    • ACon1_001541
    • CHEBI:92424
    • GTPL13376
    • 5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-trans-2-propenyl]-2(1H)-pyridinone
    • DTXSID801029762
    • GLXC-05372
    • HMS1569J10
    • HMS2096J10
    • HMS2234K24
    • HMS6018L11
    • Piperlongumine, >=97% (HPLC)
    • EX-A2925
    • HY-N2329
    • BDBM50462013
    • NSC794671
    • s7551
    • AKOS024284776
    • CCG-214375
    • EBC-217030
    • FP27075
    • NSC-794671
    • NCGC00096028-01
    • NCGC00096028-02
    • NCGC00096028-03
    • NCGC00096028-04
    • NCGC00096028-06
    • NCGC00096028-07
    • NCGC00096028-14
    • AC-32683
    • AS-74140
    • BP-25401
    • DA-66744
    • LS-14579
    • SMR001233252
    • SY057856
    • CS-0021113
    • P2361
    • EN300-7424497
    • AM-730/20761034
    • SR-01000841248
    • A1-00162
    • N-(3,4,5-Trimethoxycinnamoyl)-D3-piperidin-2-one
    • Q7197361
    • SR-01000841248-2
    • BRD-K24132293-001-05-3
    • BRD-K24132293-001-09-5
    • BRD-K24132293-001-16-0
    • 5,6-Dihydro-1-(3,4,5-trimethoxycinnamoyl)-2(1H)-pyridinone
    • 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone
    • 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone #
    • 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,5,6-trihydropyridin-2-one
    • 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
    • 5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone, 9CI
    • Piplartine; (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
    • Prop-2-en-1-one, 3-(3,4,5-trimethoxyphenyl)-1-(2,3-dihydropyridin-6(1H)-one-1-yl)-
    • 2(1H)-PYRIDINONE, 5,6-DIHYDRO-1-(1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2- PROPENYL)-, (E)-
    • 20069-09-4

  • Applications

    Piperlongumine (CAS 20069-09-4) is primarily used in pharmaceutical research as a natural product scaffold for synthesis and structure-activity relationship (SAR) studies, to explore related biological mechanisms in redox signaling and cellular pathways. It also serves as a research reagent in chemical biology for evaluating mechanisms of action of related compounds and in academic laboratories for probe development. In synthesis, it can function as a building block or starting material to access analogs and related derivatives for investigative purposes. Additionally, it is supplied to laboratories as a naturally derived compound for research use, with application subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.12
    methanol 6.18
    isopropanol 3.69
    water 0.02
    ethyl acetate 25.89
    n-propanol 4.79
    acetone 39.52
    n-butanol 4.18
    acetonitrile 30.79
    DMF 45.97
    toluene 10.97
    isobutanol 3.92
    1,4-dioxane 40.22
    methyl acetate 29.56
    THF 64.32
    2-butanone 31.52
    n-pentanol 6.16
    sec-butanol 4.61
    n-hexane 0.46
    ethylene glycol 2.88
    NMP 45.16
    cyclohexane 1.4
    DMSO 101.32
    n-butyl acetate 13.95
    n-octanol 4.04
    chloroform 78.03
    n-propyl acetate 19.02
    acetic acid 21.29
    dichloromethane 96.3
    cyclohexanone 48.09
    propylene glycol 2.24
    isopropyl acetate 12.74
    DMAc 72.11
    2-ethoxyethanol 25.46
    isopentanol 5.14
    n-heptane 0.53
    ethyl formate 23.27
    1,2-dichloroethane 63.74
    n-hexanol 6.03
    2-methoxyethanol 26.88
    isobutyl acetate 10.81
    tetrachloromethane 7.45
    n-pentyl acetate 10.37
    transcutol 28.08
    n-heptanol 4.48
    ethylbenzene 6.73
    MIBK 12.75
    2-propoxyethanol 22.79
    tert-butanol 5.86
    MTBE 5.59
    2-butoxyethanol 14.29
    propionic acid 12.2
    o-xylene 7.84
    formic acid 11.44
    diethyl ether 8.21
    m-xylene 6.34
    p-xylene 8.87
    chlorobenzene 23.77
    dimethyl carbonate 18.16
    n-octane 0.48
    formamide 23.11
    cyclopentanone 65.29
    2-pentanone 20.96
    anisole 15.83
    cyclopentyl methyl ether 14.43
    gamma-butyrolactone 71.63
    1-methoxy-2-propanol 14.84
    pyridine 51.5
    3-pentanone 20.6
    furfural 70.46
    n-dodecane 0.6
    diethylene glycol 22.67
    diisopropyl ether 2.24
    tert-amyl alcohol 5.89
    acetylacetone 38.19
    n-hexadecane 0.71
    acetophenone 25.64
    methyl propionate 23.95
    isopentyl acetate 12.86
    trichloroethylene 118.37
    n-nonanol 4.79
    cyclohexanol 7.4
    benzyl alcohol 18.19
    2-ethylhexanol 5.71
    isooctanol 4.32
    dipropyl ether 5.44
    1,2-dichlorobenzene 24.84
    ethyl lactate 13.64
    propylene carbonate 32.33
    n-methylformamide 24.56
    2-pentanol 3.0
    n-pentane 0.37
    1-propoxy-2-propanol 12.18
    1-methoxy-2-propyl acetate 19.24
    2-(2-methoxypropoxy) propanol 16.95
    mesitylene 3.81
    ε-caprolactone 37.48
    p-cymene 4.95
    epichlorohydrin 95.95
    1,1,1-trichloroethane 34.78
    2-aminoethanol 4.3
    morpholine-4-carbaldehyde 50.63
    sulfolane 84.09
    2,2,4-trimethylpentane 0.44
    2-methyltetrahydrofuran 26.93
    n-hexyl acetate 11.37
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 17.79
    sec-butyl acetate 10.5
    tert-butyl acetate 12.53
    decalin 1.1
    glycerin 7.32
    diglyme 39.62
    acrylic acid 16.45
    isopropyl myristate 5.9
    n-butyric acid 15.68
    acetyl acetate 21.8
    di(2-ethylhexyl) phthalate 9.55
    ethyl propionate 17.94
    nitromethane 66.52
    1,2-diethoxyethane 14.75
    benzonitrile 27.89
    trioctyl phosphate 6.09
    1-bromopropane 15.68
    gamma-valerolactone 73.82
    n-decanol 4.0
    triethyl phosphate 11.88
    4-methyl-2-pentanol 2.82
    propionitrile 18.86
    vinylene carbonate 36.19
    1,1,2-trichlorotrifluoroethane 57.91
    DMS 19.63
    cumene 4.87
    2-octanol 3.07
    2-hexanone 18.91
    octyl acetate 7.8
    limonene 5.88
    1,2-dimethoxyethane 46.78
    ethyl orthosilicate 9.91
    tributyl phosphate 8.18
    diacetone alcohol 17.05
    N,N-dimethylaniline 11.42
    acrylonitrile 33.38
    aniline 14.28
    1,3-propanediol 8.09
    bromobenzene 22.98
    dibromomethane 52.34
    1,1,2,2-tetrachloroethane 74.4
    2-methyl-cyclohexyl acetate 13.99
    tetrabutyl urea 12.51
    diisobutyl methanol 3.57
    2-phenylethanol 16.54
    styrene 8.46
    dioctyl adipate 11.41
    dimethyl sulfate 33.69
    ethyl butyrate 13.6
    methyl lactate 14.88
    butyl lactate 9.77
    diethyl carbonate 12.33
    propanediol butyl ether 8.6
    triethyl orthoformate 10.93
    p-tert-butyltoluene 3.89
    methyl 4-tert-butylbenzoate 17.59
    morpholine 37.3
    tert-butylamine 2.8
    n-dodecanol 3.35
    dimethoxymethane 32.83
    ethylene carbonate 29.2
    cyrene 27.45
    2-ethoxyethyl acetate 18.95
    2-ethylhexyl acetate 10.61
    1,2,4-trichlorobenzene 27.72
    4-methylpyridine 34.84
    dibutyl ether 5.98
    2,6-dimethyl-4-heptanol 3.57
    DEF 28.25
    dimethyl isosorbide 32.22
    tetrachloroethylene 53.09
    eugenol 19.74
    triacetin 17.41
    span 80 11.28
    1,4-butanediol 5.45
    1,1-dichloroethane 33.15
    2-methyl-1-pentanol 6.86
    methyl formate 28.35
    2-methyl-1-butanol 4.85
    n-decane 0.83
    butyronitrile 16.43
    3,7-dimethyl-1-octanol 4.89
    1-chlorooctane 3.96
    1-chlorotetradecane 2.26
    n-nonane 0.65
    undecane 0.69
    tert-butylcyclohexane 0.73
    cyclooctane 0.52
    cyclopentanol 9.51
    tetrahydropyran 22.63
    tert-amyl methyl ether 6.01
    2,5,8-trioxanonane 29.72
    1-hexene 2.29
    2-isopropoxyethanol 16.12
    2,2,2-trifluoroethanol 17.25
    methyl butyrate 24.02

    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