(-)-Phaseollin

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  • Identifiers

    CAS number
    13401-40-6

    Molecular formula
    C20H18O4

    SMILES
    CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4[C@H]3COC5=C4C=CC(=C5)O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 49.71%
    Phenolic 41.69%
    Spicy 38.68%
    Vanilla 28.23%
    Powdery 26.5%
    Animal 23.52%
    Creamy 22.48%
    Balsamic 21.62%
    Aromatic 21.2%
    Coumarinic 21.19%

     

    Flavor
    Bitter 94.88%
    Cedarleaf 19.38%
    Parsley 18.67%
    Lovage 18.24%
    Ripe apricot 18.02%
    Sweet-like 17.99%
    Indole 17.76%
    Very strong 17.72%
    Red fruit 17.67%
    Cereal 17.64%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    7.74 (neutral)

    Molecular weight
    322.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    789°C

    Flash point

    • 227.24 ˚C est.

  • Synonyms

    • Phaseolin
    • 13401-40-6
    • (-)-Phaseollin
    • 8OHL7771FZ
    • DTXSID701029664
    • (2R,11R)-17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol
    • (2R,11R)-17,17-dimethyl-4,12,18-trioxapentacyclo(11.8.0.02,11.05,10.014,19)henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol
    • RefChem:1049128
    • DTXCID301514873
    • Phaseollin
    • (+/-)-Phaseollin
    • I7OEP19ZWL
    • Phaseollin, (+/-)
    • UNII-I7OEP19ZWL
    • CHEMBL448350
    • Phaseolin fungicide
    • MFCD00210543
    • 3H,7H-Furo(3,2-c:5,4-f')bis(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, cis-
    • 3H,7H-Furo(3,2-c:5,4-f')bis(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, cis-(+/-)-
    • 3H,7H-Pyrano(2',3':6,7)benzofuro(3,2-C)(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, (6bR,12bR)-rel-
    • 91110-20-2
    • UNII-8OHL7771FZ
    • Phaseolin; Phaseolin (phytoalexin)
    • PHASEOLIN [MI]
    • SCHEMBL33736
    • orb1705164
    • SCHEMBL29351585
    • SCHEMBL29929606
    • PHASEOLLIN, (+/-)-
    • HY-N3087
    • BDBM50317438
    • LMPK12070020
    • AKOS032948435
    • FS-9472
    • DA-66651
    • FP137776
    • CS-0023187
    • H62734
    • 401P406
    • Q7180982
    • (6BR,12BR)-6B,12B-DIHYDRO-3,3-DIMETHYL-3H,7H-FURO(3,2-C:5,4-F')BIS(1)BENZOPYRAN-10-OL
    • 3H,7H-Furo(3,2-c:5,4-f')bis(1)benzopyran-10-ol, 6b,12b-dihydro-3,3-dimethyl-, (6bR-cis)-
    • 13401-40-6

  • Applications

    (-)-Phaseollin (CAS 13401-40-6) is a natural pterocarpan phytoalexin produced by bean plants, typically regarded as a reference natural product and as a synthetic precursor for related pterocarpans. In industrial and research contexts it is used as a scaffold for the synthesis of pterocarpan derivatives and as a lead compound in natural product–based libraries. It is evaluated for biological activities related to plant defense, such as antifungal effects, and serves as a model in studies of isoflavonoid biosynthesis and plant-pathogen interactions, supporting academic and pharmaceutical research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.76
    methanol 10.79
    isopropanol 11.15
    water 0.06
    ethyl acetate 46.66
    n-propanol 12.0
    acetone 66.2
    n-butanol 13.11
    acetonitrile 37.99
    DMF 76.19
    toluene 13.28
    isobutanol 11.41
    1,4-dioxane 99.29
    methyl acetate 51.22
    THF 157.23
    2-butanone 54.87
    n-pentanol 12.31
    sec-butanol 7.57
    n-hexane 0.4
    ethylene glycol 8.69
    NMP 56.36
    cyclohexane 1.15
    DMSO 119.67
    n-butyl acetate 42.37
    n-octanol 12.94
    chloroform 139.59
    n-propyl acetate 38.59
    acetic acid 43.97
    dichloromethane 90.56
    cyclohexanone 75.97
    propylene glycol 8.08
    isopropyl acetate 39.48
    DMAc 140.57
    2-ethoxyethanol 52.61
    isopentanol 17.46
    n-heptane 0.92
    ethyl formate 31.43
    1,2-dichloroethane 59.22
    n-hexanol 15.82
    2-methoxyethanol 74.14
    isobutyl acetate 38.08
    tetrachloromethane 7.43
    n-pentyl acetate 30.2
    transcutol 235.4
    n-heptanol 12.68
    ethylbenzene 6.5
    MIBK 38.97
    2-propoxyethanol 84.08
    tert-butanol 17.61
    MTBE 17.01
    2-butoxyethanol 46.73
    propionic acid 22.33
    o-xylene 8.21
    formic acid 16.83
    diethyl ether 20.24
    m-xylene 10.84
    p-xylene 10.9
    chlorobenzene 27.06
    dimethyl carbonate 48.23
    n-octane 0.74
    formamide 28.27
    cyclopentanone 92.21
    2-pentanone 44.67
    anisole 28.54
    cyclopentyl methyl ether 38.23
    gamma-butyrolactone 92.06
    1-methoxy-2-propanol 62.24
    pyridine 49.95
    3-pentanone 42.74
    furfural 80.15
    n-dodecane 1.51
    diethylene glycol 84.88
    diisopropyl ether 9.36
    tert-amyl alcohol 10.22
    acetylacetone 76.29
    n-hexadecane 1.83
    acetophenone 37.66
    methyl propionate 47.92
    isopentyl acetate 45.57
    trichloroethylene 135.43
    n-nonanol 15.37
    cyclohexanol 17.3
    benzyl alcohol 26.62
    2-ethylhexanol 14.77
    isooctanol 13.18
    dipropyl ether 19.99
    1,2-dichlorobenzene 29.71
    ethyl lactate 32.91
    propylene carbonate 50.68
    n-methylformamide 33.36
    2-pentanol 9.35
    n-pentane 0.43
    1-propoxy-2-propanol 53.89
    1-methoxy-2-propyl acetate 78.31
    2-(2-methoxypropoxy) propanol 68.51
    mesitylene 7.24
    ε-caprolactone 61.66
    p-cymene 9.73
    epichlorohydrin 125.49
    1,1,1-trichloroethane 44.99
    2-aminoethanol 12.26
    morpholine-4-carbaldehyde 113.23
    sulfolane 93.56
    2,2,4-trimethylpentane 0.71
    2-methyltetrahydrofuran 45.01
    n-hexyl acetate 39.36
    isooctane 0.77
    2-(2-butoxyethoxy)ethanol 83.01
    sec-butyl acetate 31.95
    tert-butyl acetate 42.25
    decalin 1.27
    glycerin 27.13
    diglyme 151.84
    acrylic acid 26.09
    isopropyl myristate 23.88
    n-butyric acid 37.04
    acetyl acetate 48.37
    di(2-ethylhexyl) phthalate 26.06
    ethyl propionate 37.36
    nitromethane 101.97
    1,2-diethoxyethane 71.44
    benzonitrile 36.39
    trioctyl phosphate 19.0
    1-bromopropane 19.0
    gamma-valerolactone 136.55
    n-decanol 12.85
    triethyl phosphate 29.91
    4-methyl-2-pentanol 11.14
    propionitrile 35.09
    vinylene carbonate 61.42
    1,1,2-trichlorotrifluoroethane 92.21
    DMS 59.94
    cumene 6.59
    2-octanol 8.63
    2-hexanone 37.59
    octyl acetate 27.4
    limonene 11.12
    1,2-dimethoxyethane 102.33
    ethyl orthosilicate 27.11
    tributyl phosphate 24.89
    diacetone alcohol 49.17
    N,N-dimethylaniline 18.7
    acrylonitrile 49.84
    aniline 22.87
    1,3-propanediol 26.49
    bromobenzene 27.91
    dibromomethane 47.35
    1,1,2,2-tetrachloroethane 104.12
    2-methyl-cyclohexyl acetate 36.03
    tetrabutyl urea 31.18
    diisobutyl methanol 12.17
    2-phenylethanol 33.08
    styrene 8.24
    dioctyl adipate 37.06
    dimethyl sulfate 65.37
    ethyl butyrate 36.52
    methyl lactate 41.65
    butyl lactate 32.07
    diethyl carbonate 33.03
    propanediol butyl ether 36.34
    triethyl orthoformate 38.53
    p-tert-butyltoluene 9.24
    methyl 4-tert-butylbenzoate 40.22
    morpholine 85.09
    tert-butylamine 7.21
    n-dodecanol 10.93
    dimethoxymethane 102.57
    ethylene carbonate 58.28
    cyrene 55.47
    2-ethoxyethyl acetate 61.87
    2-ethylhexyl acetate 36.38
    1,2,4-trichlorobenzene 38.89
    4-methylpyridine 43.7
    dibutyl ether 21.52
    2,6-dimethyl-4-heptanol 12.17
    DEF 45.29
    dimethyl isosorbide 98.78
    tetrachloroethylene 51.97
    eugenol 42.24
    triacetin 61.64
    span 80 39.28
    1,4-butanediol 12.75
    1,1-dichloroethane 46.55
    2-methyl-1-pentanol 14.66
    methyl formate 36.77
    2-methyl-1-butanol 12.41
    n-decane 2.0
    butyronitrile 27.07
    3,7-dimethyl-1-octanol 16.86
    1-chlorooctane 9.05
    1-chlorotetradecane 5.49
    n-nonane 1.44
    undecane 1.7
    tert-butylcyclohexane 1.12
    cyclooctane 0.59
    cyclopentanol 18.13
    tetrahydropyran 48.52
    tert-amyl methyl ether 13.82
    2,5,8-trioxanonane 123.1
    1-hexene 2.23
    2-isopropoxyethanol 43.86
    2,2,2-trifluoroethanol 24.83
    methyl butyrate 42.14

    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