Pimpinellin

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  • Identifiers

    CAS number
    131-12-4

    Molecular formula
    C13H10O5

    SMILES
    COC1=C(C2=C(C=CO2)C3=C1C=CC(=O)O3)OC

    Safety labels

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 54.81%
    Fruity 44.98%
    Vanilla 39.16%
    Caramellic 37.61%
    Burnt 35.62%
    Phenolic 32.67%
    Powdery 32.26%
    Creamy 29.54%
    Berry 27.25%
    Nutty 26.91%

     

    Flavor
    Bitter 87.69%
    Parsley 20.64%
    Eugenol 19.68%
    Cedarleaf 19.48%
    Sweet-like 19.08%
    Lovage 18.8%
    Ripe apricot 18.74%
    Naphthalic 18.52%
    Very strong 18.52%
    Aniseed 18.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    5.7 (weak acid)

    Molecular weight
    246.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    419°C

    Melting point expt.

    • 119 °C

    Flash point

    • 194.72 ˚C est.

    Solubility expt.

    • Practically insoluble in water
    • Soluble in alcohol

  • Synonyms

    • pimpinellin
    • 131-12-4
    • 5,6-Dimethoxy-2H-furo[2,3-H]chromen-2-one
    • 5,6-dimethoxyfuro[2,3-h]chromen-2-one
    • 2H-Furo[2,3-h]-1-benzopyran-2-one, 5,6-dimethoxy-
    • D419UK1B4L
    • 2H-Furo(2,3-h)-1-benzopyran-2-one, 5,6-dimethoxy-
    • 5,6-dimethoxy-2h-furo[2,3-h]-1-benzopyran-2-one
    • DTXSID20156831
    • 5,6-DIMETHOXY-2H-FURO(2,3-H)-1-BENZOPYRAN-2-ONE
    • 5,6-dimethoxyfuro(2,3-h)chromen-2-one
    • 5,6-dimethoxy-2H-furo(2,3-h)chromen-2-one
    • RefChem:174288
    • DTXCID2079322
    • 683-094-1
    • Pimpinecilin
    • Pimpinelline
    • CCRIS 4344
    • 6,7-Dimethoxyangelicin
    • UNII-D419UK1B4L
    • Pimpinellidine
    • MFCD00597237
    • PIMPINELIN
    • Spectrum_000417
    • PIMPINELLIN [MI]
    • Spectrum2_000720
    • Spectrum3_001234
    • Spectrum4_001957
    • Spectrum5_000769
    • BSPBio_002708
    • KBioGR_002397
    • KBioSS_000897
    • SPECTRUM300013
    • DivK1c_001025
    • 5,6-dimethoxy-2h-furo[2,3-h][1]benzopyran-2-one
    • SPBio_000939
    • CHEBI:8213
    • MEGxp0_001831
    • orb1301501
    • SCHEMBL2255899
    • CHEMBL1491809
    • HMS503M11
    • HSDB 8481
    • KBio1_001025
    • KBio2_000897
    • KBio2_003465
    • KBio2_006033
    • KBio3_002208
    • BQPRWZCEKZLBHL-UHFFFAOYSA-N
    • NINDS_001025
    • HMS1923E17
    • HMS3886B20
    • HY-N0438
    • CCG-40044
    • s9176
    • AKOS000277261
    • EBC-616715
    • SDCCGMLS-0066532.P001
    • IDI1_001025
    • NCGC00095242-01
    • NCGC00095242-02
    • NCGC00095242-03
    • AC-34304
    • DA-76893
    • FP145259
    • MS-23480
    • CS-0008956
    • NS00094646
    • C09285
    • 131P124
    • 5,6-Dimethoxy-2H-furo[2,3-H]chromen-2-one #
    • SR-05000002492
    • Q3905067
    • SR-05000002492-1
    • BRD-K93197368-001-02-9
    • BRD-K93197368-001-03-7
    • 131-12-4

  • Applications

    Pimpinellin, CAS 131-12-4, is a natural furanocoumarin that is of interest in natural product chemistry, organic synthesis, and pharmaceutical research. Practical applications under consideration include serving as a synthetic intermediate for furanocoumarin derivatives and related heterocycles, acting as a reference standard in analytical methods for furanocoumarins, and supporting medicinal chemistry development as a scaffold for derivative exploration. It is also studied for photochemical properties and has potential use in materials science as a photoactive compound. In addition, pimpinellin occurs in plant extracts and is relevant to natural product research and quality control of essential oil components.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.01
    methanol 13.74
    isopropanol 6.9
    water 0.22
    ethyl acetate 37.05
    n-propanol 7.84
    acetone 47.54
    n-butanol 7.37
    acetonitrile 28.59
    DMF 121.32
    toluene 13.14
    isobutanol 7.76
    1,4-dioxane 51.27
    methyl acetate 41.95
    THF 66.14
    2-butanone 34.42
    n-pentanol 9.63
    sec-butanol 7.55
    n-hexane 1.15
    ethylene glycol 14.27
    NMP 115.55
    cyclohexane 2.68
    DMSO 118.77
    n-butyl acetate 32.08
    n-octanol 13.11
    chloroform 60.34
    n-propyl acetate 33.59
    acetic acid 29.18
    dichloromethane 91.86
    cyclohexanone 59.92
    propylene glycol 4.92
    isopropyl acetate 22.92
    DMAc 106.51
    2-ethoxyethanol 33.5
    isopentanol 9.44
    n-heptane 2.09
    ethyl formate 33.89
    1,2-dichloroethane 70.16
    n-hexanol 14.04
    2-methoxyethanol 48.54
    isobutyl acetate 22.42
    tetrachloromethane 12.16
    n-pentyl acetate 29.31
    transcutol 38.46
    n-heptanol 13.01
    ethylbenzene 12.2
    MIBK 19.84
    2-propoxyethanol 41.0
    tert-butanol 10.35
    MTBE 10.32
    2-butoxyethanol 30.23
    propionic acid 20.64
    o-xylene 13.62
    formic acid 22.61
    diethyl ether 14.56
    m-xylene 11.31
    p-xylene 18.51
    chlorobenzene 31.44
    dimethyl carbonate 43.36
    n-octane 1.79
    formamide 45.68
    cyclopentanone 75.19
    2-pentanone 27.72
    anisole 25.15
    cyclopentyl methyl ether 28.13
    gamma-butyrolactone 101.12
    1-methoxy-2-propanol 27.48
    pyridine 55.23
    3-pentanone 28.0
    furfural 104.98
    n-dodecane 2.11
    diethylene glycol 54.42
    diisopropyl ether 5.7
    tert-amyl alcohol 10.85
    acetylacetone 50.72
    n-hexadecane 2.43
    acetophenone 40.71
    methyl propionate 41.2
    isopentyl acetate 28.25
    trichloroethylene 114.4
    n-nonanol 13.31
    cyclohexanol 14.54
    benzyl alcohol 28.21
    2-ethylhexanol 14.23
    isooctanol 12.4
    dipropyl ether 13.11
    1,2-dichlorobenzene 37.61
    ethyl lactate 27.03
    propylene carbonate 58.5
    n-methylformamide 51.96
    2-pentanol 6.18
    n-pentane 0.99
    1-propoxy-2-propanol 26.2
    1-methoxy-2-propyl acetate 39.07
    2-(2-methoxypropoxy) propanol 29.78
    mesitylene 7.87
    ε-caprolactone 57.44
    p-cymene 12.87
    epichlorohydrin 100.92
    1,1,1-trichloroethane 37.99
    2-aminoethanol 11.72
    morpholine-4-carbaldehyde 104.78
    sulfolane 126.73
    2,2,4-trimethylpentane 1.1
    2-methyltetrahydrofuran 36.62
    n-hexyl acetate 29.96
    isooctane 0.74
    2-(2-butoxyethoxy)ethanol 30.56
    sec-butyl acetate 20.29
    tert-butyl acetate 22.78
    decalin 2.59
    glycerin 18.06
    diglyme 67.33
    acrylic acid 29.26
    isopropyl myristate 13.81
    n-butyric acid 21.86
    acetyl acetate 29.88
    di(2-ethylhexyl) phthalate 20.11
    ethyl propionate 30.75
    nitromethane 75.62
    1,2-diethoxyethane 23.64
    benzonitrile 39.45
    trioctyl phosphate 15.5
    1-bromopropane 21.22
    gamma-valerolactone 96.63
    n-decanol 10.9
    triethyl phosphate 23.32
    4-methyl-2-pentanol 6.1
    propionitrile 21.89
    vinylene carbonate 63.39
    1,1,2-trichlorotrifluoroethane 82.48
    DMS 42.26
    cumene 10.55
    2-octanol 10.32
    2-hexanone 29.6
    octyl acetate 19.07
    limonene 14.86
    1,2-dimethoxyethane 67.68
    ethyl orthosilicate 19.59
    tributyl phosphate 17.41
    diacetone alcohol 28.42
    N,N-dimethylaniline 22.95
    acrylonitrile 40.17
    aniline 20.79
    1,3-propanediol 16.07
    bromobenzene 30.8
    dibromomethane 52.1
    1,1,2,2-tetrachloroethane 77.69
    2-methyl-cyclohexyl acetate 26.93
    tetrabutyl urea 25.31
    diisobutyl methanol 8.86
    2-phenylethanol 29.89
    styrene 13.88
    dioctyl adipate 21.82
    dimethyl sulfate 77.83
    ethyl butyrate 27.18
    methyl lactate 32.02
    butyl lactate 23.65
    diethyl carbonate 24.13
    propanediol butyl ether 21.1
    triethyl orthoformate 21.41
    p-tert-butyltoluene 10.71
    methyl 4-tert-butylbenzoate 36.35
    morpholine 44.99
    tert-butylamine 5.94
    n-dodecanol 8.95
    dimethoxymethane 67.97
    ethylene carbonate 51.52
    cyrene 45.57
    2-ethoxyethyl acetate 38.57
    2-ethylhexyl acetate 26.07
    1,2,4-trichlorobenzene 43.72
    4-methylpyridine 45.88
    dibutyl ether 12.68
    2,6-dimethyl-4-heptanol 8.86
    DEF 50.84
    dimethyl isosorbide 52.7
    tetrachloroethylene 66.59
    eugenol 40.28
    triacetin 35.22
    span 80 21.6
    1,4-butanediol 11.31
    1,1-dichloroethane 36.08
    2-methyl-1-pentanol 11.62
    methyl formate 61.76
    2-methyl-1-butanol 8.95
    n-decane 3.01
    butyronitrile 18.48
    3,7-dimethyl-1-octanol 11.5
    1-chlorooctane 11.65
    1-chlorotetradecane 6.0
    n-nonane 2.5
    undecane 2.5
    tert-butylcyclohexane 1.94
    cyclooctane 1.28
    cyclopentanol 17.4
    tetrahydropyran 26.96
    tert-amyl methyl ether 11.9
    2,5,8-trioxanonane 46.65
    1-hexene 4.9
    2-isopropoxyethanol 25.26
    2,2,2-trifluoroethanol 29.53
    methyl butyrate 40.11

    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