5-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one

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  • Identifiers

    CAS number
    3380-68-5

    Molecular formula
    C12H8O4

    SMILES
    COC1=CC(=O)OC2=C1C=C3C=COC3=C2

    Retention indicies (RI)

    • DB5: 2048.0

  • Odor profile

    Sweet 69.26%
    Coumarinic 41.03%
    Vanilla 37.39%
    Powdery 36.72%
    Nutty 34.71%
    Phenolic 33.49%
    Balsamic 32.69%
    Coconut 32.12%
    Creamy 30.91%
    Fruity 30.68%

    Scent© AI

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    5.62 (weak acid)

    Molecular weight
    216.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    358°C

    Flash point est.
    187.03 ˚C

  • Synonyms

    • 4-methoxypsoralen
    • 3380-68-5
    • 5-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one
    • 5-methoxyfuro[3,2-g]chromen-7-one
    • EINECS 222-183-8
    • 5-methoxy-7h-furo[3,2-g]chromen-7-one
    • CHEMBL141006
    • SCHEMBL8440887
    • DTXSID00187466
    • NS00029548
    • 4-METHOXYFURO(3',2':6,7)COUMARIN
    • Q63408819

  • Applications

    5-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one (CAS 3380-68-5) is a furocoumarin derivative used primarily as an analytical reference/standard in natural product and cosmetic matrices containing coumarins, as a UVA photosensitizer model in photobiology to probe reactive oxygen species generation, nucleic acid interactions and phototoxicity, as a structural scaffold in medicinal chemistry for psoralen-class SAR, and in phototherapy research (e.g., as a comparator to 8-methoxypsoralen in PUVA) and materials photochemistry; it is typically employed for R&D, quality control and method development (HPLC/LC-MS), UV stability/toxicity assessments, and as a natural-product marker standard, with appropriate handling due to strong photosensitizing properties and light-induced irritation risk.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.91
    methanol 13.87
    isopropanol 6.5
    water 0.19
    ethyl acetate 27.57
    n-propanol 6.43
    acetone 51.41
    n-butanol 5.86
    acetonitrile 27.19
    DMF 136.58
    toluene 9.13
    isobutanol 6.39
    1,4-dioxane 61.66
    methyl acetate 44.95
    THF 94.6
    2-butanone 37.87
    n-pentanol 5.4
    sec-butanol 6.06
    n-hexane 0.26
    ethylene glycol 15.39
    NMP 150.53
    cyclohexane 0.6
    DMSO 208.05
    n-butyl acetate 19.24
    n-octanol 4.03
    chloroform 23.56
    n-propyl acetate 21.68
    acetic acid 21.07
    dichloromethane 38.56
    cyclohexanone 45.05
    propylene glycol 7.56
    isopropyl acetate 18.26
    DMAc 210.86
    2-ethoxyethanol 33.15
    isopentanol 7.98
    n-heptane 0.46
    ethyl formate 19.89
    1,2-dichloroethane 34.19
    n-hexanol 6.18
    2-methoxyethanol 62.39
    isobutyl acetate 14.12
    tetrachloromethane 3.62
    n-pentyl acetate 10.62
    transcutol 107.03
    n-heptanol 4.39
    ethylbenzene 6.86
    MIBK 16.6
    2-propoxyethanol 33.96
    tert-butanol 11.88
    MTBE 9.58
    2-butoxyethanol 19.08
    propionic acid 16.45
    o-xylene 9.3
    formic acid 21.16
    diethyl ether 10.59
    m-xylene 7.7
    p-xylene 10.63
    chlorobenzene 13.53
    dimethyl carbonate 39.99
    n-octane 0.22
    formamide 50.0
    cyclopentanone 66.49
    2-pentanone 23.41
    anisole 26.35
    cyclopentyl methyl ether 25.94
    gamma-butyrolactone 82.77
    1-methoxy-2-propanol 37.56
    pyridine 43.49
    3-pentanone 25.99
    furfural 77.33
    n-dodecane 0.37
    diethylene glycol 46.95
    diisopropyl ether 4.05
    tert-amyl alcohol 9.83
    acetylacetone 50.77
    n-hexadecane 0.44
    acetophenone 31.07
    methyl propionate 36.17
    isopentyl acetate 19.23
    trichloroethylene 56.48
    n-nonanol 4.5
    cyclohexanol 10.08
    benzyl alcohol 21.49
    2-ethylhexanol 6.91
    isooctanol 4.72
    dipropyl ether 9.04
    1,2-dichlorobenzene 15.32
    ethyl lactate 18.72
    propylene carbonate 38.52
    n-methylformamide 47.54
    2-pentanol 4.15
    n-pentane 0.19
    1-propoxy-2-propanol 23.01
    1-methoxy-2-propyl acetate 33.65
    2-(2-methoxypropoxy) propanol 32.89
    mesitylene 5.16
    ε-caprolactone 41.63
    p-cymene 6.76
    epichlorohydrin 87.41
    1,1,1-trichloroethane 18.39
    2-aminoethanol 12.71
    morpholine-4-carbaldehyde 119.15
    sulfolane 113.09
    2,2,4-trimethylpentane 0.44
    2-methyltetrahydrofuran 38.13
    n-hexyl acetate 12.81
    isooctane 0.28
    2-(2-butoxyethoxy)ethanol 32.8
    sec-butyl acetate 15.46
    tert-butyl acetate 20.98
    decalin 1.01
    glycerin 25.76
    diglyme 71.49
    acrylic acid 22.92
    isopropyl myristate 7.91
    n-butyric acid 15.54
    acetyl acetate 24.3
    di(2-ethylhexyl) phthalate 11.92
    ethyl propionate 23.51
    nitromethane 88.51
    1,2-diethoxyethane 24.75
    benzonitrile 21.44
    trioctyl phosphate 7.33
    1-bromopropane 9.31
    gamma-valerolactone 91.48
    n-decanol 3.92
    triethyl phosphate 17.55
    4-methyl-2-pentanol 4.37
    propionitrile 17.21
    vinylene carbonate 37.32
    1,1,2-trichlorotrifluoroethane 65.74
    DMS 29.47
    cumene 5.91
    2-octanol 2.89
    2-hexanone 20.4
    octyl acetate 9.97
    limonene 7.63
    1,2-dimethoxyethane 72.17
    ethyl orthosilicate 15.08
    tributyl phosphate 9.98
    diacetone alcohol 31.23
    N,N-dimethylaniline 21.27
    acrylonitrile 29.16
    aniline 19.45
    1,3-propanediol 17.77
    bromobenzene 12.65
    dibromomethane 18.96
    1,1,2,2-tetrachloroethane 42.0
    2-methyl-cyclohexyl acetate 19.29
    tetrabutyl urea 15.0
    diisobutyl methanol 5.13
    2-phenylethanol 18.52
    styrene 8.1
    dioctyl adipate 14.69
    dimethyl sulfate 78.99
    ethyl butyrate 18.79
    methyl lactate 30.94
    butyl lactate 13.04
    diethyl carbonate 18.47
    propanediol butyl ether 15.66
    triethyl orthoformate 17.05
    p-tert-butyltoluene 5.69
    methyl 4-tert-butylbenzoate 23.04
    morpholine 55.32
    tert-butylamine 4.89
    n-dodecanol 3.34
    dimethoxymethane 72.71
    ethylene carbonate 30.94
    cyrene 38.22
    2-ethoxyethyl acetate 22.51
    2-ethylhexyl acetate 16.38
    1,2,4-trichlorobenzene 22.44
    4-methylpyridine 36.91
    dibutyl ether 6.39
    2,6-dimethyl-4-heptanol 5.13
    DEF 42.5
    dimethyl isosorbide 53.61
    tetrachloroethylene 27.81
    eugenol 24.86
    triacetin 23.74
    span 80 17.26
    1,4-butanediol 7.8
    1,1-dichloroethane 16.91
    2-methyl-1-pentanol 7.47
    methyl formate 49.73
    2-methyl-1-butanol 7.28
    n-decane 0.47
    butyronitrile 12.34
    3,7-dimethyl-1-octanol 5.95
    1-chlorooctane 2.67
    1-chlorotetradecane 1.62
    n-nonane 0.35
    undecane 0.41
    tert-butylcyclohexane 0.78
    cyclooctane 0.27
    cyclopentanol 12.52
    tetrahydropyran 25.06
    tert-amyl methyl ether 10.44
    2,5,8-trioxanonane 56.32
    1-hexene 1.73
    2-isopropoxyethanol 22.93
    2,2,2-trifluoroethanol 20.64
    methyl butyrate 27.77

    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

Botanical

Name CAS Botanical Proportion
Rue (Malaysia) 1 8014-29-7 Ruta graveolens L., fam. Rutaceae 7.24%
Parsley leaf (Germany), 1b (smooth leaf) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.1%
Parsley leaf (Germany), 1a (curly leaf) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 1.5%
Skimmia laureola (India) 2 Skimmia laureola Sieb. et Zucc., fam. Rutaceae 4.2%
Lime (Mexican, West Indian, Key) 6 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.27%
Bergamot (Turkey) 2 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.2%
Bergamot (Japan) 1 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.11%
Laggera alata var. montana (Cameroon) Laggera alata var. montana C.D. Adams, fam. Asteraceae (Compositae) 0.6%