6',7'-Dihydroxybergamottin

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  • Identifiers

    CAS number
    145414-76-2

    Molecular formula
    C21H24O6

    SMILES
    C/C(=C\COC1=C2C=CC(=O)OC2=CC3=C1C=CO3)/CCC(C(C)(C)O)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 35.52%
    Floral 35.13%
    Fruity 33.97%
    Powdery 26.74%
    Woody 26.59%
    Odorless 26.37%
    Vanilla 26.31%
    Creamy 23.54%
    Dry 23.05%
    Berry 23.03%

     

    Flavor
    Bitter 64.68%
    Odorless 24.48%
    Bland 22.68%
    Mild 22.04%
    Parsley 19.18%
    Heather 19.14%
    Cedarleaf 18.9%
    Ethyl benzoate 18.85%
    Sweet-like 18.82%
    Broom 18.77%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    9.32 (weak base)

    Molecular weight
    372.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    718°C

    Flash point

    • 249.43 ˚C est.

  • Synonyms

    • 145414-76-2
    • 6',7'-dihydroxybergamottin
    • 6,7-dihydroxybergamottin
    • 6,7-DHB
    • DTXSID001045401
    • RefChem:913624
    • DTXCID001527336
    • 5-(((2E)-6-hydroxy-3,7,7-trimethyloct-2-en-1-yl)oxy)-2H,8H-pyrano(3,2-g)chromen-2-one
    • 4-((E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy)furo(3,2-g)chromen-7-one
    • 6',7'-dihydroxy Bergamottin
    • 71339-34-9
    • 7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-
    • 4-[(E)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one
    • (E)-4-((6,7-Dihydroxy-3,7-dimethyloct-2-en-1-yl)oxy)-7H-furo[3,2-g]chromen-7-one
    • 4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octenyl]oxy]-7H-fuoro[3,2-g][1]benzopyran-7-one
    • 7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl)oxy]-
    • 4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one
    • CHEMBL513494
    • SCHEMBL30173389
    • 6??,-7??-Dihydroxybergamottin
    • CHEBI:175789
    • IXZUPBUEKFXTSD-MDWZMJQESA-N
    • 7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E,6R)-6,7-dihydroxy-3,7-dimethyl-2-octenyl]oxy]- (9CI); 4-[[(2E,6R)-6,7-Dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one; (R)-17,18-Dihydroxybergamottin
    • HY-N8354
    • 6a(2),7a(2)-Dihydroxybergamottin
    • AKOS025294521
    • AT44630
    • FD22049
    • 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy)-
    • NCGC00165947-01
    • DA-49903
    • CS-0143518
    • C22156
    • Q3599478
    • 5-[(6',7'-Dihydroxy-3',7'-dimethyl-2-octenyl)oxy]psoralen
    • 4-[(E)-6,7-dihydroxy-3,7-dimethyl-oct-2-enoxy]furo[3,2-g]chromen-7-one
    • 4-[(E)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]uro[3,2-g]chromen-7-one
    • 6 inverted exclamation mark pound not7 inverted exclamation mark -Dihydroxy Bergamottin
    • 71339-34-9

  • Applications

    6',7'-Dihydroxybergamottin is a natural furanocoumarin found in citrus essential oils (notably bergamot) and is primarily encountered in pharmaceutical research and analytical contexts. In research settings it is commonly evaluated for its CYP3A4-inhibitory activity and potential drug interaction effects, and it serves as a chemical marker for quality control and authenticity of bergamot oil and other citrus essential oils. In flavor and fragrance work, it may contribute to citrus notes and is used as a reference compound in analytical flavor studies. It is also employed as an intermediate in the synthesis of other coumarin derivatives in laboratory and industrial settings. Additionally, its photosensitizing properties make it a focus in photochemistry and phototoxicity studies. All uses are research-oriented and subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 68.15
    methanol 160.3
    isopropanol 47.98
    water 0.44
    ethyl acetate 27.96
    n-propanol 61.78
    acetone 121.68
    n-butanol 42.52
    acetonitrile 24.97
    DMF 228.32
    toluene 10.13
    isobutanol 36.96
    1,4-dioxane 125.19
    methyl acetate 50.3
    THF 260.62
    2-butanone 86.74
    n-pentanol 39.2
    sec-butanol 40.28
    n-hexane 0.4
    ethylene glycol 28.36
    NMP 94.67
    cyclohexane 1.04
    DMSO 479.59
    n-butyl acetate 12.2
    n-octanol 12.77
    chloroform 67.33
    n-propyl acetate 22.56
    acetic acid 155.06
    dichloromethane 64.59
    cyclohexanone 93.25
    propylene glycol 58.08
    isopropyl acetate 19.09
    DMAc 395.4
    2-ethoxyethanol 149.38
    isopentanol 32.86
    n-heptane 0.49
    ethyl formate 26.99
    1,2-dichloroethane 35.1
    n-hexanol 14.94
    2-methoxyethanol 245.19
    isobutyl acetate 16.35
    tetrachloromethane 3.93
    n-pentyl acetate 16.45
    transcutol 296.21
    n-heptanol 13.55
    ethylbenzene 4.41
    MIBK 27.16
    2-propoxyethanol 90.67
    tert-butanol 45.93
    MTBE 20.03
    2-butoxyethanol 56.69
    propionic acid 62.37
    o-xylene 5.95
    formic acid 87.06
    diethyl ether 17.29
    m-xylene 5.8
    p-xylene 7.43
    chlorobenzene 10.82
    dimethyl carbonate 37.5
    n-octane 0.35
    formamide 109.68
    cyclopentanone 98.01
    2-pentanone 44.43
    anisole 24.64
    cyclopentyl methyl ether 34.86
    gamma-butyrolactone 88.61
    1-methoxy-2-propanol 158.76
    pyridine 66.49
    3-pentanone 36.44
    furfural 74.32
    n-dodecane 0.46
    diethylene glycol 86.19
    diisopropyl ether 3.25
    tert-amyl alcohol 35.98
    acetylacetone 68.45
    n-hexadecane 0.52
    acetophenone 31.96
    methyl propionate 40.86
    isopentyl acetate 15.58
    trichloroethylene 76.93
    n-nonanol 14.05
    cyclohexanol 32.47
    benzyl alcohol 40.48
    2-ethylhexanol 8.05
    isooctanol 11.57
    dipropyl ether 8.6
    1,2-dichlorobenzene 10.46
    ethyl lactate 29.06
    propylene carbonate 35.86
    n-methylformamide 85.58
    2-pentanol 19.02
    n-pentane 0.39
    1-propoxy-2-propanol 52.38
    1-methoxy-2-propyl acetate 32.81
    2-(2-methoxypropoxy) propanol 65.92
    mesitylene 3.3
    ε-caprolactone 62.47
    p-cymene 3.2
    epichlorohydrin 128.34
    1,1,1-trichloroethane 15.94
    2-aminoethanol 66.18
    morpholine-4-carbaldehyde 168.76
    sulfolane 116.4
    2,2,4-trimethylpentane 0.44
    2-methyltetrahydrofuran 62.99
    n-hexyl acetate 20.4
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 91.67
    sec-butyl acetate 14.61
    tert-butyl acetate 22.8
    decalin 0.6
    glycerin 94.23
    diglyme 161.63
    acrylic acid 66.12
    isopropyl myristate 9.37
    n-butyric acid 55.36
    acetyl acetate 22.47
    di(2-ethylhexyl) phthalate 15.95
    ethyl propionate 18.12
    nitromethane 179.97
    1,2-diethoxyethane 44.24
    benzonitrile 20.85
    trioctyl phosphate 9.86
    1-bromopropane 11.43
    gamma-valerolactone 183.49
    n-decanol 10.01
    triethyl phosphate 12.07
    4-methyl-2-pentanol 11.55
    propionitrile 23.66
    vinylene carbonate 40.99
    1,1,2-trichlorotrifluoroethane 124.3
    DMS 24.27
    cumene 3.24
    2-octanol 8.18
    2-hexanone 36.0
    octyl acetate 13.25
    limonene 4.31
    1,2-dimethoxyethane 176.47
    ethyl orthosilicate 11.77
    tributyl phosphate 11.54
    diacetone alcohol 61.43
    N,N-dimethylaniline 19.11
    acrylonitrile 36.1
    aniline 27.74
    1,3-propanediol 102.12
    bromobenzene 8.82
    dibromomethane 27.55
    1,1,2,2-tetrachloroethane 65.17
    2-methyl-cyclohexyl acetate 17.66
    tetrabutyl urea 20.37
    diisobutyl methanol 5.51
    2-phenylethanol 23.87
    styrene 5.95
    dioctyl adipate 19.42
    dimethyl sulfate 57.07
    ethyl butyrate 11.8
    methyl lactate 52.95
    butyl lactate 25.67
    diethyl carbonate 9.82
    propanediol butyl ether 61.62
    triethyl orthoformate 15.21
    p-tert-butyltoluene 3.1
    methyl 4-tert-butylbenzoate 31.07
    morpholine 167.13
    tert-butylamine 12.61
    n-dodecanol 7.16
    dimethoxymethane 171.08
    ethylene carbonate 35.29
    cyrene 65.76
    2-ethoxyethyl acetate 36.25
    2-ethylhexyl acetate 10.88
    1,2,4-trichlorobenzene 17.04
    4-methylpyridine 42.7
    dibutyl ether 10.97
    2,6-dimethyl-4-heptanol 5.51
    DEF 64.18
    dimethyl isosorbide 76.2
    tetrachloroethylene 37.4
    eugenol 40.08
    triacetin 42.59
    span 80 46.31
    1,4-butanediol 49.09
    1,1-dichloroethane 22.72
    2-methyl-1-pentanol 28.9
    methyl formate 61.73
    2-methyl-1-butanol 31.74
    n-decane 0.74
    butyronitrile 19.7
    3,7-dimethyl-1-octanol 11.2
    1-chlorooctane 3.86
    1-chlorotetradecane 1.81
    n-nonane 0.56
    undecane 0.56
    tert-butylcyclohexane 0.45
    cyclooctane 0.36
    cyclopentanol 43.5
    tetrahydropyran 62.88
    tert-amyl methyl ether 16.86
    2,5,8-trioxanonane 115.75
    1-hexene 2.32
    2-isopropoxyethanol 76.97
    2,2,2-trifluoroethanol 45.5
    methyl butyrate 28.7

    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