5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

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  • Identifiers

    CAS number
    67604-48-2

    Molecular formula
    C15H12O5

    SMILES
    C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Phenolic 61.29%
    Odorless 47.95%
    Spicy 33.15%
    Sweet 31.2%
    Nutty 30.67%
    Vanilla 29.91%
    Medicinal 28.78%
    Burnt 27.0%
    Smoky 24.74%
    Bitter 24.73%

     

    Flavor
    Bitter 93.81%
    Cedarleaf 20.9%
    Lovage 20.87%
    Sweet-like 20.64%
    Parsley 20.02%
    Odorless 19.98%
    Very strong 19.71%
    Ripe apricot 19.68%
    Nitrile 19.61%
    Indole 19.61%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    10.56 (weak base)

    Molecular weight
    272.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    554°C

    Flash point

    • 243.64 ˚C est.

  • Synonyms

    • naringenin
    • 67604-48-2
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
    • (+/-)-Naringenin
    • 4',5,7-Trihydroxyflavanone
    • naringetol
    • 93602-28-9
    • rac Naringenin
    • ( inverted exclamation markA)-Naringenin
    • (-)-Naringenin
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
    • (+)-naringenin
    • CCRIS 8135
    • EINECS 266-769-1
    • MFCD00006844
    • CHEMBL32571
    • rac-Naringenin
    • MLS000028739
    • MLS000738094
    • CHEBI:50202
    • DTXSID50274239
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
    • NSC11855
    • NSC34875
    • (R,S)-Naringenin
    • SMR000059039
    • 4',7-Trihydroxyflavanone
    • Flavanone,5,7-trihydroxy-
    • BE-14348A
    • 4',5,7-trihydroxyflavan-4-one
    • Naringenin?
    • NSC-34875
    • 4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-
    • 4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-
    • Naringenin (NAR)
    • Prestwick_531
    • (??)-Naringenin
    • Opera_ID_106
    • Prestwick0_000466
    • Prestwick1_000466
    • Prestwick2_000466
    • Prestwick3_000466
    • (R,S)-Naringenin 1000 microg/mL in Acetone
    • Oprea1_194140
    • SCHEMBL20571
    • BSPBio_000572
    • MLS001146907
    • 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-one
    • SPBio_002511
    • BPBio1_000630
    • MEGxp0_000358
    • SCHEMBL1934259
    • SCHEMBL25894738
    • ACon1_000582
    • BDBM19461
    • GTPL10298
    • DTXCID50196624
    • (+/-)-Naringenin, >=95%
    • HMS1569M14
    • HMS2096M14
    • HMS2231O18
    • HMS3352B08
    • HMS3373N07
    • HMS3656G15
    • Naringenin, natural (US), 98%
    • BCP31780
    • HY-W011641R
    • MFCD00870553
    • NSC815094
    • AKOS015895052
    • (+/-)-Naringenin, analytical standard
    • CS-W012357
    • FN01176
    • HY-W011641
    • KS-5142
    • NSC-815094
    • SB17305
    • (+/-)-Naringenin, ~95% (HPCE)
    • SMP1_000060
    • NCGC00017346-02
    • NCGC00017346-03
    • NCGC00017346-04
    • NCGC00017346-09
    • NCGC00095963-01
    • NCGC00095963-02
    • NCGC00095963-03
    • AC-20273
    • SY049933
    • SY075819
    • DB-057415
    • N0072
    • NS00003069
    • EN300-717813
    • S00279
    • AE-848/32605045
    • ( inverted exclamation markA)-Naringenin (Standard)
    • BRD-A94669766-001-02-6
    • BRD-A94669766-001-04-2
    • Q57826857
    • Z1741982267
    • EC19096C-4404-4A16-9BF9-92F9F358E005
    • ( )-Naringenin; 4?,5,7-Trihydroxyflavanone; H-1-benzopyran-4-one
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one, (S)- #
    • (+/-)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4- one
    • 266-769-1

  • Applications

    Naringenin (CAS 67604-48-2) is a key natural flavonoid found abundantly in citrus peels, tomatoes and various herbs, and has attracted wide interest because of its multifaceted biological activities: potent antioxidant capacity that scavenges free radicals and shields cells from oxidative stress; pronounced anti-inflammatory action that alleviates chronic inflammation associated with cardiovascular, arthritic and dermatological disorders; modulation of lipid and glucose metabolism that lowers LDL cholesterol and improves insulin sensitivity, making it a valuable ingredient in nutraceutical formulations targeting obesity and diabetes; ability to inhibit proliferation of numerous cancer cell lines, positioning naringenin as a promising lead compound for anticancer drug development; mild antibacterial and antiviral effects that support immune defense; additionally, the molecule is employed as a natural additive in cosmetics to enhance product stability and provide photoprotection against UV-induced hyperpigmentation, and as an antioxidant, metal-chelating agent and shelf-life extender in foods, biodegradable packaging and pharmaceutical preparations, thereby improving safety and longevity of consumer products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.11
    methanol 35.4
    isopropanol 24.11
    water 0.58
    ethyl acetate 47.1
    n-propanol 4.42
    acetone 184.62
    n-butanol 7.67
    acetonitrile 141.97
    DMF 593.84
    toluene 0.76
    isobutanol 9.77
    1,4-dioxane 144.99
    methyl acetate 92.6
    THF 337.19
    2-butanone 82.17
    n-pentanol 8.8
    sec-butanol 10.57
    n-hexane 0.02
    ethylene glycol 64.87
    NMP 174.43
    cyclohexane 0.04
    DMSO 2935.24
    n-butyl acetate 24.54
    n-octanol 8.36
    chloroform 0.65
    n-propyl acetate 36.96
    acetic acid 71.0
    dichloromethane 0.49
    cyclohexanone 64.46
    propylene glycol 96.43
    isopropyl acetate 38.55
    DMAc 474.49
    2-ethoxyethanol 151.99
    isopentanol 17.18
    n-heptane 0.1
    ethyl formate 42.49
    1,2-dichloroethane 2.07
    n-hexanol 5.21
    2-methoxyethanol 316.42
    isobutyl acetate 20.84
    tetrachloromethane 0.22
    n-pentyl acetate 13.38
    transcutol 688.8
    n-heptanol 5.2
    ethylbenzene 0.64
    MIBK 42.68
    2-propoxyethanol 131.53
    tert-butanol 75.53
    MTBE 15.54
    2-butoxyethanol 45.22
    propionic acid 44.56
    o-xylene 1.19
    formic acid 55.12
    diethyl ether 5.12
    m-xylene 1.38
    p-xylene 1.26
    chlorobenzene 1.33
    dimethyl carbonate 90.62
    n-octane 0.05
    formamide 157.74
    cyclopentanone 175.15
    2-pentanone 53.4
    anisole 14.1
    cyclopentyl methyl ether 26.47
    gamma-butyrolactone 230.76
    1-methoxy-2-propanol 286.95
    pyridine 13.07
    3-pentanone 31.83
    furfural 118.67
    n-dodecane 0.2
    diethylene glycol 221.26
    diisopropyl ether 3.24
    tert-amyl alcohol 21.81
    acetylacetone 205.25
    n-hexadecane 0.24
    acetophenone 22.29
    methyl propionate 72.69
    isopentyl acetate 24.09
    trichloroethylene 5.38
    n-nonanol 8.82
    cyclohexanol 10.66
    benzyl alcohol 15.9
    2-ethylhexanol 5.43
    isooctanol 5.85
    dipropyl ether 11.66
    1,2-dichlorobenzene 2.25
    ethyl lactate 60.12
    propylene carbonate 67.36
    n-methylformamide 223.28
    2-pentanol 9.08
    n-pentane 0.02
    1-propoxy-2-propanol 92.99
    1-methoxy-2-propyl acetate 81.21
    2-(2-methoxypropoxy) propanol 97.33
    mesitylene 1.42
    ε-caprolactone 56.6
    p-cymene 1.71
    epichlorohydrin 153.07
    1,1,1-trichloroethane 2.68
    2-aminoethanol 44.62
    morpholine-4-carbaldehyde 271.15
    sulfolane 396.09
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 43.41
    n-hexyl acetate 23.28
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 143.66
    sec-butyl acetate 21.34
    tert-butyl acetate 48.75
    decalin 0.11
    glycerin 267.35
    diglyme 275.57
    acrylic acid 57.3
    isopropyl myristate 12.69
    n-butyric acid 44.19
    acetyl acetate 50.51
    di(2-ethylhexyl) phthalate 14.9
    ethyl propionate 36.13
    nitromethane 691.05
    1,2-diethoxyethane 76.4
    benzonitrile 14.32
    trioctyl phosphate 11.45
    1-bromopropane 0.42
    gamma-valerolactone 287.7
    n-decanol 7.08
    triethyl phosphate 20.42
    4-methyl-2-pentanol 10.0
    propionitrile 41.58
    vinylene carbonate 51.38
    1,1,2-trichlorotrifluoroethane 132.89
    DMS 50.35
    cumene 0.85
    2-octanol 4.0
    2-hexanone 34.93
    octyl acetate 15.68
    limonene 2.22
    1,2-dimethoxyethane 247.89
    ethyl orthosilicate 16.56
    tributyl phosphate 16.83
    diacetone alcohol 129.98
    N,N-dimethylaniline 9.31
    acrylonitrile 85.23
    aniline 5.38
    1,3-propanediol 75.92
    bromobenzene 0.77
    dibromomethane 0.23
    1,1,2,2-tetrachloroethane 7.22
    2-methyl-cyclohexyl acetate 19.79
    tetrabutyl urea 25.74
    diisobutyl methanol 7.4
    2-phenylethanol 13.8
    styrene 0.75
    dioctyl adipate 25.68
    dimethyl sulfate 176.33
    ethyl butyrate 26.28
    methyl lactate 139.44
    butyl lactate 32.4
    diethyl carbonate 22.28
    propanediol butyl ether 78.74
    triethyl orthoformate 26.87
    p-tert-butyltoluene 1.95
    methyl 4-tert-butylbenzoate 33.09
    morpholine 137.95
    tert-butylamine 8.62
    n-dodecanol 5.53
    dimethoxymethane 293.49
    ethylene carbonate 50.57
    cyrene 83.62
    2-ethoxyethyl acetate 43.35
    2-ethylhexyl acetate 15.06
    1,2,4-trichlorobenzene 4.39
    4-methylpyridine 14.09
    dibutyl ether 12.54
    2,6-dimethyl-4-heptanol 7.4
    DEF 69.08
    dimethyl isosorbide 167.35
    tetrachloroethylene 2.45
    eugenol 38.88
    triacetin 58.56
    span 80 44.78
    1,4-butanediol 40.58
    1,1-dichloroethane 1.55
    2-methyl-1-pentanol 10.39
    methyl formate 221.2
    2-methyl-1-butanol 9.72
    n-decane 0.24
    butyronitrile 20.93
    3,7-dimethyl-1-octanol 10.79
    1-chlorooctane 1.63
    1-chlorotetradecane 1.03
    n-nonane 0.15
    undecane 0.22
    tert-butylcyclohexane 0.12
    cyclooctane 0.04
    cyclopentanol 22.87
    tetrahydropyran 18.43
    tert-amyl methyl ether 11.14
    2,5,8-trioxanonane 208.91
    1-hexene 0.13
    2-isopropoxyethanol 87.44
    2,2,2-trifluoroethanol 50.51
    methyl butyrate 47.57

    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