(+)-Pinocembrin

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  • Identifiers

    CAS number
    480-39-7

    Molecular formula
    C15H12O4

    SMILES
    C1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 49.3%
    Odorless 44.28%
    Sweet 37.86%
    Spicy 37.57%
    Balsamic 29.88%
    Vanilla 28.79%
    Nutty 27.6%
    Coconut 27.03%
    Bitter 25.29%
    Coumarinic 24.48%

     

    Flavor
    Bitter 91.78%
    Lovage 21.48%
    Cedarleaf 20.74%
    Parsley 19.86%
    Ripe apricot 19.66%
    Sweet-like 19.48%
    Nitrile 19.44%
    Ethyl benzoate 19.4%
    Red fruit 19.34%
    Very strong 19.12%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    9.9 (weak base)

    Molecular weight
    256.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    503°C

    Melting point expt.

    • 192 - 193 °C

    Flash point

    • 215.03 ˚C est.

  • Synonyms

    • Pinocembrin
    • 480-39-7
    • (+)-Pinocembrin
    • Galangin flavanone
    • pinocembrine
    • (+)-pinocoembrin
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2S)-
    • (S)-2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one
    • 8T7C8CH791
    • NSC-279005
    • (2S)-5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
    • DTXSID3075412
    • CHEBI:28157
    • 5,7-dihydroxy-flavanone
    • RefChem:863359
    • GlyTouCan:G59588PU
    • DTXCID0040597
    • G59588PU
    • Dihydrochrysin
    • (S)-5,7-dihydroxy-2-phenylchroman-4-one
    • (2S)-pinocembrin
    • (S)-5,7-dihydroxyflavanone
    • (2s)-5,7-dihydroxy-2-phenyl-2,3-dihydro-4h-chromen-4-one
    • CHEMBL399910
    • (s)-pinocembrin
    • MFCD06858345
    • (2S)-5,7-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
    • (2S)-5,7-dihydroxy-2-phenyl-chroman-4-one
    • SMR000232372
    • Pinocembrin (6CI)
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (-)-
    • NSC 43318
    • NSC 279005
    • NSC 661207
    • pinocernbrin
    • NSC43318
    • UNII-8T7C8CH791
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (S)-
    • NSC-43318
    • NSC661207
    • Pinocembrin (Standard)
    • Spectrum_001879
    • SpecPlus_000896
    • 5,7-Dihydroxy flavanone
    • Spectrum2_001670
    • Spectrum3_001635
    • Spectrum4_001765
    • Spectrum5_000349
    • Oprea1_508274
    • BSPBio_003329
    • KBioGR_002249
    • KBioSS_002406
    • MLS000697595
    • MLS000728654
    • DivK1c_006992
    • SPBio_001859
    • orb1304762
    • SCHEMBL10026578
    • BDBM26667
    • HY-N0575R
    • KBio1_001936
    • KBio2_002401
    • KBio2_004969
    • KBio2_007537
    • KBio3_002549
    • MSK7406
    • HMS2205J20
    • HMS6019G03
    • HY-N0575
    • (2S)-5,7-dihydroxy-dihydroflavone
    • CCG-39668
    • LMPK12140214
    • s3941
    • STL578139
    • AKOS004111068
    • EBC-465070
    • SDCCGMLS-0066749.P001
    • NCGC00178137-01
    • AC-34601
    • AS-56293
    • DA-76897
    • ST023293
    • XP162085
    • (2S)-5,7-dihydroxy-2-phenylchroman-4-one
    • CS-0009111
    • C09827
    • SR-01000762561
    • SR-01000762561-3
    • BRD-K94689771-001-02-5
    • BRD-K94689771-001-09-0
    • Pinocembrin, analytical standard, 95% (TLC), solid
    • (2~{S})-5,7-bis(oxidanyl)-2-phenyl-2,3-dihydrochromen-4-one
    • (2S)-5,7-Dihydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (S)-(-)-
    • 480-39-7

  • Applications

    (+)-Pinocembrin (CAS 480-39-7) is a flavanone that is widely studied as a bioactive intermediate in flavonoid chemistry and is used in cosmetic formulations as an antioxidant-active ingredient; it is also investigated in pharmaceutical research as a building block for the synthesis of flavonoid derivatives and as a scaffold for medicinal chemistry work; in industrial manufacturing it can be employed as an intermediate to synthesize related flavonoid compounds; in coatings and inks, it may be evaluated as a natural antioxidant additive to improve oxidative stability; in food processing research, pinocembrin is frequently evaluated for its potential as a natural antioxidant in food systems.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.66
    methanol 34.41
    isopropanol 21.44
    water 0.25
    ethyl acetate 56.82
    n-propanol 10.36
    acetone 257.62
    n-butanol 12.31
    acetonitrile 133.69
    DMF 526.88
    toluene 3.24
    isobutanol 14.58
    1,4-dioxane 151.69
    methyl acetate 94.25
    THF 429.49
    2-butanone 106.67
    n-pentanol 13.67
    sec-butanol 12.71
    n-hexane 0.05
    ethylene glycol 50.64
    NMP 244.24
    cyclohexane 0.11
    DMSO 2484.19
    n-butyl acetate 34.9
    n-octanol 10.31
    chloroform 8.54
    n-propyl acetate 40.28
    acetic acid 84.68
    dichloromethane 6.76
    cyclohexanone 103.86
    propylene glycol 62.28
    isopropyl acetate 42.68
    DMAc 435.84
    2-ethoxyethanol 94.54
    isopentanol 22.58
    n-heptane 0.2
    ethyl formate 44.8
    1,2-dichloroethane 16.55
    n-hexanol 11.07
    2-methoxyethanol 226.51
    isobutyl acetate 26.27
    tetrachloromethane 1.37
    n-pentyl acetate 17.82
    transcutol 635.74
    n-heptanol 7.97
    ethylbenzene 2.13
    MIBK 49.85
    2-propoxyethanol 105.27
    tert-butanol 58.72
    MTBE 21.1
    2-butoxyethanol 42.44
    propionic acid 48.82
    o-xylene 3.66
    formic acid 45.86
    diethyl ether 10.74
    m-xylene 4.47
    p-xylene 3.64
    chlorobenzene 7.62
    dimethyl carbonate 95.71
    n-octane 0.1
    formamide 127.1
    cyclopentanone 243.02
    2-pentanone 68.29
    anisole 25.48
    cyclopentyl methyl ether 49.56
    gamma-butyrolactone 260.19
    1-methoxy-2-propanol 195.69
    pyridine 31.13
    3-pentanone 47.76
    furfural 154.75
    n-dodecane 0.41
    diethylene glycol 164.93
    diisopropyl ether 5.65
    tert-amyl alcohol 24.87
    acetylacetone 193.33
    n-hexadecane 0.49
    acetophenone 37.18
    methyl propionate 79.15
    isopentyl acetate 33.92
    trichloroethylene 40.05
    n-nonanol 10.92
    cyclohexanol 19.21
    benzyl alcohol 27.13
    2-ethylhexanol 10.76
    isooctanol 8.68
    dipropyl ether 16.7
    1,2-dichlorobenzene 10.07
    ethyl lactate 53.11
    propylene carbonate 96.26
    n-methylformamide 172.44
    2-pentanol 11.24
    n-pentane 0.05
    1-propoxy-2-propanol 81.6
    1-methoxy-2-propyl acetate 91.56
    2-(2-methoxypropoxy) propanol 96.24
    mesitylene 3.57
    ε-caprolactone 77.03
    p-cymene 4.82
    epichlorohydrin 224.73
    1,1,1-trichloroethane 15.7
    2-aminoethanol 40.96
    morpholine-4-carbaldehyde 260.4
    sulfolane 456.75
    2,2,4-trimethylpentane 0.28
    2-methyltetrahydrofuran 75.28
    n-hexyl acetate 31.25
    isooctane 0.31
    2-(2-butoxyethoxy)ethanol 125.52
    sec-butyl acetate 26.52
    tert-butyl acetate 52.26
    decalin 0.34
    glycerin 172.99
    diglyme 260.55
    acrylic acid 64.7
    isopropyl myristate 16.91
    n-butyric acid 50.54
    acetyl acetate 57.23
    di(2-ethylhexyl) phthalate 20.89
    ethyl propionate 43.36
    nitromethane 474.12
    1,2-diethoxyethane 75.33
    benzonitrile 30.42
    trioctyl phosphate 15.72
    1-bromopropane 2.56
    gamma-valerolactone 296.92
    n-decanol 9.15
    triethyl phosphate 26.45
    4-methyl-2-pentanol 13.01
    propionitrile 49.11
    vinylene carbonate 76.23
    1,1,2-trichlorotrifluoroethane 175.77
    DMS 64.08
    cumene 2.61
    2-octanol 5.61
    2-hexanone 42.02
    octyl acetate 21.1
    limonene 6.24
    1,2-dimethoxyethane 196.27
    ethyl orthosilicate 21.58
    tributyl phosphate 22.49
    diacetone alcohol 117.89
    N,N-dimethylaniline 17.13
    acrylonitrile 90.64
    aniline 17.0
    1,3-propanediol 63.29
    bromobenzene 5.43
    dibromomethane 3.04
    1,1,2,2-tetrachloroethane 38.38
    2-methyl-cyclohexyl acetate 28.18
    tetrabutyl urea 32.66
    diisobutyl methanol 10.52
    2-phenylethanol 26.66
    styrene 2.54
    dioctyl adipate 32.73
    dimethyl sulfate 204.82
    ethyl butyrate 33.19
    methyl lactate 113.08
    butyl lactate 34.82
    diethyl carbonate 28.86
    propanediol butyl ether 69.02
    triethyl orthoformate 30.53
    p-tert-butyltoluene 4.84
    methyl 4-tert-butylbenzoate 42.86
    morpholine 160.86
    tert-butylamine 11.88
    n-dodecanol 7.46
    dimethoxymethane 245.05
    ethylene carbonate 67.49
    cyrene 84.18
    2-ethoxyethyl acetate 47.25
    2-ethylhexyl acetate 23.24
    1,2,4-trichlorobenzene 18.31
    4-methylpyridine 34.01
    dibutyl ether 16.22
    2,6-dimethyl-4-heptanol 10.52
    DEF 79.4
    dimethyl isosorbide 157.79
    tetrachloroethylene 14.1
    eugenol 46.14
    triacetin 67.01
    span 80 53.6
    1,4-butanediol 30.42
    1,1-dichloroethane 10.27
    2-methyl-1-pentanol 15.82
    methyl formate 168.83
    2-methyl-1-butanol 14.73
    n-decane 0.49
    butyronitrile 31.23
    3,7-dimethyl-1-octanol 14.93
    1-chlorooctane 3.69
    1-chlorotetradecane 2.19
    n-nonane 0.3
    undecane 0.46
    tert-butylcyclohexane 0.42
    cyclooctane 0.08
    cyclopentanol 34.99
    tetrahydropyran 39.18
    tert-amyl methyl ether 16.49
    2,5,8-trioxanonane 197.97
    1-hexene 0.38
    2-isopropoxyethanol 62.2
    2,2,2-trifluoroethanol 53.53
    methyl butyrate 52.54

    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