Engeletin

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  • Identifiers

    CAS number
    572-31-6

    Molecular formula
    C21H22O10

    SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 73.38%
    Phenolic 33.4%
    Vanilla 32.43%
    Sweet 26.72%
    Savory 21.92%
    Spicy 21.38%
    Burnt 21.37%
    Smoky 21.03%
    Milky 20.7%
    Bitter 20.64%

     

    Flavor
    Bitter 82.15%
    Bland 29.57%
    Odorless 28.81%
    Sweet-like 25.55%
    Cedarleaf 20.63%
    Lovage 19.45%
    Parsley 19.39%
    Nitrile 18.98%
    Eugenol 18.94%
    Leaves 18.69%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    7.75 (neutral)

    Molecular weight
    434.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2136°C

    Flash point

    • 252.79 ˚C est.

  • Synonyms

    • Engeletin
    • 572-31-6
    • (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
    • (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3-dihydrochromen-4-one
    • RefChem:136831
    • Engelitin
    • (2R,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
    • (2R,3R)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-3-[(2S,3R,4R,5S,6S)-3,4,5-TRIHYDROXY-6-METHYL-OXAN-2-YL]OXY-CHROMAN-4-ONE
    • (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
    • 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (2R-trans)-
    • 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2R-trans)-
    • (2R,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
    • MFCD01632717
    • Engeletin (Standard)
    • MEGxp0_000364
    • orb1300236
    • SCHEMBL5575048
    • SCHEMBL29365448
    • ACon1_000852
    • HY-N0436R
    • DTXSID70972649
    • HY-N0436
    • s9170
    • AKOS037514632
    • CCG-269060
    • EBC-616348
    • ME33650
    • NCGC00169295-01
    • AC-34264
    • AS-75029
    • Dihydrokaempferol 3-O-?-L-rhamnopyranoside
    • CS-0008955
    • 838A673
    • Q5377536
    • (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chroman-4-one
    • (2R,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl 6-deoxy-alpha-L-mannopyranoside
    • (2R,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-d eoxy-?-L-mannopyranoside
    • (2R,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-3-yl alpha-L-mannopyranoside
    • 572-31-6

  • Applications

    Engeletin (CAS 572-31-6) is a natural flavonoid that is evaluated for several industrial applications: it may be used as an active component in cosmetics and personal care due to antioxidant properties; it is often considered a synthetic intermediate for flavonoid derivatives in pharmaceutical research; it is evaluated as an antioxidant/stabilizing additive in polymer formulations and coatings; it can serve as a precursor or intermediate in organic synthesis; and it is explored for use in printing inks and coating formulations to enhance stability and color retention.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 41.18
    methanol 157.21
    isopropanol 17.8
    water 0.38
    ethyl acetate 10.12
    n-propanol 38.87
    acetone 82.77
    n-butanol 20.34
    acetonitrile 12.95
    DMF 320.77
    toluene 0.85
    isobutanol 9.85
    1,4-dioxane 44.38
    methyl acetate 14.63
    THF 108.87
    2-butanone 37.07
    n-pentanol 6.25
    sec-butanol 11.73
    n-hexane 0.03
    ethylene glycol 95.12
    NMP 152.38
    cyclohexane 0.13
    DMSO 1118.89
    n-butyl acetate 1.87
    n-octanol 3.76
    chloroform 1.48
    n-propyl acetate 2.87
    acetic acid 174.61
    dichloromethane 1.92
    cyclohexanone 34.82
    propylene glycol 102.56
    isopropyl acetate 4.67
    DMAc 228.98
    2-ethoxyethanol 124.34
    isopentanol 7.89
    n-heptane 0.1
    ethyl formate 17.91
    1,2-dichloroethane 3.41
    n-hexanol 2.71
    2-methoxyethanol 386.34
    isobutyl acetate 0.91
    tetrachloromethane 0.28
    n-pentyl acetate 3.14
    transcutol 94.28
    n-heptanol 3.81
    ethylbenzene 0.26
    MIBK 6.63
    2-propoxyethanol 50.64
    tert-butanol 10.79
    MTBE 2.71
    2-butoxyethanol 23.37
    propionic acid 32.7
    o-xylene 0.58
    formic acid 226.91
    diethyl ether 6.18
    m-xylene 0.52
    p-xylene 0.29
    chlorobenzene 0.49
    dimethyl carbonate 19.25
    n-octane 0.07
    formamide 275.74
    cyclopentanone 73.23
    2-pentanone 23.33
    anisole 2.41
    cyclopentyl methyl ether 9.03
    gamma-butyrolactone 74.89
    1-methoxy-2-propanol 173.44
    pyridine 13.77
    3-pentanone 11.06
    furfural 48.55
    n-dodecane 0.08
    diethylene glycol 94.17
    diisopropyl ether 0.63
    tert-amyl alcohol 7.31
    acetylacetone 41.82
    n-hexadecane 0.1
    acetophenone 3.83
    methyl propionate 19.39
    isopentyl acetate 1.72
    trichloroethylene 5.68
    n-nonanol 3.81
    cyclohexanol 6.64
    benzyl alcohol 5.69
    2-ethylhexanol 1.25
    isooctanol 2.54
    dipropyl ether 2.75
    1,2-dichlorobenzene 0.47
    ethyl lactate 11.51
    propylene carbonate 13.06
    n-methylformamide 181.05
    2-pentanol 5.49
    n-pentane 0.09
    1-propoxy-2-propanol 24.12
    1-methoxy-2-propyl acetate 11.23
    2-(2-methoxypropoxy) propanol 23.7
    mesitylene 0.32
    ε-caprolactone 23.11
    p-cymene 0.3
    epichlorohydrin 57.9
    1,1,1-trichloroethane 0.88
    2-aminoethanol 123.97
    morpholine-4-carbaldehyde 141.85
    sulfolane 182.84
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 16.0
    n-hexyl acetate 4.42
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 36.11
    sec-butyl acetate 1.36
    tert-butyl acetate 5.07
    decalin 0.04
    glycerin 211.15
    diglyme 62.62
    acrylic acid 44.46
    isopropyl myristate 1.76
    n-butyric acid 27.44
    acetyl acetate 6.6
    di(2-ethylhexyl) phthalate 3.17
    ethyl propionate 3.73
    nitromethane 245.2
    1,2-diethoxyethane 9.33
    benzonitrile 2.27
    trioctyl phosphate 2.86
    1-bromopropane 1.06
    gamma-valerolactone 171.73
    n-decanol 2.71
    triethyl phosphate 2.42
    4-methyl-2-pentanol 2.12
    propionitrile 7.11
    vinylene carbonate 12.92
    1,1,2-trichlorotrifluoroethane 76.08
    DMS 5.45
    cumene 0.16
    2-octanol 1.92
    2-hexanone 4.65
    octyl acetate 3.3
    limonene 0.59
    1,2-dimethoxyethane 73.6
    ethyl orthosilicate 2.05
    tributyl phosphate 2.68
    diacetone alcohol 29.09
    N,N-dimethylaniline 1.72
    acrylonitrile 16.16
    aniline 4.41
    1,3-propanediol 131.39
    bromobenzene 0.27
    dibromomethane 0.89
    1,1,2,2-tetrachloroethane 4.78
    2-methyl-cyclohexyl acetate 2.13
    tetrabutyl urea 5.54
    diisobutyl methanol 0.98
    2-phenylethanol 3.46
    styrene 0.3
    dioctyl adipate 4.56
    dimethyl sulfate 44.45
    ethyl butyrate 2.75
    methyl lactate 54.97
    butyl lactate 8.18
    diethyl carbonate 1.87
    propanediol butyl ether 28.75
    triethyl orthoformate 3.28
    p-tert-butyltoluene 0.33
    methyl 4-tert-butylbenzoate 8.38
    morpholine 80.99
    tert-butylamine 1.69
    n-dodecanol 1.79
    dimethoxymethane 144.27
    ethylene carbonate 10.23
    cyrene 31.24
    2-ethoxyethyl acetate 8.82
    2-ethylhexyl acetate 1.03
    1,2,4-trichlorobenzene 0.94
    4-methylpyridine 6.72
    dibutyl ether 2.03
    2,6-dimethyl-4-heptanol 0.98
    DEF 32.51
    dimethyl isosorbide 32.15
    tetrachloroethylene 3.26
    eugenol 10.38
    triacetin 10.62
    span 80 17.63
    1,4-butanediol 32.41
    1,1-dichloroethane 1.23
    2-methyl-1-pentanol 3.07
    methyl formate 114.02
    2-methyl-1-butanol 7.84
    n-decane 0.16
    butyronitrile 5.48
    3,7-dimethyl-1-octanol 2.29
    1-chlorooctane 0.67
    1-chlorotetradecane 0.28
    n-nonane 0.12
    undecane 0.11
    tert-butylcyclohexane 0.03
    cyclooctane 0.07
    cyclopentanol 14.85
    tetrahydropyran 14.21
    tert-amyl methyl ether 2.91
    2,5,8-trioxanonane 47.44
    1-hexene 0.17
    2-isopropoxyethanol 30.78
    2,2,2-trifluoroethanol 40.42
    methyl butyrate 6.04

    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