Punicalagin

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  • Identifiers

    CAS number
    65995-63-3

    Molecular formula
    C48H28O30

    SMILES
    C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C4C5=C3C(=O)OC6=C(C(=C(C7=C(C(=C(C=C7C(=O)O1)O)O)O)C(=C56)C(=O)O4)O)O)O)O)O)O)O)C8C(OC(=O)C9=CC(=C(C(=C9C1=C(C(=C(C=C1C(=O)O8)O)O)O)O)O)O)C=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 76.74%
    Phenolic 33.52%
    Burnt 29.06%
    Savory 15.92%
    Smoky 15.55%
    Balsamic 15.48%
    Bitter 14.7%
    Spicy 14.59%
    Dry 13.75%
    Milky 13.75%

     

    Flavor
    Bitter 90.39%
    Odorless 32.29%
    Bland 26.52%
    Sweet-like 22.65%
    Cedarleaf 19.66%
    Lovage 19.3%
    Nitrile 19.11%
    Parsley 19.08%
    Eugenol 18.96%
    Rotten 18.83%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    4.63 (weak acid)

    Molecular weight
    1084.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    4548°C

    Flash point

    • 360.86 ˚C est.

    Solubility expt.

    • In methanol, 5 mg/mL, clear

  • Synonyms

    • DTXSID40894768
    • 9S9XW36W2A
    • RefChem:177265
    • DTXCID601324332
    • 6,7,8,11,12,23,24,27,28,29,37,43,44,45,48,49,50-heptadecahydroxy-2,14,21,33,36,39,54-heptaoxaundecacyclo(33.20.0.04,9.010,19.013,18.016,25.017,22.026,31.038,55.041,46.047,52)pentapentaconta-4,6,8,10,12,16,18,22,24,26,28,30,41,43,45,47,49,51-octadecaene-3,15,20,32,40,53-hexone
    • 65995-63-3
    • Punicalagin
    • 3,4,5,16,17,18-Hexahydroxy-8,13-dioxo-11-(3,4,5,11,17,18,19,22,23,34,35-undecahydroxy-8,14,26,31-tetraoxo-9,13,25,32-tetraoxaheptacyclo[25.8.0.02,7.015,20.021,30.024,29.028,33]pentatriaconta-1(35),2,4,6,15,17,19,21,23,27,29,33-dodecaen-10-yl)-9,12-dioxatricyclo[12.4.0.02,7]octadeca-1(18),2,4,6,14,16-hexaene-10-carbaldehyde
    • D-Glucose, cyclic4,6-[(2S,2'S)-2,2'-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo[1]benzopyrano[5,4,3-cde][1]benzopyran-1,6-diyl)bis[3,4,5-trihydroxybenzoate]]cyclic2,3-[(S)-4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate]
    • Punicalagin A&B
    • Punicalagin (Standard)
    • orb1303562
    • CHEMBL1984101
    • SCHEMBL29838615
    • HSDB 8106
    • HY-N0063R
    • HY-N0063
    • NSC676825
    • s9131
    • CCG-270636
    • EBC-616524
    • NSC-676825
    • NCI60_027272
    • CS-0007111
    • Q3410841
    • 1,2,3,12,13,14-Hexahydroxy-5,10-dioxo-8-[3,4,5,11,17,18,19,22,23,34,35-undecahydroxy-8,14,26,31-tetraoxo-9,13,25,32-tetraoxaheptacyclo[25.8.0.0~2,7~.0~15,20~.0~21,30~.0~24,29~.0~28,33~]pentatriaconta-1(35),2,4,6,15,17,19,21,23,27,29,33-dodecaen-10-yl]-5,7,8,10-tetrahydrodibenzo[f,h][1,4]dioxecine-7-carbaldehyde
    • D-Glucose, cyclic 4,6-(2,2'-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo(1)benzopyrano(5,4,3-cde)(1)benzopyran-1,6-diyl)bis(3,4,5-trihydroxybenzoate)) cyclic 2,3-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate)-, (2(S),4(S,S))-
    • 65995-63-3

  • Applications

    Punicalagin (CAS 65995-63-3) is a natural ellagitannin with strong antioxidant activity, commonly explored as an antioxidant additive in cosmetics and personal care formulations to improve stability of sensitive ingredients; it is also evaluated for food processing and beverage applications as a natural antioxidant and functional ingredient to help extend shelf life; in nutraceuticals and dietary supplements, punicalagin-rich extracts are often considered as polyphenol-rich components; in coatings and polymer systems, it can serve as a natural stabilizer against oxidation for polymers and protective coatings; and in agriculture, punicalagin-containing formulations are studied for natural antimicrobial activity to support crop protection products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.44
    methanol 2.89
    isopropanol 1.87
    water 0.26
    ethyl acetate 1.22
    n-propanol 2.02
    acetone 1.76
    n-butanol 0.88
    acetonitrile 0.65
    DMF 43.3
    toluene 0.29
    isobutanol 0.77
    1,4-dioxane 6.72
    methyl acetate 2.76
    THF 13.68
    2-butanone 2.18
    n-pentanol 0.5
    sec-butanol 1.36
    n-hexane 0.02
    ethylene glycol 9.83
    NMP 44.63
    cyclohexane 0.04
    DMSO 26.08
    n-butyl acetate 0.75
    n-octanol 0.75
    chloroform 0.4
    n-propyl acetate 0.73
    acetic acid 9.07
    dichloromethane 0.47
    cyclohexanone 1.9
    propylene glycol 9.3
    isopropyl acetate 0.73
    DMAc 38.9
    2-ethoxyethanol 8.87
    isopentanol 0.41
    n-heptane 0.05
    ethyl formate 1.31
    1,2-dichloroethane 0.42
    n-hexanol 0.38
    2-methoxyethanol 23.31
    isobutyl acetate 0.22
    tetrachloromethane 0.07
    n-pentyl acetate 1.09
    transcutol 10.63
    n-heptanol 0.74
    ethylbenzene 0.09
    MIBK 0.34
    2-propoxyethanol 7.5
    tert-butanol 1.21
    MTBE 0.73
    2-butoxyethanol 5.23
    propionic acid 4.88
    o-xylene 0.21
    formic acid 16.33
    diethyl ether 0.96
    m-xylene 0.14
    p-xylene 0.1
    chlorobenzene 0.08
    dimethyl carbonate 5.37
    n-octane 0.04
    formamide 19.23
    cyclopentanone 6.29
    2-pentanone 0.97
    anisole 0.5
    cyclopentyl methyl ether 2.33
    gamma-butyrolactone 12.95
    1-methoxy-2-propanol 15.9
    pyridine 3.54
    3-pentanone 0.93
    furfural 7.46
    n-dodecane 0.03
    diethylene glycol 10.83
    diisopropyl ether 0.16
    tert-amyl alcohol 1.09
    acetylacetone 1.86
    n-hexadecane 0.03
    acetophenone 0.71
    methyl propionate 3.16
    isopentyl acetate 0.4
    trichloroethylene 0.86
    n-nonanol 0.77
    cyclohexanol 0.89
    benzyl alcohol 0.88
    2-ethylhexanol 0.2
    isooctanol 0.43
    dipropyl ether 0.87
    1,2-dichlorobenzene 0.08
    ethyl lactate 2.22
    propylene carbonate 2.73
    n-methylformamide 13.57
    2-pentanol 0.58
    n-pentane 0.04
    1-propoxy-2-propanol 5.9
    1-methoxy-2-propyl acetate 2.95
    2-(2-methoxypropoxy) propanol 3.7
    mesitylene 0.07
    ε-caprolactone 3.31
    p-cymene 0.09
    epichlorohydrin 5.61
    1,1,1-trichloroethane 0.13
    2-aminoethanol 8.84
    morpholine-4-carbaldehyde 38.13
    sulfolane 21.77
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 3.38
    n-hexyl acetate 1.02
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 5.58
    sec-butyl acetate 0.36
    tert-butyl acetate 0.68
    decalin 0.01
    glycerin 29.13
    diglyme 10.02
    acrylic acid 8.75
    isopropyl myristate 0.35
    n-butyric acid 2.13
    acetyl acetate 0.71
    di(2-ethylhexyl) phthalate 0.45
    ethyl propionate 0.84
    nitromethane 11.83
    1,2-diethoxyethane 2.0
    benzonitrile 0.35
    trioctyl phosphate 0.42
    1-bromopropane 0.19
    gamma-valerolactone 18.37
    n-decanol 0.5
    triethyl phosphate 0.57
    4-methyl-2-pentanol 0.2
    propionitrile 0.69
    vinylene carbonate 2.66
    1,1,2-trichlorotrifluoroethane 12.43
    DMS 1.92
    cumene 0.05
    2-octanol 0.53
    2-hexanone 0.49
    octyl acetate 0.69
    limonene 0.14
    1,2-dimethoxyethane 7.65
    ethyl orthosilicate 0.51
    tributyl phosphate 0.34
    diacetone alcohol 2.5
    N,N-dimethylaniline 0.57
    acrylonitrile 1.59
    aniline 1.04
    1,3-propanediol 7.57
    bromobenzene 0.05
    dibromomethane 0.19
    1,1,2,2-tetrachloroethane 0.89
    2-methyl-cyclohexyl acetate 0.4
    tetrabutyl urea 0.94
    diisobutyl methanol 0.14
    2-phenylethanol 0.63
    styrene 0.1
    dioctyl adipate 0.71
    dimethyl sulfate 12.18
    ethyl butyrate 0.67
    methyl lactate 9.62
    butyl lactate 2.19
    diethyl carbonate 0.54
    propanediol butyl ether 6.46
    triethyl orthoformate 1.1
    p-tert-butyltoluene 0.11
    methyl 4-tert-butylbenzoate 1.64
    morpholine 12.34
    tert-butylamine 0.39
    n-dodecanol 0.33
    dimethoxymethane 14.01
    ethylene carbonate 1.79
    cyrene 4.84
    2-ethoxyethyl acetate 2.68
    2-ethylhexyl acetate 0.34
    1,2,4-trichlorobenzene 0.21
    4-methylpyridine 1.66
    dibutyl ether 0.52
    2,6-dimethyl-4-heptanol 0.14
    DEF 4.13
    dimethyl isosorbide 4.72
    tetrachloroethylene 0.59
    eugenol 1.76
    triacetin 2.31
    span 80 3.63
    1,4-butanediol 2.39
    1,1-dichloroethane 0.22
    2-methyl-1-pentanol 0.25
    methyl formate 8.37
    2-methyl-1-butanol 0.55
    n-decane 0.06
    butyronitrile 0.37
    3,7-dimethyl-1-octanol 0.27
    1-chlorooctane 0.16
    1-chlorotetradecane 0.06
    n-nonane 0.05
    undecane 0.04
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 2.39
    tetrahydropyran 2.17
    tert-amyl methyl ether 0.77
    2,5,8-trioxanonane 6.53
    1-hexene 0.07
    2-isopropoxyethanol 3.64
    2,2,2-trifluoroethanol 6.11
    methyl butyrate 1.01

    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