Cynaropicrin

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  • Identifiers

    CAS number
    35730-78-0

    Molecular formula
    C19H22O6

    SMILES
    C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 53.75%
    Sweet 27.87%
    Burnt 24.3%
    Nutty 23.78%
    Caramellic 22.74%
    Mint 22.72%
    Spicy 19.04%
    Ethereal 17.9%
    Roasted 17.45%
    Woody 16.92%

     

    Flavor
    Bitter 93.44%
    Odorless 25.58%
    Bland 20.85%
    Sweet-like 19.9%
    Cedarleaf 19.28%
    Nitrile 18.79%
    Lovage 18.51%
    Very mild 18.37%
    Basil 17.86%
    Parsley 17.74%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    5.31 (weak acid)

    Molecular weight
    346.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    555°C

    Flash point

    • 206.36 ˚C est.

  • Synonyms

    • Cynaropicrin
    • 35730-78-0
    • 2-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester
    • M9233789I9
    • [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
    • 2-Propenoic acid, 2-(hydroxymethyl)-, dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-
    • ((3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno(4,5-b)furan-4-yl) 2-(hydroxymethyl)prop-2-enoate
    • ((3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno(4,5-b)furan-4-yl) 2-(hydroxymethyl)prop-2-enoate
    • [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
    • RefChem:34088
    • 689-765-5
    • Cynaropikrin
    • CHEMBL374146
    • Cynaropicrin (Standard)
    • CHEBI:4038
    • MEGxp0_001095
    • orb1684669
    • SCHEMBL1711811
    • ACon1_000045
    • HY-N2350R
    • DTXSID20957143
    • UNII-M9233789I9
    • HY-N2350
    • BDBM50194430
    • AKOS032971358
    • CS-8041
    • EBC-513120
    • FS-8077
    • NCGC00168845-01
    • NCGC00168845-02
    • (3AR,4S,6AR,8S,9AR,9BR)-8-HYDROXY-3,6,9-TRIMETHYLIDENE-2-OXO-DODECAHYDROAZULENO[4,5-B]FURAN-4-YL 2-(HYDROXYMETHYL)PROP-2-ENOATE
    • DA-52252
    • XC160151
    • NS00094008
    • Cynaropicrin - Cynara cardunculus (artichoke)
    • C09385
    • G16186
    • BRD-K51428447-001-01-5
    • Q15410905
    • (3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate
    • 2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-
    • 8-Hydroxy-3,6,9-trimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate
    • 35730-78-0

  • Applications

    Cynaropicrin (CAS 35730-78-0) is a bitter sesquiterpene lactone primarily found in artichoke leaf extracts. In industrial practice, it is used as a natural bittering component in flavor systems, encountered in dietary supplements and nutraceutical raw materials derived from artichoke extracts for quality and authenticity control, researched as a potential lead structure in pharmaceutical development due to its reactive lactone moiety, and employed as a chemical marker to standardize Cynara-derived ingredients across food, nutraceutical, and cosmetic supply chains.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 85.82
    methanol 178.87
    isopropanol 67.49
    water 0.59
    ethyl acetate 46.16
    n-propanol 67.25
    acetone 160.7
    n-butanol 57.46
    acetonitrile 31.04
    DMF 232.58
    toluene 6.29
    isobutanol 35.45
    1,4-dioxane 118.13
    methyl acetate 46.74
    THF 347.94
    2-butanone 80.29
    n-pentanol 35.17
    sec-butanol 32.9
    n-hexane 0.25
    ethylene glycol 24.55
    NMP 124.61
    cyclohexane 0.55
    DMSO 381.95
    n-butyl acetate 28.27
    n-octanol 11.67
    chloroform 54.76
    n-propyl acetate 29.48
    acetic acid 232.89
    dichloromethane 43.22
    cyclohexanone 96.99
    propylene glycol 26.28
    isopropyl acetate 33.34
    DMAc 264.55
    2-ethoxyethanol 141.63
    isopentanol 45.16
    n-heptane 0.24
    ethyl formate 41.47
    1,2-dichloroethane 29.4
    n-hexanol 25.49
    2-methoxyethanol 245.15
    isobutyl acetate 18.19
    tetrachloromethane 4.82
    n-pentyl acetate 23.47
    transcutol 163.38
    n-heptanol 17.92
    ethylbenzene 4.03
    MIBK 40.33
    2-propoxyethanol 119.38
    tert-butanol 50.66
    MTBE 13.64
    2-butoxyethanol 65.69
    propionic acid 53.97
    o-xylene 4.9
    formic acid 142.18
    diethyl ether 20.86
    m-xylene 5.26
    p-xylene 6.27
    chlorobenzene 10.1
    dimethyl carbonate 43.74
    n-octane 0.24
    formamide 197.59
    cyclopentanone 156.49
    2-pentanone 66.7
    anisole 17.14
    cyclopentyl methyl ether 35.83
    gamma-butyrolactone 152.66
    1-methoxy-2-propanol 165.7
    pyridine 58.21
    3-pentanone 32.7
    furfural 101.2
    n-dodecane 0.28
    diethylene glycol 121.85
    diisopropyl ether 4.37
    tert-amyl alcohol 31.86
    acetylacetone 90.94
    n-hexadecane 0.32
    acetophenone 31.95
    methyl propionate 47.02
    isopentyl acetate 29.26
    trichloroethylene 75.68
    n-nonanol 12.55
    cyclohexanol 28.3
    benzyl alcohol 35.98
    2-ethylhexanol 10.46
    isooctanol 14.49
    dipropyl ether 8.18
    1,2-dichlorobenzene 11.02
    ethyl lactate 32.71
    propylene carbonate 63.58
    n-methylformamide 125.01
    2-pentanol 23.37
    n-pentane 0.24
    1-propoxy-2-propanol 59.33
    1-methoxy-2-propyl acetate 54.24
    2-(2-methoxypropoxy) propanol 52.06
    mesitylene 3.4
    ε-caprolactone 82.44
    p-cymene 3.56
    epichlorohydrin 159.31
    1,1,1-trichloroethane 18.62
    2-aminoethanol 49.54
    morpholine-4-carbaldehyde 171.16
    sulfolane 168.92
    2,2,4-trimethylpentane 0.29
    2-methyltetrahydrofuran 71.51
    n-hexyl acetate 26.0
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 76.33
    sec-butyl acetate 18.49
    tert-butyl acetate 33.78
    decalin 0.5
    glycerin 69.27
    diglyme 122.78
    acrylic acid 57.75
    isopropyl myristate 10.22
    n-butyric acid 88.88
    acetyl acetate 34.07
    di(2-ethylhexyl) phthalate 18.26
    ethyl propionate 23.41
    nitromethane 213.49
    1,2-diethoxyethane 31.32
    benzonitrile 24.27
    trioctyl phosphate 13.76
    1-bromopropane 8.59
    gamma-valerolactone 229.5
    n-decanol 8.41
    triethyl phosphate 14.88
    4-methyl-2-pentanol 15.82
    propionitrile 25.86
    vinylene carbonate 59.1
    1,1,2-trichlorotrifluoroethane 126.56
    DMS 29.42
    cumene 3.28
    2-octanol 9.3
    2-hexanone 34.02
    octyl acetate 14.7
    limonene 4.44
    1,2-dimethoxyethane 143.14
    ethyl orthosilicate 13.19
    tributyl phosphate 14.64
    diacetone alcohol 76.57
    N,N-dimethylaniline 13.05
    acrylonitrile 41.05
    aniline 20.16
    1,3-propanediol 114.79
    bromobenzene 7.49
    dibromomethane 20.85
    1,1,2,2-tetrachloroethane 53.42
    2-methyl-cyclohexyl acetate 21.06
    tetrabutyl urea 22.65
    diisobutyl methanol 6.5
    2-phenylethanol 33.48
    styrene 4.35
    dioctyl adipate 19.62
    dimethyl sulfate 78.12
    ethyl butyrate 18.84
    methyl lactate 56.26
    butyl lactate 31.53
    diethyl carbonate 14.35
    propanediol butyl ether 51.91
    triethyl orthoformate 16.23
    p-tert-butyltoluene 3.19
    methyl 4-tert-butylbenzoate 35.02
    morpholine 155.23
    tert-butylamine 9.91
    n-dodecanol 5.57
    dimethoxymethane 174.89
    ethylene carbonate 53.74
    cyrene 70.41
    2-ethoxyethyl acetate 43.8
    2-ethylhexyl acetate 18.41
    1,2,4-trichlorobenzene 16.9
    4-methylpyridine 42.84
    dibutyl ether 7.0
    2,6-dimethyl-4-heptanol 6.5
    DEF 62.53
    dimethyl isosorbide 77.98
    tetrachloroethylene 34.85
    eugenol 42.73
    triacetin 34.04
    span 80 40.37
    1,4-butanediol 43.23
    1,1-dichloroethane 20.63
    2-methyl-1-pentanol 28.47
    methyl formate 100.59
    2-methyl-1-butanol 34.35
    n-decane 0.49
    butyronitrile 26.91
    3,7-dimethyl-1-octanol 11.11
    1-chlorooctane 2.93
    1-chlorotetradecane 1.19
    n-nonane 0.37
    undecane 0.35
    tert-butylcyclohexane 0.37
    cyclooctane 0.24
    cyclopentanol 44.0
    tetrahydropyran 56.76
    tert-amyl methyl ether 12.15
    2,5,8-trioxanonane 83.69
    1-hexene 1.9
    2-isopropoxyethanol 72.59
    2,2,2-trifluoroethanol 75.34
    methyl butyrate 37.75

    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