Helenalin

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  • Identifiers

    CAS number
    6754-13-8

    Molecular formula
    C15H18O4

    SMILES
    C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)O)C(=C)C(=O)O2

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 42.41%
    Spicy 34.28%
    Burnt 33.58%
    Caramellic 30.39%
    Sweet 30.15%
    Nutty 27.63%
    Woody 25.68%
    Roasted 22.74%
    Mint 20.77%
    Phenolic 20.35%

     

    Flavor
    Bitter 92.47%
    Cedarleaf 20.65%
    Lovage 19.7%
    Sweet-like 19.32%
    Fenugreek 19.06%
    Basil 18.93%
    Nitrile 18.75%
    Leaves 18.56%
    Ripe apricot 18.46%
    Red fruit 18.32%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    5.91 (weak acid)

    Molecular weight
    262.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    693°C

    Melting point expt.

    • 167-168 °C

    Flash point

    • 170.29 ˚C est.

    Solubility expt.

    • SLIGHTLY SOL IN WATER; SOL IN ALCOHOL, CHLOROFORM, HOT BENZENE

  • Synonyms

    • HELENALIN
    • 6754-13-8
    • Helenalin A
    • PF 56
    • 4GUY9L896T
    • NSC-85236
    • 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone
    • CHEBI:5635
    • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
    • DTXSID50217868
    • Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone
    • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
    • Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-
    • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione
    • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione
    • RefChem:145455
    • DTXCID00140359
    • HSDB 3490
    • NSC85236
    • NSC 85236
    • MLS000728512
    • Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
    • SMR000445626
    • (3aR,5R,5aR,8aR,9S,9aS)-9-Hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-dione
    • (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
    • MLS002701927
    • BRN 0028081
    • UNII-4GUY9L896T
    • NF-kappaB inhibitor
    • HELENALIN [MI]
    • HELENALIN [HSDB]
    • (-)-HELENALIN
    • BSPBio_001312
    • (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
    • 4-18-00-01434 (Beilstein Handbook Reference)
    • cid_23205
    • SCHEMBL161593
    • CHEMBL338474
    • orb1707223
    • BDBM43484
    • HMS1791B14
    • HMS1989B14
    • HMS2236C04
    • EX-A10269
    • HB3927
    • MFCD01674580
    • AKOS040741831
    • Ambrosa-2,11(13)-dien-12-oic acid, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone
    • NCGC00163416-01
    • NCGC00163416-02
    • Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-
    • FH177939
    • MS-23694
    • NCI60_041870
    • HY-119970
    • CS-0078850
    • NS00094722
    • C09473
    • G13013
    • Q387505
    • WLN: T C575 DYVO MV KUTJ A1 BQ DU1 I1
    • BRD-K26302255-001-02-3
    • Ambrosa-2, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone
    • 6.ALPHA.,8.BETA.-DIHYDROXY-4-OXOAMBROSA-2,11(13)-DIEN-12-OIC ACID 12,8-LACTONE
    • (3aR,5R,5aR,8aR,9S,9aS)-5,8a-dimethyl-1-methylidene-9-oxidanyl-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
    • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-quinone
    • (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
    • (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
    • (3AS-(3A.ALPHA.,4.ALPHA.,4A.BETA.,7A.ALPHA.,8.ALPHA.,9A.ALPHA.))-3,3A,4,4A,7A,8,9,9A-OCTAHYDRO-4-HYDROXY-4A,8-DIMETHYL-3-METHYLENEAZULENO(6,5-B)FURAN-2,5-DIONE
    • 4-Hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
    • Azuleno[6,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-
    • 6754-13-8

  • Applications

    Helenalin (CAS 6754-13-8) is a natural sesquiterpene lactone primarily studied in pharmacology and natural product chemistry; real-world applications focus on (i) pharmaceutical research for anti-inflammatory activity and related mechanisms, (ii) medicinal chemistry as a lead compound or pharmacophore for structure-activity optimization, (iii) analytical/natural product reference standard for Arnica-derived materials, (iv) synthetic chemistry as an intermediate or precursor for other sesquiterpene lactones, and (v) safety assessment and regulatory research in the context of evaluating extracts and bioactivity; due to its toxicity and safety considerations, consumer uses are limited and any application in products is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 23.54
    methanol 80.63
    isopropanol 36.59
    water 0.95
    ethyl acetate 52.34
    n-propanol 30.55
    acetone 93.77
    n-butanol 34.7
    acetonitrile 39.13
    DMF 284.98
    toluene 60.3
    isobutanol 24.86
    1,4-dioxane 150.37
    methyl acetate 64.66
    THF 288.37
    2-butanone 83.47
    n-pentanol 22.68
    sec-butanol 20.06
    n-hexane 0.61
    ethylene glycol 19.96
    NMP 197.7
    cyclohexane 2.2
    DMSO 248.15
    n-butyl acetate 41.29
    n-octanol 15.33
    chloroform 171.5
    n-propyl acetate 37.13
    acetic acid 58.96
    dichloromethane 154.14
    cyclohexanone 150.85
    propylene glycol 14.6
    isopropyl acetate 45.01
    DMAc 163.08
    2-ethoxyethanol 60.72
    isopentanol 35.02
    n-heptane 0.85
    ethyl formate 46.72
    1,2-dichloroethane 83.8
    n-hexanol 33.97
    2-methoxyethanol 127.41
    isobutyl acetate 29.19
    tetrachloromethane 19.2
    n-pentyl acetate 35.37
    transcutol 94.59
    n-heptanol 21.16
    ethylbenzene 20.08
    MIBK 51.2
    2-propoxyethanol 94.09
    tert-butanol 41.45
    MTBE 16.68
    2-butoxyethanol 50.97
    propionic acid 42.1
    o-xylene 32.0
    formic acid 48.82
    diethyl ether 20.76
    m-xylene 41.62
    p-xylene 29.53
    chlorobenzene 67.67
    dimethyl carbonate 63.92
    n-octane 0.7
    formamide 80.29
    cyclopentanone 224.43
    2-pentanone 67.62
    anisole 46.71
    cyclopentyl methyl ether 62.94
    gamma-butyrolactone 225.74
    1-methoxy-2-propanol 99.99
    pyridine 126.35
    3-pentanone 51.17
    furfural 169.43
    n-dodecane 0.96
    diethylene glycol 104.04
    diisopropyl ether 9.71
    tert-amyl alcohol 20.94
    acetylacetone 106.17
    n-hexadecane 1.16
    acetophenone 59.93
    methyl propionate 59.89
    isopentyl acetate 41.35
    trichloroethylene 178.49
    n-nonanol 17.0
    cyclohexanol 38.03
    benzyl alcohol 55.27
    2-ethylhexanol 19.84
    isooctanol 18.63
    dipropyl ether 13.63
    1,2-dichlorobenzene 59.82
    ethyl lactate 34.12
    propylene carbonate 97.39
    n-methylformamide 114.54
    2-pentanol 19.94
    n-pentane 0.76
    1-propoxy-2-propanol 52.45
    1-methoxy-2-propyl acetate 63.82
    2-(2-methoxypropoxy) propanol 50.75
    mesitylene 22.6
    ε-caprolactone 100.6
    p-cymene 16.0
    epichlorohydrin 206.39
    1,1,1-trichloroethane 62.72
    2-aminoethanol 27.22
    morpholine-4-carbaldehyde 196.29
    sulfolane 231.92
    2,2,4-trimethylpentane 0.94
    2-methyltetrahydrofuran 87.15
    n-hexyl acetate 39.78
    isooctane 1.1
    2-(2-butoxyethoxy)ethanol 55.33
    sec-butyl acetate 28.36
    tert-butyl acetate 45.48
    decalin 2.25
    glycerin 44.62
    diglyme 107.48
    acrylic acid 49.32
    isopropyl myristate 19.23
    n-butyric acid 59.81
    acetyl acetate 54.9
    di(2-ethylhexyl) phthalate 29.27
    ethyl propionate 36.36
    nitromethane 130.89
    1,2-diethoxyethane 32.44
    benzonitrile 72.59
    trioctyl phosphate 22.2
    1-bromopropane 27.09
    gamma-valerolactone 232.19
    n-decanol 13.15
    triethyl phosphate 24.21
    4-methyl-2-pentanol 18.6
    propionitrile 40.47
    vinylene carbonate 105.51
    1,1,2-trichlorotrifluoroethane 110.82
    DMS 53.78
    cumene 14.93
    2-octanol 13.44
    2-hexanone 41.04
    octyl acetate 24.42
    limonene 17.78
    1,2-dimethoxyethane 102.68
    ethyl orthosilicate 21.62
    tributyl phosphate 22.63
    diacetone alcohol 66.91
    N,N-dimethylaniline 34.39
    acrylonitrile 72.53
    aniline 64.47
    1,3-propanediol 53.01
    bromobenzene 65.59
    dibromomethane 77.42
    1,1,2,2-tetrachloroethane 120.97
    2-methyl-cyclohexyl acetate 36.44
    tetrabutyl urea 34.05
    diisobutyl methanol 14.31
    2-phenylethanol 59.85
    styrene 23.25
    dioctyl adipate 30.56
    dimethyl sulfate 110.94
    ethyl butyrate 32.31
    methyl lactate 53.84
    butyl lactate 33.86
    diethyl carbonate 26.65
    propanediol butyl ether 36.09
    triethyl orthoformate 26.18
    p-tert-butyltoluene 14.82
    methyl 4-tert-butylbenzoate 54.54
    morpholine 126.77
    tert-butylamine 15.15
    n-dodecanol 10.03
    dimethoxymethane 164.05
    ethylene carbonate 89.19
    cyrene 77.02
    2-ethoxyethyl acetate 51.42
    2-ethylhexyl acetate 32.56
    1,2,4-trichlorobenzene 70.56
    4-methylpyridine 113.31
    dibutyl ether 12.06
    2,6-dimethyl-4-heptanol 14.31
    DEF 67.12
    dimethyl isosorbide 94.32
    tetrachloroethylene 78.86
    eugenol 56.42
    triacetin 49.64
    span 80 39.52
    1,4-butanediol 22.77
    1,1-dichloroethane 68.22
    2-methyl-1-pentanol 24.32
    methyl formate 109.48
    2-methyl-1-butanol 24.58
    n-decane 1.43
    butyronitrile 39.49
    3,7-dimethyl-1-octanol 17.56
    1-chlorooctane 8.43
    1-chlorotetradecane 4.19
    n-nonane 1.04
    undecane 1.15
    tert-butylcyclohexane 1.72
    cyclooctane 1.02
    cyclopentanol 50.52
    tetrahydropyran 73.02
    tert-amyl methyl ether 15.07
    2,5,8-trioxanonane 79.96
    1-hexene 3.46
    2-isopropoxyethanol 45.15
    2,2,2-trifluoroethanol 44.3
    methyl butyrate 46.63

    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