Heliotrine, N-oxide

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  • Identifiers

    CAS number
    6209-65-0

    Molecular formula
    C16H27NO6

    SMILES
    C[C@H]([C@@](C(C)C)(C(=O)OCC1=CC[N+]2([C@H]1[C@H](CC2)O)[O-])O)OC

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 61.81%
    Cooling 32.18%
    Mint 27.32%
    Milky 23.4%
    Sweet 23.16%
    Buttery 18.88%
    Savory 17.59%
    Woody 17.38%
    Creamy 16.09%
    Alcoholic 15.92%

     

    Flavor
    Bitter 73.96%
    Odorless 31.24%
    Bland 25.92%
    Fruity 25.03%
    Sweet-like 23.6%
    Mild 20.02%
    Cedarleaf 19.86%
    Heather 18.58%
    Broom 18.43%
    Parsley 18.41%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    5.29 (weak acid)

    Molecular weight
    329.39 g/mol

    Flash point

    • -342.04 ˚C est.

  • Synonyms

    • Heliotrine N-oxide
    • 6209-65-0
    • Heliotrine, N-oxide
    • DTXSID50977677
    • RefChem:922781
    • DTXCID501776150
    • (1S-(1 alpha,7(2R*,3S*),7a alpha))-2-hydroxy-2-(1-methoxyethyl)-3-methylbutanoic acid, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester
    • ((7S,8S)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl)methyl 2-hydroxy-2-(1-methoxyethyl)-3-methylbutanoate
    • Heliotrine, 4-oxide
    • NSC30621
    • [(7S,8R)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
    • Heliotrine Impurity 2
    • Seneciphylline Impurity 2
    • orb1690409
    • CHEMBL2289736
    • CHEBI:184053
    • NSC-30621
    • AKOS040758239
    • DA-53927
    • Heliotrine-N-oxide 100 microg/mL in Water
    • HY-133590
    • CS-0128290
    • NS00066994
    • (1S,7aR)-1-hydroxy-7-((((2S,3R)-2-hydroxy-2-isopropyl-3-methoxybutanoyl)oxy)methyl)-2,3,5,7a-tetrahydropyrrolizine 4(1H)-oxide
    • 6209-65-0

  • Applications

    Heliotrine, N-oxide (CAS 6209-65-0) is a pyrrolizidine alkaloid derivative whose use is typically restricted to research and synthetic applications due to notable toxicity and is not a consumer-grade additive. Real-world applications include serving as an intermediate in the synthesis of more complex pyrrolizidine derivatives, and as an analytical reference material for chromatographic and toxicological studies. It may also be used as a synthetic precursor in medicinal chemistry research under strict regulatory oversight, and is considered within appropriate safety and handling frameworks. Application scope depends on local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 158.47
    methanol 348.08
    isopropanol 78.36
    water 13.37
    ethyl acetate 66.49
    n-propanol 96.06
    acetone 147.3
    n-butanol 70.27
    acetonitrile 79.58
    DMF 288.29
    toluene 12.13
    isobutanol 52.25
    1,4-dioxane 130.37
    methyl acetate 60.62
    THF 218.27
    2-butanone 65.4
    n-pentanol 38.58
    sec-butanol 50.77
    n-hexane 0.78
    ethylene glycol 97.68
    NMP 155.3
    cyclohexane 1.92
    DMSO 441.02
    n-butyl acetate 24.76
    n-octanol 19.83
    chloroform 208.31
    n-propyl acetate 28.56
    acetic acid 459.9
    dichloromethane 190.08
    cyclohexanone 106.51
    propylene glycol 65.22
    isopropyl acetate 39.67
    DMAc 207.73
    2-ethoxyethanol 175.95
    isopentanol 47.32
    n-heptane 0.78
    ethyl formate 75.59
    1,2-dichloroethane 99.41
    n-hexanol 31.59
    2-methoxyethanol 339.5
    isobutyl acetate 18.53
    tetrachloromethane 22.79
    n-pentyl acetate 27.24
    transcutol 229.67
    n-heptanol 22.65
    ethylbenzene 6.77
    MIBK 42.17
    2-propoxyethanol 134.67
    tert-butanol 64.26
    MTBE 19.67
    2-butoxyethanol 82.84
    propionic acid 92.77
    o-xylene 9.76
    formic acid 547.49
    diethyl ether 36.21
    m-xylene 10.44
    p-xylene 8.74
    chlorobenzene 26.8
    dimethyl carbonate 51.55
    n-octane 0.67
    formamide 507.59
    cyclopentanone 142.57
    2-pentanone 64.66
    anisole 22.32
    cyclopentyl methyl ether 43.1
    gamma-butyrolactone 189.47
    1-methoxy-2-propanol 191.77
    pyridine 71.65
    3-pentanone 39.05
    furfural 178.36
    n-dodecane 0.7
    diethylene glycol 173.67
    diisopropyl ether 7.5
    tert-amyl alcohol 44.2
    acetylacetone 106.18
    n-hexadecane 0.8
    acetophenone 38.14
    methyl propionate 61.67
    isopentyl acetate 24.95
    trichloroethylene 214.66
    n-nonanol 19.85
    cyclohexanol 43.2
    benzyl alcohol 43.83
    2-ethylhexanol 13.77
    isooctanol 18.16
    dipropyl ether 12.26
    1,2-dichlorobenzene 31.97
    ethyl lactate 39.54
    propylene carbonate 83.4
    n-methylformamide 222.25
    2-pentanol 32.02
    n-pentane 1.16
    1-propoxy-2-propanol 65.52
    1-methoxy-2-propyl acetate 56.29
    2-(2-methoxypropoxy) propanol 63.5
    mesitylene 5.83
    ε-caprolactone 102.7
    p-cymene 6.14
    epichlorohydrin 225.31
    1,1,1-trichloroethane 59.06
    2-aminoethanol 142.79
    morpholine-4-carbaldehyde 208.46
    sulfolane 219.02
    2,2,4-trimethylpentane 0.99
    2-methyltetrahydrofuran 69.78
    n-hexyl acetate 35.23
    isooctane 0.69
    2-(2-butoxyethoxy)ethanol 92.08
    sec-butyl acetate 18.09
    tert-butyl acetate 38.44
    decalin 1.13
    glycerin 164.37
    diglyme 164.74
    acrylic acid 120.31
    isopropyl myristate 11.5
    n-butyric acid 122.61
    acetyl acetate 59.88
    di(2-ethylhexyl) phthalate 21.74
    ethyl propionate 29.51
    nitromethane 441.23
    1,2-diethoxyethane 37.32
    benzonitrile 42.31
    trioctyl phosphate 14.94
    1-bromopropane 30.45
    gamma-valerolactone 245.61
    n-decanol 12.68
    triethyl phosphate 16.11
    4-methyl-2-pentanol 20.05
    propionitrile 46.54
    vinylene carbonate 90.31
    1,1,2-trichlorotrifluoroethane 244.84
    DMS 38.44
    cumene 5.48
    2-octanol 13.87
    2-hexanone 29.28
    octyl acetate 16.95
    limonene 8.35
    1,2-dimethoxyethane 144.55
    ethyl orthosilicate 14.43
    tributyl phosphate 16.62
    diacetone alcohol 80.26
    N,N-dimethylaniline 16.76
    acrylonitrile 75.64
    aniline 31.38
    1,3-propanediol 178.59
    bromobenzene 23.06
    dibromomethane 97.72
    1,1,2,2-tetrachloroethane 151.14
    2-methyl-cyclohexyl acetate 21.46
    tetrabutyl urea 24.5
    diisobutyl methanol 9.25
    2-phenylethanol 41.55
    styrene 7.23
    dioctyl adipate 22.58
    dimethyl sulfate 99.64
    ethyl butyrate 21.26
    methyl lactate 74.32
    butyl lactate 35.99
    diethyl carbonate 15.76
    propanediol butyl ether 75.28
    triethyl orthoformate 17.88
    p-tert-butyltoluene 5.7
    methyl 4-tert-butylbenzoate 45.01
    morpholine 159.98
    tert-butylamine 20.58
    n-dodecanol 8.53
    dimethoxymethane 189.26
    ethylene carbonate 74.67
    cyrene 83.61
    2-ethoxyethyl acetate 52.8
    2-ethylhexyl acetate 17.45
    1,2,4-trichlorobenzene 40.06
    4-methylpyridine 53.68
    dibutyl ether 10.61
    2,6-dimethyl-4-heptanol 9.25
    DEF 79.67
    dimethyl isosorbide 95.78
    tetrachloroethylene 109.83
    eugenol 55.2
    triacetin 53.55
    span 80 50.8
    1,4-butanediol 73.78
    1,1-dichloroethane 71.34
    2-methyl-1-pentanol 29.93
    methyl formate 169.29
    2-methyl-1-butanol 43.06
    n-decane 1.25
    butyronitrile 43.6
    3,7-dimethyl-1-octanol 17.54
    1-chlorooctane 7.18
    1-chlorotetradecane 2.67
    n-nonane 1.03
    undecane 0.9
    tert-butylcyclohexane 0.85
    cyclooctane 0.8
    cyclopentanol 58.1
    tetrahydropyran 61.69
    tert-amyl methyl ether 18.33
    2,5,8-trioxanonane 111.69
    1-hexene 3.71
    2-isopropoxyethanol 83.03
    2,2,2-trifluoroethanol 242.91
    methyl butyrate 38.99

    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