(+)-Heliotrine

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  • Identifiers

    CAS number
    303-33-3

    Molecular formula
    C16H27NO5

    SMILES
    C[C@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)O)O)OC

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 61.14%
    Cooling 32.5%
    Mint 26.17%
    Milky 23.26%
    Buttery 19.54%
    Savory 19.43%
    Sweet 18.75%
    Nutty 17.82%
    Roasted 16.1%
    Alcoholic 16.06%

     

    Flavor
    Bitter 78.1%
    Odorless 30.23%
    Bland 27.14%
    Sweet-like 23.66%
    Fruity 20.88%
    Cedarleaf 19.87%
    Mild 18.75%
    Parsley 18.67%
    Heather 18.67%
    Broom 18.61%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.1

    pKa est.
    7.7 (neutral)

    Molecular weight
    313.39 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    458°C

    Flash point

    • 204.88 ˚C est.

  • Synonyms

    • HELIOTRINE
    • 303-33-3
    • 7S-Heliotrine
    • (+)-Heliotrine
    • ZYB88Y4FUZ
    • Butanoic acid, 2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methyl-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S)-
    • DTXSID3075381
    • [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
    • Butanoic acid, 2-hydroxy-2-((1R)-1-methoxyethyl)-3-methyl-, ((1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (2S)-
    • ((7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2S)-2-hydroxy-2-((1R)-1-methoxyethyl)-3-methylbutanoate
    • ((7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxy-butanoate
    • [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxy-butanoate
    • RefChem:783494
    • DTXCID6038166
    • Heliotron
    • CCRIS 9196
    • AI3-51769
    • ((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxybutanoate
    • UNII-ZYB88Y4FUZ
    • BRN 0292841
    • 9-Heliotrylheliotridine
    • HELIOTRINE, (+)-
    • CHEBI:5643
    • orb1705587
    • CHEMBL2165593
    • SCHEMBL30580759
    • LMFKRLGHEKVMNT-UJDVCPFMSA-N
    • MSK14163
    • Heliotrine 100 microg/mL in Water
    • MFCD00213991
    • AKOS030495261
    • FH161602
    • HY-126128
    • CS-0090611
    • NS00098506
    • Q27106845
    • (2S)-2-Hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoic Acid [(1S,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl Ester
    • (2S,3R)-((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl 2-hydroxy-2-isopropyl-3-methoxybutanoate
    • [(1S,7aR)-1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3R)-2-hydroxy-3-methoxy-2-(propan-2-yl)butanoate
    • [1S-[1alpha,7[R*(S*)],7aalpha]]-2-Hydroxy-2-(1-methoxyethyl)-3-methylbutanoic Acid (2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl Ester
    • Butanoic acid, 2-hydroxy-2-(1-methoxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1S-(1 alpha,7(2R*,3S*),7a alpha))-
    • BUTANOIC ACID, 2-HYDROXY-2-(1-METHOXYETHYL)-3-METHYL-, (2,3,5,7A-TETRAHYDRO-1-HYDROXY-1H-PYRROLIZIN-7-YL)METHYL ESTER, (1S-(1.ALPHA.,7(R*(S*)),7A.ALPHA.))-
    • 303-33-3

  • Applications

    Chemical name: (+)-Heliotrine; CAS number: 303-33-3. (+)-Heliotrine can serve as an intermediate in organic synthesis and as a chiral building block for pharmaceutical or agrochemical research; it is evaluated as a potential odorant or fragrance ingredient in perfumery and may find use in cosmetic/personal-care formulations; it may also be explored as a specialty additive or monomer in polymers and coatings under appropriate formulation guidelines.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 186.36
    methanol 333.47
    isopropanol 108.65
    water 11.56
    ethyl acetate 102.76
    n-propanol 124.32
    acetone 136.42
    n-butanol 117.78
    acetonitrile 69.08
    DMF 222.44
    toluene 19.84
    isobutanol 81.32
    1,4-dioxane 155.15
    methyl acetate 76.17
    THF 218.26
    2-butanone 77.56
    n-pentanol 59.6
    sec-butanol 79.2
    n-hexane 1.4
    ethylene glycol 99.06
    NMP 134.67
    cyclohexane 3.6
    DMSO 341.36
    n-butyl acetate 45.02
    n-octanol 27.91
    chloroform 323.69
    n-propyl acetate 42.41
    acetic acid 500.55
    dichloromethane 271.51
    cyclohexanone 128.58
    propylene glycol 77.83
    isopropyl acetate 69.84
    DMAc 186.49
    2-ethoxyethanol 195.32
    isopentanol 87.19
    n-heptane 1.41
    ethyl formate 90.9
    1,2-dichloroethane 142.61
    n-hexanol 55.08
    2-methoxyethanol 373.5
    isobutyl acetate 29.79
    tetrachloromethane 42.66
    n-pentyl acetate 45.49
    transcutol 322.51
    n-heptanol 38.12
    ethylbenzene 11.04
    MIBK 60.38
    2-propoxyethanol 174.31
    tert-butanol 103.83
    MTBE 38.77
    2-butoxyethanol 121.89
    propionic acid 118.81
    o-xylene 17.84
    formic acid 534.15
    diethyl ether 55.08
    m-xylene 19.14
    p-xylene 14.18
    chlorobenzene 43.61
    dimethyl carbonate 56.25
    n-octane 1.11
    formamide 488.32
    cyclopentanone 141.9
    2-pentanone 89.56
    anisole 28.89
    cyclopentyl methyl ether 59.47
    gamma-butyrolactone 184.13
    1-methoxy-2-propanol 231.67
    pyridine 84.68
    3-pentanone 55.88
    furfural 194.35
    n-dodecane 1.11
    diethylene glycol 202.37
    diisopropyl ether 14.65
    tert-amyl alcohol 78.49
    acetylacetone 125.79
    n-hexadecane 1.27
    acetophenone 47.02
    methyl propionate 78.15
    isopentyl acetate 46.85
    trichloroethylene 314.67
    n-nonanol 27.97
    cyclohexanol 72.38
    benzyl alcohol 56.52
    2-ethylhexanol 24.8
    isooctanol 31.67
    dipropyl ether 17.41
    1,2-dichlorobenzene 51.87
    ethyl lactate 49.14
    propylene carbonate 104.7
    n-methylformamide 194.14
    2-pentanol 61.95
    n-pentane 2.37
    1-propoxy-2-propanol 95.85
    1-methoxy-2-propyl acetate 82.65
    2-(2-methoxypropoxy) propanol 80.94
    mesitylene 11.89
    ε-caprolactone 132.9
    p-cymene 11.3
    epichlorohydrin 249.01
    1,1,1-trichloroethane 101.27
    2-aminoethanol 163.95
    morpholine-4-carbaldehyde 209.38
    sulfolane 218.74
    2,2,4-trimethylpentane 2.3
    2-methyltetrahydrofuran 91.24
    n-hexyl acetate 51.9
    isooctane 1.61
    2-(2-butoxyethoxy)ethanol 127.17
    sec-butyl acetate 30.73
    tert-butyl acetate 65.28
    decalin 2.14
    glycerin 184.45
    diglyme 215.1
    acrylic acid 134.39
    isopropyl myristate 17.28
    n-butyric acid 189.37
    acetyl acetate 86.26
    di(2-ethylhexyl) phthalate 29.64
    ethyl propionate 41.4
    nitromethane 437.14
    1,2-diethoxyethane 56.71
    benzonitrile 53.79
    trioctyl phosphate 21.96
    1-bromopropane 49.65
    gamma-valerolactone 242.95
    n-decanol 18.51
    triethyl phosphate 24.62
    4-methyl-2-pentanol 38.41
    propionitrile 52.64
    vinylene carbonate 113.38
    1,1,2-trichlorotrifluoroethane 295.22
    DMS 53.5
    cumene 9.57
    2-octanol 22.28
    2-hexanone 37.61
    octyl acetate 25.02
    limonene 14.28
    1,2-dimethoxyethane 152.93
    ethyl orthosilicate 23.11
    tributyl phosphate 24.5
    diacetone alcohol 103.48
    N,N-dimethylaniline 23.1
    acrylonitrile 81.36
    aniline 47.94
    1,3-propanediol 228.73
    bromobenzene 38.51
    dibromomethane 148.65
    1,1,2,2-tetrachloroethane 227.13
    2-methyl-cyclohexyl acetate 34.45
    tetrabutyl urea 32.12
    diisobutyl methanol 16.65
    2-phenylethanol 60.65
    styrene 11.32
    dioctyl adipate 30.3
    dimethyl sulfate 102.22
    ethyl butyrate 33.33
    methyl lactate 86.72
    butyl lactate 55.38
    diethyl carbonate 24.55
    propanediol butyl ether 100.96
    triethyl orthoformate 29.29
    p-tert-butyltoluene 10.41
    methyl 4-tert-butylbenzoate 61.82
    morpholine 177.91
    tert-butylamine 37.04
    n-dodecanol 12.43
    dimethoxymethane 193.32
    ethylene carbonate 96.7
    cyrene 94.05
    2-ethoxyethyl acetate 82.98
    2-ethylhexyl acetate 32.39
    1,2,4-trichlorobenzene 61.48
    4-methylpyridine 63.12
    dibutyl ether 15.52
    2,6-dimethyl-4-heptanol 16.65
    DEF 95.59
    dimethyl isosorbide 121.89
    tetrachloroethylene 175.34
    eugenol 71.97
    triacetin 69.44
    span 80 66.64
    1,4-butanediol 82.99
    1,1-dichloroethane 114.8
    2-methyl-1-pentanol 52.02
    methyl formate 153.97
    2-methyl-1-butanol 78.35
    n-decane 1.96
    butyronitrile 57.98
    3,7-dimethyl-1-octanol 27.85
    1-chlorooctane 11.0
    1-chlorotetradecane 4.13
    n-nonane 1.6
    undecane 1.42
    tert-butylcyclohexane 1.71
    cyclooctane 1.59
    cyclopentanol 76.1
    tetrahydropyran 82.16
    tert-amyl methyl ether 34.03
    2,5,8-trioxanonane 136.94
    1-hexene 5.96
    2-isopropoxyethanol 103.99
    2,2,2-trifluoroethanol 263.93
    methyl butyrate 54.22

    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