[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3Z,5R,6S,14aR,14bR)-

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  • Identifiers

    CAS number
    15503-86-3

    Molecular formula
    C18H25NO7

    SMILES
    C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CO)O)C

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 43.76%
    Sweet 43.08%
    Caramellic 39.95%
    Burnt 28.19%
    Nutty 26.28%
    Roasted 25.6%
    Spicy 23.18%
    Vanilla 21.47%
    Lactonic 20.75%
    Popcorn 20.71%

     

    Flavor
    Bitter 83.08%
    Sweet-like 21.17%
    Cedarleaf 20.75%
    Fenugreek 19.93%
    Leaves 19.91%
    Seedy 19.66%
    Lovage 19.64%
    Extremely sweet 19.54%
    Cotton candy 19.5%
    Alkaline 19.5%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    6.23 (neutral)

    Molecular weight
    367.4 g/mol

    Melting point expt.

    • 138 DEGdeg C (Decomp)

    Flash point

    • -314.71 ˚C est.

    Solubility expt.

    • Sol in water and ethanol; sparingly sol in non-polar solvents
    • In water, 5,200 mg/L @ 25 °C /Estimated/

  • Synonyms

    • 15503-86-3
    • [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3Z,5R,6S,14aR,14bR)-
    • C18H25NO7
    • (5R,6S,9a1R,14aR,Z)-3-Ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-2,7-dioxo-3,4,5,6,7,9,9a1,11,12,13,14,14a-dodecahydro-2H-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide
    • [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3Z,5R,6S,14aR,14bR)-; Isatidine (6CI,7CI); Retrorsine, N-oxide (8CI); Senecionan-11,16-dione, 12,18-dihydroxy-, 4-oxide; Retrorsine oxide
    • Retrorsine Impurity 1
    • CHEBI:5977
    • orb1696913
    • SCHEMBL30473053
    • MSK14175
    • FR161591
    • HY-116832
    • Retrorsine-N-oxide 100 microg/mL in Water
    • CS-0066628
    • NS00100976
    • Q27106956
    • (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • (3Z,5R,6S,14aR)-3-Ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-12-oxo-3,4,5,6,13,14,14a,14b-octahydro-9H-12lambda~5~-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7(11H,12H)-dione
    • (3Z,5R,6S,14aR,14bR)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione 12-oxide
    • (5R,6S,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-2,7-dioxo-2,3,4,5,6,7,9,9a1,11,13,14,14a-dodecahydro-12H-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide
    • 15503-86-3

  • Applications

    Potential applications of this compound include use as a synthetic intermediate and chiral building block in pharmaceutical chemistry, enabling access to bicyclic imide-containing scaffolds and diversity-oriented libraries. It can also serve as a functionalized precursor in specialty polymers and high-performance materials, supporting polyimide or polyamide chemistries used in coatings and electronics packaging. In coatings, inks, and adhesives, it may be employed as a reactive monomer or crosslinking modifier to impart rigidity and thermal stability in formulated systems. In research and development, it is often evaluated for stereocontrolled synthesis and as a scaffold for exploring structure–activity relationships in drug discovery programs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 201.83
    methanol 411.51
    isopropanol 104.76
    water 6.34
    ethyl acetate 109.98
    n-propanol 139.17
    acetone 237.43
    n-butanol 111.19
    acetonitrile 104.51
    DMF 563.35
    toluene 22.2
    isobutanol 75.41
    1,4-dioxane 155.86
    methyl acetate 111.29
    THF 267.69
    2-butanone 119.39
    n-pentanol 60.87
    sec-butanol 78.91
    n-hexane 1.06
    ethylene glycol 125.95
    NMP 402.89
    cyclohexane 2.7
    DMSO 667.51
    n-butyl acetate 46.66
    n-octanol 24.07
    chloroform 199.89
    n-propyl acetate 52.73
    acetic acid 879.3
    dichloromethane 189.67
    cyclohexanone 182.85
    propylene glycol 115.97
    isopropyl acetate 59.97
    DMAc 412.15
    2-ethoxyethanol 222.26
    isopentanol 70.32
    n-heptane 1.21
    ethyl formate 135.01
    1,2-dichloroethane 112.69
    n-hexanol 49.13
    2-methoxyethanol 481.14
    isobutyl acetate 27.71
    tetrachloromethane 22.7
    n-pentyl acetate 43.54
    transcutol 303.92
    n-heptanol 32.97
    ethylbenzene 9.73
    MIBK 60.7
    2-propoxyethanol 194.56
    tert-butanol 71.64
    MTBE 23.83
    2-butoxyethanol 112.11
    propionic acid 192.69
    o-xylene 16.19
    formic acid 840.36
    diethyl ether 49.75
    m-xylene 15.07
    p-xylene 11.68
    chlorobenzene 34.19
    dimethyl carbonate 122.94
    n-octane 0.82
    formamide 853.91
    cyclopentanone 234.05
    2-pentanone 117.49
    anisole 33.15
    cyclopentyl methyl ether 62.15
    gamma-butyrolactone 314.37
    1-methoxy-2-propanol 297.53
    pyridine 139.73
    3-pentanone 71.22
    furfural 281.52
    n-dodecane 0.83
    diethylene glycol 242.06
    diisopropyl ether 9.95
    tert-amyl alcohol 59.67
    acetylacetone 168.38
    n-hexadecane 0.93
    acetophenone 62.24
    methyl propionate 122.8
    isopentyl acetate 38.72
    trichloroethylene 258.54
    n-nonanol 25.09
    cyclohexanol 66.93
    benzyl alcohol 69.86
    2-ethylhexanol 20.71
    isooctanol 24.17
    dipropyl ether 18.52
    1,2-dichlorobenzene 38.03
    ethyl lactate 71.42
    propylene carbonate 153.65
    n-methylformamide 411.57
    2-pentanol 50.73
    n-pentane 1.94
    1-propoxy-2-propanol 93.97
    1-methoxy-2-propyl acetate 86.63
    2-(2-methoxypropoxy) propanol 89.43
    mesitylene 8.28
    ε-caprolactone 185.76
    p-cymene 8.32
    epichlorohydrin 299.61
    1,1,1-trichloroethane 63.73
    2-aminoethanol 184.51
    morpholine-4-carbaldehyde 409.46
    sulfolane 386.38
    2,2,4-trimethylpentane 1.21
    2-methyltetrahydrofuran 99.79
    n-hexyl acetate 50.16
    isooctane 0.84
    2-(2-butoxyethoxy)ethanol 127.52
    sec-butyl acetate 29.55
    tert-butyl acetate 49.4
    decalin 1.56
    glycerin 266.83
    diglyme 208.25
    acrylic acid 257.22
    isopropyl myristate 16.59
    n-butyric acid 229.03
    acetyl acetate 96.71
    di(2-ethylhexyl) phthalate 34.09
    ethyl propionate 49.85
    nitromethane 773.34
    1,2-diethoxyethane 51.28
    benzonitrile 62.87
    trioctyl phosphate 24.2
    1-bromopropane 37.76
    gamma-valerolactone 435.39
    n-decanol 17.2
    triethyl phosphate 26.89
    4-methyl-2-pentanol 27.54
    propionitrile 72.01
    vinylene carbonate 182.82
    1,1,2-trichlorotrifluoroethane 361.94
    DMS 65.45
    cumene 7.08
    2-octanol 18.43
    2-hexanone 51.0
    octyl acetate 26.89
    limonene 12.02
    1,2-dimethoxyethane 188.7
    ethyl orthosilicate 22.31
    tributyl phosphate 26.97
    diacetone alcohol 113.09
    N,N-dimethylaniline 28.37
    acrylonitrile 127.31
    aniline 61.33
    1,3-propanediol 249.14
    bromobenzene 27.03
    dibromomethane 98.75
    1,1,2,2-tetrachloroethane 165.99
    2-methyl-cyclohexyl acetate 34.02
    tetrabutyl urea 37.59
    diisobutyl methanol 12.19
    2-phenylethanol 60.21
    styrene 12.23
    dioctyl adipate 34.35
    dimethyl sulfate 226.26
    ethyl butyrate 35.99
    methyl lactate 174.85
    butyl lactate 60.87
    diethyl carbonate 28.59
    propanediol butyl ether 106.07
    triethyl orthoformate 28.71
    p-tert-butyltoluene 7.63
    methyl 4-tert-butylbenzoate 61.29
    morpholine 226.2
    tert-butylamine 24.58
    n-dodecanol 11.84
    dimethoxymethane 308.44
    ethylene carbonate 148.28
    cyrene 139.76
    2-ethoxyethyl acetate 82.07
    2-ethylhexyl acetate 26.98
    1,2,4-trichlorobenzene 55.8
    4-methylpyridine 101.69
    dibutyl ether 13.79
    2,6-dimethyl-4-heptanol 12.19
    DEF 162.18
    dimethyl isosorbide 128.0
    tetrachloroethylene 126.13
    eugenol 75.24
    triacetin 78.91
    span 80 77.15
    1,4-butanediol 98.3
    1,1-dichloroethane 80.29
    2-methyl-1-pentanol 45.15
    methyl formate 319.62
    2-methyl-1-butanol 68.48
    n-decane 1.43
    butyronitrile 67.28
    3,7-dimethyl-1-octanol 21.67
    1-chlorooctane 8.11
    1-chlorotetradecane 3.38
    n-nonane 1.12
    undecane 1.05
    tert-butylcyclohexane 1.09
    cyclooctane 1.06
    cyclopentanol 89.22
    tetrahydropyran 86.49
    tert-amyl methyl ether 25.44
    2,5,8-trioxanonane 149.33
    1-hexene 5.4
    2-isopropoxyethanol 104.11
    2,2,2-trifluoroethanol 343.14
    methyl butyrate 70.45

    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