Integerrimine

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  • Identifiers

    CAS number
    480-79-5

    Molecular formula
    C18H25NO5

    SMILES
    C/C=C/1\C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(C)O)C

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Sweet 50.79%
    Caramellic 48.05%
    Nutty 36.34%
    Burnt 34.58%
    Roasted 33.89%
    Coumarinic 27.65%
    Odorless 27.36%
    Spicy 27.3%
    Coconut 26.43%
    Lactonic 25.03%

     

    Flavor
    Bitter 80.66%
    Cedarleaf 20.62%
    Lovage 20.35%
    Fenugreek 20.14%
    Leaves 19.99%
    Cotton candy 19.98%
    Seedy 19.98%
    Extremely sweet 19.93%
    Ripe apricot 19.81%
    Sweet-like 19.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.1

    pKa est.
    8.18 (weak base)

    Molecular weight
    335.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    502°C

    Flash point

    • 209.48 ˚C est.

  • Synonyms

    • Integerrimine
    • Squalidine
    • Squalidin
    • Intergerrimine
    • Inegerrimine
    • (15E)-12-Hydroxysenecionan-11,16-dione
    • NSC 79540
    • UNII-3179A6U4PN
    • 3179A6U4PN
    • Senecionan-11,16-dione, 12-hydroxy-, (15E)-
    • DTXSID601016480
    • NSC-79540
    • (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-5,6-DIMETHYL-, (3E,5R,6R,14AR,14BR)-
    • RefChem:39573
    • DTXCID801474670
    • SENECIONINE C15-TRANS ISOMER
    • 480-79-5
    • (-)-Integerrimine
    • (1R,4E,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • (15Z)-12-hydroxysenecionan-11,16-dione
    • Senecionan-11,16-dione, 12-hydroxy-;Aureine;Senecionin
    • CHEBI:5935
    • CHEMBL488203
    • orb1684524
    • SCHEMBL27505085
    • MSK160719
    • DA-74500
    • XI161635
    • SENECIONINE C15-TRANS ISOMER [MI]
    • HY-122772
    • CS-0088878
    • NS00094202
    • Q27106934
    • (5R,6R,9a1R,14aR,E)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
    • 480-79-5

  • Applications

    Integerrimine (CAS 480-79-5) is a natural alkaloid that is mainly of interest in research and development contexts: it can serve as an intermediate in organic synthesis and as a scaffolding block for derivative compounds; it is used as a reference material in analytical characterization of plant extracts (e.g., in HPLC/GC methods); it is employed in medicinal chemistry and chemical biology studies to explore structure-activity relationships and biological interactions; and it may be evaluated in natural-product library screening and related bioactivity assessments in academic or industrial research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 205.5
    methanol 357.95
    isopropanol 145.53
    water 2.47
    ethyl acetate 205.63
    n-propanol 174.34
    acetone 252.94
    n-butanol 174.29
    acetonitrile 111.01
    DMF 543.83
    toluene 98.28
    isobutanol 131.32
    1,4-dioxane 284.03
    methyl acetate 178.33
    THF 346.0
    2-butanone 184.64
    n-pentanol 108.05
    sec-butanol 129.78
    n-hexane 2.7
    ethylene glycol 73.32
    NMP 376.15
    cyclohexane 7.06
    DMSO 395.79
    n-butyl acetate 106.88
    n-octanol 42.04
    chloroform 545.47
    n-propyl acetate 110.47
    acetic acid 757.91
    dichloromethane 391.44
    cyclohexanone 288.31
    propylene glycol 76.11
    isopropyl acetate 147.63
    DMAc 455.53
    2-ethoxyethanol 266.56
    isopentanol 146.27
    n-heptane 2.42
    ethyl formate 177.57
    1,2-dichloroethane 210.65
    n-hexanol 94.09
    2-methoxyethanol 462.6
    isobutyl acetate 74.39
    tetrachloromethane 60.7
    n-pentyl acetate 97.46
    transcutol 543.93
    n-heptanol 62.53
    ethylbenzene 38.5
    MIBK 124.1
    2-propoxyethanol 270.27
    tert-butanol 115.91
    MTBE 62.91
    2-butoxyethanol 178.52
    propionic acid 233.44
    o-xylene 60.89
    formic acid 536.39
    diethyl ether 99.62
    m-xylene 65.42
    p-xylene 50.3
    chlorobenzene 115.31
    dimethyl carbonate 156.89
    n-octane 1.58
    formamide 626.04
    cyclopentanone 302.06
    2-pentanone 190.86
    anisole 82.09
    cyclopentyl methyl ether 140.08
    gamma-butyrolactone 384.62
    1-methoxy-2-propanol 320.08
    pyridine 281.59
    3-pentanone 129.61
    furfural 379.65
    n-dodecane 1.79
    diethylene glycol 256.27
    diisopropyl ether 26.81
    tert-amyl alcohol 108.88
    acetylacetone 251.79
    n-hexadecane 2.06
    acetophenone 129.76
    methyl propionate 186.31
    isopentyl acetate 99.6
    trichloroethylene 555.54
    n-nonanol 45.39
    cyclohexanol 145.61
    benzyl alcohol 142.4
    2-ethylhexanol 46.75
    isooctanol 50.89
    dipropyl ether 33.95
    1,2-dichlorobenzene 114.08
    ethyl lactate 92.39
    propylene carbonate 232.7
    n-methylformamide 342.39
    2-pentanol 108.28
    n-pentane 4.51
    1-propoxy-2-propanol 146.75
    1-methoxy-2-propyl acetate 161.88
    2-(2-methoxypropoxy) propanol 137.58
    mesitylene 33.91
    ε-caprolactone 284.23
    p-cymene 24.09
    epichlorohydrin 405.45
    1,1,1-trichloroethane 174.51
    2-aminoethanol 144.05
    morpholine-4-carbaldehyde 491.34
    sulfolane 376.67
    2,2,4-trimethylpentane 3.79
    2-methyltetrahydrofuran 187.35
    n-hexyl acetate 107.16
    isooctane 2.85
    2-(2-butoxyethoxy)ethanol 201.05
    sec-butyl acetate 82.84
    tert-butyl acetate 119.75
    decalin 4.92
    glycerin 184.63
    diglyme 338.96
    acrylic acid 267.29
    isopropyl myristate 37.14
    n-butyric acid 344.45
    acetyl acetate 193.56
    di(2-ethylhexyl) phthalate 63.32
    ethyl propionate 96.14
    nitromethane 713.06
    1,2-diethoxyethane 118.35
    benzonitrile 139.57
    trioctyl phosphate 42.09
    1-bromopropane 91.13
    gamma-valerolactone 548.22
    n-decanol 31.45
    triethyl phosphate 50.45
    4-methyl-2-pentanol 67.51
    propionitrile 106.3
    vinylene carbonate 281.07
    1,1,2-trichlorotrifluoroethane 446.61
    DMS 127.74
    cumene 26.75
    2-octanol 36.81
    2-hexanone 102.24
    octyl acetate 53.03
    limonene 29.74
    1,2-dimethoxyethane 257.82
    ethyl orthosilicate 45.79
    tributyl phosphate 50.05
    diacetone alcohol 175.25
    N,N-dimethylaniline 64.92
    acrylonitrile 164.91
    aniline 158.69
    1,3-propanediol 237.31
    bromobenzene 101.74
    dibromomethane 221.85
    1,1,2,2-tetrachloroethane 369.29
    2-methyl-cyclohexyl acetate 71.36
    tetrabutyl urea 63.83
    diisobutyl methanol 28.92
    2-phenylethanol 124.6
    styrene 46.42
    dioctyl adipate 62.41
    dimethyl sulfate 246.31
    ethyl butyrate 71.64
    methyl lactate 180.42
    butyl lactate 101.06
    diethyl carbonate 58.14
    propanediol butyl ether 146.15
    triethyl orthoformate 58.68
    p-tert-butyltoluene 21.72
    methyl 4-tert-butylbenzoate 111.14
    morpholine 347.54
    tert-butylamine 48.69
    n-dodecanol 21.98
    dimethoxymethane 329.27
    ethylene carbonate 233.29
    cyrene 177.32
    2-ethoxyethyl acetate 166.53
    2-ethylhexyl acetate 74.07
    1,2,4-trichlorobenzene 146.15
    4-methylpyridine 256.14
    dibutyl ether 31.94
    2,6-dimethyl-4-heptanol 28.92
    DEF 229.54
    dimethyl isosorbide 199.81
    tetrachloroethylene 274.64
    eugenol 122.46
    triacetin 137.23
    span 80 116.53
    1,4-butanediol 91.95
    1,1-dichloroethane 200.02
    2-methyl-1-pentanol 104.06
    methyl formate 282.33
    2-methyl-1-butanol 139.07
    n-decane 2.89
    butyronitrile 112.45
    3,7-dimethyl-1-octanol 47.25
    1-chlorooctane 17.27
    1-chlorotetradecane 7.74
    n-nonane 2.13
    undecane 2.19
    tert-butylcyclohexane 3.57
    cyclooctane 2.86
    cyclopentanol 144.45
    tetrahydropyran 185.91
    tert-amyl methyl ether 61.39
    2,5,8-trioxanonane 217.22
    1-hexene 15.64
    2-isopropoxyethanol 162.48
    2,2,2-trifluoroethanol 316.09
    methyl butyrate 126.35

    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