Jacobine

Overview IFRA Request a quote

  • Identifiers

    CAS number
    6870-67-3

    Molecular formula
    C18H25NO6

    SMILES
    C[C@@H]1C[C@]2([C@@H](O2)C)C(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@]1(C)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 46.07%
    Sweet 44.43%
    Odorless 39.78%
    Nutty 35.29%
    Roasted 32.15%
    Burnt 31.97%
    Popcorn 24.51%
    Buttery 22.68%
    Lactonic 20.41%
    Coumarinic 20.14%

     

    Flavor
    Bitter 83.19%
    Sweet-like 21.8%
    Fatty 21.22%
    Cedarleaf 21.17%
    Naphthalic 20.65%
    Fenugreek 20.51%
    Cotton candy 20.51%
    Alkaline 20.12%
    Seedy 20.11%
    Extremely sweet 20.08%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    7.39 (neutral)

    Molecular weight
    351.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    658°C

    Melting point expt.

    • 228 °C

    Flash point

    • 171.84 ˚C est.

    Solubility expt.

    • Sol in chloroform; sparingly sol in ethanol, water and ether
    • In water, 1.5X10+5 mg/L @ 25 °C /Estimated/

  • Synonyms

    • JACOBINE
    • 6870-67-3
    • NSC 89936
    • GM32U80H1R
    • DTXSID501020078
    • NSC-89936
    • 15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
    • (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
    • Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15alpha,20R)-
    • (1R,3'S,4S,6R,7R,17R)-7-hydroxy-3',6,7-trimethylspiro(2,9-dioxa-14-azatricyclo(9.5.1.014,17)heptadec-11-ene-4,2'-oxirane)-3,8-dione
    • (1R,3'S,4S,6R,7R,17R)-7-hydroxy-3',6,7-trimethylspiro[2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-4,2'-oxirane]-3,8-dione
    • RefChem:150303
    • DTXCID201477919
    • (15 alpha,20R)15,20-epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione
    • Jacobine.
    • CCRIS 5777
    • HSDB 3500
    • BRN 0054580
    • (2S,3S,5'R,6'R,9a1'R,14a'R)-6'-hydroxy-3,5',6'-trimethyl-5',6',9',9a1',11',13',14',14a'-octahydro-2'H-spiro[oxirane-2,3'-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine]-2',7'(4'H)-dione
    • 471-14-7
    • Jacobine Impurity 1
    • JACOBINE [IARC]
    • UNII-GM32U80H1R
    • 4-27-00-06827 (Beilstein Handbook Reference)
    • CHEBI:6080
    • orb1682296
    • MSK14167
    • AKOS027326873
    • 12beta-Hydroxy-12alpha,13beta-dimethylsenec-1-enine-15S-spiro-2'-(3'R-methyloxiran)
    • Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)-
    • BJ161539
    • DA-64608
    • HY-124058
    • CS-0084068
    • NS00066968
    • Q27107031
    • (15S,20S)-12-Hydroxy-15,20-dihydro-15,20-epoxysenecionan-11,16-dione
    • (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione
    • Jacobine; Spiro[[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-3(2H),2'-oxirane]-2,7(4H)-dione, 5,6,9,11,13,14,14a,14b-octahydro-6-hydroxy-3',5,6-trimethyl-, (2'S,3'S,5R,6R,14aR,14bR)-; Jacobine (6CI,7CI,8CI); Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydr
    • SENECIONAN-11,16-DIONE, 15,20-EPOXY-15,20-DIHYDRO-12-HYDROXY-, (15.ALPHA.,20S)-
    • SPIRO((1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-3(2H),2'-OXIRANE)-2,7(4H)-DIONE, 5,6,9,11,13,14,14A,14B-OCTAHYDRO-6-HYDROXY-3',5,6-TRIMETHYL-, (2'S,3'S,5R,6R,14AR,14BR)-
    • 6870-67-3

  • Applications

    Jacobine (CAS 6870-67-3) is a specialty organic compound with potential industrial applications as an intermediate in organic synthesis for pharmaceuticals and other specialty chemicals; it may serve as a solvent or reaction medium in niche manufacturing processes; it can be used as a processing additive or stabilizer for polymers and coatings formulations; it is evaluated for synthesis of agrochemicals or pesticides; and it may be considered as a component in cleaning formulations or as an additive in certain plastic or resin systems, subject to regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 123.01
    methanol 200.79
    isopropanol 80.53
    water 1.42
    ethyl acetate 166.34
    n-propanol 97.92
    acetone 216.27
    n-butanol 85.73
    acetonitrile 121.71
    DMF 432.87
    toluene 47.69
    isobutanol 65.57
    1,4-dioxane 199.85
    methyl acetate 156.88
    THF 275.48
    2-butanone 158.91
    n-pentanol 58.46
    sec-butanol 70.09
    n-hexane 1.49
    ethylene glycol 71.13
    NMP 338.24
    cyclohexane 3.79
    DMSO 382.67
    n-butyl acetate 67.47
    n-octanol 25.27
    chloroform 318.72
    n-propyl acetate 80.83
    acetic acid 587.17
    dichloromethane 259.11
    cyclohexanone 211.31
    propylene glycol 60.01
    isopropyl acetate 104.83
    DMAc 389.48
    2-ethoxyethanol 197.88
    isopentanol 70.72
    n-heptane 1.66
    ethyl formate 133.19
    1,2-dichloroethane 138.4
    n-hexanol 51.32
    2-methoxyethanol 363.16
    isobutyl acetate 47.9
    tetrachloromethane 33.26
    n-pentyl acetate 58.31
    transcutol 343.23
    n-heptanol 35.17
    ethylbenzene 20.8
    MIBK 85.27
    2-propoxyethanol 189.77
    tert-butanol 64.34
    MTBE 41.1
    2-butoxyethanol 118.07
    propionic acid 179.56
    o-xylene 30.37
    formic acid 513.42
    diethyl ether 72.31
    m-xylene 30.22
    p-xylene 27.24
    chlorobenzene 66.69
    dimethyl carbonate 129.46
    n-octane 0.86
    formamide 593.85
    cyclopentanone 252.83
    2-pentanone 144.3
    anisole 58.39
    cyclopentyl methyl ether 90.97
    gamma-butyrolactone 322.68
    1-methoxy-2-propanol 229.56
    pyridine 205.87
    3-pentanone 101.63
    furfural 312.58
    n-dodecane 0.98
    diethylene glycol 194.53
    diisopropyl ether 17.42
    tert-amyl alcohol 60.68
    acetylacetone 202.21
    n-hexadecane 1.14
    acetophenone 92.48
    methyl propionate 151.03
    isopentyl acetate 61.16
    trichloroethylene 368.12
    n-nonanol 27.71
    cyclohexanol 72.86
    benzyl alcohol 93.72
    2-ethylhexanol 26.37
    isooctanol 28.82
    dipropyl ether 24.35
    1,2-dichlorobenzene 67.14
    ethyl lactate 74.93
    propylene carbonate 169.42
    n-methylformamide 290.4
    2-pentanol 51.48
    n-pentane 2.4
    1-propoxy-2-propanol 99.34
    1-methoxy-2-propyl acetate 125.12
    2-(2-methoxypropoxy) propanol 99.48
    mesitylene 15.57
    ε-caprolactone 210.73
    p-cymene 13.99
    epichlorohydrin 330.9
    1,1,1-trichloroethane 99.64
    2-aminoethanol 109.89
    morpholine-4-carbaldehyde 401.71
    sulfolane 309.55
    2,2,4-trimethylpentane 1.91
    2-methyltetrahydrofuran 136.59
    n-hexyl acetate 67.23
    isooctane 1.3
    2-(2-butoxyethoxy)ethanol 135.14
    sec-butyl acetate 56.73
    tert-butyl acetate 79.4
    decalin 2.62
    glycerin 158.52
    diglyme 248.11
    acrylic acid 233.52
    isopropyl myristate 23.88
    n-butyric acid 218.12
    acetyl acetate 155.76
    di(2-ethylhexyl) phthalate 41.07
    ethyl propionate 76.26
    nitromethane 695.43
    1,2-diethoxyethane 74.18
    benzonitrile 95.35
    trioctyl phosphate 27.53
    1-bromopropane 52.49
    gamma-valerolactone 452.56
    n-decanol 19.28
    triethyl phosphate 38.46
    4-methyl-2-pentanol 33.55
    propionitrile 91.05
    vinylene carbonate 205.95
    1,1,2-trichlorotrifluoroethane 366.08
    DMS 91.22
    cumene 14.18
    2-octanol 19.44
    2-hexanone 72.7
    octyl acetate 35.85
    limonene 17.82
    1,2-dimethoxyethane 205.68
    ethyl orthosilicate 32.53
    tributyl phosphate 31.83
    diacetone alcohol 124.8
    N,N-dimethylaniline 43.73
    acrylonitrile 148.91
    aniline 90.22
    1,3-propanediol 155.64
    bromobenzene 57.79
    dibromomethane 137.14
    1,1,2,2-tetrachloroethane 222.16
    2-methyl-cyclohexyl acetate 50.65
    tetrabutyl urea 42.15
    diisobutyl methanol 16.01
    2-phenylethanol 82.31
    styrene 25.64
    dioctyl adipate 44.43
    dimethyl sulfate 201.1
    ethyl butyrate 53.85
    methyl lactate 149.01
    butyl lactate 62.99
    diethyl carbonate 44.87
    propanediol butyl ether 94.5
    triethyl orthoformate 43.42
    p-tert-butyltoluene 12.45
    methyl 4-tert-butylbenzoate 76.94
    morpholine 241.28
    tert-butylamine 25.62
    n-dodecanol 13.24
    dimethoxymethane 261.32
    ethylene carbonate 163.85
    cyrene 136.57
    2-ethoxyethyl acetate 113.7
    2-ethylhexyl acetate 45.2
    1,2,4-trichlorobenzene 94.15
    4-methylpyridine 164.8
    dibutyl ether 19.24
    2,6-dimethyl-4-heptanol 16.01
    DEF 169.88
    dimethyl isosorbide 151.67
    tetrachloroethylene 168.58
    eugenol 85.92
    triacetin 106.21
    span 80 76.78
    1,4-butanediol 67.16
    1,1-dichloroethane 115.1
    2-methyl-1-pentanol 51.8
    methyl formate 242.46
    2-methyl-1-butanol 66.18
    n-decane 1.66
    butyronitrile 84.74
    3,7-dimethyl-1-octanol 27.24
    1-chlorooctane 10.07
    1-chlorotetradecane 4.37
    n-nonane 1.21
    undecane 1.23
    tert-butylcyclohexane 1.8
    cyclooctane 1.57
    cyclopentanol 84.42
    tetrahydropyran 118.49
    tert-amyl methyl ether 38.67
    2,5,8-trioxanonane 160.96
    1-hexene 8.15
    2-isopropoxyethanol 112.46
    2,2,2-trifluoroethanol 252.07
    methyl butyrate 96.33

    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