Monocrotaline

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  • Identifiers

    CAS number
    315-22-0

    Molecular formula
    C16H23NO6

    SMILES
    C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 50.06%
    Odorless 43.83%
    Caramellic 37.59%
    Nutty 28.55%
    Burnt 28.15%
    Roasted 24.18%
    Spicy 23.09%
    Vanilla 22.9%
    Coconut 22.5%
    Creamy 22.1%

     

    Flavor
    Bitter 84.07%
    Sweet-like 22.79%
    Cedarleaf 21.53%
    Fatty 20.61%
    Cotton candy 20.49%
    Fenugreek 20.48%
    Seedy 20.34%
    Extremely sweet 20.2%
    Odorless 20.18%
    Ripe apricot 20.1%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    6.28 (neutral)

    Molecular weight
    325.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    817°C

    Melting point expt.

    • 197-198 °C (decomposes)
    • MP: 184 °C (decomp); specific optical rotation: -38.4 deg @ 28 °C/D (concentration by volume = 5.2 g in 100 ml water) /Monocrotaline hydrochloride/

    Flash point

    • 226.88 ˚C est.

    Solubility expt.

    • Readily sol in water /Monocrotaline hydrochloride/
    • Slightly sol in water (1.2%); sparingly sol in non-polar org solvents (0.09% in oleyl alcohol, 0.012% in dodecane); sol in ethanol and chloroform
    • In water, 3.7X10+5 mg/L @ 25 °C /Estimated/

  • Synonyms

    • monocrotaline
    • 315-22-0
    • Monocrotalin
    • NCI-C56462
    • A 6080
    • Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate
    • CHEBI:6980
    • DTXSID9020902
    • 73077K8HYV
    • (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
    • NSC-28693
    • NSC 28693
    • DTXCID50902
    • 12-beta,13-beta-Dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine
    • 14,19-Dihydro-12,13-dihydroxy(13-alpha,14-alpha)-20-norcrotalanan-11,15-dione
    • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-
    • (3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
    • 2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-
    • 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-
    • (3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-(1,6)dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione
    • RefChem:159547
    • Testosterone oenanthate
    • Crotaline
    • (-)-Monocrotaline
    • MFCD00084656
    • MLS002153902
    • 14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
    • (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
    • (3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
    • NCGC00164256-01
    • CCRIS 416
    • HSDB 3513
    • SR-01000838886
    • (2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
    • BRN 0048732
    • UNII-73077K8HYV
    • CAS-315-22-0
    • Prestwick_338
    • Spectrum_001224
    • Monocrotaline Impurity 2
    • Prestwick0_000603
    • Prestwick1_000603
    • Prestwick2_000603
    • Prestwick3_000603
    • Spectrum2_000906
    • Spectrum3_000947
    • Spectrum4_001057
    • Spectrum5_001233
    • MONOCROTALINE [MI]
    • MONOCROTALINE [HSDB]
    • MONOCROTALINE [IARC]
    • BSPBio_000506
    • KBioGR_001354
    • KBioSS_001704
    • 4-27-00-06660 (Beilstein Handbook Reference)
    • DivK1c_000959
    • SCHEMBL164486
    • SPECTRUM1502252
    • SPBio_000752
    • SPBio_002725
    • BPBio1_000558
    • CHEMBL521035
    • MEGxp0_001899
    • ACon0_000305
    • ACon1_000179
    • HMS502P21
    • KBio1_000959
    • KBio2_001704
    • KBio2_004272
    • KBio2_006840
    • KBio3_002014
    • Monocrotaline, analytical standard
    • NINDS_000959
    • HMS1569J08
    • HMS1921P04
    • HMS2096J08
    • HMS2235J12
    • HY-N0750
    • MSK14173
    • Tox21_112094
    • Tox21_201509
    • Tox21_302874
    • BDBM50480309
    • CCG-39621
    • s3812
    • AKOS015969712
    • AKOS032962048
    • Tox21_112094_1
    • CS-6164
    • FM64904
    • FS-5652
    • SDCCGMLS-0066675.P001
    • 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-
    • IDI1_000959
    • NCGC00179538-01
    • NCGC00179538-02
    • NCGC00179538-03
    • NCGC00256518-01
    • NCGC00259060-01
    • NCGC00262539-03
    • (3R,4R,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-Octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
    • AC-34918
    • SMR001233251
    • SY065743
    • JACS 72: 158 (1950)
    • F002602
    • SR-01000838886-3
    • SR-01000838886-4
    • BRD-K65508953-001-05-5
    • BRD-K65508953-001-08-9
    • Q27107379
    • (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0??,??]hexadec-10-ene-3,7-dione
    • (3R,4R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
    • 109525-74-8
    • 2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13A,13B-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-, (3R-(3R*,4R*,5R*,13AR*,13BR*))-
    • rel-(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
    • 315-22-0

  • Applications

    Monocrotaline (CAS 315-22-0) is primarily used as a research tool in toxicology and pharmacology to evaluate toxic mechanisms and model tissue injury, including hepatic damage and vascular remodeling; it is commonly employed to induce pulmonary arterial hypertension in animal models to study PAH, and may serve as an intermediate in the synthesis of related pyrrolizidine alkaloid derivatives; it is also used as a reference material in the development and validation of analytical methods for pyrrolizidine alkaloid toxicology in laboratory settings; all uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 171.47
    methanol 434.01
    isopropanol 99.81
    water 8.45
    ethyl acetate 90.4
    n-propanol 112.92
    acetone 191.67
    n-butanol 96.82
    acetonitrile 63.72
    DMF 697.47
    toluene 36.22
    isobutanol 69.69
    1,4-dioxane 242.18
    methyl acetate 85.01
    THF 376.05
    2-butanone 99.83
    n-pentanol 57.0
    sec-butanol 61.92
    n-hexane 1.33
    ethylene glycol 90.31
    NMP 419.83
    cyclohexane 4.25
    DMSO 638.78
    n-butyl acetate 36.47
    n-octanol 21.09
    chloroform 253.46
    n-propyl acetate 45.93
    acetic acid 574.91
    dichloromethane 206.92
    cyclohexanone 198.3
    propylene glycol 71.83
    isopropyl acetate 54.99
    DMAc 404.56
    2-ethoxyethanol 229.86
    isopentanol 74.58
    n-heptane 1.11
    ethyl formate 112.31
    1,2-dichloroethane 109.76
    n-hexanol 43.87
    2-methoxyethanol 472.61
    isobutyl acetate 28.13
    tetrachloromethane 28.84
    n-pentyl acetate 35.05
    transcutol 266.8
    n-heptanol 30.48
    ethylbenzene 15.24
    MIBK 61.77
    2-propoxyethanol 195.84
    tert-butanol 81.31
    MTBE 26.04
    2-butoxyethanol 110.95
    propionic acid 125.37
    o-xylene 23.87
    formic acid 690.66
    diethyl ether 46.38
    m-xylene 27.45
    p-xylene 22.73
    chlorobenzene 42.95
    dimethyl carbonate 101.91
    n-octane 0.71
    formamide 830.92
    cyclopentanone 263.71
    2-pentanone 104.62
    anisole 47.34
    cyclopentyl methyl ether 90.91
    gamma-butyrolactone 326.95
    1-methoxy-2-propanol 286.89
    pyridine 170.17
    3-pentanone 63.02
    furfural 301.77
    n-dodecane 0.7
    diethylene glycol 233.57
    diisopropyl ether 10.8
    tert-amyl alcohol 59.47
    acetylacetone 154.42
    n-hexadecane 0.84
    acetophenone 74.65
    methyl propionate 99.09
    isopentyl acetate 34.78
    trichloroethylene 283.91
    n-nonanol 21.7
    cyclohexanol 85.27
    benzyl alcohol 89.76
    2-ethylhexanol 18.17
    isooctanol 22.91
    dipropyl ether 15.42
    1,2-dichlorobenzene 44.25
    ethyl lactate 55.18
    propylene carbonate 142.16
    n-methylformamide 423.5
    2-pentanol 47.55
    n-pentane 1.89
    1-propoxy-2-propanol 91.06
    1-methoxy-2-propyl acetate 71.0
    2-(2-methoxypropoxy) propanol 77.2
    mesitylene 14.95
    ε-caprolactone 181.89
    p-cymene 9.28
    epichlorohydrin 306.64
    1,1,1-trichloroethane 70.09
    2-aminoethanol 146.21
    morpholine-4-carbaldehyde 446.95
    sulfolane 369.76
    2,2,4-trimethylpentane 1.25
    2-methyltetrahydrofuran 132.71
    n-hexyl acetate 40.93
    isooctane 1.05
    2-(2-butoxyethoxy)ethanol 111.43
    sec-butyl acetate 30.16
    tert-butyl acetate 48.47
    decalin 2.18
    glycerin 202.76
    diglyme 214.1
    acrylic acid 163.86
    isopropyl myristate 14.59
    n-butyric acid 175.2
    acetyl acetate 80.76
    di(2-ethylhexyl) phthalate 27.98
    ethyl propionate 43.28
    nitromethane 594.85
    1,2-diethoxyethane 47.38
    benzonitrile 66.03
    trioctyl phosphate 19.71
    1-bromopropane 35.03
    gamma-valerolactone 460.77
    n-decanol 14.46
    triethyl phosphate 22.67
    4-methyl-2-pentanol 31.23
    propionitrile 47.34
    vinylene carbonate 160.71
    1,1,2-trichlorotrifluoroethane 335.24
    DMS 50.63
    cumene 10.31
    2-octanol 16.01
    2-hexanone 49.95
    octyl acetate 21.66
    limonene 12.13
    1,2-dimethoxyethane 249.7
    ethyl orthosilicate 20.86
    tributyl phosphate 20.42
    diacetone alcohol 108.42
    N,N-dimethylaniline 38.41
    acrylonitrile 88.87
    aniline 85.5
    1,3-propanediol 209.04
    bromobenzene 35.92
    dibromomethane 105.36
    1,1,2,2-tetrachloroethane 209.18
    2-methyl-cyclohexyl acetate 32.52
    tetrabutyl urea 32.06
    diisobutyl methanol 11.9
    2-phenylethanol 65.34
    styrene 18.4
    dioctyl adipate 28.34
    dimethyl sulfate 191.35
    ethyl butyrate 28.96
    methyl lactate 129.19
    butyl lactate 45.68
    diethyl carbonate 22.79
    propanediol butyl ether 86.33
    triethyl orthoformate 25.8
    p-tert-butyltoluene 9.09
    methyl 4-tert-butylbenzoate 57.15
    morpholine 293.39
    tert-butylamine 26.51
    n-dodecanol 9.73
    dimethoxymethane 342.0
    ethylene carbonate 127.82
    cyrene 134.36
    2-ethoxyethyl acetate 63.86
    2-ethylhexyl acetate 25.18
    1,2,4-trichlorobenzene 62.12
    4-methylpyridine 142.61
    dibutyl ether 11.92
    2,6-dimethyl-4-heptanol 11.9
    DEF 150.34
    dimethyl isosorbide 127.36
    tetrachloroethylene 150.63
    eugenol 70.83
    triacetin 55.77
    span 80 61.28
    1,4-butanediol 80.42
    1,1-dichloroethane 82.84
    2-methyl-1-pentanol 45.84
    methyl formate 331.32
    2-methyl-1-butanol 59.58
    n-decane 1.28
    butyronitrile 51.72
    3,7-dimethyl-1-octanol 19.6
    1-chlorooctane 6.62
    1-chlorotetradecane 2.67
    n-nonane 0.98
    undecane 0.91
    tert-butylcyclohexane 1.37
    cyclooctane 1.64
    cyclopentanol 113.68
    tetrahydropyran 122.26
    tert-amyl methyl ether 26.91
    2,5,8-trioxanonane 140.72
    1-hexene 6.28
    2-isopropoxyethanol 111.86
    2,2,2-trifluoroethanol 242.83
    methyl butyrate 64.77

    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