Lasiocarpine

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  • Identifiers

    CAS number
    303-34-4

    Molecular formula
    C21H33NO7

    SMILES
    C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 51.03%
    Mint 25.57%
    Sweet 25.44%
    Cooling 24.07%
    Milky 21.67%
    Woody 19.89%
    Buttery 18.68%
    Fresh 17.84%
    Lactonic 17.43%
    Creamy 17.01%

     

    Flavor
    Bitter 79.5%
    Odorless 30.35%
    Bland 26.61%
    Fruity 23.77%
    Sweet-like 21.62%
    Mild 19.81%
    Very mild 19.29%
    Cedarleaf 19.23%
    Heather 19.08%
    Broom 19.06%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    7.1 (neutral)

    Molecular weight
    411.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    493°C

    Melting point expt.

    • 206 to 207 °F (NTP, 1992)
    • 96.4-97 °C

    Flash point

    • 225.28 ˚C est.

    Solubility expt.

    • less than 0.1 mg/mL at 68 °F (NTP, 1992)
    • SOL IN WATER /LASIOCARPINE HYDROCHLORIDE/
    • SOL IN MOST NON-POLAR ORG SOLVENTS & ETHANOL; SPARINGLY SOL IN WATER (0.68%) & LIGHT PETROLEUM
    • Soluble on ether, alcohol, and benzene.

  • Synonyms

    • LASIOCARPINE
    • 7-Angelyleuropine
    • 303-34-4
    • Europine 7-angelate
    • NCI-C01478
    • NSC 30625
    • NSC-30625
    • AI3-51770
    • S770100Q96
    • Heliotridine ester with lasiocarpum and angelic acid
    • (Z)-2-Methylcrotonic acid, 2,3-dihydroxy-2-(1-methoxyethyl)-3-methylbutyrate (ester)
    • (7alpha-Angelyloxy-5,6,7,8alpha-tetrahydro-3H-pyrrolizin-1-yl)methyl-2,3-dihydroxy-2-(1'-methoxyethyl)-3-methylbutyrate
    • 2,3,5,7alphabeta-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol-1-angelate-7-(2,3-dihydroxy-2(1-methoxyethyl))-3-methyl-butyrate
    • [(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate
    • DTXSID1020772
    • ((7S,8R)-7-((Z)-2-methylbut-2-enoyl)oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2R)-2,3-dihydroxy-2-((1S)-1-methoxyethyl)-3-methylbutanoate
    • RefChem:41015
    • DTXCID70772
    • 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1alpha(Z),7(S*(R*)),7Aalpha))-
    • RCRA waste number U143
    • MLS002639334
    • CCRIS 355
    • NSC30625
    • HSDB 6062
    • UNII-S770100Q96
    • Heliotridine ester with lasiocarpum & angelic acid
    • LASIOCARPINE [MI]
    • RCRA waste no. U143
    • LASIOCARPINE [HSDB]
    • LASIOCARPINE [IARC]
    • SCHEMBL168932
    • CHEMBL1999554
    • Lasiocarpine (7-Angelyleuropine)
    • QHOZSLCIKHUPSU-LPLKQDONSA-N
    • MSK14169
    • HELIOSUPINE METHYL ETHER [MI]
    • Lasiocarpine 100 microg/mL in Water
    • AKOS030501885
    • 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1S-(1alpha(Z),7(2S*,3R*),7aalpha))-
    • FL168452
    • NS00066989
    • WLN: T55 AN CUTJ D1OVXQXQ1 & 1 & Y1 & O1 FOVY1 & U2
    • (1S,7aR)-7-((((R)-2,3-dihydroxy-2-((S)-1-methoxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (Z)-2-methylbut-2-enoate
    • (Z)-(1S,7aR)-7-(((2,3-dihydroxy-2-((S)-1-methoxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl 2-methylbut-2-enoate
    • 2-Butenoic acid, 2-methy-,(1S,7aR)-7-(((2R)-2,3-dihydroxy-2-((1S)-1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-ester, (2Z)-
    • 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1-METHOXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A-TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1S-(1.ALPHA.(Z),7(S*(R*)),7A.ALPHA.))-
    • 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1S-(1alpha(Z),7(2S*,3R*),7a alpha))-
    • 2-Butenoic acid, 7-[[2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, [1S-[1.alpha.(Z),7(2S*,3R*),7a.alpha.]]-
    • 2-Butenoic acid,2-methyl-,(1S,7aR)-7-[[(2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ylester, (2Z)-
    • 303-34-4

  • Applications

    Lasiocarpine (CAS 303-34-4) is primarily encountered in toxicology and analytical contexts rather than as a routine industrial additive. In research settings it is used as a representative pyrrolizidine alkaloid to study hepatotoxic mechanisms and to calibrate analytical methods for detecting pyrrolizidine alkaloids. It also serves as a reference compound in method development and validation for monitoring these alkaloids in crops, herbal medicines, and food products. Because it can occur as a contaminant in plant-derived materials, it is relevant to risk assessment in agriculture and food safety. In pharmacology/toxicology studies it may be employed as a model compound for safety evaluation of pyrrolizidine alkaloids.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 160.84
    methanol 209.99
    isopropanol 129.76
    water 0.67
    ethyl acetate 98.23
    n-propanol 165.32
    acetone 196.65
    n-butanol 136.52
    acetonitrile 68.26
    DMF 253.05
    toluene 27.17
    isobutanol 99.33
    1,4-dioxane 169.67
    methyl acetate 92.16
    THF 318.67
    2-butanone 146.9
    n-pentanol 85.78
    sec-butanol 122.52
    n-hexane 1.83
    ethylene glycol 32.81
    NMP 236.62
    cyclohexane 3.48
    DMSO 328.58
    n-butyl acetate 42.16
    n-octanol 27.97
    chloroform 319.81
    n-propyl acetate 46.44
    acetic acid 366.98
    dichloromethane 224.74
    cyclohexanone 189.99
    propylene glycol 53.54
    isopropyl acetate 63.12
    DMAc 291.5
    2-ethoxyethanol 190.68
    isopentanol 87.48
    n-heptane 1.11
    ethyl formate 82.36
    1,2-dichloroethane 132.23
    n-hexanol 54.7
    2-methoxyethanol 287.06
    isobutyl acetate 30.52
    tetrachloromethane 36.75
    n-pentyl acetate 49.6
    transcutol 226.0
    n-heptanol 35.17
    ethylbenzene 12.13
    MIBK 65.4
    2-propoxyethanol 169.12
    tert-butanol 93.06
    MTBE 45.13
    2-butoxyethanol 112.41
    propionic acid 110.7
    o-xylene 17.38
    formic acid 204.53
    diethyl ether 68.5
    m-xylene 16.41
    p-xylene 15.86
    chlorobenzene 46.71
    dimethyl carbonate 56.96
    n-octane 0.83
    formamide 211.49
    cyclopentanone 204.09
    2-pentanone 125.25
    anisole 29.42
    cyclopentyl methyl ether 74.71
    gamma-butyrolactone 214.06
    1-methoxy-2-propanol 207.9
    pyridine 114.82
    3-pentanone 84.89
    furfural 177.24
    n-dodecane 0.76
    diethylene glycol 134.03
    diisopropyl ether 11.51
    tert-amyl alcohol 87.81
    acetylacetone 134.11
    n-hexadecane 0.87
    acetophenone 47.5
    methyl propionate 88.95
    isopentyl acetate 41.62
    trichloroethylene 294.3
    n-nonanol 28.37
    cyclohexanol 84.25
    benzyl alcohol 57.51
    2-ethylhexanol 22.1
    isooctanol 28.12
    dipropyl ether 18.14
    1,2-dichlorobenzene 48.17
    ethyl lactate 41.69
    propylene carbonate 99.9
    n-methylformamide 160.51
    2-pentanol 70.1
    n-pentane 2.69
    1-propoxy-2-propanol 87.66
    1-methoxy-2-propyl acetate 66.55
    2-(2-methoxypropoxy) propanol 71.83
    mesitylene 8.55
    ε-caprolactone 168.9
    p-cymene 8.22
    epichlorohydrin 290.44
    1,1,1-trichloroethane 104.83
    2-aminoethanol 91.7
    morpholine-4-carbaldehyde 238.35
    sulfolane 252.72
    2,2,4-trimethylpentane 2.08
    2-methyltetrahydrofuran 147.17
    n-hexyl acetate 58.48
    isooctane 1.05
    2-(2-butoxyethoxy)ethanol 102.25
    sec-butyl acetate 31.12
    tert-butyl acetate 53.07
    decalin 1.79
    glycerin 101.74
    diglyme 167.05
    acrylic acid 110.9
    isopropyl myristate 15.71
    n-butyric acid 174.86
    acetyl acetate 67.35
    di(2-ethylhexyl) phthalate 28.63
    ethyl propionate 41.87
    nitromethane 359.93
    1,2-diethoxyethane 51.08
    benzonitrile 49.3
    trioctyl phosphate 20.26
    1-bromopropane 66.05
    gamma-valerolactone 329.17
    n-decanol 17.52
    triethyl phosphate 18.12
    4-methyl-2-pentanol 32.55
    propionitrile 62.16
    vinylene carbonate 100.98
    1,1,2-trichlorotrifluoroethane 262.82
    DMS 44.74
    cumene 8.47
    2-octanol 20.78
    2-hexanone 60.33
    octyl acetate 25.33
    limonene 12.37
    1,2-dimethoxyethane 151.85
    ethyl orthosilicate 18.06
    tributyl phosphate 22.66
    diacetone alcohol 99.11
    N,N-dimethylaniline 22.96
    acrylonitrile 75.89
    aniline 54.3
    1,3-propanediol 153.6
    bromobenzene 40.01
    dibromomethane 142.35
    1,1,2,2-tetrachloroethane 226.54
    2-methyl-cyclohexyl acetate 30.69
    tetrabutyl urea 32.95
    diisobutyl methanol 11.65
    2-phenylethanol 55.0
    styrene 13.32
    dioctyl adipate 28.58
    dimethyl sulfate 102.94
    ethyl butyrate 28.93
    methyl lactate 77.92
    butyl lactate 49.44
    diethyl carbonate 18.44
    propanediol butyl ether 87.69
    triethyl orthoformate 23.04
    p-tert-butyltoluene 7.61
    methyl 4-tert-butylbenzoate 56.76
    morpholine 231.16
    tert-butylamine 33.76
    n-dodecanol 10.9
    dimethoxymethane 181.46
    ethylene carbonate 85.39
    cyrene 88.9
    2-ethoxyethyl acetate 80.95
    2-ethylhexyl acetate 29.65
    1,2,4-trichlorobenzene 62.5
    4-methylpyridine 98.16
    dibutyl ether 16.82
    2,6-dimethyl-4-heptanol 11.65
    DEF 126.47
    dimethyl isosorbide 104.09
    tetrachloroethylene 156.71
    eugenol 62.02
    triacetin 63.84
    span 80 61.0
    1,4-butanediol 67.34
    1,1-dichloroethane 119.81
    2-methyl-1-pentanol 63.16
    methyl formate 119.08
    2-methyl-1-butanol 96.21
    n-decane 1.55
    butyronitrile 62.57
    3,7-dimethyl-1-octanol 23.82
    1-chlorooctane 10.49
    1-chlorotetradecane 3.46
    n-nonane 1.28
    undecane 1.04
    tert-butylcyclohexane 1.39
    cyclooctane 1.14
    cyclopentanol 100.11
    tetrahydropyran 120.53
    tert-amyl methyl ether 38.51
    2,5,8-trioxanonane 106.7
    1-hexene 9.45
    2-isopropoxyethanol 102.92
    2,2,2-trifluoroethanol 157.05
    methyl butyrate 58.99

    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