Echimidine

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  • Identifiers

    CAS number
    520-68-3

    Molecular formula
    C20H31NO7

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

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 55.24%
    Sweet 29.44%
    Cooling 23.1%
    Milky 23.01%
    Mint 22.7%
    Buttery 19.33%
    Creamy 18.08%
    Lactonic 17.9%
    Woody 17.4%
    Savory 16.39%

     

    Flavor
    Bitter 81.12%
    Odorless 35.49%
    Bland 28.87%
    Sweet-like 22.44%
    Very mild 21.28%
    Mild 20.16%
    Cedarleaf 19.01%
    Fruity 18.93%
    Heather 18.82%
    Broom 18.78%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    7.15 (neutral)

    Molecular weight
    397.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    584°C

    Flash point

    • 243.61 ˚C est.

  • Synonyms

    • ECHIMIDINE
    • 520-68-3
    • (+)-Echimidine
    • 31NEL09379
    • DTXSID501020028
    • [(7R,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-hydroxyethyl]-3-methylbutanoate
    • 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-hydroxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (1R-(1alpha(Z),7(2R*,3S*),7abeta))-
    • ((7R,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-hydroxyethyl)-3-methyl-butanoate
    • ((7R,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-hydroxyethyl)-3-methylbutanoate
    • [(7R,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-hydroxyethyl]-3-methyl-butanoate
    • RefChem:35347
    • DTXCID301477879
    • C20H31NO7
    • (1R,7aR)-7-((((R)-2,3-Dihydroxy-2-((S)-1-hydroxyethyl)-3-methylbutanoyl)oxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (Z)-2-methylbut-2-enoate
    • HSDB 3483
    • 7-Angelyl-9-echimidinylretronecine
    • UNII-31NEL09379
    • 2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-hydroxyethyl)-3-methyl-1-oxobutoxy)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester
    • Echimidine Impurity 2
    • ECHIMIDINE [HSDB]
    • ECHIMIDINE, (+)-
    • CHEBI:4744
    • orb1682705
    • SCHEMBL3414540
    • CHEMBL2269162
    • Echimidine 100 microg/mL in Water
    • MFCD02656389
    • AKOS040761651
    • DA-52796
    • FE161548
    • HY-124050
    • CS-0084054
    • NS00067006
    • Q27106462
    • (1R,7aR)-7-[({(2R)-2,3-Dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl}oxy)methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate
    • 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1- HYDROXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A- TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER
    • 2-BUTENOIC ACID, 2-METHYL-, 7-((2,3-DIHYDROXY-2-(1- HYDROXYETHYL)-3-METHYL-1-OXOBUTOXY)METHYL)-2,3,5,7A- TETRAHYDRO-1H-PYRROLIZIN-1-YL ESTER, (1R- (1.ALPHA.(Z),7(2R*,3S*),7A.BETA.))-
    • L-THREO-PENTITOL, 1,5-DIDEOXY-2-C-METHYL-3-C-((((1R,7AR)-2,3,5,7A-TETRAHYDRO-1-(((2Z)-2-METHYL-1-OXO-2-BUTEN-1-YL)OXY)-1H-PYRROLIZIN-7-YL)METHOXY)CARBONYL)-
    • L-THREO-PENTITOL, 1,5-DIDEOXY-2-C-METHYL-3-C-((((1R,7AR)-2,3,5,7A-TETRAHYDRO-1-(((2Z)-2-METHYL-1-OXO-2-BUTENYL)OXY)-1H-PYRROLIZIN-7-YL)METHOXY)CARBONYL)-
    • 520-68-3

  • Applications

    Echimidine (CAS 520-68-3) is a naturally occurring pyrrolizidine alkaloid found in certain plant species and is associated with toxicity, which limits its industrial use. In practice, it is often handled as a reference standard and encountered in analytical workflows. Typical applications include: developing and validating analytical methods to detect echimidine and other pyrrolizidine alkaloids in plant materials and botanical extracts; conducting toxicology and safety assessments to understand hepatotoxic risk; studying natural product chemistry, structure–activity relationships, and biosynthesis; serving as a reference material for quality control and regulatory compliance in botanical products; and supporting academic research on plant defense compounds and secondary metabolism. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 242.82
    methanol 419.56
    isopropanol 140.27
    water 1.42
    ethyl acetate 80.53
    n-propanol 192.69
    acetone 189.87
    n-butanol 148.97
    acetonitrile 48.59
    DMF 394.63
    toluene 15.97
    isobutanol 101.5
    1,4-dioxane 162.33
    methyl acetate 75.65
    THF 366.49
    2-butanone 126.75
    n-pentanol 81.35
    sec-butanol 120.08
    n-hexane 1.54
    ethylene glycol 62.29
    NMP 308.51
    cyclohexane 2.32
    DMSO 472.24
    n-butyl acetate 30.58
    n-octanol 25.05
    chloroform 209.99
    n-propyl acetate 34.04
    acetic acid 486.84
    dichloromethane 161.06
    cyclohexanone 167.93
    propylene glycol 98.39
    isopropyl acetate 48.19
    DMAc 352.2
    2-ethoxyethanol 236.22
    isopentanol 84.14
    n-heptane 0.97
    ethyl formate 77.04
    1,2-dichloroethane 92.88
    n-hexanol 50.62
    2-methoxyethanol 463.79
    isobutyl acetate 20.87
    tetrachloromethane 20.66
    n-pentyl acetate 38.28
    transcutol 283.27
    n-heptanol 32.66
    ethylbenzene 7.58
    MIBK 57.76
    2-propoxyethanol 191.29
    tert-butanol 92.6
    MTBE 36.35
    2-butoxyethanol 116.84
    propionic acid 127.9
    o-xylene 10.7
    formic acid 381.85
    diethyl ether 58.88
    m-xylene 10.97
    p-xylene 8.87
    chlorobenzene 26.03
    dimethyl carbonate 54.63
    n-octane 0.69
    formamide 371.96
    cyclopentanone 213.69
    2-pentanone 113.81
    anisole 23.23
    cyclopentyl methyl ether 72.13
    gamma-butyrolactone 226.33
    1-methoxy-2-propanol 299.65
    pyridine 95.6
    3-pentanone 70.01
    furfural 182.95
    n-dodecane 0.55
    diethylene glycol 177.64
    diisopropyl ether 9.09
    tert-amyl alcohol 84.96
    acetylacetone 122.21
    n-hexadecane 0.61
    acetophenone 39.2
    methyl propionate 87.37
    isopentyl acetate 30.48
    trichloroethylene 212.71
    n-nonanol 24.81
    cyclohexanol 74.65
    benzyl alcohol 50.37
    2-ethylhexanol 18.06
    isooctanol 23.52
    dipropyl ether 15.91
    1,2-dichlorobenzene 28.08
    ethyl lactate 39.4
    propylene carbonate 87.63
    n-methylformamide 248.05
    2-pentanol 67.13
    n-pentane 2.36
    1-propoxy-2-propanol 89.78
    1-methoxy-2-propyl acetate 59.9
    2-(2-methoxypropoxy) propanol 70.74
    mesitylene 5.55
    ε-caprolactone 156.64
    p-cymene 5.34
    epichlorohydrin 285.46
    1,1,1-trichloroethane 56.11
    2-aminoethanol 165.26
    morpholine-4-carbaldehyde 289.51
    sulfolane 281.33
    2,2,4-trimethylpentane 1.59
    2-methyltetrahydrofuran 139.82
    n-hexyl acetate 47.12
    isooctane 0.83
    2-(2-butoxyethoxy)ethanol 114.77
    sec-butyl acetate 22.37
    tert-butyl acetate 44.5
    decalin 1.24
    glycerin 181.78
    diglyme 183.65
    acrylic acid 135.37
    isopropyl myristate 11.57
    n-butyric acid 175.77
    acetyl acetate 48.43
    di(2-ethylhexyl) phthalate 22.72
    ethyl propionate 32.22
    nitromethane 410.55
    1,2-diethoxyethane 46.38
    benzonitrile 33.09
    trioctyl phosphate 15.95
    1-bromopropane 43.79
    gamma-valerolactone 379.72
    n-decanol 14.91
    triethyl phosphate 13.8
    4-methyl-2-pentanol 30.78
    propionitrile 43.29
    vinylene carbonate 87.13
    1,1,2-trichlorotrifluoroethane 280.94
    DMS 37.52
    cumene 5.55
    2-octanol 18.63
    2-hexanone 47.97
    octyl acetate 19.81
    limonene 8.78
    1,2-dimethoxyethane 174.63
    ethyl orthosilicate 13.77
    tributyl phosphate 17.35
    diacetone alcohol 104.8
    N,N-dimethylaniline 18.53
    acrylonitrile 60.32
    aniline 44.2
    1,3-propanediol 234.74
    bromobenzene 20.11
    dibromomethane 91.75
    1,1,2,2-tetrachloroethane 163.75
    2-methyl-cyclohexyl acetate 23.46
    tetrabutyl urea 25.94
    diisobutyl methanol 9.48
    2-phenylethanol 45.75
    styrene 8.04
    dioctyl adipate 22.52
    dimethyl sulfate 103.66
    ethyl butyrate 21.4
    methyl lactate 93.48
    butyl lactate 46.6
    diethyl carbonate 12.68
    propanediol butyl ether 99.55
    triethyl orthoformate 18.2
    p-tert-butyltoluene 5.09
    methyl 4-tert-butylbenzoate 48.95
    morpholine 261.04
    tert-butylamine 29.8
    n-dodecanol 9.03
    dimethoxymethane 245.35
    ethylene carbonate 71.28
    cyrene 90.73
    2-ethoxyethyl acetate 69.39
    2-ethylhexyl acetate 20.13
    1,2,4-trichlorobenzene 38.23
    4-methylpyridine 76.87
    dibutyl ether 13.23
    2,6-dimethyl-4-heptanol 9.48
    DEF 133.92
    dimethyl isosorbide 109.43
    tetrachloroethylene 113.73
    eugenol 56.24
    triacetin 55.37
    span 80 61.92
    1,4-butanediol 88.9
    1,1-dichloroethane 72.33
    2-methyl-1-pentanol 55.4
    methyl formate 157.63
    2-methyl-1-butanol 92.6
    n-decane 1.19
    butyronitrile 44.82
    3,7-dimethyl-1-octanol 20.79
    1-chlorooctane 7.8
    1-chlorotetradecane 2.4
    n-nonane 1.0
    undecane 0.76
    tert-butylcyclohexane 0.98
    cyclooctane 0.85
    cyclopentanol 103.81
    tetrahydropyran 104.81
    tert-amyl methyl ether 34.86
    2,5,8-trioxanonane 113.29
    1-hexene 7.52
    2-isopropoxyethanol 108.21
    2,2,2-trifluoroethanol 176.84
    methyl butyrate 48.0

    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