Retrorsine

Overview IFRA Request a quote

  • Identifiers

    CAS number
    480-54-6

    Molecular formula
    C18H25NO6

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

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Caramellic 43.71%
    Sweet 42.63%
    Odorless 38.17%
    Nutty 33.85%
    Roasted 31.39%
    Burnt 29.98%
    Popcorn 24.63%
    Spicy 23.28%
    Lactonic 21.23%
    Coconut 20.93%

     

    Flavor
    Bitter 85.4%
    Sweet-like 21.04%
    Cedarleaf 20.45%
    Lovage 19.84%
    Fenugreek 19.7%
    Leaves 19.6%
    Seedy 19.54%
    Cotton candy 19.42%
    Extremely sweet 19.32%
    Parsley 19.19%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    7.8 (neutral)

    Molecular weight
    351.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    973°C

    Melting point expt.

    • 212 °C

    Flash point

    • 239.79 ˚C est.

    Solubility expt.

    • Soluble in chloroform; slightly soluble in acetone, ethanol, water
    • Practically insoluble in ether.
    • In water, 3.08X10+4 mg/L @ 25 °C /Estimated/

  • Synonyms

    • RETRORSINE
    • beta-Longilobine
    • 480-54-6
    • XJ86XWL8IY
    • cis-Retronecic acid ester of retronecine
    • 12,18-Dihydroxy-senecionan-11,16-dione
    • Senecionan-11,16-dione, 12,18-dihydroxy-
    • DTXSID6021242
    • trans-15-Ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-enine
    • NSC-107659
    • 3-Ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-hydroxymethyl-5-methyl(1,6)dioxacyclododeca(2,3,4-gh)pyrrolizidine-2,7-dione
    • (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    • (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo(9.5.1.014,17)heptadec-11-ene-3,8-dione
    • RefChem:930688
    • DTXCID501242
    • 610-403-9
    • 12,18-Dihydroxysenecionan-11,16-dione
    • Retrorsin
    • (15Z)-12,18-dihydroxysenecionan-11,16-dione
    • CCRIS 4338
    • HSDB 3530
    • UNII-XJ86XWL8IY
    • NSC 107659
    • Retrorcine
    • Prestwick_562
    • Retrorsine (Standard)
    • RETRORSINE [MI]
    • Prestwick2_000637
    • Prestwick3_000637
    • RETRORSINE [HSDB]
    • RETRORSINE [IARC]
    • BSPBio_000634
    • MLS002153926
    • SCHEMBL133058
    • BPBio1_000698
    • CHEBI:8822
    • CHEMBL496894
    • orb1684265
    • Retrorsine, >=90% (HPLC)
    • HY-N6638R
    • HMS1545M22
    • HMS1569P16
    • HMS2096P16
    • HMS2231J18
    • HY-N6638
    • MSK40320
    • Retrorsine 100 microg/mL in Water
    • AKOS024282552
    • CCG-208491
    • NCGC00142486-03
    • FR161611
    • MS-25432
    • SMR001233270
    • ST057072
    • CS-0062871
    • G12795
    • SR-01000841220
    • SR-01000841220-3
    • BRD-K42142750-001-01-5
    • BRD-K42142750-001-04-9
    • Q27108154
    • (Z)-ethylidene-hydroxy-(hydroxymethyl)-methyl-[?]dione
    • (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-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-
    • (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0??,??]heptadec-11-ene-3,8-dione
    • (5R,6S,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
    • (7S,1R,6R,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14- azatricyclo[9.5.1.0<14,17>]heptadec-11-ene-3,8-dione
    • 480-54-6

  • Applications

    Retrorsine is primarily used in scientific research as a hepatotoxic pyrrolizidine alkaloid to model liver injury in animal studies and to investigate related mechanisms; it serves as a reference standard for developing and validating analytical methods to quantify pyrrolizidine alkaloids in plants, herbs, and related products; metabolism and pharmacokinetic studies rely on it to understand PA biotransformation and tissue distribution; and it supports risk assessment research on PA exposure in environmental and consumer product contexts, all subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 131.78
    methanol 254.93
    isopropanol 86.98
    water 2.78
    ethyl acetate 89.56
    n-propanol 114.01
    acetone 140.86
    n-butanol 109.69
    acetonitrile 54.57
    DMF 326.08
    toluene 24.63
    isobutanol 74.83
    1,4-dioxane 120.85
    methyl acetate 82.63
    THF 173.1
    2-butanone 96.21
    n-pentanol 58.79
    sec-butanol 74.16
    n-hexane 1.09
    ethylene glycol 75.54
    NMP 247.13
    cyclohexane 2.78
    DMSO 355.37
    n-butyl acetate 48.85
    n-octanol 23.37
    chloroform 197.97
    n-propyl acetate 45.22
    acetic acid 546.82
    dichloromethane 162.41
    cyclohexanone 158.13
    propylene glycol 75.28
    isopropyl acetate 58.73
    DMAc 282.23
    2-ethoxyethanol 167.38
    isopentanol 83.91
    n-heptane 1.22
    ethyl formate 100.77
    1,2-dichloroethane 99.71
    n-hexanol 53.34
    2-methoxyethanol 333.08
    isobutyl acetate 28.57
    tetrachloromethane 24.45
    n-pentyl acetate 49.7
    transcutol 296.6
    n-heptanol 37.34
    ethylbenzene 10.62
    MIBK 60.67
    2-propoxyethanol 164.71
    tert-butanol 69.13
    MTBE 25.9
    2-butoxyethanol 112.2
    propionic acid 148.19
    o-xylene 19.41
    formic acid 483.97
    diethyl ether 40.78
    m-xylene 19.34
    p-xylene 13.38
    chlorobenzene 37.25
    dimethyl carbonate 87.31
    n-octane 0.83
    formamide 486.76
    cyclopentanone 165.52
    2-pentanone 97.09
    anisole 28.33
    cyclopentyl methyl ether 56.32
    gamma-butyrolactone 211.07
    1-methoxy-2-propanol 222.18
    pyridine 115.7
    3-pentanone 62.41
    furfural 206.83
    n-dodecane 0.82
    diethylene glycol 182.83
    diisopropyl ether 10.92
    tert-amyl alcohol 62.14
    acetylacetone 126.94
    n-hexadecane 0.93
    acetophenone 53.52
    methyl propionate 93.52
    isopentyl acetate 46.16
    trichloroethylene 229.19
    n-nonanol 25.32
    cyclohexanol 75.9
    benzyl alcohol 64.23
    2-ethylhexanol 24.6
    isooctanol 29.78
    dipropyl ether 15.72
    1,2-dichlorobenzene 42.04
    ethyl lactate 58.93
    propylene carbonate 123.47
    n-methylformamide 237.36
    2-pentanol 56.98
    n-pentane 2.12
    1-propoxy-2-propanol 91.3
    1-methoxy-2-propyl acetate 83.81
    2-(2-methoxypropoxy) propanol 83.04
    mesitylene 11.18
    ε-caprolactone 154.27
    p-cymene 10.4
    epichlorohydrin 212.08
    1,1,1-trichloroethane 63.51
    2-aminoethanol 123.19
    morpholine-4-carbaldehyde 287.14
    sulfolane 253.53
    2,2,4-trimethylpentane 1.64
    2-methyltetrahydrofuran 82.27
    n-hexyl acetate 52.41
    isooctane 1.2
    2-(2-butoxyethoxy)ethanol 123.92
    sec-butyl acetate 30.87
    tert-butyl acetate 52.5
    decalin 1.79
    glycerin 184.57
    diglyme 192.03
    acrylic acid 184.64
    isopropyl myristate 17.64
    n-butyric acid 209.13
    acetyl acetate 85.1
    di(2-ethylhexyl) phthalate 35.67
    ethyl propionate 42.58
    nitromethane 439.97
    1,2-diethoxyethane 50.58
    benzonitrile 58.02
    trioctyl phosphate 25.65
    1-bromopropane 37.11
    gamma-valerolactone 308.57
    n-decanol 17.7
    triethyl phosphate 26.16
    4-methyl-2-pentanol 33.84
    propionitrile 54.6
    vinylene carbonate 144.16
    1,1,2-trichlorotrifluoroethane 289.05
    DMS 60.7
    cumene 8.48
    2-octanol 20.88
    2-hexanone 46.85
    octyl acetate 27.88
    limonene 13.96
    1,2-dimethoxyethane 138.23
    ethyl orthosilicate 22.97
    tributyl phosphate 28.45
    diacetone alcohol 106.23
    N,N-dimethylaniline 25.26
    acrylonitrile 87.92
    aniline 62.5
    1,3-propanediol 191.5
    bromobenzene 29.96
    dibromomethane 88.77
    1,1,2,2-tetrachloroethane 158.7
    2-methyl-cyclohexyl acetate 34.94
    tetrabutyl urea 37.02
    diisobutyl methanol 14.9
    2-phenylethanol 61.39
    styrene 12.09
    dioctyl adipate 33.01
    dimethyl sulfate 147.34
    ethyl butyrate 34.08
    methyl lactate 129.7
    butyl lactate 63.46
    diethyl carbonate 27.29
    propanediol butyl ether 101.09
    triethyl orthoformate 28.97
    p-tert-butyltoluene 9.58
    methyl 4-tert-butylbenzoate 61.22
    morpholine 166.52
    tert-butylamine 25.82
    n-dodecanol 12.25
    dimethoxymethane 190.5
    ethylene carbonate 119.03
    cyrene 114.57
    2-ethoxyethyl acetate 84.41
    2-ethylhexyl acetate 32.54
    1,2,4-trichlorobenzene 57.76
    4-methylpyridine 91.53
    dibutyl ether 13.3
    2,6-dimethyl-4-heptanol 14.9
    DEF 126.16
    dimethyl isosorbide 116.0
    tetrachloroethylene 122.58
    eugenol 70.46
    triacetin 71.33
    span 80 73.48
    1,4-butanediol 73.79
    1,1-dichloroethane 75.16
    2-methyl-1-pentanol 53.1
    methyl formate 184.8
    2-methyl-1-butanol 81.6
    n-decane 1.34
    butyronitrile 57.38
    3,7-dimethyl-1-octanol 24.21
    1-chlorooctane 8.02
    1-chlorotetradecane 3.49
    n-nonane 1.02
    undecane 1.01
    tert-butylcyclohexane 1.32
    cyclooctane 1.23
    cyclopentanol 80.42
    tetrahydropyran 76.53
    tert-amyl methyl ether 28.09
    2,5,8-trioxanonane 130.97
    1-hexene 5.46
    2-isopropoxyethanol 92.53
    2,2,2-trifluoroethanol 239.05
    methyl butyrate 59.25

    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