Narciclasine

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  • Identifiers

    CAS number
    29477-83-6

    Molecular formula
    C14H13NO7

    SMILES
    C1OC2=C(O1)C(=C3C(=C2)C4=C[C@@H]([C@H]([C@H]([C@@H]4NC3=O)O)O)O)O

    Safety labels

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 77.52%
    Spicy 20.92%
    Burnt 20.41%
    Sweet 20.4%
    Phenolic 19.73%
    Savory 18.07%
    Vanilla 17.93%
    Bitter 15.85%
    Smoky 15.06%
    Milky 14.86%

     

    Flavor
    Bitter 91.11%
    Bland 26.46%
    Odorless 23.01%
    Sweet-like 22.25%
    Cedarleaf 19.17%
    Lovage 18.39%
    Parsley 17.83%
    Nitrile 17.63%
    Ripe apricot 17.3%
    Cereal 17.28%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.2

    pKa est.
    7.14 (neutral)

    Molecular weight
    307.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2917°C

    Flash point

    • 312.74 ˚C est.

  • Synonyms

    • Narciclasine
    • 29477-83-6
    • Lycoricidinol
    • Lycoricidin-A
    • Narciclasina
    • NSC 266535
    • BRN 1087400
    • Lycorcidinol
    • Nacriclasine
    • NSC266535
    • 3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one
    • (2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
    • CHEMBL98745
    • (2s,3r,4s,4ar)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j]phenanthridin-6(2h)-one
    • CHEBI:70169
    • DTXSID70183677
    • MFCD01729949
    • [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR)-
    • (1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S-(2-alpha,3-beta,4-beta,4a-beta))-
    • (2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one
    • MLS002703039
    • (2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-2H-(1,3)dioxolo(4,5-j)phenanthridin-6-one
    • [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR)-; [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, [2S-(2a,3ss,4ss,4ass)]-; (+)-Lycoricidinol; (+)-Narciclasine; Lycoricidinol
    • [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, [2S-(2.alpha.,3.beta.,4.beta.,4a.beta.)]-
    • Narciclasine (Standard)
    • SCHEMBL625165
    • cid_619061
    • DTXCID10106168
    • Narciclasine, >=98% (HPLC)
    • 2,3,4,4a-Tetrahydro[1,3]dioxolo[4,5-j]phenanthridine-2,3,4,6,7-pentol-, (2S-(2.alpha.,3.beta.,4.beta.,4a.beta.))-
    • BDBM50293603
    • HY-16563R
    • AKOS024457767
    • CS-1051
    • FT74001
    • NSC-266535
    • (2S,3R,4S,4aR)-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one
    • (2S-(2-alpha,3-beta,4-beta,4a-beta))-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one
    • BP-25400
    • DA-56009
    • HY-16563
    • MS-24449
    • NCI60_002146
    • NS00094773
    • C08533
    • BRD-K06792661-001-01-9
    • Q18379239
    • (1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S-(2alpha,3beta,4beta,4abeta))-
    • [1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR)
    • [1,5-j]phenanthridin-6(2H)-one, 3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-, [2S-(2.alpha.,3.beta.,4.beta.,4a.beta.)]-
    • 2,3,4,4a-Tetrahydro(1,3)dioxolo(4,5-j)phenanthridine-2,3,4,6,7-pentol-, (2S-(2alpha,3beta,4beta,4abeta))-
    • 3KF

  • Applications

    Narciclasine (CAS 29477-83-6) is used in pharmaceutical and chemical biology research as a tool to study protein synthesis inhibition via the eEF1A factor, and it is evaluated as a lead scaffold for SAR studies in anticancer research; it is also used as a reference standard in natural product analytics (e.g., LC-MS, HPLC) and as a basis for synthesizing derivatives to expand libraries of analogs and explore structural variation.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.21
    methanol 4.65
    isopropanol 1.26
    water 0.9
    ethyl acetate 0.65
    n-propanol 1.17
    acetone 1.63
    n-butanol 0.94
    acetonitrile 0.95
    DMF 28.43
    toluene 0.13
    isobutanol 0.42
    1,4-dioxane 2.82
    methyl acetate 0.77
    THF 6.44
    2-butanone 1.13
    n-pentanol 0.53
    sec-butanol 0.56
    n-hexane 0.02
    ethylene glycol 10.78
    NMP 26.76
    cyclohexane 0.06
    DMSO 47.74
    n-butyl acetate 0.92
    n-octanol 1.16
    chloroform 0.06
    n-propyl acetate 0.65
    acetic acid 8.44
    dichloromethane 0.07
    cyclohexanone 3.03
    propylene glycol 4.52
    isopropyl acetate 0.6
    DMAc 31.08
    2-ethoxyethanol 11.37
    isopentanol 0.68
    n-heptane 0.08
    ethyl formate 1.54
    1,2-dichloroethane 0.13
    n-hexanol 0.9
    2-methoxyethanol 30.79
    isobutyl acetate 0.24
    tetrachloromethane 0.06
    n-pentyl acetate 1.11
    transcutol 13.5
    n-heptanol 1.55
    ethylbenzene 0.1
    MIBK 0.84
    2-propoxyethanol 11.44
    tert-butanol 1.2
    MTBE 0.2
    2-butoxyethanol 7.89
    propionic acid 1.84
    o-xylene 0.17
    formic acid 41.43
    diethyl ether 0.43
    m-xylene 0.14
    p-xylene 0.13
    chlorobenzene 0.06
    dimethyl carbonate 2.6
    n-octane 0.07
    formamide 52.31
    cyclopentanone 5.05
    2-pentanone 1.07
    anisole 0.31
    cyclopentyl methyl ether 1.13
    gamma-butyrolactone 6.82
    1-methoxy-2-propanol 15.2
    pyridine 1.64
    3-pentanone 0.67
    furfural 7.72
    n-dodecane 0.06
    diethylene glycol 24.57
    diisopropyl ether 0.14
    tert-amyl alcohol 0.62
    acetylacetone 2.66
    n-hexadecane 0.07
    acetophenone 0.93
    methyl propionate 1.49
    isopentyl acetate 0.81
    trichloroethylene 0.19
    n-nonanol 1.24
    cyclohexanol 0.9
    benzyl alcohol 0.92
    2-ethylhexanol 0.55
    isooctanol 0.89
    dipropyl ether 0.81
    1,2-dichlorobenzene 0.09
    ethyl lactate 2.74
    propylene carbonate 2.36
    n-methylformamide 15.59
    2-pentanol 0.48
    n-pentane 0.02
    1-propoxy-2-propanol 6.13
    1-methoxy-2-propyl acetate 3.13
    2-(2-methoxypropoxy) propanol 5.88
    mesitylene 0.12
    ε-caprolactone 3.31
    p-cymene 0.21
    epichlorohydrin 2.39
    1,1,1-trichloroethane 0.05
    2-aminoethanol 7.46
    morpholine-4-carbaldehyde 27.69
    sulfolane 17.56
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.15
    n-hexyl acetate 1.31
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 9.0
    sec-butyl acetate 0.32
    tert-butyl acetate 0.87
    decalin 0.02
    glycerin 24.61
    diglyme 14.28
    acrylic acid 3.51
    isopropyl myristate 0.6
    n-butyric acid 2.03
    acetyl acetate 0.61
    di(2-ethylhexyl) phthalate 0.98
    ethyl propionate 0.66
    nitromethane 12.24
    1,2-diethoxyethane 1.72
    benzonitrile 0.61
    trioctyl phosphate 1.09
    1-bromopropane 0.07
    gamma-valerolactone 17.22
    n-decanol 0.9
    triethyl phosphate 1.04
    4-methyl-2-pentanol 0.36
    propionitrile 0.7
    vinylene carbonate 2.32
    1,1,2-trichlorotrifluoroethane 10.07
    DMS 1.46
    cumene 0.08
    2-octanol 0.83
    2-hexanone 0.67
    octyl acetate 1.01
    limonene 0.29
    1,2-dimethoxyethane 9.16
    ethyl orthosilicate 0.83
    tributyl phosphate 0.93
    diacetone alcohol 5.08
    N,N-dimethylaniline 0.43
    acrylonitrile 1.65
    aniline 0.52
    1,3-propanediol 11.24
    bromobenzene 0.04
    dibromomethane 0.04
    1,1,2,2-tetrachloroethane 0.24
    2-methyl-cyclohexyl acetate 0.92
    tetrabutyl urea 2.33
    diisobutyl methanol 0.42
    2-phenylethanol 1.29
    styrene 0.08
    dioctyl adipate 1.16
    dimethyl sulfate 6.14
    ethyl butyrate 0.93
    methyl lactate 7.43
    butyl lactate 2.76
    diethyl carbonate 0.78
    propanediol butyl ether 7.46
    triethyl orthoformate 1.19
    p-tert-butyltoluene 0.2
    methyl 4-tert-butylbenzoate 2.55
    morpholine 5.82
    tert-butylamine 0.28
    n-dodecanol 0.63
    dimethoxymethane 10.71
    ethylene carbonate 1.94
    cyrene 8.42
    2-ethoxyethyl acetate 2.17
    2-ethylhexyl acetate 0.59
    1,2,4-trichlorobenzene 0.16
    4-methylpyridine 0.92
    dibutyl ether 0.63
    2,6-dimethyl-4-heptanol 0.42
    DEF 4.15
    dimethyl isosorbide 7.88
    tetrachloroethylene 0.29
    eugenol 3.59
    triacetin 2.39
    span 80 4.34
    1,4-butanediol 3.56
    1,1-dichloroethane 0.05
    2-methyl-1-pentanol 0.35
    methyl formate 8.51
    2-methyl-1-butanol 0.44
    n-decane 0.1
    butyronitrile 0.61
    3,7-dimethyl-1-octanol 0.62
    1-chlorooctane 0.25
    1-chlorotetradecane 0.12
    n-nonane 0.09
    undecane 0.07
    tert-butylcyclohexane 0.01
    cyclooctane 0.04
    cyclopentanol 1.4
    tetrahydropyran 1.15
    tert-amyl methyl ether 0.27
    2,5,8-trioxanonane 10.88
    1-hexene 0.06
    2-isopropoxyethanol 3.95
    2,2,2-trifluoroethanol 6.57
    methyl butyrate 1.09

    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