Cytochalasin D

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  • Identifiers

    CAS number
    22144-77-0

    Molecular formula
    C30H37NO6

    SMILES
    C[C@H]1C/C=C/[C@H]2[C@@H](C(=C)[C@H]([C@@H]3[C@@]2([C@@H](/C=C/[C@@](C1=O)(C)O)OC(=O)C)C(=O)N[C@H]3CC4=CC=CC=C4)C)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 49.0%
    Spicy 25.51%
    Nutty 22.69%
    Sweet 22.02%
    Caramellic 21.93%
    Burnt 21.24%
    Woody 20.86%
    Roasted 19.85%
    Vanilla 18.6%
    Popcorn 17.97%

     

    Flavor
    Bitter 83.7%
    Cedarleaf 20.05%
    Minty 19.96%
    Lovage 19.22%
    Sweet-like 19.16%
    Fenugreek 18.97%
    Leaves 18.87%
    Orange flower 18.81%
    Nitrile 18.78%
    Orange blossom 18.76%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    5.76 (weak acid)

    Molecular weight
    507.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    1030°C

    Melting point expt.

    • 491 to 500 °F (decomposes) (NTP, 1992)
    • 267-271 °C

    Flash point

    • 248.15 ˚C est.

  • Synonyms

    • cytochalasin D
    • 22144-77-0
    • Cytohalasin D
    • Lygosporin A
    • SY9F0FZ3TO
    • (-)-CYTOCHALASIN D
    • (11)Cytochalasa-6(12),13,19-triene-1,17-dione, 21-(acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E,21R)-
    • NSC-209835
    • 1H-Cycloundec(d)isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-
    • 1H-Cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3-alpha4,5,6,6-alpha,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
    • DTXSID8037099
    • 1H-Cycloundec(d)isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S-(3R*,3aS*,4R*,6R*,6aS*,7E,10R*,12S*,13E,15S*,15aS*))-
    • 7,18-Dihydroxy-10-phenyl-5,16,18-trimethyl-(11)cytochalas-21-acetoxy-6(12),13,19-trien-17-one
    • CHEBI:529996
    • ((1R,2R,3E,5R,7S,9E,11R,12S,14S,15R,16S)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo(9.7.0.01,15)octadeca-3,9-dien-2-yl) acetate
    • [(1R,2R,3E,5R,7S,9E,11R,12S,14S,15R,16S)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate
    • RefChem:130328
    • DTXCID6017099
    • ((1R,2R,3E,5R,7S,9E,11R,14S,15R,16S)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo(9.7.0.01,15)octadeca-3,9-dien-2-yl) acetate
    • 244-804-1
    • 3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1,11-dioxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca(e)isoindol-15-yl acetate
    • MFCD00077706
    • NSC209835
    • UNII-SY9F0FZ3TO
    • HSDB 3549
    • 3eks
    • EINECS 244-804-1
    • NSC 209835
    • SCHEMBL33529
    • CYTOCHALASIN D [HSDB]
    • CHEMBL260287
    • SDZRWUKZFQQKKV-JHADDHBZSA-N
    • HY-N6682
    • EX-A10663
    • AKOS030213128
    • FC29349
    • Cytochalasin D, from Zygosporium mansonii
    • CS-0012977
    • NS00011653
    • F82057
    • Q5201339
    • (benzyl-dihydroxy-trimethyl-methylene-dioxo-[?]yl) acetate
    • Cytochalasin D, from Zygosporium mansonii, >=98% (TLC and HPLC), powder
    • [(1R,2R,3E,5R,7S,9E,11R,12S,14S,15R,16S)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate
    • 1H-Cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3-alpha,4,5,6,6-alpha,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
    • 1H-Cycloundec[d]isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6-12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-
    • 7(S),18(R)-Dihydroxy-16(S),18-dimethyl-10-phenyl(11)cytochalasa-6(12),13(E),19(E)-triene-1,17-dione 21(R)-acetate
    • 22144-77-0

  • Applications

    Cytochalasin D (CAS 22144-77-0) is primarily used as a biochemical tool in life sciences research to inhibit actin polymerization and disrupt the actin cytoskeleton, enabling studies of cell shape, adhesion, and motility; it is widely employed in cancer research to probe mechanisms of cell migration and invasion in vitro; it serves in endocytosis and phagocytosis assays to dissect cytoskeletal requirements; it functions as a laboratory reagent for actin-related biochemical assays and imaging-based experiments; and it is often used in pharmaceutical research and early drug-discovery workflows as a tool compound to explore actin-dependent pathways, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 197.98
    methanol 306.06
    isopropanol 120.27
    water 0.26
    ethyl acetate 77.08
    n-propanol 190.43
    acetone 180.36
    n-butanol 136.47
    acetonitrile 46.28
    DMF 506.87
    toluene 20.39
    isobutanol 87.77
    1,4-dioxane 163.21
    methyl acetate 88.82
    THF 474.39
    2-butanone 150.24
    n-pentanol 75.32
    sec-butanol 80.05
    n-hexane 0.97
    ethylene glycol 46.66
    NMP 466.95
    cyclohexane 1.28
    DMSO 448.99
    n-butyl acetate 31.15
    n-octanol 13.37
    chloroform 153.85
    n-propyl acetate 38.81
    acetic acid 477.4
    dichloromethane 113.46
    cyclohexanone 213.93
    propylene glycol 76.55
    isopropyl acetate 42.09
    DMAc 474.86
    2-ethoxyethanol 185.82
    isopentanol 63.16
    n-heptane 0.61
    ethyl formate 79.24
    1,2-dichloroethane 72.68
    n-hexanol 39.08
    2-methoxyethanol 394.84
    isobutyl acetate 21.27
    tetrachloromethane 15.79
    n-pentyl acetate 31.56
    transcutol 146.16
    n-heptanol 20.9
    ethylbenzene 7.64
    MIBK 42.44
    2-propoxyethanol 166.11
    tert-butanol 48.87
    MTBE 22.43
    2-butoxyethanol 81.88
    propionic acid 137.73
    o-xylene 10.09
    formic acid 232.19
    diethyl ether 50.98
    m-xylene 9.7
    p-xylene 8.99
    chlorobenzene 29.8
    dimethyl carbonate 88.84
    n-octane 0.33
    formamide 220.47
    cyclopentanone 321.21
    2-pentanone 114.79
    anisole 26.6
    cyclopentyl methyl ether 82.4
    gamma-butyrolactone 347.63
    1-methoxy-2-propanol 263.58
    pyridine 125.78
    3-pentanone 73.41
    furfural 201.21
    n-dodecane 0.26
    diethylene glycol 134.7
    diisopropyl ether 6.1
    tert-amyl alcohol 42.91
    acetylacetone 102.84
    n-hexadecane 0.3
    acetophenone 38.16
    methyl propionate 107.84
    isopentyl acetate 26.87
    trichloroethylene 158.43
    n-nonanol 13.87
    cyclohexanol 54.35
    benzyl alcohol 55.94
    2-ethylhexanol 13.36
    isooctanol 14.43
    dipropyl ether 15.18
    1,2-dichlorobenzene 25.84
    ethyl lactate 40.48
    propylene carbonate 119.12
    n-methylformamide 277.86
    2-pentanol 47.57
    n-pentane 1.33
    1-propoxy-2-propanol 78.73
    1-methoxy-2-propyl acetate 59.63
    2-(2-methoxypropoxy) propanol 45.55
    mesitylene 4.35
    ε-caprolactone 185.56
    p-cymene 4.03
    epichlorohydrin 306.3
    1,1,1-trichloroethane 47.03
    2-aminoethanol 125.77
    morpholine-4-carbaldehyde 389.57
    sulfolane 375.3
    2,2,4-trimethylpentane 0.62
    2-methyltetrahydrofuran 143.61
    n-hexyl acetate 34.74
    isooctane 0.38
    2-(2-butoxyethoxy)ethanol 68.38
    sec-butyl acetate 22.19
    tert-butyl acetate 32.61
    decalin 0.83
    glycerin 125.43
    diglyme 116.2
    acrylic acid 147.66
    isopropyl myristate 8.77
    n-butyric acid 185.54
    acetyl acetate 50.67
    di(2-ethylhexyl) phthalate 19.18
    ethyl propionate 34.8
    nitromethane 343.96
    1,2-diethoxyethane 34.39
    benzonitrile 35.6
    trioctyl phosphate 12.75
    1-bromopropane 37.02
    gamma-valerolactone 505.45
    n-decanol 8.36
    triethyl phosphate 14.32
    4-methyl-2-pentanol 18.66
    propionitrile 54.07
    vinylene carbonate 121.41
    1,1,2-trichlorotrifluoroethane 240.77
    DMS 35.16
    cumene 4.69
    2-octanol 10.6
    2-hexanone 50.35
    octyl acetate 16.31
    limonene 6.3
    1,2-dimethoxyethane 146.67
    ethyl orthosilicate 13.28
    tributyl phosphate 13.14
    diacetone alcohol 73.2
    N,N-dimethylaniline 20.22
    acrylonitrile 77.18
    aniline 54.49
    1,3-propanediol 192.16
    bromobenzene 22.98
    dibromomethane 65.23
    1,1,2,2-tetrachloroethane 123.98
    2-methyl-cyclohexyl acetate 23.44
    tetrabutyl urea 21.43
    diisobutyl methanol 6.16
    2-phenylethanol 43.9
    styrene 9.68
    dioctyl adipate 19.73
    dimethyl sulfate 134.77
    ethyl butyrate 22.35
    methyl lactate 108.59
    butyl lactate 38.85
    diethyl carbonate 15.74
    propanediol butyl ether 67.51
    triethyl orthoformate 18.34
    p-tert-butyltoluene 3.69
    methyl 4-tert-butylbenzoate 38.12
    morpholine 291.98
    tert-butylamine 13.95
    n-dodecanol 4.99
    dimethoxymethane 279.36
    ethylene carbonate 99.33
    cyrene 90.46
    2-ethoxyethyl acetate 57.56
    2-ethylhexyl acetate 19.62
    1,2,4-trichlorobenzene 38.42
    4-methylpyridine 103.73
    dibutyl ether 8.47
    2,6-dimethyl-4-heptanol 6.16
    DEF 135.75
    dimethyl isosorbide 74.77
    tetrachloroethylene 78.6
    eugenol 43.92
    triacetin 40.48
    span 80 44.2
    1,4-butanediol 75.05
    1,1-dichloroethane 66.4
    2-methyl-1-pentanol 42.33
    methyl formate 186.54
    2-methyl-1-butanol 70.58
    n-decane 0.55
    butyronitrile 50.74
    3,7-dimethyl-1-octanol 10.29
    1-chlorooctane 4.13
    1-chlorotetradecane 1.24
    n-nonane 0.44
    undecane 0.36
    tert-butylcyclohexane 0.6
    cyclooctane 0.41
    cyclopentanol 100.93
    tetrahydropyran 124.36
    tert-amyl methyl ether 21.94
    2,5,8-trioxanonane 66.86
    1-hexene 6.83
    2-isopropoxyethanol 84.35
    2,2,2-trifluoroethanol 125.58
    methyl butyrate 50.56

    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