Fumagillin

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  • Identifiers

    CAS number
    23110-15-8

    Molecular formula
    C26H34O7

    SMILES
    CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O)OC)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Spicy 32.14%
    Sweet 28.26%
    Odorless 26.42%
    Fruity 23.17%
    Herbal 21.37%
    Fresh 20.34%
    Tropical 20.27%
    Peach 20.26%
    Warm 19.22%
    Citrus 19.15%

     

    Flavor
    Bitter 44.26%
    Odorless 21.49%
    Oriental 19.55%
    Heather 19.43%
    Nitrile 19.3%
    Broom 19.25%
    Genet 19.09%
    Cedarleaf 19.08%
    Lovage 19.0%
    Basil 18.93%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.0

    pKa est.
    5.97 (weak acid)

    Molecular weight
    458.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    351°C

    Melting point expt.

    • 190-192

    Flash point

    • 199.07 ˚C est.

  • Synonyms

    • fumagillin
    • 23110-15-8
    • Fugillin
    • Fumidil
    • Fumagilina
    • Fumagilline
    • Fumagillinum
    • Fumagillina
    • Amebacilin
    • DTXSID7040736
    • ZGN-201
    • NSC-9168
    • 2,4,6,8-Decatetraenedioic acid, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2,5)oct-6-yl ester
    • 7OW73204U1
    • DTXCID5020736
    • CHEBI:48635
    • (2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
    • 2,4,6,8-DECATETRAENEDIOIC ACID, MONO((3R,4S,5S,6R)-5-METHOXY-4-((2R,3R)-2-METHYL-3-(3-METHYL-2-BUTENYL)OXIRANYL)-1-OXASPIRO(2.5)OCT-6-YL) ESTER, (2E,4E,6E,8E)-
    • Fumidil-B
    • (2E,4E,6E,8E)-10-(((3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro(2.5)oct-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
    • (2E,4E,6E,8E)-10-(((3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro(2.5)octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
    • (2E,4E,6E,8E)-10-[[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy]-10-oxodeca-2,4,6,8-tetraenoic acid
    • RefChem:56275
    • P01AX10
    • 245-433-8
    • (-)-Fumagillin
    • (2E,4E,6E,8E)-10-(((3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
    • Amebacillin
    • Fugilin
    • CHEMBL32838
    • Fumagillin DCH
    • Flisint
    • (2E,4E,6E,8E)-10-(((3R,4S,5S,6R)-5-Methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraeno
    • (2E,4E,6E,8E)-10-{[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
    • CAS-23110-15-8
    • Fumagillina [DCIT]
    • U 5762
    • Fumagilina [INN-Spanish]
    • Fumagilline [INN-French]
    • Fumagillinum [INN-Latin]
    • Fumagillin [INN:BAN:DCF]
    • C26H34O7
    • Fumagillin?
    • CCRIS 9025
    • MFCD03990453
    • UNII-7OW73204U1
    • NCGC00163699-01
    • (2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
    • H-3
    • NSC 9168
    • EINECS 245-433-8
    • Fumagillin (Standard)
    • FUMAGILLIN [MI]
    • FUMAGILLIN [INN]
    • 127913-45-5
    • FUMAGILLIN [MART.]
    • SCHEMBL8130
    • FUMAGILLIN [WHO-DD]
    • orb1300416
    • HY-B0751R
    • EX-A2890
    • HY-B0751
    • Tox21_112066
    • Tox21_302410
    • BDBM50113436
    • HB3901
    • s7784
    • AKOS024456768
    • DB02640
    • EBC-372060
    • FF41669
    • LMPR0103060003
    • MSK000355-100A
    • NCGC00163699-02
    • NCGC00163699-07
    • NCGC00255568-01
    • AC-35866
    • BS-16576
    • DA-63630
    • SR-90144
    • SY074331
    • NS00011722
    • D81922
    • Fumagillin Solution in Acetonitrile, 100ug/mL
    • Q120199
    • (2E,4E,6E,8E)-10-[[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy]-10-oxo-deca-2,4,6,8-tetraenoic acid
    • (2E,4E,6E,8E)-Mono[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] 2,4,6,8-deca tetraenedioic acid ester
    • 2,4,6,8-DECATETRAENEDIOIC ACID, 1-((3R,4S,5S,6R)-5-METHOXY-4-((2R,3R)-2-METHYL-3-(3-METHYL-2-BUTEN-1-YL)-2-OXIRANYL)-1-OXASPIRO(2.5)OCT-6-YL) ESTER, (2E,4E,6E,8E)-
    • 2,4,6,8-DECATETRAENEDIOIC ACID, MONO(4-(1,2-EPOXY-1,5-DIMETHYL-4-HEXENYL)-5-METHOXY-1-OXASPIRO(2.5)OCT-6-YL) ESTER
    • 2,4,6,8-Decatetraenedioic acid, mono(4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2.5)oct-6-yl) ester (VAN)
    • 2,4,6,8-DECATETRAENEDIOIC ACID, MONO(5-METHOXY-4-(2-METHYL-3-(3-METHYL-2-BUTENYL)OXIRANYL)-1-OXASPIRO(2.5)OCT-6-YL) ESTER, (3R- (3.ALPHA.,4.ALPHA.(2R*,3R*),5.BETA.,6.BETA.(2E,4E,6E,8E)))-
    • 2,4,6,8-Decatetraenedioic acid, mono(5-methoxy-4-(2-methyl-3-(3-methyl-2-butenyl)oxiranyl)-1-oxaspiro(2.5)oct-6-yl) ester, (3R-(3alp
    • 2,4,6,8-Decatetraenedioic acid, mono[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester, (2E,4E,6E,8E)-
    • Antibiotic obtained from cultures of Aspergillus fumigatus, or the same substance produced by any other means
    • 23110-15-8

  • Applications

    Fumagillin (CAS 23110-15-8) is a natural-product antibiotic produced by Aspergillus fumigatus, used primarily in apiculture to control Nosema infections in honey bee colonies. Beyond agriculture, it is studied and used as a research tool in pharmaceutical and biomedical research, notably as a MetAP2 inhibitor in anti-angiogenic studies and to probe the mechanism of enzyme action. In the laboratory it serves as a reference compound and investigative agent in enzyme- and parasitology-related assays, and is regarded as a potential lead in medicinal chemistry programs exploring anti-angiogenic drug discovery. Its applications illustrate its multi-disciplinary utility, subject to regulatory and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 33.15
    methanol 25.05
    isopropanol 19.82
    water 0.02
    ethyl acetate 25.16
    n-propanol 33.39
    acetone 52.64
    n-butanol 28.17
    acetonitrile 19.42
    DMF 52.95
    toluene 9.45
    isobutanol 19.34
    1,4-dioxane 38.37
    methyl acetate 28.79
    THF 143.42
    2-butanone 69.22
    n-pentanol 26.13
    sec-butanol 24.6
    n-hexane 0.47
    ethylene glycol 3.55
    NMP 83.61
    cyclohexane 0.95
    DMSO 131.87
    n-butyl acetate 16.27
    n-octanol 7.69
    chloroform 119.63
    n-propyl acetate 20.03
    acetic acid 56.8
    dichloromethane 95.91
    cyclohexanone 88.43
    propylene glycol 8.7
    isopropyl acetate 15.92
    DMAc 150.74
    2-ethoxyethanol 49.09
    isopentanol 19.34
    n-heptane 0.33
    ethyl formate 20.29
    1,2-dichloroethane 49.36
    n-hexanol 15.03
    2-methoxyethanol 49.48
    isobutyl acetate 14.57
    tetrachloromethane 7.31
    n-pentyl acetate 14.85
    transcutol 57.37
    n-heptanol 9.11
    ethylbenzene 5.58
    MIBK 20.56
    2-propoxyethanol 47.78
    tert-butanol 14.44
    MTBE 12.08
    2-butoxyethanol 29.68
    propionic acid 27.83
    o-xylene 5.45
    formic acid 17.73
    diethyl ether 16.42
    m-xylene 4.18
    p-xylene 7.09
    chlorobenzene 16.9
    dimethyl carbonate 12.67
    n-octane 0.21
    formamide 22.75
    cyclopentanone 91.29
    2-pentanone 40.33
    anisole 16.21
    cyclopentyl methyl ether 22.5
    gamma-butyrolactone 75.15
    1-methoxy-2-propanol 38.3
    pyridine 49.0
    3-pentanone 32.99
    furfural 50.95
    n-dodecane 0.28
    diethylene glycol 24.48
    diisopropyl ether 2.69
    tert-amyl alcohol 18.21
    acetylacetone 35.73
    n-hexadecane 0.31
    acetophenone 24.37
    methyl propionate 25.49
    isopentyl acetate 17.55
    trichloroethylene 98.61
    n-nonanol 8.38
    cyclohexanol 21.06
    benzyl alcohol 23.25
    2-ethylhexanol 8.26
    isooctanol 7.96
    dipropyl ether 7.05
    1,2-dichlorobenzene 14.84
    ethyl lactate 16.33
    propylene carbonate 33.12
    n-methylformamide 27.32
    2-pentanol 12.51
    n-pentane 0.47
    1-propoxy-2-propanol 26.82
    1-methoxy-2-propyl acetate 24.5
    2-(2-methoxypropoxy) propanol 27.76
    mesitylene 2.07
    ε-caprolactone 60.64
    p-cymene 3.06
    epichlorohydrin 106.75
    1,1,1-trichloroethane 30.81
    2-aminoethanol 12.8
    morpholine-4-carbaldehyde 57.66
    sulfolane 99.14
    2,2,4-trimethylpentane 0.45
    2-methyltetrahydrofuran 52.77
    n-hexyl acetate 18.32
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 33.11
    sec-butyl acetate 13.69
    tert-butyl acetate 14.74
    decalin 0.73
    glycerin 14.04
    diglyme 51.9
    acrylic acid 24.05
    isopropyl myristate 7.04
    n-butyric acid 41.5
    acetyl acetate 15.73
    di(2-ethylhexyl) phthalate 11.85
    ethyl propionate 17.47
    nitromethane 62.45
    1,2-diethoxyethane 17.98
    benzonitrile 19.5
    trioctyl phosphate 7.56
    1-bromopropane 27.25
    gamma-valerolactone 111.07
    n-decanol 5.86
    triethyl phosphate 10.18
    4-methyl-2-pentanol 7.04
    propionitrile 22.23
    vinylene carbonate 31.17
    1,1,2-trichlorotrifluoroethane 70.69
    DMS 12.72
    cumene 3.87
    2-octanol 4.96
    2-hexanone 34.18
    octyl acetate 10.14
    limonene 4.59
    1,2-dimethoxyethane 51.05
    ethyl orthosilicate 9.53
    tributyl phosphate 9.08
    diacetone alcohol 26.78
    N,N-dimethylaniline 11.12
    acrylonitrile 25.12
    aniline 18.48
    1,3-propanediol 23.99
    bromobenzene 15.89
    dibromomethane 56.1
    1,1,2,2-tetrachloroethane 77.91
    2-methyl-cyclohexyl acetate 16.94
    tetrabutyl urea 13.95
    diisobutyl methanol 3.74
    2-phenylethanol 18.94
    styrene 7.05
    dioctyl adipate 14.09
    dimethyl sulfate 25.35
    ethyl butyrate 13.97
    methyl lactate 19.82
    butyl lactate 15.79
    diethyl carbonate 10.02
    propanediol butyl ether 20.47
    triethyl orthoformate 11.76
    p-tert-butyltoluene 2.31
    methyl 4-tert-butylbenzoate 19.67
    morpholine 63.29
    tert-butylamine 5.61
    n-dodecanol 3.98
    dimethoxymethane 36.11
    ethylene carbonate 26.54
    cyrene 38.62
    2-ethoxyethyl acetate 22.81
    2-ethylhexyl acetate 13.6
    1,2,4-trichlorobenzene 21.69
    4-methylpyridine 38.97
    dibutyl ether 6.91
    2,6-dimethyl-4-heptanol 3.74
    DEF 36.36
    dimethyl isosorbide 39.49
    tetrachloroethylene 38.78
    eugenol 20.99
    triacetin 21.44
    span 80 20.78
    1,4-butanediol 12.87
    1,1-dichloroethane 41.79
    2-methyl-1-pentanol 21.77
    methyl formate 18.28
    2-methyl-1-butanol 21.85
    n-decane 0.48
    butyronitrile 24.07
    3,7-dimethyl-1-octanol 7.5
    1-chlorooctane 3.63
    1-chlorotetradecane 1.38
    n-nonane 0.36
    undecane 0.35
    tert-butylcyclohexane 0.48
    cyclooctane 0.26
    cyclopentanol 27.8
    tetrahydropyran 46.43
    tert-amyl methyl ether 11.76
    2,5,8-trioxanonane 35.65
    1-hexene 3.91
    2-isopropoxyethanol 32.61
    2,2,2-trifluoroethanol 17.08
    methyl butyrate 25.27

    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