Itaconic Anhydride

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  • Identifiers

    CAS number
    25300-97-4

    Molecular formula
    C5H4O3

    SMILES
    C=C1CC(=O)OC1=O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 56.33%
    Burnt 52.53%
    Sweet 46.47%
    Nutty 37.78%
    Odorless 35.05%
    Buttery 29.76%
    Sharp 29.18%
    Tobacco 27.74%
    Sour 24.14%
    Coumarinic 23.99%

     

    Flavor
    Caramel 26.37%
    Maple 24.27%
    Cotton candy 22.1%
    Extremely sweet 21.99%
    Fenugreek 21.97%
    Odorless 21.71%
    Buttery 21.7%
    Seedy 21.6%
    Maple syrup 21.41%
    Sugar 20.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    8.23 (weak base)

    Molecular weight
    112.08 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    223°C

    Flash point

    • 87.43 ˚C est.

  • Synonyms

    • Itaconic anhydride
    • 3-methylideneoxolane-2,5-dione
    • Itaconic acid anhydride
    • Methylenesuccinic anhydride
    • Dihydro-3-methylene-2,5-furandione
    • 2,5-Furandione, dihydro-3-methylene-
    • Succinic anhydride, methylene-
    • Y455KS1U7Q
    • ITACONIC-ANHYDRIDE
    • NSC-43979
    • 25300-97-4
    • UNII-Y455KS1U7Q
    • DTXSID8062230
    • EINECS 218-518-2
    • NSC 43979
    • 3-METHYLIDENEDIHYDROFURAN-2,5-DIONE
    • RefChem:150199
    • Succinic anhydride, methylene
    • Dihydro3methylene2,5furandione
    • DTXCID2036538
    • 2,5Furandione, dihydro3methylene
    • 218-518-2
    • InChI=1/C5H4O3/c1-3-2-4(6)8-5(3)7/h1-2H
    • OFNISBHGPNMTMS-UHFFFAOYSA-N
    • 2170-03-8
    • 2-Methylenesuccinic anhydride
    • 3-methylenedihydrofuran-2,5-dione
    • MFCD00005530
    • 3,4-Dihydro-3-methylene-2,5-furandione
    • 3-Methylenedihydro-2,5-furandione
    • 3-methylenetetrahydrofuran-2,5-dione
    • CHEMBL87967
    • 3-Methylene-dihydro-furan-2,5-dione
    • Adipic Acid Impurity 4
    • Itaconic anhydride, 95%
    • 2, dihydro-3-methylene-
    • Itaconic Anhydride (ITA)
    • SCHEMBL25233
    • orb1301891
    • NSC43972
    • NSC43979
    • BDBM50108508
    • NSC-43972
    • 3-Methylenedihydro-2,5-furandione #
    • AKOS015900399
    • EBC-613042
    • FI29334
    • GS-3259
    • 3-methylene-tetrahydro-furan-2,5-dione
    • SY009111
    • DB-045673
    • CS-0073152
    • I0203
    • NS00026942
    • EN300-99171
    • A20230
    • H10043
    • F615091
    • Q15726050
    • F0001-0774
    • Benzoyl chloride, 2-chloro-5-nitro-;2-Chloro-5-Nitrobenzoyl;2-Chloro-5-nitrobenzoic acid chloride
    • 2170-03-8

  • Applications

    Itaconic Anhydride (CAS 25300-97-4) is used primarily as a reactive monomer and intermediate for bio-based polymers and high-performance resins. It can be incorporated into unsaturated polyesters, alkyds, and related polymer systems to introduce carboxyl functionality and enable crosslinking; it also serves as a versatile crosslinking or curing component in epoxy/anhydride formulations for coatings and adhesives. In industrial manufacturing, it is employed to synthesize specialty polymers, functional monomers, and other chemical intermediates, and it can be a precursor for further derivatization such as esters and ring-opening polymerizations. Itaconic Anhydride is sometimes evaluated as a reactive diluent or plasticizer in resin formulations and as a building block for sustainable, bio-based materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 330.07
    methanol 463.77
    isopropanol 236.35
    water 46.75
    ethyl acetate 118.93
    n-propanol 223.26
    acetone 253.81
    n-butanol 192.72
    acetonitrile 213.63
    DMF 621.32
    toluene 12.04
    isobutanol 146.06
    1,4-dioxane 149.26
    methyl acetate 158.86
    THF 221.0
    2-butanone 182.12
    n-pentanol 183.14
    sec-butanol 238.94
    n-hexane 3.95
    ethylene glycol 145.53
    NMP 475.61
    cyclohexane 1.18
    DMSO 430.02
    n-butyl acetate 45.49
    n-octanol 68.77
    chloroform 47.63
    n-propyl acetate 90.71
    acetic acid 447.07
    dichloromethane 73.87
    cyclohexanone 116.17
    propylene glycol 206.22
    isopropyl acetate 64.41
    DMAc 499.3
    2-ethoxyethanol 381.61
    isopentanol 165.01
    n-heptane 2.49
    ethyl formate 129.63
    1,2-dichloroethane 52.17
    n-hexanol 77.8
    2-methoxyethanol 573.48
    isobutyl acetate 46.81
    tetrachloromethane 3.75
    n-pentyl acetate 44.65
    transcutol 540.57
    n-heptanol 48.92
    ethylbenzene 13.92
    MIBK 88.1
    2-propoxyethanol 217.97
    tert-butanol 231.82
    MTBE 91.76
    2-butoxyethanol 120.63
    propionic acid 184.73
    o-xylene 14.5
    formic acid 289.02
    diethyl ether 80.38
    m-xylene 14.45
    p-xylene 18.44
    chlorobenzene 20.12
    dimethyl carbonate 88.58
    n-octane 1.68
    formamide 441.02
    cyclopentanone 174.5
    2-pentanone 136.67
    anisole 88.69
    cyclopentyl methyl ether 77.56
    gamma-butyrolactone 258.62
    1-methoxy-2-propanol 439.83
    pyridine 85.34
    3-pentanone 78.72
    furfural 258.89
    n-dodecane 2.42
    diethylene glycol 222.85
    diisopropyl ether 21.26
    tert-amyl alcohol 232.48
    acetylacetone 147.99
    n-hexadecane 2.51
    acetophenone 104.43
    methyl propionate 127.87
    isopentyl acetate 42.69
    trichloroethylene 92.42
    n-nonanol 60.22
    cyclohexanol 76.06
    benzyl alcohol 102.73
    2-ethylhexanol 38.32
    isooctanol 41.45
    dipropyl ether 29.16
    1,2-dichlorobenzene 25.41
    ethyl lactate 94.39
    propylene carbonate 145.11
    n-methylformamide 378.53
    2-pentanol 140.64
    n-pentane 3.61
    1-propoxy-2-propanol 127.57
    1-methoxy-2-propyl acetate 74.29
    2-(2-methoxypropoxy) propanol 158.38
    mesitylene 9.98
    ε-caprolactone 135.88
    p-cymene 10.31
    epichlorohydrin 230.26
    1,1,1-trichloroethane 26.16
    2-aminoethanol 246.61
    morpholine-4-carbaldehyde 403.7
    sulfolane 293.47
    2,2,4-trimethylpentane 3.24
    2-methyltetrahydrofuran 152.22
    n-hexyl acetate 85.52
    isooctane 2.58
    2-(2-butoxyethoxy)ethanol 213.15
    sec-butyl acetate 56.12
    tert-butyl acetate 77.81
    decalin 2.88
    glycerin 245.53
    diglyme 264.18
    acrylic acid 203.02
    isopropyl myristate 34.39
    n-butyric acid 162.96
    acetyl acetate 65.58
    di(2-ethylhexyl) phthalate 40.07
    ethyl propionate 89.88
    nitromethane 622.74
    1,2-diethoxyethane 79.05
    benzonitrile 70.53
    trioctyl phosphate 30.6
    1-bromopropane 27.67
    gamma-valerolactone 303.88
    n-decanol 45.31
    triethyl phosphate 30.13
    4-methyl-2-pentanol 79.65
    propionitrile 114.58
    vinylene carbonate 133.51
    1,1,2-trichlorotrifluoroethane 182.63
    DMS 67.46
    cumene 13.86
    2-octanol 40.96
    2-hexanone 119.23
    octyl acetate 47.8
    limonene 13.36
    1,2-dimethoxyethane 346.94
    ethyl orthosilicate 25.68
    tributyl phosphate 37.92
    diacetone alcohol 182.03
    N,N-dimethylaniline 67.15
    acrylonitrile 166.3
    aniline 48.53
    1,3-propanediol 281.45
    bromobenzene 13.25
    dibromomethane 34.18
    1,1,2,2-tetrachloroethane 64.56
    2-methyl-cyclohexyl acetate 41.57
    tetrabutyl urea 57.13
    diisobutyl methanol 23.36
    2-phenylethanol 69.2
    styrene 16.12
    dioctyl adipate 53.36
    dimethyl sulfate 152.16
    ethyl butyrate 45.82
    methyl lactate 146.0
    butyl lactate 64.96
    diethyl carbonate 35.36
    propanediol butyl ether 176.37
    triethyl orthoformate 32.0
    p-tert-butyltoluene 10.05
    methyl 4-tert-butylbenzoate 84.12
    morpholine 225.63
    tert-butylamine 87.52
    n-dodecanol 32.44
    dimethoxymethane 257.05
    ethylene carbonate 90.16
    cyrene 162.64
    2-ethoxyethyl acetate 69.92
    2-ethylhexyl acetate 29.96
    1,2,4-trichlorobenzene 34.85
    4-methylpyridine 108.44
    dibutyl ether 38.61
    2,6-dimethyl-4-heptanol 23.36
    DEF 188.11
    dimethyl isosorbide 166.65
    tetrachloroethylene 30.59
    eugenol 115.56
    triacetin 95.5
    span 80 108.72
    1,4-butanediol 163.22
    1,1-dichloroethane 42.98
    2-methyl-1-pentanol 151.11
    methyl formate 258.02
    2-methyl-1-butanol 160.86
    n-decane 3.45
    butyronitrile 102.57
    3,7-dimethyl-1-octanol 60.27
    1-chlorooctane 17.33
    1-chlorotetradecane 7.8
    n-nonane 2.99
    undecane 2.87
    tert-butylcyclohexane 3.54
    cyclooctane 0.8
    cyclopentanol 111.56
    tetrahydropyran 79.75
    tert-amyl methyl ether 87.35
    2,5,8-trioxanonane 205.36
    1-hexene 20.5
    2-isopropoxyethanol 221.51
    2,2,2-trifluoroethanol 151.89
    methyl butyrate 124.05

    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