Fumaric Acid

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  • Identifiers

    CAS number
    110-17-8

    Molecular formula
    C4H4O4

    SMILES
    C(=C/C(=O)O)\C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Sour 63.63%
    Odorless 50.56%
    Winey 43.74%
    Caramellic 43.38%
    Sharp 40.65%
    Burnt 40.48%
    Pungent 27.69%
    Buttery 26.22%
    Clean 26.13%
    Nutty 26.04%

    Scent© AI

  • Properties

    XLogP3-AA
    -0.3

    Molecular weight
    116.07 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 572 to 576 °F (NTP, 1992)
    • 287 dec °C
    • 286-302 °C (closed capillary, rapid heating)
    • 287 °C decomposes
    • 549 °C

    Boiling point

    • 329 °F at 1.7 mmHg ; sublimes (NTP, 1992)
    • 522 °C
    • Sublimes at 200 °C

    Flash point est.
    176.96 ˚C

    Flash point expt.

    • 273 °C (open cup)
    • 230 °C (closed cup)
    • 273 °C

    Solubility expt.

    • less than 1 mg/mL at 72 °F (NTP, 1992)
    • 7000 mg/L (at 25 °C)
    • Soluble in ethanol, concentrated sulfuric acid; slightly soluble in ethyl ether, acetone
    • Soluble in alcohol 5.76 g/100 g at 30 °C. Insoluble in chloroform and benzene
    • in 100 g 95% alcohol at 30 °C: 5.76g; in 100 g acetone at 30 °C: 1.72 g; in 100 g ether at 25 °C: 0.72 g
    • Almost insoluble in olive oil, ... carbon tetrachloride, xylene, ... molten camphor, liquid ammonia.
    • In water, 7X10-3 mg/L at 25 °C
    • 7.0 mg/mL
    • Solubility in water, g/100ml at 25 °C: 0.63 (poor)
    • insoluble to slightly soluble in water; soluble in alcohol; slightly soluble in oils.

  • Synonyms

    • fumaric acid
    • 110-17-8
    • trans-Butenedioic acid
    • Allomaleic acid
    • fumarate
    • Boletic acid
    • Lichenic acid
    • (2E)-but-2-enedioic acid
    • Tumaric acid
    • 2-Butenedioic acid
    • trans-1,2-Ethylenedicarboxylic acid
    • (E)-2-Butenedioic acid
    • Allomalenic acid
    • But-2-enedioic acid
    • trans-2-Butenedioic acid
    • Fumaricum acidum
    • 2-Butenedioic acid, (E)-
    • Kyselina fumarova
    • 2-Butenedioic acid (E)-
    • USAF EK-P-583
    • Butenedioic acid, (E)-
    • FEMA No. 2488
    • Butenedioic acid
    • (2E)-2-butenedioic acid
    • (E)-but-2-enedioic acid
    • Caswell No. 465E
    • FEMA Number 2488
    • NSC-2752
    • Fumarsaeure
    • Allomaleic-acid
    • Boletic-acid
    • 2-Butenedioic acid (2E)-
    • 1,2-Ethylenedicarboxylic acid, (E)
    • CCRIS 1039
    • HSDB 710
    • 2-(E)-Butenedioic acid
    • trans-but-2-enedioic acid
    • Futrans-2-Butenedioic Acid
    • U-1149
    • Sodium fumarate
    • (E)-Butenedioic acid
    • 1,2-Ethenedicarboxylic acid, trans-
    • EPA Pesticide Chemical Code 051201
    • AI3-24236
    • 6915-18-0
    • EINECS 203-743-0
    • BRN 0605763
    • Fumaric acid (NF)
    • Fumaric acid [NF]
    • INS NO.297
    • DTXSID3021518
    • UNII-88XHZ13131
    • CHEBI:18012
    • INS-297
    • NSC2752
    • ethylenedicarboxylic acid
    • MFCD00002700
    • 88XHZ13131
    • E297
    • DTXCID601518
    • E-297
    • 2(TRANS)-BUTENEDIOIC ACID
    • EC 203-743-0
    • 4-02-00-02202 (Beilstein Handbook Reference)
    • fum
    • Lichenic acid (VAN)
    • FUMARIC ACID (II)
    • FUMARIC ACID [II]
    • (E)-2-Butenedioate
    • Fumaric acid 1000 microg/mL in Acetonitrile:Water
    • Kyselina fumarova [Czech]
    • FUMARIC ACID (MART.)
    • FUMARIC ACID [MART.]
    • FUMARIC ACID (USP-RS)
    • FUMARIC ACID [USP-RS]
    • (2E)-but-2-enedioate
    • Maleic acid-2,3-13C2
    • FUMARIC ACID (USP IMPURITY)
    • FUMARIC ACID [USP IMPURITY]
    • but-2-enedioicacid
    • CAS-110-17-8
    • fumarate, 10
    • Maleic-2,3-d2 acid
    • trans-1,2-Ethenedicarboxylic acid
    • MALIC ACID IMPURITY A (EP IMPURITY)
    • MALIC ACID IMPURITY A [EP IMPURITY]
    • (E)-1,2-Ethylenedicarboxylic acid
    • trans-1,2-Ethylenediccarboxylic acid
    • E-2-Butenedioic acid
    • Fumaric acid (8CI)
    • FC 33 (acid)
    • SODIUM AUROTHIOMALATE IMPURITY B (EP IMPURITY)
    • SODIUM AUROTHIOMALATE IMPURITY B [EP IMPURITY]
    • fumarsaure
    • Allomaleate
    • Boletate
    • Lichenate
    • Acido lichenico
    • fumeric acid
    • Acido boletico
    • Acido fumarico
    • Acido allomaleico
    • trans-Butenedioate
    • NCGC00091192-02
    • trans-2-Butendisaure
    • trans-2-Butenedioate
    • 2-(E)-Butenedioate
    • Fumaric acid, 99%
    • Acido trans butendioico
    • Fumaric acid (Standard)
    • trans-Ethylendicarbonsaure
    • (Trans)-butenedioic acid
    • F0067
    • Fumaric acid, >=99%
    • FEMA Number: 2488
    • bmse000083
    • FUMARIC ACID [MI]
    • WLN: QV1U1VQ-T
    • FUMARIC ACID [FCC]
    • SCHEMBL1177
    • FUMARIC ACID [FHFI]
    • FUMARIC ACID [HSDB]
    • Butanedioic acid trans-Isomer
    • FUMARIC ACID [VANDF]
    • MLS002454406
    • 1,2-ethylenedicarboxylic acid
    • 2-butenedioic acid, (2E)-
    • (2E)-2-Butenedioic acid #

  • Applications

    Fumaric acid (CAS 110-17-8) is an unsaturated dicarboxylic acid naturally occurring in tart fruits and widely used as an acidulant, flavor enhancer, buffering and antimicrobial agent in beverages, bakery mixes, confectionery and instant noodles; in animal nutrition it acidifies the gut, improves feed efficiency and suppresses pathogenic bacteria; in pharmaceuticals it serves as a precursor to fumarate salts for treating iron-deficiency anemia, psoriasis and multiple sclerosis and as a pH-adjusting excipient in effervescent tablets; in chemical industry it is a key monomer for unsaturated polyester resins, alkyds, 3-D printing resins, plasticizers, lubricants, paper and textile sizing, and modified phenolic resins; it is also employed in metal surface treatment, boiler scale removal, electroplating additives, water-repellent paper manufacturing and as an intermediate to maleic, malic and adipic acids, thereby contributing to the production of lightweight, durable, safe and environmentally friendly materials.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 38.89
    methanol 83.35
    isopropanol 28.99
    water 70.4
    ethyl acetate 2.56
    n-propanol 24.14
    acetone 9.44
    n-butanol 18.96
    acetonitrile 7.94
    DMF 167.53
    toluene 1.35
    isobutanol 15.32
    1,4-dioxane 18.32
    methyl acetate 8.88
    THF 28.13
    2-butanone 8.63
    n-pentanol 13.68
    sec-butanol 19.2
    n-hexane 1.61
    ethylene glycol 48.89
    NMP 61.63
    cyclohexane 0.74
    DMSO 207.37
    n-butyl acetate 4.52
    n-octanol 9.23
    chloroform 5.21
    n-propyl acetate 4.01
    acetic acid 11.04
    dichloromethane 9.79
    cyclohexanone 7.14
    propylene glycol 28.09
    isopropyl acetate 2.08
    DMAc 123.75
    2-ethoxyethanol 38.43
    isopentanol 13.51
    n-heptane 1.38
    ethyl formate 17.44
    1,2-dichloroethane 8.29
    n-hexanol 10.01
    2-methoxyethanol 74.82
    isobutyl acetate 1.9
    tetrachloromethane 2.5
    n-pentyl acetate 4.24
    transcutol 22.3
    n-heptanol 9.07
    ethylbenzene 2.12
    MIBK 3.63
    2-propoxyethanol 26.08
    tert-butanol 29.51
    MTBE 10.14
    2-butoxyethanol 21.21
    propionic acid 9.69
    o-xylene 2.55
    formic acid 46.31
    diethyl ether 6.1
    m-xylene 1.4
    p-xylene 2.65
    chlorobenzene 1.21
    dimethyl carbonate 9.5
    n-octane 0.88
    formamide 62.93
    cyclopentanone 12.75
    2-pentanone 4.56
    anisole 7.79
    cyclopentyl methyl ether 7.49
    gamma-butyrolactone 17.55
    1-methoxy-2-propanol 35.65
    pyridine 8.03
    3-pentanone 3.95
    furfural 26.65
    n-dodecane 0.87
    diethylene glycol 39.29
    diisopropyl ether 1.64
    tert-amyl alcohol 22.04
    acetylacetone 4.57
    n-hexadecane 0.89
    acetophenone 6.75
    methyl propionate 5.9
    isopentyl acetate 3.98
    trichloroethylene 5.9
    n-nonanol 8.19
    cyclohexanol 7.91
    benzyl alcohol 9.16
    2-ethylhexanol 5.01
    isooctanol 6.41
    dipropyl ether 5.33
    1,2-dichlorobenzene 1.9
    ethyl lactate 8.25
    propylene carbonate 8.2
    n-methylformamide 68.19
    2-pentanol 8.89
    n-pentane 1.3
    1-propoxy-2-propanol 16.02
    1-methoxy-2-propyl acetate 5.52
    2-(2-methoxypropoxy) propanol 20.9
    mesitylene 1.39
    ε-caprolactone 8.24
    p-cymene 2.04
    epichlorohydrin 20.62
    1,1,1-trichloroethane 2.68
    2-aminoethanol 51.46
    morpholine-4-carbaldehyde 51.96
    sulfolane 38.44
    2,2,4-trimethylpentane 0.7
    2-methyltetrahydrofuran 12.49
    n-hexyl acetate 5.58
    isooctane 0.42
    2-(2-butoxyethoxy)ethanol 20.66
    sec-butyl acetate 2.13
    tert-butyl acetate 3.3
    decalin 0.77
    glycerin 46.18
    diglyme 43.65
    acrylic acid 10.68
    isopropyl myristate 3.08
    n-butyric acid 7.3
    acetyl acetate 1.54
    di(2-ethylhexyl) phthalate 4.93
    ethyl propionate 4.0
    nitromethane 21.26
    1,2-diethoxyethane 7.33
    benzonitrile 4.72
    trioctyl phosphate 4.83
    1-bromopropane 4.82
    gamma-valerolactone 21.9
    n-decanol 6.48
    triethyl phosphate 5.7
    4-methyl-2-pentanol 4.84
    propionitrile 8.51
    vinylene carbonate 8.76
    1,1,2-trichlorotrifluoroethane 24.46
    DMS 4.38
    cumene 2.16
    2-octanol 5.98
    2-hexanone 5.48
    octyl acetate 4.49
    limonene 2.4
    1,2-dimethoxyethane 65.56
    ethyl orthosilicate 5.44
    tributyl phosphate 4.43
    diacetone alcohol 9.82
    N,N-dimethylaniline 11.53
    acrylonitrile 11.92
    aniline 4.72
    1,3-propanediol 40.21
    bromobenzene 0.9
    dibromomethane 5.68
    1,1,2,2-tetrachloroethane 7.66
    2-methyl-cyclohexyl acetate 4.11
    tetrabutyl urea 9.34
    diisobutyl methanol 3.71
    2-phenylethanol 7.18
    styrene 1.99
    dioctyl adipate 4.77
    dimethyl sulfate 27.52
    ethyl butyrate 3.82
    methyl lactate 14.41
    butyl lactate 7.53
    diethyl carbonate 4.06
    propanediol butyl ether 17.75
    triethyl orthoformate 5.06
    p-tert-butyltoluene 2.12
    methyl 4-tert-butylbenzoate 10.43
    morpholine 26.79
    tert-butylamine 17.36
    n-dodecanol 5.11
    dimethoxymethane 44.26
    ethylene carbonate 7.09
    cyrene 16.6
    2-ethoxyethyl acetate 4.72
    2-ethylhexyl acetate 3.06
    1,2,4-trichlorobenzene 2.23
    4-methylpyridine 9.09
    dibutyl ether 5.16
    2,6-dimethyl-4-heptanol 3.71
    DEF 18.54
    dimethyl isosorbide 22.94
    tetrachloroethylene 6.03
    eugenol 15.43
    triacetin 4.95
    span 80 11.02
    1,4-butanediol 24.16
    1,1-dichloroethane 3.63
    2-methyl-1-pentanol 9.75
    methyl formate 48.59
    2-methyl-1-butanol 13.76
    n-decane 1.21
    butyronitrile 7.79
    3,7-dimethyl-1-octanol 5.75
    1-chlorooctane 3.1
    1-chlorotetradecane 1.59
    n-nonane 1.15
    undecane 1.01
    tert-butylcyclohexane 0.8
    cyclooctane 0.44
    cyclopentanol 13.74
    tetrahydropyran 7.9
    tert-amyl methyl ether 8.68
    2,5,8-trioxanonane 36.75
    1-hexene 3.36
    2-isopropoxyethanol 17.66
    2,2,2-trifluoroethanol 14.18
    methyl butyrate 7.26

    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