Xanthine

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  • Identifiers

    CAS number
    69-89-6

    Molecular formula
    C5H4N4O2

    SMILES
    C1=NC2=C(N1)C(=O)NC(=O)N2

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 67.76%
    Burnt 33.42%
    Bitter 24.63%
    Nutty 22.8%
    Pungent 19.99%
    Cooked 17.85%
    Musty 16.4%
    Roasted 14.98%
    Aromatic 13.44%
    Sour 13.1%

     

    Flavor
    Bitter 89.39%
    Odorless 37.62%
    Nitrile 18.95%
    Rotten 18.62%
    Bread crust 18.55%
    Formyl 18.34%
    Very strong 18.33%
    Indole 17.83%
    Cereal 17.8%
    Moth ball 17.71%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    11.78 (strong base)

    Molecular weight
    152.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    592°C

    Melting point expt.

    • > 300 °C

    Flash point

    • 299.03 ˚C est.

    Solubility expt.

    • 69 mg/L (at 16 °C)
    • 0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt)

  • Synonyms

    • xanthine
    • 69-89-6
    • 2,6-Dihydroxypurine
    • 2,6-dioxopurine
    • Xanthin
    • Xanthic oxide
    • 1H-Purine-2,6-diol
    • 9H-Purine-2,6-diol
    • Isoxanthine
    • Pseudoxanthine
    • 3,7-Dihydro-1H-purine-2,6-dione
    • Purine-2,6-diol
    • 1H-Purine-2,6-dione, 3,7-dihydro-
    • 3,7-dihydropurine-2,6-dione
    • 2,6(1,3)-Purinedion
    • 3,9-dihydro-1H-purine-2,6-dione
    • 2,6-Dioxo-1,2,3,6-tetrahydropurine
    • 1H-Purine-2,6-dione, 3,9-dihydro-
    • 9H-Purine-2,6-(1H,3H)-dione
    • Purine-2,6(1H,3H)-dione
    • 9H-Purine-2,6(1H,3H)-dione
    • 1AVZ07U9S7
    • DTXSID4035120
    • NSC-14664
    • 2,3,6,7-tetrahydro-1H-purine-2,6-dione
    • RefChem:902259
    • DTXCID2015120
    • CHEBI:15318
    • 200-718-6
    • 1H-Purine-2,6(3H,7H)-dione
    • USAF CB-17
    • XAN
    • 9H-xanthine
    • Purine-2(3H),6(1H)-dione
    • MFCD00078453
    • Purine-2,6-(1H,3H)-dione
    • NSC 14664
    • EPA Pesticide Chemical Code 116900
    • AI3-52268
    • 2,3,6,9-tetrahydro-1H-purine-2,6-dione
    • 7H-purine-2,6-diol
    • CHEMBL1424
    • 3,9-dihydropurine-2,6-dione
    • CHEBI:17712
    • purine, 2,6-dihydroxy-
    • 1,3-dihydropurine-2,6-dione
    • Xanthine (VAN)
    • CCRIS 994
    • EINECS 200-718-6
    • UNII-1AVZ07U9S7
    • Dioxopurine
    • Dioxypurin
    • 7H-xanthine
    • 2-Oxohypoxanthine
    • 2,6-dioxypurine
    • 2,6-Dihydroxypurin
    • Xanthine (Standard)
    • Xanthine, 98%
    • Purine-2,3H)-dione
    • Xanthine, >=99%
    • 2uz9
    • XANTHINE [MI]
    • bmse000127
    • MolMap_000070
    • XANTHINE [WHO-DD]
    • Xanthine, p.a., 99%
    • 9H-Purine-2,3H)-dione
    • Cambridge id 5126190
    • SCHEMBL4965
    • SCHEMBL4966
    • Xanthine (VAN) (8CI)
    • 2,2,3,6-tetrahydropurine
    • Oprea1_474175
    • 1H,3H,7H-XANTHINE
    • 1H,3H,9H-XANTHINE
    • SCHEMBL170835
    • SCHEMBL662729
    • SCHEMBL662730
    • SCHEMBL918381
    • Xanthine, BioUltra, >=99%
    • GTPL4557
    • orb1310405
    • SCHEMBL1246788
    • SCHEMBL2733971
    • SCHEMBL6501028
    • SCHEMBL7011289
    • SCHEMBL29180270
    • 3,7-dihydro-purine-2,6-dione
    • 3,9-Dihydro-purine-2,6-dione
    • BDBM82009
    • CHEBI:48517
    • LRFVTYWOQMYALW-UHFFFAOYSA-
    • MSK6930
    • 2,6-Dihydroxypurine; Isoxanthine
    • HMS1659G11
    • HMS3604G12
    • HMS5081J20
    • SMSSF-0052556
    • ALBB-038637
    • BB_SC-09416
    • CAS_1188
    • HY-W017389R
    • NSC_1188
    • NSC14664
    • 1H-purine-2,6(3H, 7H)-dione
    • BBL028159
    • BDBM50227193
    • EBC-06199
    • SBB004054
    • STL064827
    • STL453051
    • AKOS000498219
    • AKOS005208756
    • AKOS015896921
    • AC-8422
    • CCG-266216
    • CS-W018105
    • DB02134
    • EBC-152276
    • FS-3231
    • FX01318
    • HY-W017389
    • SDCCGMLS-0065805.P001
    • CID 5280342
    • 2,6-Dioxo-1,2,3, 6-tetrahydropurine
    • NCGC00164338-01
    • 3,9-dihydro-2H-purine-2,6(1H)-dione
    • 69-89-6

  • Applications

    Xanthine (CAS 69-89-6) is used as an intermediate in the synthesis of methylxanthine derivatives such as caffeine, theophylline, and theobromine; it also serves as a precursor for purine-based fine chemicals and heterocyclic building blocks in specialty chemical manufacturing. In analytical chemistry, xanthine is used as a reference standard or internal standard for HPLC/LC-MS methods to quantify purine compounds. In biological and enzymatic research it functions as a substrate in xanthine oxidase assays and related metabolic studies. In pharmaceutical research it is viewed as a building block for the development of xanthine-based drugs and related medicinal chemistry programs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.02
    methanol 0.05
    isopropanol 0.02
    water 0.09
    ethyl acetate 0.01
    n-propanol 0.02
    acetone 0.01
    n-butanol 0.03
    acetonitrile 0.02
    DMF 1.94
    toluene 0.0
    isobutanol 0.02
    1,4-dioxane 0.03
    methyl acetate 0.03
    THF 0.18
    2-butanone 0.04
    n-pentanol 0.03
    sec-butanol 0.03
    n-hexane 0.0
    ethylene glycol 0.29
    NMP 6.17
    cyclohexane 0.0
    DMSO 6.98
    n-butyl acetate 0.07
    n-octanol 0.02
    chloroform 0.0
    n-propyl acetate 0.03
    acetic acid 0.05
    dichloromethane 0.01
    cyclohexanone 0.06
    propylene glycol 0.28
    isopropyl acetate 0.01
    DMAc 3.36
    2-ethoxyethanol 0.47
    isopentanol 0.04
    n-heptane 0.0
    ethyl formate 0.05
    1,2-dichloroethane 0.01
    n-hexanol 0.03
    2-methoxyethanol 0.94
    isobutyl acetate 0.02
    tetrachloromethane 0.0
    n-pentyl acetate 0.03
    transcutol 0.64
    n-heptanol 0.03
    ethylbenzene 0.0
    MIBK 0.03
    2-propoxyethanol 0.62
    tert-butanol 0.04
    MTBE 0.01
    2-butoxyethanol 0.42
    propionic acid 0.07
    o-xylene 0.0
    formic acid 0.44
    diethyl ether 0.0
    m-xylene 0.0
    p-xylene 0.01
    chlorobenzene 0.0
    dimethyl carbonate 0.08
    n-octane 0.0
    formamide 0.61
    cyclopentanone 0.18
    2-pentanone 0.02
    anisole 0.02
    cyclopentyl methyl ether 0.03
    gamma-butyrolactone 0.4
    1-methoxy-2-propanol 0.66
    pyridine 0.03
    3-pentanone 0.02
    furfural 0.83
    n-dodecane 0.0
    diethylene glycol 1.44
    diisopropyl ether 0.0
    tert-amyl alcohol 0.05
    acetylacetone 0.03
    n-hexadecane 0.0
    acetophenone 0.05
    methyl propionate 0.03
    isopentyl acetate 0.09
    trichloroethylene 0.01
    n-nonanol 0.02
    cyclohexanol 0.02
    benzyl alcohol 0.04
    2-ethylhexanol 0.04
    isooctanol 0.03
    dipropyl ether 0.04
    1,2-dichlorobenzene 0.0
    ethyl lactate 0.29
    propylene carbonate 0.2
    n-methylformamide 0.46
    2-pentanol 0.02
    n-pentane 0.0
    1-propoxy-2-propanol 0.51
    1-methoxy-2-propyl acetate 0.18
    2-(2-methoxypropoxy) propanol 1.0
    mesitylene 0.0
    ε-caprolactone 0.11
    p-cymene 0.01
    epichlorohydrin 0.15
    1,1,1-trichloroethane 0.0
    2-aminoethanol 0.26
    morpholine-4-carbaldehyde 2.1
    sulfolane 3.16
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.05
    n-hexyl acetate 0.03
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 0.66
    sec-butyl acetate 0.02
    tert-butyl acetate 0.02
    decalin 0.0
    glycerin 2.03
    diglyme 1.27
    acrylic acid 0.14
    isopropyl myristate 0.03
    n-butyric acid 0.05
    acetyl acetate 0.01
    di(2-ethylhexyl) phthalate 0.13
    ethyl propionate 0.04
    nitromethane 0.18
    1,2-diethoxyethane 0.05
    benzonitrile 0.04
    trioctyl phosphate 0.08
    1-bromopropane 0.0
    gamma-valerolactone 0.68
    n-decanol 0.02
    triethyl phosphate 0.21
    4-methyl-2-pentanol 0.02
    propionitrile 0.03
    vinylene carbonate 0.12
    1,1,2-trichlorotrifluoroethane 0.72
    DMS 0.07
    cumene 0.01
    2-octanol 0.02
    2-hexanone 0.05
    octyl acetate 0.04
    limonene 0.01
    1,2-dimethoxyethane 0.73
    ethyl orthosilicate 0.15
    tributyl phosphate 0.11
    diacetone alcohol 0.2
    N,N-dimethylaniline 0.04
    acrylonitrile 0.07
    aniline 0.01
    1,3-propanediol 0.25
    bromobenzene 0.0
    dibromomethane 0.0
    1,1,2,2-tetrachloroethane 0.01
    2-methyl-cyclohexyl acetate 0.1
    tetrabutyl urea 0.24
    diisobutyl methanol 0.03
    2-phenylethanol 0.05
    styrene 0.0
    dioctyl adipate 0.08
    dimethyl sulfate 0.69
    ethyl butyrate 0.08
    methyl lactate 0.51
    butyl lactate 0.24
    diethyl carbonate 0.09
    propanediol butyl ether 0.51
    triethyl orthoformate 0.15
    p-tert-butyltoluene 0.01
    methyl 4-tert-butylbenzoate 0.23
    morpholine 0.08
    tert-butylamine 0.01
    n-dodecanol 0.02
    dimethoxymethane 0.23
    ethylene carbonate 0.08
    cyrene 1.61
    2-ethoxyethyl acetate 0.06
    2-ethylhexyl acetate 0.07
    1,2,4-trichlorobenzene 0.01
    4-methylpyridine 0.03
    dibutyl ether 0.02
    2,6-dimethyl-4-heptanol 0.03
    DEF 0.14
    dimethyl isosorbide 1.74
    tetrachloroethylene 0.01
    eugenol 0.49
    triacetin 0.12
    span 80 0.32
    1,4-butanediol 0.18
    1,1-dichloroethane 0.0
    2-methyl-1-pentanol 0.04
    methyl formate 0.22
    2-methyl-1-butanol 0.04
    n-decane 0.0
    butyronitrile 0.03
    3,7-dimethyl-1-octanol 0.03
    1-chlorooctane 0.0
    1-chlorotetradecane 0.0
    n-nonane 0.0
    undecane 0.0
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.05
    tetrahydropyran 0.01
    tert-amyl methyl ether 0.02
    2,5,8-trioxanonane 1.4
    1-hexene 0.0
    2-isopropoxyethanol 0.2
    2,2,2-trifluoroethanol 0.16
    methyl butyrate 0.08

    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