Vidarabine

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  • Identifiers

    CAS number
    5536-17-4

    Molecular formula
    C10H13N5O4

    SMILES
    C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N

    Safety labels

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 81.11%
    Sweet 23.21%
    Bitter 19.01%
    Savory 18.95%
    Milky 15.73%
    Cooked 14.71%
    Burnt 14.66%
    Vanilla 14.25%
    Meaty 13.95%
    Caramellic 13.33%

     

    Flavor
    Bitter 81.36%
    Odorless 41.2%
    Bland 28.22%
    Sweet-like 26.3%
    Cedarleaf 19.24%
    Bread crust 18.98%
    Cereal 18.9%
    Alkaline 18.9%
    Very slight 18.71%
    Scallion 18.69%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.1

    pKa est.
    3.46 (weak acid)

    Molecular weight
    267.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2067°C

    Melting point expt.

    • 500 to 518 °F (NTP, 1992)
    • 257.0-257.5 °C (0.4 H2O)
    • 257.00 °C. @ 760.00 mm Hg

    Flash point

    • 358.42 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 70 °F (NTP, 1992)
    • The monohydrate occurs as a white, crystalline powder and has a solubility of approximately 0.45 mg/mL in water at 25 °C. /Vidarabine monohydrate/
    • 1.40e+01 g/L
    • >40.1 [ug/mL] (The mean of the results at pH 7.4)

  • Synonyms

    • Vidarabine
    • 5536-17-4
    • Adenine arabinoside
    • Ara-A
    • Arabinosyladenine
    • Vira-A
    • Spongoadenosine
    • Araadenosine
    • Arasena-A
    • Vidarabin
    • 9-beta-D-Arabinofuranosyladenine
    • Vidarabine anhydrous
    • Vidarabina
    • Vidarabinum
    • beta-D-Arabinosyladenine
    • NSC-404241
    • 9-beta-D-arabinofuranosyl-9H-purin-6-amine
    • 9-Arabinosyladenine
    • 9-beta-Arabinoadenosine
    • Vidarabine, anhydrous
    • beta-D-Arabinofuranosyladenine
    • CI-673
    • Adenine beta-D-arabinofuranoside
    • Adenine-9-beta-D-arabinofuranoside
    • 3XQD2MEW34
    • Adenine, 9-beta-D-arabinofuranosyl-
    • 9H-Purin-6-amine, 9-beta-D-arabinofuranosyl-
    • Arabinofuranosyladenine
    • (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    • 6-Amino-9-beta-D-arabinofuranosylpurine
    • 2-(6-Amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
    • CI 673
    • NSC-247519
    • NSC-757383
    • (2R,3S,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    • CHEBI:45327
    • alpha-Ara A
    • beta-Ara A
    • Ara A
    • Vira A
    • ViraA
    • CHEBI:9978
    • alpha Ara A
    • 9-beta-D-Arabinofuranosyl-9H-purine-6-amine monohydrate
    • beta Ara A
    • 9-beta-Arabinofuranosyladenine
    • Arabinoside, Adenine
    • 9-beta-D-Arabinofuranosyladenine monohydrate
    • 9 beta Arabinofuranosyladenine
    • alpha D Arabinofuranosyladenine
    • 9 beta D Arabinofuranosyladenine
    • Beta Ara-A
    • RefChem:901851
    • Adenine Arabinoside Anhydrous
    • J05AB03
    • S01AD06
    • 9-beta-D-arabinofuranosyladenine Anyhydrous
    • 226-893-9
    • FA2DM6879K
    • NSC404241
    • Adenine 9-beta-D-arabinofuranoside
    • Arabinosyl adenine
    • (2R,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
    • Arabinoside adenine
    • Vidarabine [INN]
    • MFCD00065471
    • 6-Amino-9-b-D-arabinofuranosylpurine
    • 9beta-D-Arabinofuranosyladenine
    • araA
    • 9-BETA-D-ARABINOFURANOSYL-ADENINE
    • Vira ATM
    • Vidarabine (Vira-A)
    • Adenine 9-beta;-D-arabinofuranoside
    • Vidarabine (JAN)
    • CHEMBL1090
    • Adenine-beta-D-arabinofuranoside
    • 9-(beta-D-Arabinofuranosyl)adenine
    • 9H-Purin-6-amine, 9-.beta.-D-arabinofuranosyl-
    • Vidarabina [DCIT]
    • RAB
    • Vidarabine (monohydrate)
    • Vidarabinum [INN-Latin]
    • (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
    • (+)-Cyclaradine
    • SMR000471872
    • CCRIS 3383
    • Armes (TN)
    • HSDB 6514
    • Adenine, 9beta-D-arabinofuranosyl-
    • EINECS 226-893-9
    • UNII-3XQD2MEW34
    • NSC 247519
    • BRN 0624881
    • AI3-52821
    • 9H-Purin-6-amine, 9beta-D-arabinofuranosyl-
    • DTXSID80873976
    • Vidarabine (Standard)
    • 9-.beta.-D-Arabinofuranosyl-9H-purin-6-amine
    • Spectrum_001894
    • VIDARABINE [MI]
    • Spectrum2_001336
    • Spectrum3_000580
    • Spectrum4_000782
    • Spectrum5_001429
    • VIDARABINE [HSDB]
    • VIDARABINE [WHO-DD]
    • BSPBio_002000
    • KBioGR_001224
    • KBioSS_002424
    • MLS001066352
    • MLS001333133
    • MLS001333134
    • DivK1c_000191
    • SCHEMBL110914
    • SPECTRUM1500609
    • SPBio_001491
    • 9-ss-D-Arabinofuranosyladenine
    • GTPL4806
    • orb1308405
    • 9-ss -D-Arabinofuranosyladenine
    • SCHEMBL29372659
    • 9-(b-D-Arabinofuranosyl)adenine
    • HMS500J13
    • HY-B0277R
    • KBio1_000191
    • KBio2_002418
    • KBio2_004986
    • 5536-17-4

  • Applications

    Vidarabine (CAS 5536-17-4) is used as a nucleoside building block in pharmaceutical synthesis, commonly evaluated as an intermediate for developing nucleoside analogs based on adenosine; in life sciences and biochemical research, it serves as a substrate or tool for enzyme assays involving polymerases and nucleoside metabolism; in chemical manufacturing, it can function as a starting material to prepare more complex nucleoside derivatives; in medicinal chemistry research, it is often used as a reference to optimize the structure and properties of adenosine-like analogs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.38
    methanol 3.94
    isopropanol 0.88
    water 6.45
    ethyl acetate 0.1
    n-propanol 1.54
    acetone 0.17
    n-butanol 1.32
    acetonitrile 0.42
    DMF 30.76
    toluene 0.06
    isobutanol 0.85
    1,4-dioxane 0.75
    methyl acetate 0.26
    THF 2.52
    2-butanone 0.58
    n-pentanol 0.65
    sec-butanol 1.18
    n-hexane 0.03
    ethylene glycol 11.64
    NMP 120.0
    cyclohexane 0.09
    DMSO 13.8
    n-butyl acetate 0.3
    n-octanol 0.25
    chloroform 0.1
    n-propyl acetate 0.19
    acetic acid 11.67
    dichloromethane 0.12
    cyclohexanone 2.43
    propylene glycol 18.11
    isopropyl acetate 0.08
    DMAc 35.18
    2-ethoxyethanol 6.87
    isopentanol 0.81
    n-heptane 0.12
    ethyl formate 0.62
    1,2-dichloroethane 0.13
    n-hexanol 0.75
    2-methoxyethanol 19.86
    isobutyl acetate 0.09
    tetrachloromethane 0.07
    n-pentyl acetate 0.24
    transcutol 5.09
    n-heptanol 0.68
    ethylbenzene 0.05
    MIBK 0.2
    2-propoxyethanol 5.04
    tert-butanol 0.63
    MTBE 0.11
    2-butoxyethanol 3.71
    propionic acid 3.0
    o-xylene 0.11
    formic acid 128.0
    diethyl ether 0.14
    m-xylene 0.06
    p-xylene 0.09
    chlorobenzene 0.05
    dimethyl carbonate 0.61
    n-octane 0.05
    formamide 74.91
    cyclopentanone 3.95
    2-pentanone 0.29
    anisole 0.14
    cyclopentyl methyl ether 0.73
    gamma-butyrolactone 6.56
    1-methoxy-2-propanol 8.64
    pyridine 1.52
    3-pentanone 0.36
    furfural 10.65
    n-dodecane 0.02
    diethylene glycol 15.42
    diisopropyl ether 0.04
    tert-amyl alcohol 0.89
    acetylacetone 0.27
    n-hexadecane 0.02
    acetophenone 0.49
    methyl propionate 0.45
    isopentyl acetate 0.29
    trichloroethylene 0.25
    n-nonanol 0.29
    cyclohexanol 1.57
    benzyl alcohol 0.8
    2-ethylhexanol 0.43
    isooctanol 0.46
    dipropyl ether 0.39
    1,2-dichlorobenzene 0.08
    ethyl lactate 1.55
    propylene carbonate 1.97
    n-methylformamide 15.78
    2-pentanol 0.55
    n-pentane 0.05
    1-propoxy-2-propanol 2.91
    1-methoxy-2-propyl acetate 0.68
    2-(2-methoxypropoxy) propanol 2.61
    mesitylene 0.05
    ε-caprolactone 3.03
    p-cymene 0.13
    epichlorohydrin 1.94
    1,1,1-trichloroethane 0.04
    2-aminoethanol 12.03
    morpholine-4-carbaldehyde 27.22
    sulfolane 27.61
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 1.2
    n-hexyl acetate 0.2
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 3.67
    sec-butyl acetate 0.09
    tert-butyl acetate 0.11
    decalin 0.02
    glycerin 63.73
    diglyme 5.64
    acrylic acid 6.9
    isopropyl myristate 0.11
    n-butyric acid 2.0
    acetyl acetate 0.08
    di(2-ethylhexyl) phthalate 0.35
    ethyl propionate 0.18
    nitromethane 7.01
    1,2-diethoxyethane 0.34
    benzonitrile 0.54
    trioctyl phosphate 0.33
    1-bromopropane 0.09
    gamma-valerolactone 12.93
    n-decanol 0.23
    triethyl phosphate 0.53
    4-methyl-2-pentanol 0.27
    propionitrile 0.48
    vinylene carbonate 1.72
    1,1,2-trichlorotrifluoroethane 15.19
    DMS 0.29
    cumene 0.05
    2-octanol 0.3
    2-hexanone 0.28
    octyl acetate 0.18
    limonene 0.22
    1,2-dimethoxyethane 2.83
    ethyl orthosilicate 0.45
    tributyl phosphate 0.31
    diacetone alcohol 1.4
    N,N-dimethylaniline 0.26
    acrylonitrile 1.15
    aniline 0.51
    1,3-propanediol 10.87
    bromobenzene 0.03
    dibromomethane 0.07
    1,1,2,2-tetrachloroethane 0.3
    2-methyl-cyclohexyl acetate 0.42
    tetrabutyl urea 0.76
    diisobutyl methanol 0.22
    2-phenylethanol 0.78
    styrene 0.05
    dioctyl adipate 0.25
    dimethyl sulfate 3.07
    ethyl butyrate 0.36
    methyl lactate 5.07
    butyl lactate 1.36
    diethyl carbonate 0.28
    propanediol butyl ether 4.09
    triethyl orthoformate 0.56
    p-tert-butyltoluene 0.11
    methyl 4-tert-butylbenzoate 0.85
    morpholine 3.12
    tert-butylamine 0.24
    n-dodecanol 0.17
    dimethoxymethane 2.12
    ethylene carbonate 1.05
    cyrene 9.62
    2-ethoxyethyl acetate 0.4
    2-ethylhexyl acetate 0.25
    1,2,4-trichlorobenzene 0.17
    4-methylpyridine 0.71
    dibutyl ether 0.16
    2,6-dimethyl-4-heptanol 0.22
    DEF 2.07
    dimethyl isosorbide 3.66
    tetrachloroethylene 0.32
    eugenol 1.65
    triacetin 0.5
    span 80 2.31
    1,4-butanediol 4.46
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 0.46
    methyl formate 4.86
    2-methyl-1-butanol 1.07
    n-decane 0.04
    butyronitrile 0.4
    3,7-dimethyl-1-octanol 0.2
    1-chlorooctane 0.06
    1-chlorotetradecane 0.03
    n-nonane 0.04
    undecane 0.03
    tert-butylcyclohexane 0.01
    cyclooctane 0.04
    cyclopentanol 3.0
    tetrahydropyran 0.65
    tert-amyl methyl ether 0.23
    2,5,8-trioxanonane 4.41
    1-hexene 0.07
    2-isopropoxyethanol 1.91
    2,2,2-trifluoroethanol 9.78
    methyl butyrate 0.42

    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