AZT (threo)

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  • Identifiers

    CAS number
    73971-82-1

    Molecular formula
    C10H13N5O4

    SMILES
    CC1=CN(C(=O)NC1=O)[C@H]2C[C@H]([C@H](O2)CO)N=[N+]=[N-]

  • Odor profile

    Fragrance
    Odorless 71.63%
    Roasted 24.6%
    Popcorn 22.78%
    Nutty 22.17%
    Burnt 20.67%
    Bitter 18.94%
    Cooked 18.57%
    Savory 17.55%
    Pungent 17.34%
    Meaty 14.86%

     

    Flavor
    Bitter 88.81%
    Odorless 31.55%
    Bland 20.16%
    Nitrile 19.46%
    Bread crust 19.34%
    Taco 19.09%
    Sweet-like 19.09%
    Cedarleaf 18.99%
    Roasted peanuts 18.84%
    Lovage 18.17%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.0

    pKa est.
    6.8 (neutral)

    Molecular weight
    267.24 g/mol

    Flash point

    • 258.62 ˚C est.

  • Synonyms

    • AZT (threo)
    • 73971-82-1
    • 3'-Epizidovudine
    • AzddXyloT
    • P8P26XQA0R
    • UNII-P8P26XQA0R
    • 3'-epi-Azido-3'-deoxythymidine
    • 3'-EPIAZT
    • 1-(3'-Azido-2',3'-dideoxy-beta-D-threo-pentofuranosyl)thymine
    • DTXSID10224710
    • 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
    • 2,4(1H,3H)-Pyrimidinedione, 1-(3-azido-2,3-dideoxy-.beta.-D-threo-pentofuranosyl)-5-methyl-
    • 2,4(1H,3H)-Pyrimidinedione, 1-(3-azido-2,3-dideoxy-beta-D-threo-pentofuranosyl)-5-methyl-
    • 1-(3-AZIDO-2,3-DIDEOXY-.BETA.-D-THREO-PENTOFURANOSYL)-5-METHYL-2,4(1H,3H)-PYRIMIDINEDIONE
    • 1-[(2R,4R,5S)-4-AZIDO-5-(HYDROXYMETHYL)OXOLAN-2-YL]-5-METHYL-PYRIMIDINE-2,4-DIONE
    • 1-((2R,4R,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
    • Azidothymidine; AZT
    • Lopac0_000015
    • CHEMBL26318
    • SCHEMBL13497993
    • DTXCID40147201
    • HMS3260C11
    • AKOS015960720
    • CCG-204111
    • LP00015
    • NA05636
    • SDCCGSBI-0050004.P002
    • NCGC00093540-01
    • HY-17413
    • PD002824
    • EU-0100015
    • A 2169
    • SR-01000075597
    • SR-01000075597-1
    • Q27896268
    • 1-(3'-Azido-2',3'-dideoxy-.beta.-D-threo-pentofuranosyl)thymine
    • AZT;3'-Azido-3'-deoxythymidine;Azitidine;3'-Azido-3'-deoxy-thymidine
    • 1-(3-AZIDO-2,3-DIDEOXY-BETA-D-THREO-PENTOFURANOSYL)-5-METHYL-2,4(1H,3H)-PYRIMIDINEDIONE
    • 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
    • 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione
    • 2,4(1H,3H)-Pyrimidinedione, 1-(3-azido-2,3-dideoxy-ss-D-threo-pentofuranosyl)-5-methyl-; 1-(3-Azido-2,3-dideoxy-ss-D-threo-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione; 3'-epi-Azido-3'-deoxythymidine; 3'-epi-Zidovudine

  • Applications

    AZT (threo), CAS 73971-82-1, is primarily used as a nucleoside-analog building block in medicinal chemistry and pharmaceutical research. In industry and academia, it is commonly employed as a synthesis intermediate for nucleoside analogs, especially in glycosylation and protecting-group strategies, and as a scaffold for exploring structure-activity relationships of azido nucleosides. It can serve as a chiral starting material in small-scale organic syntheses and method development, and is sometimes used as a reference material or analytical standard in nucleoside analysis. Use is subject to local regulations and formulation limits; it should not be construed as a therapeutic claim.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.25
    methanol 3.16
    isopropanol 0.89
    water 1.72
    ethyl acetate 0.32
    n-propanol 0.97
    acetone 1.91
    n-butanol 0.96
    acetonitrile 2.35
    DMF 47.5
    toluene 0.18
    isobutanol 0.71
    1,4-dioxane 1.31
    methyl acetate 0.99
    THF 4.62
    2-butanone 2.67
    n-pentanol 0.77
    sec-butanol 0.8
    n-hexane 0.02
    ethylene glycol 3.2
    NMP 47.47
    cyclohexane 0.02
    DMSO 147.02
    n-butyl acetate 0.81
    n-octanol 0.21
    chloroform 1.44
    n-propyl acetate 0.75
    acetic acid 11.15
    dichloromethane 2.29
    cyclohexanone 6.18
    propylene glycol 3.18
    isopropyl acetate 0.29
    DMAc 75.8
    2-ethoxyethanol 8.52
    isopentanol 1.05
    n-heptane 0.01
    ethyl formate 2.04
    1,2-dichloroethane 1.34
    n-hexanol 0.42
    2-methoxyethanol 17.36
    isobutyl acetate 0.45
    tetrachloromethane 0.2
    n-pentyl acetate 0.52
    transcutol 8.08
    n-heptanol 0.38
    ethylbenzene 0.17
    MIBK 0.97
    2-propoxyethanol 6.24
    tert-butanol 0.9
    MTBE 0.18
    2-butoxyethanol 3.53
    propionic acid 2.62
    o-xylene 0.24
    formic acid 41.49
    diethyl ether 0.15
    m-xylene 0.21
    p-xylene 0.39
    chlorobenzene 0.34
    dimethyl carbonate 1.64
    n-octane 0.01
    formamide 56.46
    cyclopentanone 9.47
    2-pentanone 1.23
    anisole 0.6
    cyclopentyl methyl ether 0.63
    gamma-butyrolactone 11.06
    1-methoxy-2-propanol 7.89
    pyridine 3.72
    3-pentanone 1.04
    furfural 19.71
    n-dodecane 0.01
    diethylene glycol 11.81
    diisopropyl ether 0.05
    tert-amyl alcohol 0.85
    acetylacetone 1.77
    n-hexadecane 0.01
    acetophenone 2.1
    methyl propionate 1.1
    isopentyl acetate 1.05
    trichloroethylene 3.44
    n-nonanol 0.27
    cyclohexanol 0.67
    benzyl alcohol 2.14
    2-ethylhexanol 0.34
    isooctanol 0.36
    dipropyl ether 0.29
    1,2-dichlorobenzene 0.53
    ethyl lactate 2.75
    propylene carbonate 4.49
    n-methylformamide 18.17
    2-pentanol 0.36
    n-pentane 0.01
    1-propoxy-2-propanol 3.22
    1-methoxy-2-propyl acetate 1.84
    2-(2-methoxypropoxy) propanol 5.25
    mesitylene 0.15
    ε-caprolactone 4.96
    p-cymene 0.22
    epichlorohydrin 9.57
    1,1,1-trichloroethane 0.53
    2-aminoethanol 3.87
    morpholine-4-carbaldehyde 28.46
    sulfolane 35.32
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.11
    n-hexyl acetate 0.53
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 5.08
    sec-butyl acetate 0.38
    tert-butyl acetate 0.5
    decalin 0.02
    glycerin 13.68
    diglyme 9.11
    acrylic acid 5.04
    isopropyl myristate 0.28
    n-butyric acid 2.61
    acetyl acetate 0.42
    di(2-ethylhexyl) phthalate 1.22
    ethyl propionate 0.69
    nitromethane 19.21
    1,2-diethoxyethane 0.77
    benzonitrile 2.17
    trioctyl phosphate 0.69
    1-bromopropane 0.37
    gamma-valerolactone 25.46
    n-decanol 0.21
    triethyl phosphate 1.26
    4-methyl-2-pentanol 0.32
    propionitrile 1.6
    vinylene carbonate 5.13
    1,1,2-trichlorotrifluoroethane 21.88
    DMS 1.14
    cumene 0.19
    2-octanol 0.2
    2-hexanone 1.44
    octyl acetate 0.43
    limonene 0.23
    1,2-dimethoxyethane 8.05
    ethyl orthosilicate 0.92
    tributyl phosphate 0.88
    diacetone alcohol 3.2
    N,N-dimethylaniline 0.79
    acrylonitrile 3.97
    aniline 0.9
    1,3-propanediol 5.77
    bromobenzene 0.26
    dibromomethane 1.04
    1,1,2,2-tetrachloroethane 2.52
    2-methyl-cyclohexyl acetate 1.11
    tetrabutyl urea 1.83
    diisobutyl methanol 0.22
    2-phenylethanol 1.47
    styrene 0.19
    dioctyl adipate 0.88
    dimethyl sulfate 7.97
    ethyl butyrate 0.91
    methyl lactate 5.47
    butyl lactate 1.99
    diethyl carbonate 0.89
    propanediol butyl ether 3.59
    triethyl orthoformate 0.99
    p-tert-butyltoluene 0.17
    methyl 4-tert-butylbenzoate 2.47
    morpholine 3.37
    tert-butylamine 0.22
    n-dodecanol 0.16
    dimethoxymethane 5.24
    ethylene carbonate 3.27
    cyrene 11.88
    2-ethoxyethyl acetate 1.02
    2-ethylhexyl acetate 0.74
    1,2,4-trichlorobenzene 0.92
    4-methylpyridine 2.64
    dibutyl ether 0.2
    2,6-dimethyl-4-heptanol 0.22
    DEF 4.38
    dimethyl isosorbide 8.59
    tetrachloroethylene 1.46
    eugenol 3.86
    triacetin 1.52
    span 80 2.91
    1,4-butanediol 3.08
    1,1-dichloroethane 0.57
    2-methyl-1-pentanol 0.89
    methyl formate 9.5
    2-methyl-1-butanol 0.92
    n-decane 0.02
    butyronitrile 1.47
    3,7-dimethyl-1-octanol 0.3
    1-chlorooctane 0.07
    1-chlorotetradecane 0.04
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 1.25
    tetrahydropyran 0.56
    tert-amyl methyl ether 0.28
    2,5,8-trioxanonane 7.61
    1-hexene 0.1
    2-isopropoxyethanol 3.46
    2,2,2-trifluoroethanol 8.14
    methyl butyrate 1.58

    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