Azacytidine

Overview IFRA Request a quote

  • Identifiers

    CAS number
    320-67-2

    Molecular formula
    C8H12N4O5

    SMILES
    C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 83.66%
    Sweet 19.58%
    Bitter 19.34%
    Savory 16.99%
    Milky 14.27%
    Burnt 13.38%
    Popcorn 13.25%
    Cooked 12.65%
    Nutty 12.36%
    Meaty 12.28%

     

    Flavor
    Bitter 77.22%
    Odorless 42.81%
    Bland 25.03%
    Sweet-like 24.96%
    Very mild 19.99%
    Cedarleaf 19.39%
    Very slight 19.09%
    Alkaline 19.01%
    Bread crust 19.01%
    Nitrile 18.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.2

    pKa est.
    3.96 (weak acid)

    Molecular weight
    244.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1726°C

    Melting point expt.

    • 442 to 446 °F (decomposes) (NTP, 1992)
    • 229 °C
    • 228-230 °C (decomposes)

    Flash point

    • 291.6 ˚C est.

    Solubility expt.

    • 5 to 10 mg/mL at 70 °F (NTP, 1992)
    • 89000 mg/L
    • 1.21e+01 g/L
    • DMSO 52.7 (mg/mL)
    • Distilled H2O 13.7-14.0 (mg/mL)
    • 0.1 N HCL 27.7-28.0 (mg/mL)
    • 0.1 N NaOH 42.0-43.8 (mg/mL)
    • 35% Ethyl alcohol 14.2-15.0 (mg/mL)
    • >36.6 [ug/mL] (The mean of the results at pH 7.4)

  • Synonyms

    • 5-azacytidine
    • Azacitidine
    • 320-67-2
    • Azacytidine
    • Ladakamycin
    • Mylosar
    • 5-azacitidine
    • Azacitidina
    • Azacitidinum
    • Antibiotic U 18496
    • Onureg
    • U-18496
    • NSC 102816
    • 4-Amino-1-beta-d-ribofuranosyl-1,3,5-triazin-2(1H)-one
    • 4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one
    • DTXSID9020116
    • NSC102816
    • 5-AZCR
    • 5 AZC
    • M801H13NRU
    • U 18496
    • U-18,496
    • DTXCID10116
    • 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
    • CHEBI:2038
    • 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
    • NCI-C01569
    • s-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-
    • 5 Azacytidine
    • 1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-
    • azacitidine for
    • 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydro-1,3,5-triazin-2-one
    • 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,3,5-triazin-2-one
    • RefChem:57658
    • AZACITIDINE AZACITIDINE
    • L01BC07
    • 4-Amino-1-beta-D-ribofuranosyl-D-triazin-2(1H)-one
    • 5'-AZACYTIDINE
    • Vidaza
    • Azacitidinum [INN-Latin]
    • Azacitidina [INN-Spanish]
    • NSC-102816
    • C8H12N4O5
    • MFCD00006539
    • 5-AZAC
    • 4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one
    • WR-183027
    • NCGC00090851-04
    • 1,3,5-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-
    • 5-Aza-xylo-cytidine
    • CCRIS 60
    • 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2-one
    • SMR000857239
    • 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
    • Vidaza (TN)
    • HSDB 6879
    • 5-aza-CR
    • SR-01000075662
    • EINECS 206-280-2
    • Azacitidine;5-AzaC;Ladakamycin
    • BRN 0620461
    • UNII-M801H13NRU
    • Azacitidine (JAN/USAN/INN)
    • Azacitidine [USAN:INN:BAN]
    • 4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one
    • 5-Azacytidine?
    • NS-17
    • 1-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-amino-1,3,5-tri azin-2-one
    • CAS-320-67-2
    • 5-AzadCyD
    • Azacitidine (Vidaza)
    • 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one
    • Azacitidine, 5-AzaC
    • Spectrum_001262
    • 4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one
    • AZACITIDINE [MI]
    • Spectrum2_000786
    • Spectrum3_001509
    • Spectrum4_000922
    • Spectrum5_001166
    • AZACITIDINE [INN]
    • AZACITIDINE [JAN]
    • 5-Azacytidine (Standard)
    • AZACITIDINE [HSDB]
    • AZACITIDINE [IARC]
    • AZACITIDINE [USAN]
    • MolMap_000062
    • 4-Amino-1-.beta.-D-ribofuranosyl-s-triazin-2(1H)-one
    • A 2385
    • AZACITIDINE [VANDF]
    • SCHEMBL3741
    • AZACITIDINE [MART.]
    • CHEMBL1489
    • Azacitidine (5-Azacytidine)
    • Lopac0_000035
    • AZACITIDINE [USP-RS]
    • AZACITIDINE [WHO-DD]
    • BSPBio_003157
    • KBioGR_001444
    • KBioGR_002556
    • KBioSS_001742
    • KBioSS_002565
    • MLS001333121
    • MLS001333122
    • MLS002153249
    • MLS002548894
    • DivK1c_000125
    • SCHEMBL433074
    • SPECTRUM1502111
    • SPBio_000892
    • AZACITIDINE [EMA EPAR]
    • GTPL6796
    • orb1308921
    • BCBcMAP01_000083
    • HMS500G07
    • KBio1_000125
    • KBio2_001742
    • KBio2_002556
    • KBio2_004310
    • KBio2_005124
    • KBio2_006878
    • KBio2_007692
    • KBio3_002657
    • KBio3_003034
    • NMUSYJAQQFHJEW-KVTDHHQDSA-
    • AZACITIDINE [ORANGE BOOK]
    • pyrimidine antimetabolite: inhibits nucleic acid replication
    • 320-67-2

  • Applications

    Azacytidine (CAS 320-67-2) is used in pharmaceutical research and manufacturing as a nucleoside-analogue building block and a precursor for the synthesis of nucleotide/nucleoside-analogue derivatives; in chemical biology and molecular biology research as a reagent and substrate for assays; as an intermediate in the synthesis of nucleotides and related nucleoside-analogue compounds; to support process development and scale-up in drug production; and in academic laboratories as a reference reagent for nucleoside chemistry.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.15
    methanol 4.27
    isopropanol 0.53
    water 68.86
    ethyl acetate 0.08
    n-propanol 0.72
    acetone 0.21
    n-butanol 0.59
    acetonitrile 0.32
    DMF 75.15
    toluene 0.06
    isobutanol 0.34
    1,4-dioxane 0.59
    methyl acetate 0.19
    THF 1.43
    2-butanone 0.31
    n-pentanol 0.24
    sec-butanol 0.45
    n-hexane 0.02
    ethylene glycol 4.85
    NMP 122.84
    cyclohexane 0.07
    DMSO 133.58
    n-butyl acetate 0.23
    n-octanol 0.14
    chloroform 0.09
    n-propyl acetate 0.12
    acetic acid 11.72
    dichloromethane 0.13
    cyclohexanone 1.61
    propylene glycol 7.09
    isopropyl acetate 0.07
    DMAc 46.04
    2-ethoxyethanol 3.91
    isopentanol 0.37
    n-heptane 0.08
    ethyl formate 0.59
    1,2-dichloroethane 0.13
    n-hexanol 0.38
    2-methoxyethanol 15.41
    isobutyl acetate 0.05
    tetrachloromethane 0.09
    n-pentyl acetate 0.14
    transcutol 2.76
    n-heptanol 0.34
    ethylbenzene 0.04
    MIBK 0.16
    2-propoxyethanol 3.33
    tert-butanol 0.48
    MTBE 0.08
    2-butoxyethanol 2.01
    propionic acid 1.85
    o-xylene 0.11
    formic acid 216.82
    diethyl ether 0.12
    m-xylene 0.07
    p-xylene 0.07
    chlorobenzene 0.03
    dimethyl carbonate 0.76
    n-octane 0.03
    formamide 153.42
    cyclopentanone 2.23
    2-pentanone 0.21
    anisole 0.1
    cyclopentyl methyl ether 0.53
    gamma-butyrolactone 4.24
    1-methoxy-2-propanol 6.11
    pyridine 0.93
    3-pentanone 0.26
    furfural 9.07
    n-dodecane 0.01
    diethylene glycol 10.22
    diisopropyl ether 0.04
    tert-amyl alcohol 0.47
    acetylacetone 0.29
    n-hexadecane 0.01
    acetophenone 0.34
    methyl propionate 0.38
    isopentyl acetate 0.23
    trichloroethylene 0.24
    n-nonanol 0.16
    cyclohexanol 0.74
    benzyl alcohol 0.37
    2-ethylhexanol 0.23
    isooctanol 0.22
    dipropyl ether 0.28
    1,2-dichlorobenzene 0.06
    ethyl lactate 1.11
    propylene carbonate 1.68
    n-methylformamide 24.92
    2-pentanol 0.25
    n-pentane 0.04
    1-propoxy-2-propanol 1.9
    1-methoxy-2-propyl acetate 0.7
    2-(2-methoxypropoxy) propanol 1.84
    mesitylene 0.06
    ε-caprolactone 1.72
    p-cymene 0.11
    epichlorohydrin 1.2
    1,1,1-trichloroethane 0.05
    2-aminoethanol 6.51
    morpholine-4-carbaldehyde 30.72
    sulfolane 30.42
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.52
    n-hexyl acetate 0.14
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 2.07
    sec-butyl acetate 0.06
    tert-butyl acetate 0.13
    decalin 0.02
    glycerin 35.33
    diglyme 4.17
    acrylic acid 4.64
    isopropyl myristate 0.07
    n-butyric acid 1.28
    acetyl acetate 0.1
    di(2-ethylhexyl) phthalate 0.24
    ethyl propionate 0.14
    nitromethane 10.8
    1,2-diethoxyethane 0.21
    benzonitrile 0.28
    trioctyl phosphate 0.22
    1-bromopropane 0.07
    gamma-valerolactone 10.41
    n-decanol 0.12
    triethyl phosphate 0.47
    4-methyl-2-pentanol 0.14
    propionitrile 0.27
    vinylene carbonate 1.73
    1,1,2-trichlorotrifluoroethane 14.89
    DMS 0.25
    cumene 0.04
    2-octanol 0.14
    2-hexanone 0.15
    octyl acetate 0.11
    limonene 0.17
    1,2-dimethoxyethane 2.54
    ethyl orthosilicate 0.36
    tributyl phosphate 0.24
    diacetone alcohol 1.31
    N,N-dimethylaniline 0.22
    acrylonitrile 0.7
    aniline 0.32
    1,3-propanediol 6.19
    bromobenzene 0.02
    dibromomethane 0.08
    1,1,2,2-tetrachloroethane 0.28
    2-methyl-cyclohexyl acetate 0.32
    tetrabutyl urea 0.59
    diisobutyl methanol 0.15
    2-phenylethanol 0.46
    styrene 0.03
    dioctyl adipate 0.17
    dimethyl sulfate 5.56
    ethyl butyrate 0.27
    methyl lactate 4.34
    butyl lactate 0.75
    diethyl carbonate 0.24
    propanediol butyl ether 2.06
    triethyl orthoformate 0.4
    p-tert-butyltoluene 0.11
    methyl 4-tert-butylbenzoate 0.76
    morpholine 2.09
    tert-butylamine 0.16
    n-dodecanol 0.09
    dimethoxymethane 3.23
    ethylene carbonate 0.94
    cyrene 6.43
    2-ethoxyethyl acetate 0.23
    2-ethylhexyl acetate 0.18
    1,2,4-trichlorobenzene 0.12
    4-methylpyridine 0.52
    dibutyl ether 0.09
    2,6-dimethyl-4-heptanol 0.15
    DEF 2.31
    dimethyl isosorbide 3.24
    tetrachloroethylene 0.32
    eugenol 1.12
    triacetin 0.37
    span 80 1.31
    1,4-butanediol 2.02
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 0.17
    methyl formate 7.79
    2-methyl-1-butanol 0.39
    n-decane 0.02
    butyronitrile 0.24
    3,7-dimethyl-1-octanol 0.12
    1-chlorooctane 0.04
    1-chlorotetradecane 0.02
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.01
    cyclooctane 0.03
    cyclopentanol 1.17
    tetrahydropyran 0.38
    tert-amyl methyl ether 0.15
    2,5,8-trioxanonane 3.32
    1-hexene 0.04
    2-isopropoxyethanol 1.05
    2,2,2-trifluoroethanol 14.96
    methyl butyrate 0.3

    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