Firefly Luciferin

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  • Identifiers

    CAS number
    2591-17-5

    Molecular formula
    C11H8N2O3S2

    SMILES
    C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 58.55%
    Meaty 50.66%
    Roasted 47.11%
    Cooked 37.87%
    Nutty 37.19%
    Savory 33.28%
    Sulfurous 27.49%
    Burnt 23.58%
    Beefy 20.84%
    Popcorn 20.7%

     

    Flavor
    Bitter 74.68%
    Odorless 35.75%
    Roasted 29.55%
    Nutty 25.81%
    Cooked 23.04%
    Bland 21.91%
    Taco 21.26%
    Bread crust 21.04%
    Scallion 20.87%
    Roasted peanuts 20.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    5.43 (weak acid)

    Molecular weight
    280.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    685°C

    Flash point

    • 272.15 ˚C est.

  • Synonyms

    • 2591-17-5
    • Firefly luciferin
    • Photinus luciferin
    • (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
    • (S)-4,5-Dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazole-4-carboxylic acid
    • 5TBB02N29K
    • (S)-4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid
    • CHEBI:17165
    • DTXSID00894865
    • (S)-4,5-Dihydro-2-(6-hydroxy-1,3-benzothiazol-2-yl)thiazole-4-carboxylic acid
    • RefChem:388980
    • DTXCID901324474
    • 219-981-3
    • D-Luciferin
    • Luciferin
    • (S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
    • MFCD00042929
    • D-(-)-Luciferin
    • (S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid
    • C11H8N2O3S2
    • CHEMBL443738
    • D-Luciferin Firefly
    • (4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
    • D-Luciferin, free acid
    • D-firefly luciferin
    • D(-)-LUCIFERIN
    • 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (4S)-
    • D-Luciferin, Potassium Salt
    • UNII-5TBB02N29K
    • Beetle Luciferin
    • EINECS 219-981-3
    • D-Luciferin,freeacid
    • D-Luciferin, synthetic
    • SCHEMBL49401
    • SCHEMBL565455
    • FIREFLY LUCIFERIN [MI]
    • orb1304335
    • EX-A617
    • GLXC-06895
    • 4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxy
    • firefly luciferin (ketone tautomer)
    • BDBM50440036
    • HY-12591A
    • s7763
    • TD8085
    • (2Z,4S)-2-(6-oxo-1,3-benzothiazol-2-ylidene)thiazolidine-4-carboxylic acid
    • (4S)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid
    • AKOS015916008
    • AKOS037644789
    • AC-8545
    • CCG-267246
    • CS-4970
    • FL08607
    • 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (S)-
    • AS-54711
    • PD087236
    • SY060664
    • A5030
    • NS00046724
    • ST50405784
    • EN300-99574
    • C02740
    • L-8200
    • M03620
    • A818071
    • D-Luciferin, synthetic, BioXtra, >=99% (HPLC)
    • Q3265801
    • Q63390514
    • (4S)-2-(6-hydroxybenzothiazol-2-yl)-1,3-thiazoline-4-carboxylic acid
    • 2591-17-5

  • Applications

    Firefly Luciferin (CAS 2591-17-5) is primarily used as the luciferin substrate for luciferase-based bioluminescence assays in life sciences. It enables in vitro and in vivo imaging and reporter gene studies to quantify gene expression, cell viability, and enzyme activity. It underpins luminometric analytical tools and biosensors for ATP detection and other enzymatic assays, supports high-throughput screening in drug discovery workflows, and is employed in diagnostic and research kits that convert biochemical activity into measurable light signals. In addition, it is routinely supplied for educational demonstrations in teaching laboratories to illustrate bioluminescent reactions, with handling and formulation guided by applicable regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.83
    methanol 8.44
    isopropanol 3.68
    water 0.14
    ethyl acetate 2.95
    n-propanol 5.89
    acetone 3.79
    n-butanol 6.33
    acetonitrile 1.81
    DMF 121.26
    toluene 0.34
    isobutanol 3.22
    1,4-dioxane 8.09
    methyl acetate 4.08
    THF 34.64
    2-butanone 7.53
    n-pentanol 5.62
    sec-butanol 5.65
    n-hexane 0.03
    ethylene glycol 12.93
    NMP 38.16
    cyclohexane 0.05
    DMSO 42.26
    n-butyl acetate 4.75
    n-octanol 4.67
    chloroform 0.3
    n-propyl acetate 5.13
    acetic acid 6.83
    dichloromethane 0.42
    cyclohexanone 12.55
    propylene glycol 12.07
    isopropyl acetate 2.79
    DMAc 100.08
    2-ethoxyethanol 46.15
    isopentanol 5.28
    n-heptane 0.1
    ethyl formate 4.68
    1,2-dichloroethane 0.48
    n-hexanol 4.19
    2-methoxyethanol 83.3
    isobutyl acetate 2.51
    tetrachloromethane 0.04
    n-pentyl acetate 5.95
    transcutol 98.44
    n-heptanol 5.47
    ethylbenzene 0.47
    MIBK 4.07
    2-propoxyethanol 39.77
    tert-butanol 3.38
    MTBE 1.39
    2-butoxyethanol 29.82
    propionic acid 5.7
    o-xylene 0.39
    formic acid 16.41
    diethyl ether 1.33
    m-xylene 0.35
    p-xylene 0.61
    chlorobenzene 0.38
    dimethyl carbonate 5.3
    n-octane 0.08
    formamide 32.99
    cyclopentanone 20.87
    2-pentanone 5.99
    anisole 3.35
    cyclopentyl methyl ether 4.77
    gamma-butyrolactone 21.37
    1-methoxy-2-propanol 55.24
    pyridine 7.31
    3-pentanone 3.17
    furfural 23.83
    n-dodecane 0.14
    diethylene glycol 51.31
    diisopropyl ether 0.43
    tert-amyl alcohol 5.27
    acetylacetone 7.77
    n-hexadecane 0.16
    acetophenone 6.75
    methyl propionate 5.97
    isopentyl acetate 4.17
    trichloroethylene 1.21
    n-nonanol 5.36
    cyclohexanol 5.02
    benzyl alcohol 8.08
    2-ethylhexanol 2.87
    isooctanol 4.22
    dipropyl ether 2.48
    1,2-dichlorobenzene 0.52
    ethyl lactate 11.97
    propylene carbonate 7.68
    n-methylformamide 32.13
    2-pentanol 3.48
    n-pentane 0.03
    1-propoxy-2-propanol 24.57
    1-methoxy-2-propyl acetate 10.48
    2-(2-methoxypropoxy) propanol 29.17
    mesitylene 0.28
    ε-caprolactone 14.06
    p-cymene 0.6
    epichlorohydrin 13.73
    1,1,1-trichloroethane 0.13
    2-aminoethanol 19.92
    morpholine-4-carbaldehyde 58.59
    sulfolane 26.46
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 7.29
    n-hexyl acetate 6.57
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 45.63
    sec-butyl acetate 2.88
    tert-butyl acetate 3.25
    decalin 0.06
    glycerin 39.5
    diglyme 56.89
    acrylic acid 7.22
    isopropyl myristate 3.14
    n-butyric acid 7.4
    acetyl acetate 1.51
    di(2-ethylhexyl) phthalate 5.51
    ethyl propionate 4.4
    nitromethane 12.71
    1,2-diethoxyethane 10.56
    benzonitrile 4.27
    trioctyl phosphate 4.14
    1-bromopropane 0.29
    gamma-valerolactone 49.9
    n-decanol 4.15
    triethyl phosphate 3.37
    4-methyl-2-pentanol 2.26
    propionitrile 3.03
    vinylene carbonate 6.69
    1,1,2-trichlorotrifluoroethane 19.45
    DMS 5.26
    cumene 0.39
    2-octanol 4.16
    2-hexanone 6.25
    octyl acetate 4.81
    limonene 0.75
    1,2-dimethoxyethane 45.35
    ethyl orthosilicate 3.16
    tributyl phosphate 4.57
    diacetone alcohol 15.56
    N,N-dimethylaniline 3.2
    acrylonitrile 6.18
    aniline 2.9
    1,3-propanediol 25.15
    bromobenzene 0.23
    dibromomethane 0.19
    1,1,2,2-tetrachloroethane 1.29
    2-methyl-cyclohexyl acetate 4.72
    tetrabutyl urea 10.21
    diisobutyl methanol 1.64
    2-phenylethanol 7.29
    styrene 0.5
    dioctyl adipate 6.32
    dimethyl sulfate 8.89
    ethyl butyrate 4.74
    methyl lactate 19.52
    butyl lactate 14.52
    diethyl carbonate 3.11
    propanediol butyl ether 33.43
    triethyl orthoformate 5.24
    p-tert-butyltoluene 0.55
    methyl 4-tert-butylbenzoate 10.12
    morpholine 22.0
    tert-butylamine 0.94
    n-dodecanol 3.05
    dimethoxymethane 34.22
    ethylene carbonate 5.08
    cyrene 26.26
    2-ethoxyethyl acetate 10.99
    2-ethylhexyl acetate 3.02
    1,2,4-trichlorobenzene 0.91
    4-methylpyridine 5.28
    dibutyl ether 3.42
    2,6-dimethyl-4-heptanol 1.64
    DEF 17.32
    dimethyl isosorbide 31.29
    tetrachloroethylene 0.76
    eugenol 18.62
    triacetin 9.45
    span 80 18.76
    1,4-butanediol 13.09
    1,1-dichloroethane 0.18
    2-methyl-1-pentanol 4.75
    methyl formate 15.52
    2-methyl-1-butanol 5.34
    n-decane 0.2
    butyronitrile 3.43
    3,7-dimethyl-1-octanol 3.48
    1-chlorooctane 0.69
    1-chlorotetradecane 0.44
    n-nonane 0.14
    undecane 0.17
    tert-butylcyclohexane 0.04
    cyclooctane 0.03
    cyclopentanol 6.99
    tetrahydropyran 4.55
    tert-amyl methyl ether 2.25
    2,5,8-trioxanonane 46.66
    1-hexene 0.27
    2-isopropoxyethanol 20.76
    2,2,2-trifluoroethanol 3.98
    methyl butyrate 7.65

    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