Thymoquinone

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  • Identifiers

    CAS number
    490-91-5

    Molecular formula
    C10H12O2

    SMILES
    CC1=CC(=O)C(=CC1=O)C(C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1252.0

  • Odor profile

    Caramellic 75.97%
    Sweet 67.31%
    Burnt 54.38%
    Mint 41.63%
    Tobacco 33.36%
    Roasted 33.34%
    Coffee 31.96%
    Nutty 30.18%
    Spicy 27.46%
    Phenolic 26.8%

    Scent© AI

  • Properties

    XLogP3-AA
    2.0

    Molecular weight
    164.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 44 - 45 °C

    Boiling point

    • 230.00 to 232.00 °C. @ 760.00 mm Hg

    Flash point est.
    111.64 ˚C

  • Synonyms

    • Thymoquinone
    • 490-91-5
    • Thymoquinon
    • p-Cymene-2,5-dione
    • 2-Isopropyl-5-methyl-1,4-benzoquinone
    • p-Mentha-3,6-diene-2,5-dione
    • 2,5-CYCLOHEXADIENE-1,4-DIONE, 2-METHYL-5-(1-METHYLETHYL)-
    • 2-Isopropyl-5-methylbenzoquinone
    • 2-Isopropyl-5-methylcyclohexa-2,5-diene-1,4-dione
    • 2-Isopropyl-5-methyl-p-benzoquinone
    • 5-Isopropyl-2-methyl-1,4-benzoquinone
    • 2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
    • 2-Isopropyl-5-methylbenzo-1,4-quinone
    • NSC 2228
    • 2-Methyl-5-isopropyl-p-benzoquinone
    • CCRIS 7152
    • NSC-2228
    • EINECS 207-721-1
    • O60IE26NUF
    • 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
    • BRN 1939047
    • AI3-17758
    • NSC2228
    • 2,5-Cyclohexadiene-1,4-dione, 5-isopropyl-2-methyl-
    • MFCD00001602
    • UNII-O60IE26NUF
    • 2-Methyl-5-isopropyl-1,4-benzoquinone
    • 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione
    • CHEBI:113532
    • 5-Isopropyl-2-methyl-p-benzoquinone
    • 5-Isopropyl-2-methyl-2,5-Cyclohexadiene-1,4-dione
    • thymolquinone
    • Thymoil
    • 4hco
    • p-Mentha-3,5-dione
    • Spectrum_001237
    • Thymoquinone (Standard)
    • SpecPlus_000457
    • Thymoquinone, >=98%
    • Spectrum2_000700
    • Spectrum3_001345
    • Spectrum4_001895
    • Spectrum5_000550
    • BSPBio_003129
    • KBioGR_002455
    • KBioSS_001717
    • DivK1c_006553
    • SCHEMBL542535
    • THYMOQUINONE [WHO-DD]
    • SPBio_000859
    • CHEMBL1672002
    • DTXSID9060079
    • HY-D0803R
    • KBio1_001497
    • KBio2_001717
    • KBio2_004285
    • KBio2_006853
    • KBio3_002349
    • Thymoquinone, analytical standard
    • 2-Methyl-5-iso-propylbenzoquinone
    • BDBM166686
    • BCP16946
    • HY-D0803
    • WLN: L6V DVJ B1 EY1&1
    • 2,4-dione, 5-isopropyl-2-methyl-
    • CCG-40027
    • s4761
    • AKOS003368628
    • FT09858
    • NCGC00178250-01
    • NCGC00178250-05
    • AS-11327
    • DA-68178
    • p-Mentha-3,6-diene-2,5-dione (8CI)
    • 2-Isopropyl-5-methylbenzo-1,4-quinone #
    • 2,4-dione, 2-methyl-5-(1-methylethyl)-
    • CS-0012226
    • NS00031853
    • T0795
    • EN300-264364
    • T72517
    • SR-05000002192
    • Q7799650
    • SR-05000002192-2
    • BRD-K97566842-001-03-5
    • Thymoquinone; 2-isopropyl-5-methylbenzo-1,4-quinone
    • Z1255372388
    • 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione (F8)
    • 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione, 9CI
    • InChI=1/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H
    • 207-721-1

  • Applications

    Thymoquinone (CAS 490-91-5), the principal bioactive quinone of Nigella sativa (black seed), is widely used in research and product development for its antioxidant, anti-inflammatory, antimicrobial/antifungal, and immunomodulatory activities; it is investigated as an adjuvant/lead in oncology (anti-proliferative, pro-apoptotic, anti-metastatic, and modulation of pathways such as NF-κB and PI3K/Akt), hepatorenal protection (reducing oxidative stress and modulating detox enzymes), cardiovascular support (improving dyslipidemia and endothelial inflammation), neuroprotection (with potential in Alzheimer’s/Parkinson’s models), and metabolic health (supporting glycemic control and insulin resistance in preclinical models), and is applied in pharmaceutical/nutraceutical formulations via micro/nano-encapsulation to improve solubility and bioavailability; it also serves as an analytical standard, quality reference material, and biological control in preclinical pharmacology screens; note that therapeutic uses remain under investigation and require clinical evidence plus proper safety, interaction, and dosing evaluation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 47.78
    methanol 38.63
    isopropanol 74.86
    water 0.57
    ethyl acetate 61.71
    n-propanol 60.98
    acetone 96.53
    n-butanol 80.73
    acetonitrile 94.82
    DMF 260.4
    toluene 109.58
    isobutanol 57.99
    1,4-dioxane 152.36
    methyl acetate 105.24
    THF 181.11
    2-butanone 118.89
    n-pentanol 60.28
    sec-butanol 84.01
    n-hexane 8.1
    ethylene glycol 11.1
    NMP 211.54
    cyclohexane 15.84
    DMSO 69.52
    n-butyl acetate 84.13
    n-octanol 51.98
    chloroform 368.19
    n-propyl acetate 59.68
    acetic acid 54.55
    dichloromethane 281.37
    cyclohexanone 177.96
    propylene glycol 13.06
    isopropyl acetate 45.81
    DMAc 216.77
    2-ethoxyethanol 53.75
    isopentanol 69.68
    n-heptane 7.63
    ethyl formate 78.98
    1,2-dichloroethane 143.8
    n-hexanol 80.99
    2-methoxyethanol 77.11
    isobutyl acetate 43.51
    tetrachloromethane 56.84
    n-pentyl acetate 59.23
    transcutol 98.79
    n-heptanol 46.74
    ethylbenzene 76.25
    MIBK 59.14
    2-propoxyethanol 92.13
    tert-butanol 84.36
    MTBE 61.89
    2-butoxyethanol 65.7
    propionic acid 55.9
    o-xylene 82.23
    formic acid 18.4
    diethyl ether 49.5
    m-xylene 80.41
    p-xylene 103.78
    chlorobenzene 123.3
    dimethyl carbonate 40.85
    n-octane 6.38
    formamide 36.52
    cyclopentanone 189.99
    2-pentanone 81.3
    anisole 101.04
    cyclopentyl methyl ether 71.87
    gamma-butyrolactone 187.26
    1-methoxy-2-propanol 65.75
    pyridine 190.97
    3-pentanone 70.79
    furfural 190.58
    n-dodecane 6.57
    diethylene glycol 60.81
    diisopropyl ether 21.36
    tert-amyl alcohol 80.92
    acetylacetone 81.8
    n-hexadecane 7.74
    acetophenone 104.39
    methyl propionate 67.77
    isopentyl acetate 82.61
    trichloroethylene 332.07
    n-nonanol 46.25
    cyclohexanol 83.3
    benzyl alcohol 87.83
    2-ethylhexanol 56.56
    isooctanol 39.47
    dipropyl ether 35.75
    1,2-dichlorobenzene 114.99
    ethyl lactate 40.28
    propylene carbonate 122.56
    n-methylformamide 74.61
    2-pentanol 54.67
    n-pentane 7.66
    1-propoxy-2-propanol 68.1
    1-methoxy-2-propyl acetate 72.91
    2-(2-methoxypropoxy) propanol 70.38
    mesitylene 50.09
    ε-caprolactone 144.3
    p-cymene 46.33
    epichlorohydrin 189.7
    1,1,1-trichloroethane 169.38
    2-aminoethanol 22.76
    morpholine-4-carbaldehyde 164.29
    sulfolane 161.49
    2,2,4-trimethylpentane 7.49
    2-methyltetrahydrofuran 127.51
    n-hexyl acetate 83.28
    isooctane 5.97
    2-(2-butoxyethoxy)ethanol 75.11
    sec-butyl acetate 45.66
    tert-butyl acetate 56.17
    decalin 15.39
    glycerin 22.21
    diglyme 119.74
    acrylic acid 51.72
    isopropyl myristate 38.31
    n-butyric acid 80.07
    acetyl acetate 49.54
    di(2-ethylhexyl) phthalate 45.1
    ethyl propionate 56.68
    nitromethane 103.91
    1,2-diethoxyethane 57.65
    benzonitrile 131.69
    trioctyl phosphate 31.88
    1-bromopropane 93.06
    gamma-valerolactone 194.76
    n-decanol 36.46
    triethyl phosphate 43.83
    4-methyl-2-pentanol 36.56
    propionitrile 86.95
    vinylene carbonate 125.95
    1,1,2-trichlorotrifluoroethane 103.94
    DMS 71.26
    cumene 50.69
    2-octanol 39.85
    2-hexanone 73.52
    octyl acetate 48.33
    limonene 54.24
    1,2-dimethoxyethane 120.19
    ethyl orthosilicate 40.28
    tributyl phosphate 33.96
    diacetone alcohol 73.64
    N,N-dimethylaniline 77.42
    acrylonitrile 114.09
    aniline 95.79
    1,3-propanediol 45.27
    bromobenzene 132.92
    dibromomethane 203.46
    1,1,2,2-tetrachloroethane 228.26
    2-methyl-cyclohexyl acetate 66.35
    tetrabutyl urea 50.61
    diisobutyl methanol 33.5
    2-phenylethanol 97.1
    styrene 82.44
    dioctyl adipate 52.69
    dimethyl sulfate 57.99
    ethyl butyrate 65.77
    methyl lactate 39.26
    butyl lactate 50.79
    diethyl carbonate 55.46
    propanediol butyl ether 52.68
    triethyl orthoformate 47.99
    p-tert-butyltoluene 42.18
    methyl 4-tert-butylbenzoate 85.8
    morpholine 137.7
    tert-butylamine 53.61
    n-dodecanol 29.11
    dimethoxymethane 88.43
    ethylene carbonate 98.29
    cyrene 82.81
    2-ethoxyethyl acetate 66.26
    2-ethylhexyl acetate 68.28
    1,2,4-trichlorobenzene 131.06
    4-methylpyridine 197.09
    dibutyl ether 41.01
    2,6-dimethyl-4-heptanol 33.5
    DEF 99.21
    dimethyl isosorbide 124.83
    tetrachloroethylene 144.54
    eugenol 84.64
    triacetin 70.1
    span 80 59.66
    1,4-butanediol 23.53
    1,1-dichloroethane 164.47
    2-methyl-1-pentanol 65.01
    methyl formate 75.72
    2-methyl-1-butanol 68.98
    n-decane 9.85
    butyronitrile 97.58
    3,7-dimethyl-1-octanol 48.57
    1-chlorooctane 39.47
    1-chlorotetradecane 18.44
    n-nonane 8.82
    undecane 7.94
    tert-butylcyclohexane 13.62
    cyclooctane 6.04
    cyclopentanol 81.76
    tetrahydropyran 115.83
    tert-amyl methyl ether 56.37
    2,5,8-trioxanonane 96.65
    1-hexene 32.73
    2-isopropoxyethanol 49.41
    2,2,2-trifluoroethanol 31.11
    methyl butyrate 82.56

    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

Botanical

Name CAS Botanical Proportion
Nigella sativa seed Nigella sativa L., fam. Ranunculaceae 24.5%
Thyme (Italy) 1 8007-46-3 Thymus vulgaris L., fam. Lamiaceae (Labiatae) 0.01%
Savory, winter (Italy) 3 90106-57-3 Satureja montana L., fam. Lamiaceae (Labiatae) 0.17%
Origanum husnuca-baserii (Turkey) Origanum husnucan-baserii H. Duman, Z. Aytac et A. Duran, fam. Lamiaceae 0.07%
Oregano, spanish (Israel) 4 8007-11-2 Coridothymus capitatus Rchb. (Thymus capitatus Hoffm. et Link.), Lamiaceae 1.0%
Thymus pubescens (Iran) 1 Thymus pubescens Boiss. et Kotschy ex Celak, fam. Lamiaceae (Labiatae) 2.7%
Savory, winter (Bulgaria) 90106-57-3 Satureja montana L. ssp. kitaibelii Wierzb., fam. Lamiaceae (Labiatae) 0.3%