Thymoquinone

Thymoquinone
Names
Preferred IUPAC name
2-Methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
Other names
Thymoquinone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.020
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3 checkY
    Key: KEQHJBNSCLWCAE-UHFFFAOYSA-N checkY
SMILES
  • CC1=CC(=O)C(=CC1=O)C(C)C
Properties
Chemical formula
C10H12O2
Molar mass 164.204 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Thymoquinone is a phytochemical compound found in the plant Nigella sativa. It is also found in select cultivated Monarda fistulosa plants, which can be steam distilled to produce an essential oil. Thymoquinone is also a major oxidation product of both thymol and its structural isomer, carvacrol.[1][2]

It has been classified as a pan-assay interference compound, which binds indiscriminately to many proteins.[3] It is under basic research to further identify its biological properties.[4]

See also

  • Dithymoquinone, a dimer of thymoquinone
  • 2,5-Dimethoxy-p-cymene

References

  1. ^ Günay T, Çimen Y, Karabacak RB, Türk H (2016). "Oxidation of Thymol and Carvacrol to Thymoquinone with KHSO5 Catalyzed by Iron Phthalocyanine Tetrasulfonate in a Methanol–Water Mixture". Catalysis Letters. 146 (11): 2306–2312. doi:10.1007/s10562-016-1850-2. ISSN 1011-372X. Retrieved 22 February 2026.
  2. ^ Kani İ (2025). "Homogeneous catalytic oxidation of thymol with dinuclear Cu(II)-2-phenyl propionate-bipyridine complex". Polyhedron. 266 117312. doi:10.1016/j.poly.2024.117312. Retrieved 22 February 2026.
  3. ^ Baell JB (March 2016). "Feeling Nature's PAINS: Natural Products, Natural Product Drugs, and Pan Assay Interference Compounds (PAINS)". Journal of Natural Products. 79 (3): 616–28. doi:10.1021/acs.jnatprod.5b00947. PMID 26900761.
  4. ^ "Kalonji". Drugs.com. 2 July 2025. Retrieved 23 February 2026.