thymoquinone
2,5-cyclohexadiene-1,4-dione, 2-methyl-5-(1-methylethyl)-
Identification
| Name | thymoquinone |
| IUPAC | 2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione |
| CAS Number | 490-91-5 |
| EINECS | 207-721-1 |
| FDA UNII | O60IE26NUF |
| Molecular Formula | C10 H12 O2 |
| Molecular Weight | 164.20404000 |
| MDL Number | MFCD00001602 |
| Nikkaji Number | J6.047J |
| Beilstein | 1939047 |
| XlogP3 | 2.00 (est) |
Regulatory
Physical Properties
| Appearance | white to tan crystalline powder (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 45.00 to 47.00 °C. @ 760.00 mm Hg |
| Boiling Point | 230.00 to 232.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.060000 mmHg @ 25.00 °C. (est) |
| Flash Point | 219.00 °F. TCC ( 103.89 °C. ) |
| logP (o/w) | 2.200 |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | intraperitoneal-rat LD50 10 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for thymoquinone usage levels up to | not for fragrance use. |
| Recommendation for thymoquinone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2,5-
cyclohexadiene-1,4-dione, 2-methyl-5- (1-methylethyl)-
2,5-
cyclohexadiene-1,4-dione, 2-methyl-5-(1-methylethyl)-
2,5-
cyclohexadiene-1,4-dione, 5-isopropyl-2-methyl-
p-
cymene-2,5-dione
para-
cymene-2,5-dione
p-
mentha-3,6-diene-2,5-dione
para-
mentha-3,6-diene-2,5-dione
p-
mentha-3,6-diene-2,5-dione (8CI)
2-
methyl-5-(1-methyl ethyl)-2,5-cyclohexadiene-1,4-dione
2-
methyl-5-(methylethyl)cyclohexa-2,5-diene-1,4-dione
2-
methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
2-
methyl-5-iso-propylbenzoquinone
2-
methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
5-iso
propyl-2-methyl-1,4-benzoquinone
2-iso
propyl-5-methyl-1,4-benzoquinone
2-iso
propyl-5-methyl-p-benzoquinone
2-iso
propyl-5-methyl-para-benzoquinone
2-iso
propyl-5-methylbenzo-1,4-quinone
2-iso
propyl-5-methylbenzoquinone
PubMed:
Volatile compounds of black cumin seeds (Nigella sativa L.) from microwave-heating and conventional roasting.
PubMed:
Potential of spice-derived phytochemicals for cancer prevention.
PubMed:
Thermodynamic analysis of thymoquinone binding to human serum albumin.
PubMed:
The effect of air-drying on glycosidically bound volatiles from seasonally collected origano (Origanum vulgare ssp. hirtum) from Croatia.
PubMed:
Antioxidant activity of Nigella sativa essential oil.
PubMed:
Inactivation of Cronobacter sakazakii in reconstituted infant formula by combination of thymoquinone and mild heat.
PubMed:
Health-promoting value and food applications of black cumin essential oil: an overview.
PubMed:
Black Cumin (Nigella sativa) and Its Active Constituent, Thymoquinone: An Overview on the Analgesic and Anti-inflammatory Effects.
PubMed:
Immunomodulatory and cytotoxic effects of Nigella sativa and thymoquinone on rat splenocytes.
PubMed:
Thymoquinone ameliorates testicular tissue inflammation induced by chronic administration of oral sodium nitrite.
PubMed:
The effect of thymoquinone treatment on the combined renal and pulmonary toxicity of cisplatin and diesel exhaust particles.
PubMed:
Neuroprotective effect of thymoquinone in acrylamide-induced neurotoxicity in Wistar rats.
PubMed:
Cardio-protective and anti-cancer therapeutic potential of Nigella sativa.
PubMed:
Thymoquinone induces caspase-independent, autophagic cell death in CPT-11-resistant lovo colon cancer via mitochondrial dysfunction and activation of JNK and p38.
PubMed:
Identification of indole-3-carboxylic acids as non-ATP-competitive Polo-like kinase 1 (Plk1) inhibitors.
PubMed:
Protective effect of thymoquinone against high-fructose diet-induced metabolic syndrome in rats.
PubMed:
Thymoquinone induces cell death in human squamous carcinoma cells via caspase activation-dependent apoptosis and LC3-II activation-dependent autophagy.
PubMed:
Therapeutic Implications of Black Seed and Its Constituent Thymoquinone in the Prevention of Cancer through Inactivation and Activation of Molecular Pathways.
PubMed:
Stable isotope dilution gas chromatography-mass spectrometry for quantification of thymoquinone in black cumin seed oil.
PubMed:
Thymoquinone vapor significantly affects the results of Staphylococcus aureus sensitivity tests using the standard broth microdilution method.
PubMed:
Thymoquinone induces heme oxygenase-1 expression in HaCaT cells via Nrf2/ARE activation: Akt and AMPKα as upstream targets.
PubMed:
Study on the potential toxicity of a thymoquinone-rich fraction nanoemulsion in Sprague Dawley rats.
PubMed:
A review on therapeutic potential of Nigella sativa: A miracle herb.
PubMed:
Isolation of volatiles from Nigella sativa seeds using microwave-assisted extraction: effect of whole extracts on canine and murine CYP1A.
PubMed:
Hypolipidemic and antioxidant activities of thymoquinone and limonene in atherogenic suspension fed rats.
PubMed:
Nigella sativa (black cumin) seed extract alleviates symptoms of allergic diarrhea in mice, involving opioid receptors.
PubMed:
Volatile compounds of black cumin seeds (Nigella sativa L.) from microwave-heating and conventional roasting.
PubMed:
Mitigation of obesity-promoted diseases by Nigella sativa and thymoquinone.
PubMed:
Regulation of renal organic anion and cation transporters by thymoquinone in cisplatin induced kidney injury.
PubMed:
Selective extraction of oxygenated compounds from oregano with sub-critical water.
PubMed:
Inhibition of the formation of advanced glycation end products by thymoquinone.
PubMed:
In vitro antifungal effect of black cumin seed quinones against dairy spoilage yeasts at different acidity levels.
PubMed:
Chemical composition of Nigella sativa L. seed extracts obtained by supercritical carbon dioxide.
PubMed:
Nigella sativa: reduces the risk of various maladies.
PubMed:
Thymoquinone supplementation reverses acetaminophen-induced oxidative stress, nitric oxide production and energy decline in mice liver.
PubMed:
Antioxidant activities of the supercritical and conventional Satureja montana extracts.
PubMed:
Depsides and other polar constituents from Origanum dictamnus L. and their in vitro antimicrobial activity in clinical strains.
PubMed:
In vitro growth-inhibitory effect of plant-derived extracts and compounds against Paenibacillus larvae and their acute oral toxicity to adult honey bees.
PubMed:
Thymoquinone-induced suicidal erythrocyte death.
PubMed:
Comparison of chemical composition and antibacterial activity of Nigella sativa seed essential oils obtained by different extraction methods.
PubMed:
Composition of essential oil compounds from different Syrian populations of Origanum syriacum L. (Lamiaceae).
PubMed:
Potential of spice-derived phytochemicals for cancer prevention.
PubMed:
Anticlastogenic activity of thymoquinone against benzo(a)pyrene in mice.
PubMed:
Immunomodulatory and therapeutic properties of the Nigella sativa L. seed.
PubMed:
Effect of solution conductivity on the volatile constituents of Origanum dictamnus L. in nutrient film culture.