| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:37 UTC |
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| Update date | 2019-11-26 03:08:15 UTC |
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| Primary ID | FDB013274 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Thymoquinone |
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| Description | Thymoquinone, also known as TQ, belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. Thymoquinone is found, on average, in the highest concentration within winter savories (Satureja montana). Thymoquinone has also been detected, but not quantified in, herbs and spices. This could make thymoquinone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Thymoquinone. |
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| CAS Number | 490-91-5 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 2-Isopropyl-5-methyl-1,4-benzoquinone | ChEBI | | 2-Isopropyl-5-methyl-p-benzoquinone | ChEBI | | 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione | ChEBI | | 5-Isopropyl-2-methyl-2,5-cyclohexadiene-1,4-dione | ChEBI | | p-Cymene-2,5-dione | ChEBI | | p-Mentha-3,6-diene-2,5-dione | ChEBI | | Thymoquinon | ChEBI | | TQ | ChEBI | | 2-Isopropyl-5-methylbenzo-1,4-quinone | HMDB | | 2-Isopropyl-5-methylbenzoquinone | HMDB, MeSH | | 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione, 9ci | HMDB | | 2-Methyl-5-isopropyl-1,4-benzoquinone | HMDB | | 2-Methyl-5-isopropyl-P-benzoquinone | HMDB, MeSH | | 5-Isopropyl-2-methyl-1,4-benzoquinone | HMDB | | 5-Isopropyl-2-methyl-P-benzoquinone | HMDB | | P-Mentha-3,6-diene-2,5-dione (8ci) | HMDB | | Polythymoquinone | HMDB | | Thymoil | HMDB | | Thymolquinone | HMDB | | Dihydrothymoquinone | MeSH, HMDB | | Thymoquinone | MeSH | | 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione, 9CI | db_source | | 2-Methyl-5-isopropyl-p-benzoquinone | biospider | | 2,5-Cyclohexadiene-1,4-dione, 2-methyl-5-(1-methylethyl)- | biospider | | 2,5-Cyclohexadiene-1,4-dione, 5-isopropyl-2-methyl- | biospider | | 5-Isopropyl-2-methyl-p-benzoquinone | biospider | | p-Mentha-3,6-diene-2,5-dione (8CI) | biospider |
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| Predicted Properties | |
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| Chemical Formula | C10H12O2 |
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| IUPAC name | 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione |
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| InChI Identifier | InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3 |
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| InChI Key | KEQHJBNSCLWCAE-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C)C1=CC(=O)C(C)=CC1=O |
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| Average Molecular Weight | 164.2011 |
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| Monoisotopic Molecular Weight | 164.083729628 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbonyl compounds |
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| Direct Parent | P-benzoquinones |
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| Alternative Parents | |
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| Substituents | - P-benzoquinone
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: Biological role: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 73.15%; H 7.37%; O 19.49% | DFC |
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| Melting Point | Mp 44-45° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | 2.20 | SANGSTER (1993) |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | 282 (e 2450) (EtOH) (Berdy) | DFC |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Thymoquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00xr-6900000000-764f3b8a1150b1cac052 | Spectrum | | Predicted GC-MS | Thymoquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Thymoquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-96f0c8e4e4f4a8455abe | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-5900000000-441064ba80ff42a70cfe | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-9200000000-c6d527c2a9a79f901029 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-d9e63c8d82efebaf41b1 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-98b2dccaab2bbdb236fe | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014r-9500000000-19dae31b3a18d5f7735c | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-8db47caa9667c101bd0f | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-5a485fdf30f3fb6eef66 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9500000000-e6c8bd2fffd875c29cff | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-7a4cd3c2c5dcf8576412 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00xr-3900000000-c1e3ac1b0edf80cd5e27 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9100000000-897472ebb650188b991d | 2021-09-24 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 9861 |
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| ChEMBL ID | CHEMBL1672002 |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 10281 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB34732 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HQQ33-S:HQQ33-S |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | THYMOQUINONE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00010876 |
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| HET ID | IMW |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| Anti-arthritic | 52217 | An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life. | DUKE | | Anti-asthmatic | 49167 | An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health. | DUKE | | Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | | Anti-bronchitic | 52217 | An agent that relieves bronchial congestion and inflammation, commonly used in managing respiratory disorders such as bronchitis, asthma, and chronic obstructive pulmonary disease (COPD), to reduce coughing, wheezing, and shortness of breath. | DUKE | | Anti eicosanoid | 35222 | An agent that inhibits the production or activity of eicosanoids, reducing inflammation and allergic responses. Therapeutically, it's used to manage conditions like asthma, arthritis, and allergic disorders, providing relief from symptoms such as pain and inflammation. | DUKE | | Anti histaminic | 37956 | An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis. | DUKE | | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | | Anti-rheumatic | 52217 | An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions. | DUKE | | Anti-spasmodic | 52217 | An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort. | DUKE | | Carcinogenic | 50903 | An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment. | DUKE | | Choleretic | | An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function. | DUKE | | Cyclooxygenase inhibitor | 35544 | An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation. | DUKE | | Lipoxygenase inhibitor | 35856 | An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases. | DUKE | | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | | Toxic | 52209 | A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells. | DUKE | | Uricosuric | | A substance that increases uric acid excretion in the urine, reducing blood plasma concentration. It plays a biological role in preventing uric acid buildup. Therapeutically, it's used to treat gout and hyperuricemia, managing symptoms and preventing complications. Key medical uses include reducing uric acid levels and alleviating gout attacks. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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