Thymoquinone

Thymoquinone
Names
	IUPAC name 2-Isopropyl-5-methylbenzo-1,4-quinone
	Other names Thymoquinone
Identifiers
CAS Number	490-91-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:113532;
ChEMBL	ChEMBL1672002 ;
ChemSpider	9861 ;
ECHA InfoCard	100.007.020
PubChem CID	10281;
UNII	O60IE26NUF ;
CompTox Dashboard (EPA)	DTXSID9060079 ;
	InChI InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3 Key: KEQHJBNSCLWCAE-UHFFFAOYSA-N ;
	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).
	verify (what is ?)
	Infobox references

Thymoquinone is a phytochemical compound found in the plant Nigella sativa. It is also found in select cultivated Monarda fistulosa plants grown in the U.S. which can be steam distilled to produce an essential oil.

In laboratory experiments in cells and in animals, it has shown antiinflammatory and antioxidant effects, and it has been studied in models of cardiovascular diseases and diabetes,[1] neurodegenerative diseases and stroke,[2] and cancer.[3] A 2016 study suggests thymoquinone may have opioid tolerance-reduction effects.[4]

It has been classified as a pan-assay interference compound, which binds indiscriminately to many proteins.[5]

References

Farkhondeh T, Samarghandian S, Borji A (September 2017). "An overview on cardioprotective and anti-diabetic effects of thymoquinone". Asian Pacific Journal of Tropical Medicine. 10 (9): 849–854. doi:10.1016/j.apjtm.2017.08.020. PMID 29080612.
Khazdair MR (2015-01-01). "The Protective Effects of Nigella sativa and Its Constituents on Induced Neurotoxicity". Journal of Toxicology. 2015: 841823. doi:10.1155/2015/841823. PMC 4641935. PMID 26604923.
Asaduzzaman Khan M, Tania M, Fu S, Fu J (August 2017). "Thymoquinone, as an anticancer molecule: from basic research to clinical investigation". Oncotarget. 8 (31): 51907–51919. doi:10.18632/oncotarget.17206. PMC 5584300. PMID 28881699.
Hosseinzadeh H, Parvardeh S, Masoudi A, Moghimi M, Mahboobifard F (2016). "Attenuation of morphine tolerance and dependence by thymoquinone in mice". Avicenna Journal of Phytomedicine. 6 (1): 55–66. PMC 4884218. PMID 27247922.
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.

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[1] Farkhondeh T, Samarghandian S, Borji A (September 2017). "An overview on cardioprotective and anti-diabetic effects of thymoquinone". Asian Pacific Journal of Tropical Medicine. 10 (9): 849–854. doi:10.1016/j.apjtm.2017.08.020. PMID 29080612.

[2] Khazdair MR (2015-01-01). "The Protective Effects of Nigella sativa and Its Constituents on Induced Neurotoxicity". Journal of Toxicology. 2015: 841823. doi:10.1155/2015/841823. PMC 4641935. PMID 26604923.

[3] Asaduzzaman Khan M, Tania M, Fu S, Fu J (August 2017). "Thymoquinone, as an anticancer molecule: from basic research to clinical investigation". Oncotarget. 8 (31): 51907–51919. doi:10.18632/oncotarget.17206. PMC 5584300. PMID 28881699.

[4] Hosseinzadeh H, Parvardeh S, Masoudi A, Moghimi M, Mahboobifard F (2016). "Attenuation of morphine tolerance and dependence by thymoquinone in mice". Avicenna Journal of Phytomedicine. 6 (1): 55–66. PMC 4884218. PMID 27247922.

[5] 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.

Thymoquinone

See also

References