Thymoquinone

Base Information

• Chemical Name: Thymoquinone
• CAS No.: 490-91-5
• Molecular Formula: C10H12 O2
• Molecular Weight: 164.204
• Hs Code.: 29146990
• European Community (EC) Number: 207-721-1
• NSC Number: 2228
• UNII: O60IE26NUF
• DSSTox Substance ID: DTXSID9060079
• Nikkaji Number: J6.047J
• Wikipedia: Thymoquinone
• Wikidata: Q7799650
• Metabolomics Workbench ID: 46663
• ChEMBL ID: CHEMBL1672002
• Mol file: 490-91-5.mol

Synonyms:2-isopropyl-5-methylbenzoquinone;2-methyl-5-isopropyl-p-benzoquinone;dihydrothymoquinone;thymoquinone

Chemical Property of Thymoquinone

Chemical Property:

• Appearance/Colour: orange to brown crystals
• Vapor Pressure: 0.0603mmHg at 25°C
• Melting Point: 45-47 ºC(lit.)
• Refractive Index: 1.5155 (estimate)
• Boiling Point: 232 ºC at 760 mmHg
• Flash Point: 103.9 ºC
• PSA: 34.14000
• Density: 1.065 g/cm³
• LogP: 1.66690
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly, Heated), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 293

Purity/Quality:

5%,10%,10:1,20:1, ^*data from raw suppliers

Thymoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)C(=CC1=O)C(C)C
• Description: Thymoquinone is an allergen In different cedar species.
• Uses: Thymoquinone is a phytochemical compound found in the plant Nigella sativa. Thymoquinone has antioxidant effects and has been shown to protect against heart, liver and kidney damage in animal studies, as well as having possible anti-cancer effects. Thymoquinone also has analgesic and anticonvulsant effects in animal models. Thymoquinone is an angiogenesis inhibitor. Thymoquinone is a phytochemical compound found in the plant Nigella sativa. Thymoquinone has antioxidant effects and has been shown to protect against heart, liver and kidney damage in animal studies, as well as having possible anti-cancer effects. Thymoquinone also has analgesic and anticonvulsant effects in animal models. Thymoquinone is an angiogenesis inhibitor. An IRAK1 inhibitor with in vivo and in vitro anti-inflammatory activities. Dyes and metabolites.

Technology Process of Thymoquinone

There total 87 articles about Thymoquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

thymol (89-83-8) → thymoquinone (490-91-5)

Guidance literature:

With [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II); oxygen; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2014.07.088

Reference yield: 90.0%

carvacrol (499-75-2) → thymoquinone (490-91-5)

Guidance literature:

With oxygen; salcomine; In N,N-dimethyl-formamide; Ambient temperature;

Reference yield: 65.0%

thymol (89-83-8) → thymoquinone (490-91-5) + 2-(4-hydroxy-5-isopropyl-2-methylphenyl)-6-isopropyl-3-methyl-1,4-benzoquinone (98268-32-7) + 3-hydroxy-5,5'-diisopropyl-2,2'-dimethyl-4,4'-diphenoquinone (98268-34-9)

Guidance literature:

With oxygen; copper dichloride; In ethanol; at 60 ℃; for 48h; Product distribution; var. solvents;

DOI:10.1021/jo00222a038

upstream raw materials:

ethanol

carvacrol

thymol

thymohydroquinone

Downstream raw materials:

2-isopropyl-5-methyl-[1,4]benzoquinone; compound with 2-isopropyl-5-methyl-hydroquinone

2-isopropyl-5-methyl-[1,4]benzoquinone-4-(O-methyl oxime )

2-isopropyl-5-methyl-[1,4]benzoquinone-4-benzoylhydrazone

2-isopropyl-5-methyl-[1,4]benzoquinone disemicarbazone

Refernces

• 1、 Günay, Tu??e,?imen, Yasemin,Karabacak, R. Bengü,Türk, Hayrettin. "Oxidation of Thymol and Carvacrol to Thymoquinone with KHSO5 Catalyzed by Iron Phthalocyanine Tetrasulfonate in a Methanol–Water Mixture". . p. 2306 - 2312. Retrieved 2016.
• 2、 Neves, Cláudia M. B.,Tomé, Jo?o P. C.,Hou, Zhanyao,Dehaen, Wim,Hoogenboom, Richard,Neves, M. Gra?a P. M. S.,Sim?es, Mário M. Q.. "Oxidation of Monoterpenes Catalysed by a Water-Soluble MnIII PEG-Porphyrin in a Biphasic Medium". . p. 2804 - 2809. Retrieved 2018.
• 3、 Ay, Burak,Yildiz, Emel,Jones, Stephanie,Zubieta, Jon. "Hydrothermal synthesis of a novel μ-dihydroxo-bis(2,6- pyridinedicarboxylatoaquachromium(III)) complex and investigation of its catalytic activity". . p. 15 - 19. Retrieved 2012.
• 4、 Wellauer, Jo?l,Miladinov, Dragan,Buchholz, Thomas,Schütz, Jan,Stemmler, René T.,Medlock, Jonathan A.,Bonrath, Werner,Sparr, Christof. "Organophotocatalytic Aerobic Oxygenation of Phenols in a Visible-Light Continuous-Flow Photoreactor". supporting information. p. 9748 - 9752. Retrieved 2021/05/27.
• 5、 -. "PHOTOOXIDATION OF PHENOLIC COMPOUNDS". Page/Page column 17-18. . Retrieved 2021/11/26.