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Sigma-Aldrich

Thymoquinone

≥98%

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Synonym(s):
2-Isopropyl-5-methyl-1,4-benzoquinone
Empirical Formula (Hill Notation):
C10H12O2
CAS Number:
490-91-5
Molecular Weight:
164.20
EC Number:
207-721-1
MDL number:
MFCD00001602
UNSPSC Code:
12171500
PubChem Substance ID:
24856596
NACRES:
NA.47

Quality Level

100

Assay

≥98%

form

solid

color

yellow

bp

230-232 °C (lit.)

mp

45-47 °C (lit.)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

CC(C)C1=CC(=O)C(C)=CC1=O

InChI

1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3

InChI key

KEQHJBNSCLWCAE-UHFFFAOYSA-N

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General description

Thymoquinone (TQ), also known as 2-isopropyl-5-methyl-1, 4-benzoquinone, is present in a crystalline triclinic form. It is the bioactive constituent of the volatile oil of black seed. TQ exhibits anti-inflammatory, antioxidant and anti-neoplastic effects both in vitro and in vivo.

Application

Thymoquinone has been used as an inhibitor of Escherichia coli ATP synthase and cell growth. It is also used as a drug against lower limb ischemia-reperfusion injury of the sciatic nerve and femoral muscle.
Thymoquinone is employed in preclinical studies as a neuroprotective and anticonvulsant agent.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Inna I Severina et al.
FEBS letters, 587(13), 2018-2024 (2013-05-15)
Since the times of the Bible, an extract of black cumin seeds was used as a medicine to treat many human pathologies. Thymoquinone (2-demethylplastoquinone derivative) was identified as an active antioxidant component of this extract. Recently, it was shown that
Samir Attoub et al.
Fundamental & clinical pharmacology, 27(5), 557-569 (2012-07-14)
Phytochemical compounds are emerging as a new generation of anticancer agents with limited toxicity in cancer patients. The purpose of this study was to investigate the potential impact of thymoquinone (TQ), the major constituent of black seed, on survival, invasion
Anjali Singh et al.
Colloids and surfaces. B, Biointerfaces, 102, 822-832 (2012-10-30)
This research aims to formulate and characterize solid lipid nanoparticles (SLNs) of Thymoquinone (THQ-SLNs) for the effective treatment of liver cirrhosis. Formulations were prepared using solvent injection method and optimized by the Box-Behnken experimental design to get the desired particle
Hala Gali-Muhtasib et al.
The international journal of biochemistry & cell biology, 38(8), 1249-1253 (2005-11-30)
There has been growing interest in naturally occurring compounds with anti-cancer potential. Black seed is one of the most extensively studied plants. This annual herb grows in countries bordering the Mediterranean Sea and India. Thymoquinone (TQ) is the bioactive constituent
Sanjar Alam et al.
International journal of nanomedicine, 7, 5705-5718 (2012-11-28)
Chitosan (CS) nanoparticles of thymoquinone (TQ) were prepared by the ionic gelation method and are characterized on the basis of surface morphology, in vitro or ex vivo release, dynamic light scattering, and X-ray diffractometry (XRD) studies. Dynamic laser light scattering
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