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274666

Sigma-Aldrich

Thymoquinone

≥98%

Synonym(s):

2-Isopropyl-5-methyl-1,4-benzoquinone

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About This Item

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

219.2 °F - closed cup

Flash Point(C)

104 °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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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
Chern Chiuh Woo et al.
Biochemical pharmacology, 83(4), 443-451 (2011-10-19)
Thymoquinone is an active ingredient isolated from Nigella sativa and has been investigated for its anti-oxidant, anti-inflammatory and anticancer activities in both in vitro and in vivo models since its first extraction in 1960s. Its anti-oxidant/anti-inflammatory effect has been reported
Thymoquinone: A promising anti-cancer drug from natural sources
Gali-Muhtasib H
The International Journal of Biochemistry & Cell Biology, 38, 1249-1253 (2006)
Regine Schneider-Stock et al.
Drug discovery today, 19(1), 18-30 (2013-09-05)
Thymoquinone (TQ), the main active constituent of black seed essential oil, exhibits promising effects against inflammatory diseases and cancer. TQ, modulates signaling pathways that are key to cancer progression, and enhances the anticancer potential of clinical drugs while reducing their
Thymoquinone Inhibits Escherichia coli ATP Synthase and Cell Growth
Ahmad Z
PLoS ONE, 10 (2015)
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