Basic information
- CAS
490-91-5- Standard SMILES
CC1=CC(=O)C(C(C)C)=CC1=O- InChIKey
KEQHJBNSCLWCAE-UHFFFAOYSA-N- Molecular formula
- C10H12O2
- Average molar mass
- 164.2 g/mol
- Monoisotopic mass
- 164.08372962
Overview
Thymoquinone is a member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity. It has a role as an antioxidant, an antidepressant, an antineoplastic agent, an adjuvant, an anti-inflammatory agent, a plant metabolite and a cardioprotective agent.
Names & identifiers
- Preferred name
- Thymoquinone
- IUPAC
- 2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
- English name
- THYMOQUINONE
- Molecular formula
- C10H12O2
- Molecular weight
- 164.2
Names & synonyms
Thymoquinone490-91-5Thymoquinonp-Cymene-2,5-dionep-Mentha-3,6-diene-2,5-dione2-Isopropyl-5-methylbenzoquinone2,5-CYCLOHEXADIENE-1,4-DIONE, 2-METHYL-5-(1-METHYLETHYL)-2-Isopropyl-5-methyl-p-benzoquinone2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione2-Methyl-5-isopropyl-p-benzoquinone2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dioneNSC-2228
Show more names
5-ISOPROPYL-2-METHYL-1,4-BENZOQUINONENSC 2228thymolquinoneAURORA KA-6714Semen NigellaeNigellae Semen。Thymoquinone,99%Thymoquinone >
O60IE26NUFDTXSID9060079CHEBI:113532RefChem:6310DTXCID1040661207-721-12-Isopropyl-5-methyl-1,4-benzoquinone2-Isopropyl-5-methylcyclohexa-2,5-diene-1,4-dione
Database identifiers
- CAS
490-91-5
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 293
Experimental & physicochemical properties
LogP
2.20
2.2
Boiling Point230.00 to 232.00 °C. @ 760.00 mm Hg
Melting Point44 - 45 °C
Physical DescriptionSolid
Collision Cross Section138.66 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 45 · 45-47 °C(lit.)
- Boiling point
- 230 · 230-232 °C(lit.)
- Density
- 1.0326 · 1.0326 (rough estimate)
- refractive index
- 1.5155 · 1.5155 (estimate)
- Flash point
- 219 °F · 219 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly, Heated), Ethanol (Slightly), Methanol (Slightly)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GU5330000
- hs_code
- 29146990
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of Action
Thymoquinone is a natural compound with widespread protective effects, including anti-oxidative, anti-inflammatory, immunomodulatory, anti-cancer, and anti-microbial. It is able to induce apoptosis, regulate pro- and anti- apopotitic genes, and inhibit cancer metastasis through JNK and p38 activation. Its anti-inflammatory effects are attributed to its inhibition of inflammatory cytokines and processes, including pathways associated with 5-LO, COX, and PGD2.
Cellular LocationsCytoplasm
Uses & manufacturing
General Manufacturing Information2,5-Cyclohexadiene-1,4-dione, 2-methyl-5-(1-methylethyl)-: ACTIVE
Applications
DescriptionThymoquinone is an allergen In different cedar species.
UsesThymoquinone 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.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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