Chrysin
Basic information
- CAS
480-40-0- Standard SMILES
O=c1cc(-c2ccccc2)oc2cc(O)cc(O)c12- InChIKey
RTIXKCRFFJGDFG-UHFFFAOYSA-N- Molecular formula
- C15H10O4
- Average molar mass
- 254.24 g/mol
- Monoisotopic mass
- 254.0579088
Overview
Chrysin is a dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7. It has a role as an antioxidant, an antineoplastic agent, a hepatoprotective agent, an anti-inflammatory agent, a plant metabolite and an EC 2.7.11.18 (myosin-light-chain kinase) inhibitor. It is a dihydroxyflavone and a 7-hydroxyflavonol.
Names & identifiers
- Preferred name
- Chrysin
- IUPAC
- 5,7-dihydroxy-2-phenylchromen-4-one
- English name
- Chrysin
- Molecular formula
- C15H10O4
- Molecular weight
- 254.24
Names & synonyms
chrysin480-40-05,7-DihydroxyflavoneChrysine5,7-dihydroxy-2-phenylchromen-4-one4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-phenyl-5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-oneFLAVONE, 5,7-DIHYDROXY-DTXSID1022396NSC-4074363CN01F5ZJ5DTXCID902396
Show more names
5,7-DIHYDROXY-2-PHENYL-CHROMEN-4-ONEhrysinNSC 407436Chrysin-RMCHRYSIN(RG)
CHEBI:750955,7-dihydroxy-flavoneRefChem:5686207-549-75,7-Dihydroxy-2-phenyl-4H-chromen-4-oneCrysinChrysinic acidMFCD00006834
Database identifiers
- CAS
480-40-0- PubChem CID
- 5281607
- DTXSID
DTXSID1022396- ChEMBL
CHEMBL117- ChEBI
CHEBI:75095- UNII
- 3CN01F5ZJ5
- EC Number
- 207-549-7
- Nikkaji
- J1.544J
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 384
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Wood Dusts & Extracts
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
LogP
3.520
3.52
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point285.50 °C. @ 760.00 mm Hg
Physical DescriptionLight yellow solid; [Merck Index] Yellow powder; [Alfa Aesar MSDS]
Collision Cross Section
157.7 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1022396]
151.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
167.64 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
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
This chemical does not meet GHS hazard criteria for 80% (8 of 10) of all reports.
Warning
H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 10 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (20%)
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- F
- 10
- wgk
- 3
- rtecs
- LK8329050
- hs_code
- 29329990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
Chemistry & industry
Pharmacology
Metabolism/MetabolitesChrysin has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid.
Cellular LocationsMembrane
Uses & manufacturing
UsesFrom heartwood of Pinus monticola; [Merck Index]
Applications
DescriptionChrysin is a natural flavonoid with antioxidant, anti-inflammatory, and anticancer properties. It blocks COX-2 gene expression, PGE2 production, and hydroxyl radical formation in LPS-induced RAW 264.7 cells. Chrysin inhibits insulin-induced HIF-1α expression (~50% at 10 μM) in human prostate cancer DU145 cells and blocks DU145 xenograft-induced angiogenesis in vivo. In a mouse model of ischemia/reperfusion injury, chrysin decreased pro-inflammatory gene expression and oxidative stress, resulting in a reduction of infarct volume and neurological defects.
UsesChrysin is a flavanoid with anti-inflammatory effect and potential protective effects against cancer and cardiovascular disease. Studies show that Chrysin is central benzodiazepine receptor ligand with possible anxiolytic effects. Chrysin was initially believed to have aromatase inhibitor but recent in vivo studies have disproved that. Dyes and metabolites.
Upstream & downstream products
Upstream raw materials
Related reactions
3 records
Compound notes
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