Basic information
- Standard SMILES
COc1cc(O)c2c(c1)O[C@H](c1ccccc1)CC2=O- InChIKey
ORJDDOBAOGKRJV-AWEZNQCLSA-N- Molecular formula
- C16H14O4
- Average molar mass
- 270.28 g/mol
Overview
Pinostrobin is a monohydroxyflavanone that is (2S)-flavanone substituted by a hydroxy group at position 5 and a methoxy group at position 7 respectively. It has a role as an antidote and a plant metabolite. It is a monomethoxyflavanone and a monohydroxyflavanone. It is functionally related to a (2S)-flavanone.
Names & identifiers
- Preferred name
- (-)-Pinostrobin
- IUPAC
- (2S)-5-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
- English name
- Pinostrobin
- Molecular formula
- C16H14O4
- Molecular weight
- 270.28
Names & synonyms
Show more names
Database identifiers
- CAS
480-37-5、75291-74-6- PubChem CID
- 73201
- DTXSID
DTXSID50963979- ChEMBL
CHEMBL254613- ChEBI
CHEBI:80491- UNII
- SZD9LZS694
- EC Number
- 207-548-1
- Nikkaji
- J196.197G
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 350
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 100 °C · 100°C
- Boiling point
- 494.9 · 494.9±45.0 °C(Predicted)
- Density
- 1.284 · 1.284±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 20 mg/ml; · DMF: 20 mg/ml; DMF:PBS (pH 7.2)(1:3): 0.25 mg/ml; DMSO: 12 mg/ml
- form
- A crystalline solid
- pka
- 7.4 · 7.40±0.40(Predicted)
- color
- White to yellow
- InChI
- InChI=1S/C16H14O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-8,14,17H,9H2,1H3/t14-/m0/s1
- InChIKey
- ORJDDOBAOGKRJV-AWEZNQCLSA-N
- SMILES
- [C@H]1(C2=CC=CC=C2)OC2=CC(OC)=CC(O)=C2C(=O)C1
- LogP
- 3.591 · 3.591 (est)
- FDA UNII
- 9 LZS694 · SZD9LZS694
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): 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 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionPinostrobin is a flavonoid with diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties. It induces quinone reductase (QR) in murine hepatoma cells with a QR doubling concentration of 500 nM. Pinostrobin inhibits TNF-α and IL-1β production in RAW 264.7 macrophages (IC50s = 17.28 and 23.5 μM, respectively) and in LPS-stimulated rats (48.6 and 55% reduction, respectively). Pinostrobin also shows selective cytotoxicity for CCRF-CEM leukemia cells (IC50 = 10.2 μM) in a panel of eight cancer cell lines (IC50s = >30 μM).
UsesPinostrombin is a useful research chemical that can be used for chemical fingerprinting, isolating, and characterizing of polyphenol compounds. It can also be used as a potential compound for TMPRSS2 inhibition for Covid-19 therapy.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: A monohydroxyflavanone that is (2S)-flavanone substituted by a hydroxy group at position 5 and a methoxy group at position 7 respectively.
Related reactions
No reaction records under the current filter.
Linked notes
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