CAS 4250-77-5 6-Hydroxyflavanone (HCID 2734580)

Overview

6-hydroxyflavanone is a monohydroxyflavanone that is flavanone substituted by a hydroxy group at position 6. It has a role as a fungal xenobiotic metabolite.

Names & identifiers

Preferred name: 6-Hydroxyflavanone
IUPAC: 6-hydroxy-2-phenyl-2,3-dihydrochromen-4-one
English name: 6-HYDROXYFLAVANONE
Molecular formula: C15H12O3
Molecular weight: 240.25

Names & synonyms

6-Hydroxyflavanone4250-77-56-hydroxy-2-phenylchroman-4-one6-hydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-oneFlavanone, 6-hydroxy-4H-1-Benzopyran-4-one, 2,3-dihydro-6-hydroxy-2-phenyl-1F174812MPDTXSID1022429CHEBI:34471RefChem:543429(+-)-6-HydroxyflavanoneDTXCID202429

Show more names

6'-HYDROXYFLAVANONE6-OH FlavanoneHYDROXYFLAVANONE, 6-6-Hydroxyflavanone>6-Hydroxyflavanone 99%6-Hydroxyflavanone,98+%HYDROXYFLAVANONE, 6-(RG)6-Hydroxyflavanone, ≥ 98.0%

624-472-8(+/-)-6-Hydroxyflavanone6-hydroxy-2-phenyl-2,3-dihydrochromen-4-oneMFCD00017485UNII-1F174812MP6-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one6-hydroxy-2-phenyl-chroman-4-oneCHEMBL195033

Database identifiers

CAS: 4250-77-5
PubChem CID: 2734580
DTXSID: DTXSID1022429
ChEMBL: CHEMBL195033
ChEBI: CHEBI:34471
UNII: 1F174812MP
EC Number: 624-472-8
Nikkaji: J285.121K

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 46.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 18
Formal charge: 0
Complexity: 309

Physicochemical properties

Melting point: 220 · 220-222 °C (dec.) (lit.)
Boiling point: 464.3 · 464.3±45.0 °C(Predicted)
Density: 1.288 · 1.288±0.06 g/cm3(Predicted)
pka: 9.53 · 9.53±0.40(Predicted)
form: powder to crystal
color: White to Orange to Green
BRN: 87354 · 87354
InChI: 1S/C15H12O3/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-8,15-16H,9H2
InChIKey: XYHWPQUEOOBIOW-UHFFFAOYSA-N
SMILES: Oc1ccc2OC(CC(=O)c2c1)c3ccccc3
LogP: 2.955 · 2.955 (est)
CAS DataBase Reference: 4250 · 4250-77-5(CAS DataBase Reference)
FDA UNII: 1 F174812MP · 1F174812MP
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
HS Code: 29329900 · 29329900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

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 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29329900
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses6-Hydroxyflavanone (6-HF) has been used for the enantiomeric separation of flavonoids using polysaccharide-based chiral stationary phases by nano-liquid chromatography (nano-LC). Racemic 6-HF may be used in the synthesis of 6-propionoxy-flavanone (6-PF). 6-HF may be employed as synthetic flavone to investigate the mechanism of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) induced cytotoxic and apoptotic effects in HeLa cancer cells.

General Description6-Hydroxyflavanone is a flavonoid. Its biotransformation by Aspergillus niger strains have been described. Crystal structure of S and R enanti-omers of 6-hydroxyflavanone has been reported to have four crystallographic sites of the unit cell in an approximate 3:1/1:3 ratio. It was identified as a metabolite of flavnone on incubation with rat liver microsomes by positive ion electrospray LC/MS analysis.