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419796

6-Hydroxyflavanone

Name: 6-Hydroxyflavanone
Brand: ALDRICH

99%

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₂O₃

CAS Number:

4250-77-5

Molecular Weight:

240.25

NACRES:

NA.22

PubChem Substance ID:

24866277

UNSPSC Code:

12352100

MDL number:

MFCD00017485

Assay:

99%

Form:

solid

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Properties

Quality Level

100

assay

99%

form

solid

mp

220-222 °C (dec.) (lit.)

functional group

ketone, phenyl

SMILES string

Oc1ccc2OC(CC(=O)c2c1)c3ccccc3

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

InChI key

XYHWPQUEOOBIOW-UHFFFAOYSA-N

Gene Information

rat ... Ar(24208)

Description

General description

6-Hydroxyflavanone is a flavonoid. Its biotransformation by Aspergillus niger strains have been described. Crystal structure of S and R enantiomers 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.

Application

6-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.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Microbial transformations of flavanone and 6-hydroxyflavanone by Aspergillus niger strains.

Kostrzewa-Suslow E, et al.

Journal of Molecular Catalysis. B, Enzymatic, 39(1), 18-23 (2006)

New metabolic pathways for flavanones catalyzed by rat liver microsomes.

Dejan Nikolic et al.

Drug metabolism and disposition: the biological fate of chemicals, 32(4), 387-397 (2004-03-25)

Flavonoids represent a diverse group of natural pigments widely distributed in the plant kingdom and are an important component of human diet due to their high content in fruits and vegetables. Since many flavonoids have been shown to be potent

Synthetic flavanones augment the anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL).

Ewelina Szliszka et al.

Molecules (Basel, Switzerland), 17(10), 11693-11711 (2012-10-03)

Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is considered as the most promising anticancer agent in the TNF superfamily because of its selective cytotoxicity against tumor cells versus normal primary cells. However, as more tumor cells are reported to be resistant

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Global Trade Item Number

SKU	GTIN
419796-1G	04061832092737