Skip to Content
Merck
All Photos(1)

Documents

419796

Sigma-Aldrich

6-Hydroxyflavanone

99%

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C15H12O3
CAS Number:
Molecular Weight:
240.25
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

solid

mp

220-222 °C (dec.) (lit.)

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)

Looking for similar products? Visit Product Comparison Guide

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

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Disordered 6-hydroxyflavanone.
Bialonska A, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(2), 430-431 (2007)
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
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
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)
Kahina Si-Ahmed et al.
Analytica chimica acta, 738, 85-94 (2012-07-14)
Three polysaccharide-based chiral stationary phases, Sepapak(®) 1, Sepapak(®) 2 and Sepapak(®) 3 have been evaluated in the present work for the stereoisomer separation of a group of 12 flavonoids including flavanones (flavanone, 4'-methoxyflavanone, 6-methoxyflavanone, 7-methoxyflavanone, 2'-hydroxyflavanone, 4'-hydroxyflavanone, 6-hydroxyflavanone, 7-hydroxyflavanone, hesperetin

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service