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H4530

Sigma-Aldrich

7-Hydroxyflavone

≥98%

Synonym(s):

7-Hydroxy-2-phenyl-4H-1-benzopyran-4-one, NSC 94258

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About This Item

Empirical Formula (Hill Notation):
C15H10O3
CAS Number:
6665-86-7
Molecular Weight:
238.24
EC Number:
229-705-3
MDL number:
MFCD00006835
UNSPSC Code:
12352100
PubChem Substance ID:
57654239
NACRES:
NA.22

Assay

≥98%

mp

245-247 °C (lit.)

SMILES string

Oc1ccc2C(=O)C=C(Oc2c1)c3ccccc3

InChI

1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H

InChI key

MQGPSCMMNJKMHQ-UHFFFAOYSA-N

Gene Information

mouse ... Hexa(15211)
rat ... Ar(24208) , Gabra2(29706)

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Application

Reactant:
  • Acting as a biologically valuable acceptor in O-glycosidation reactions
  • Involved in synthesis of fully phosphorylated flavones for use as pancreatic cholesterol esterase inhibitors
  • For O-methylation with di-Me carbonate
  • Linked by a polymethylene chain for synthesis of α1-adrenoceptor antagonists
  • Involved in Baylis-Hillman reactions
  • Involved in phase-transfer catalyzed glucosylation for synthesis of glucosylated flavonoids

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCL3814
SLCF7488
SLBZ8857
066H0962
053K3665

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Nga Ta et al.
The Journal of steroid biochemistry and molecular biology, 107(1-2), 127-129 (2007-07-13)
Previous studies have shown chrysin, 7-hydroxyflavone and 7,4'-dihydroxyflavone to be the most potent flavonoid inhibitors of aromatase. However, very poor oral bioavailability is a major limitation for the successful use of dietary flavonoids as chemopreventive agents. We have recently shown
R Le Lain et al.
Journal of enzyme inhibition, 16(1), 35-45 (2001-08-11)
In a screening programme for inhibitors of human testis 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3), as potential agents for the treatment of hormone-dependent prostatic cancer, we have used crude human testis microsomal 17beta-hydroxysteroid dehydrogenase as a convenient source of the enzyme.
T K Vinh et al.
Journal of enzyme inhibition, 16(5), 417-424 (2002-03-28)
A series of 4-aryl substituted 7-hydroxy-flavones were prepared using the three-step Baker-Venkataraman synthesis in good overall yields. The flavones were all evaluated in vitro for inhibitory activity against aromatase (P450AROM, CYP19), using human placental microsomes, and for inhibitory activity against
J Thomas Sanderson et al.
Toxicological sciences : an official journal of the Society of Toxicology, 82(1), 70-79 (2004-08-21)
Flavonoids and related structures (e.g., flavones, isoflavones, flavanones, catechins) exert various biological effects, including anticarcinogenic, antioxidant and (anti-)estrogenic effects, and modulation of sex hormone homeostasis. A key enzyme in the synthesis of estrogens from androgens is aromatase (cytochrome P450 19;
Shun-Fa Yang et al.
Archives of oral biology, 53(3), 287-294 (2007-10-16)
Oral squamous cell carcinoma (OSCC) is one of the most common head and neck cancers with a poor prognosis due to frequent lymph node metastasis and local invasion. A growing number of in vitro studies have been conducted on the
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