2-hydroxyflavanone
4H-1-benzopyran-4-one, 2,3-dihydro-2-(2-hydroxyphenyl)-
Identification
| Name | 2-hydroxyflavanone |
| IUPAC | 2-(2-hydroxyphenyl)-2,3-dihydrochromen-4-one |
| CAS Number | 17348-76-4 |
| FDA UNII | Search |
| Molecular Formula | C15 H12 O3 |
| Molecular Weight | 240.25824000 |
| MDL Number | MFCD00017702 |
| Nikkaji Number | J285.124E |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 376.87 °C. @ 760.00 mm Hg (est) |
| Flash Point | 289.00 °F. TCC ( 142.60 °C. ) (est) |
| logP (o/w) | 2.978 (est) |
| Soluble in | water, 416.5 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 2-hydroxyflavanone usage levels up to | not for fragrance use. |
| Recommendation for 2-hydroxyflavanone flavor usage levels up to | not for flavor use. |
Penta International Corporation
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 2,3-dihydro-2-(2-hydroxyphenyl)-
2-(2-
hydroxy-phenyl)-chroman-4-one
2'-
hydroxyflavanone
2'-
hydroxyflavone
2-(2-
hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
2-(2-
hydroxyphenyl)-2,3-dihydrochromen-4-one
2-(2-
hydroxyphenyl)chroman-4-one
PubMed:
Purification, molecular cloning and functional characterization of flavonoid C-glucosyltransferases from Fagopyrum esculentum M. (buckwheat) cotyledon.
PubMed:
2'-hydroxyflavanone inhibits prostate tumor growth through inactivation of AKT/STAT3 signaling and induction of cell apoptosis.
PubMed:
Functional characterization of a Plagiochasma appendiculatum flavone synthase I showing flavanone 2-hydroxylase activity.
PubMed:
Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice.
PubMed:
Anthracycline resistance mediated by reductive metabolism in cancer cells: the role of aldo-keto reductase 1C3.
PubMed:
2'-hydroxyflavanone induces apoptosis of human osteosarcoma 143 B cells by activating the extrinsic TRAIL- and intrinsic mitochondria-mediated pathways.
PubMed:
[Inhibitory effect of 2'-hydroxyflavanone on proliferation, invasion and migration of bladder cancer cells in vitro via blocking AKT/STAT3 signaling pathway].
PubMed:
Nonsteroidal anti-inflammatory drug activated gene-1 (NAG-1) modulators from natural products as anti-cancer agents.
PubMed:
Repression of cell proliferation and androgen receptor activity in prostate cancer cells by 2'-hydroxyflavanone.
PubMed:
The influence of β-cyclodextrin encapsulation on the binding of 2'-hydroxyflavanone with calf thymus DNA.
PubMed:
Evaluation of novel amylose and cellulose-based chiral stationary phases for the stereoisomer separation of flavanones by means of nano-liquid chromatography.
PubMed:
2'-Hydroxyflavanone induces apoptosis through Egr-1 involving expression of Bax, p21, and NAG-1 in colon cancer cells.
PubMed:
Aldo-keto reductase 1C3 is expressed in differentiated human epidermis, affects keratinocyte differentiation, and is upregulated in atopic dermatitis.
PubMed:
2'-hydroxyflavanone inhibits proliferation, tumor vascularization and promotes normal differentiation in VHL-mutant renal cell carcinoma.
PubMed:
CYP93G2 is a flavanone 2-hydroxylase required for C-glycosylflavone biosynthesis in rice.
PubMed:
Optical isomer separation of flavanones and flavanone glycosides by nano-liquid chromatography using a phenyl-carbamate-propyl-beta-cyclodextrin chiral stationary phase.
PubMed:
The C-glycosylation of flavonoids in cereals.
PubMed:
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.
PubMed:
Chiral separation of hydroxyflavanones in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors.
PubMed:
[Effects of flavonoids with different structures on proliferation of leukemia cell line HL-60].
PubMed:
Flavanone and 2'-OH flavanone inhibit metastasis of lung cancer cells via down-regulation of proteinases activities and MAPK pathway.
PubMed:
A new 2-hydroxyflavanone from Mosla soochouensis.
PubMed:
Rapid hepatic metabolism of 7-ketocholesterol by 11beta-hydroxysteroid dehydrogenase type 1: species-specific differences between the rat, human, and hamster enzyme.
PubMed:
A rapid screening assay for inhibitors of 11beta-hydroxysteroid dehydrogenases (11beta-HSD): flavanone selectively inhibits 11beta-HSD1 reductase activity.
PubMed:
A novel 2-hydroxyflavanone from collinsonia canadensis
PubMed:
Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food.
PubMed:
Purification and characterization of flavone synthase I, a 2-oxoglutarate-dependent desaturase.