Prunetin

Names

[ CAS No. ]:
552-59-0

[ Name ]:
Prunetin

[Synonym ]:
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
Prunusetin
5,4'-dihydroxy-7-methoxyisoflavone
Prunetin
7-methoxy-4',5-dihydroxyisoflavone
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
7-O-methyl-genistein
4',5-dihydroxy-7-methoxyisoflavone
4',5-dihydroxy-7-methoxygenistein
4H-1-Benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-
EINECS 209-018-5
MFCD00016951

Biological Activity

[Description]:

Prunetin, an O-methylated isoflavone, possesses anti-inflammatory activity. Prunetin is a potent human aldehyde dehydrogenases inhibitor[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Aldehyde Dehydrogenase (ALDH)

Research Areas >> Inflammation/Immunology

[In Vitro]

Prunetin inhibited LPS-induced inflammatory cytokine production and MUC5 AC expression and secretion by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells[1].

[References]

[1]. Hu H, et al. Prunetin inhibits lipopolysaccharide-induced inflammatory cytokine production and MUC5AC expression by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells. Biomed Pharmacother. 2018 Oct;106:1469-1477.

[2]. Sheikh S, et al. Allosteric inhibition of human liver aldehyde dehydrogenase by the isoflavone prunetin. Biochem Pharmacol. 1997 Feb 21;53(4):471-8.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
546.5±50.0 °C at 760 mmHg

[ Melting Point ]:
240-242ºC

[ Molecular Formula ]:
C₁₆H₁₂O₅

[ Molecular Weight ]:
284.263

[ Flash Point ]:
209.7±23.6 °C

[ Exact Mass ]:
284.068481

[ PSA ]:
79.90000

[ LogP ]:
3.53

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.669

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3100050

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-

CAS REGISTRY NUMBER :: 552-59-0

BEILSTEIN REFERENCE NO. :: 0292155

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C16-H12-O5

MOLECULAR WEIGHT :: 284.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 13,51,1979

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DJ3100050

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

Preparation and evaluation of surface-bonded tricationic ionic liquid silica as stationary phases for high-performance liquid chromatography.

J. Chromatogr. A. 1396 , 62-71, (2015)

Two tricationic ionic liquids were prepared and then bonded onto the surface of supporting silica materials through "thiol-ene" click chemistry as new stationary phases for high-performance liquid chr...

Absorption of red clover isoflavones in human subjects: results from a pilot study.

Br. J. Nutr. 103(11) , 1569-72, (2010)

In addition to soya-derived preparations, red clover-based dietary supplements have gained considerable interest as an alternative isoflavone (IF) source. While metabolism and bioavailability of the m...

The phytoestrogen prunetin affects body composition and improves fitness and lifespan in male Drosophila melanogaster.

FASEB J. 30 , 948-58, (2016)

Dietary isoflavones, a group of secondary plant compounds that exhibit phytoestrogenic properties, are primarily found in soy. Prunetin, a representative isoflavone, was recently found to affect cell ...