Herbacetin

Names

[ CAS No. ]:
527-95-7

[ Name ]:
Herbacetin

[Synonym ]:
3,5,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
8-Hydroxykaempferol
4H-1-Benzopyran-4-one, 3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-
Herbacetin
3,4',5,7,8-Pentahydroxyflavone
3,4´,5,7,8-pentahydroxyflavone
3,5,7,8,4'-pentahydroxyflavone

Biological Activity

[Description]:

Herbacetin is a natural flavonoid from flaxseed, exerts various pharmacological activities, including antioxidant, anti-inflammatory and anticancer effects[1]. Herbacetin is an Ornithine decarboxylase (ODC) allosteric inhibitor, directly binds to Asp44, Asp243, and Glu384 on ODC. Ornithine decarboxylase (ODC) is a rate-limiting enzyme in the first step of polyamine biosynthesis[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[Target]

IC50: Ornithine decarboxylase[2]

[In Vivo]

Herbacetin (orally administration; 20mg/kg) significantly reduces the body weight, plasma glucose, plasma insulin, and HOMA-IR activity in obesity associated insulin resistant mice (OIR). (Herbacetin dissolves in 0.5% DMSO)[1]. Herbacetin (intraperitoneal injection; 0.4, 2, 10 or 20 mg/kg; B.W.) decreases the number and size of polyps in APCMin+ mice with no overt toxicity[2].

[References]

[1]. Veeramani C, et al. Herbacetin, a flaxseed flavonoid, ameliorates high percent dietary fat induced insulin resistance and lipid accumulation through the regulation of hepatic lipid metabolizing and lipid-regulating enzymes. Chem Biol Interact. 2018 May 25;288:49-56.

[2]. Kim DJ, et al. Herbacetin Is a Novel Allosteric Inhibitor of Ornithine Decarboxylase with Antitumor Activity. Cancer Res. 2016 Mar 1;76(5):1146-1157.

Chemical & Physical Properties

[ Density]:
1.799

[ Boiling Point ]:
618.7±55.0 °C at 760 mmHg

[ Melting Point ]:
284ºC

[ Molecular Formula ]:
C₁₅H₁₀O₇

[ Molecular Weight ]:
302.236

[ Flash Point ]:
239.0±25.0 °C

[ Exact Mass ]:
302.042664

[ PSA ]:
131.36000

[ LogP ]:
1.14

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.823

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ RIDADR ]:
UN 2811 6.1 / PGIII

[ HS Code ]:
2914501900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914501900

[ Summary ]:
2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Related Compounds

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