HISPIDIN

Base Information

• Chemical Name: HISPIDIN
• CAS No.: 555-55-5
• Molecular Formula: C₁₃H₁₀O₅
• Molecular Weight: 246.219
• Mol file: 555-55-5.mol

Synonyms:Hispidin (7CI);6-(3,4-Dihydroxystyryl)-4-hydroxy-2-pyrone;2H-Pyran-2-one,6-[(1E)-2-(3,4-dihydroxyphenyl) ethenyl]-4-hydroxy-;6-[(E)-2-(3,4-Dihydroxyphenyl)vinyl]-4-hydroxy-2H-pyran-2-one;6-[(E)-2-(3,4-Dihydroxyphenyl)ethenyl]-4-hydroxy-2H-pyran-2-one;

Chemical Property of HISPIDIN

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 4.05E-13mmHg at 25°C
• Melting Point: 312-315 °C
• Refractive Index: 1.854
• Boiling Point: 554.246 °C at 760 mmHg
• PKA: 4.90±0.30(Predicted)
• Flash Point: 220.129 °C
• PSA: 90.90000
• Density: 1.658 g/cm³
• LogP: 1.92700
• Storage Temp.: −20°C
• Solubility.: DMSO: >10 mg/mL

Purity/Quality:

98%,99%, ^*data from raw suppliers

Hispidin >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Hispidin is a polyphenol originally isolated from P. hispidus that has diverse biological activities, including antioxidant, anti-inflammatory, and cytoprotective properties. In a trolox equivalent antioxidant capacity (TEAC) assay, hispidin scavenges radicals at 14.47 equivalents of trolox . It inhibits transcriptional activity of NF-κB, decreases inducible nitric oxide synthase (iNOS) expression, and decreases the generation of reactive oxygen species (ROS) in LPS-induced macrophage RAW 264.7 cells. Hispidin inhibits apoptosis and increases insulin secretion in hydrogen peroxide-treated RINm5F pancreatic β-cells. It inhibits protein kinase C β (PKCβ; IC50 = 2 μM) with no activity against alkaline phosphatase. Hispidin also inhibits β-secretase (BACE1; IC50 = 4.9 μM) and prolyl endopeptidase (PE; IC50 = 16 μM) but not other serine proteases when used at a concentration of 40 μM (0.6, 0, 8.2, and 3.1% inhibition of chymotrypsin, trypsin, elastase, and tumor necrosis factor-α converting enzyme (TACE), respectively).
• Uses: Hispidin is a naturally occuring precursor to fungal luciferin responsible for luminosity in mushrooms.

Technology Process of HISPIDIN

There total 3 articles about HISPIDIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

4-methoxy-6-(3',4'-dihydroxystyryl)-2-pyrone (149947-22-8) → hispidin (87888-40-2,555-55-5)

Guidance literature:

With sodium hydride; ethanethiol; In N,N-dimethyl-formamide; paraffin; for 1h; Heating;

DOI:10.1055/s-1994-25654

Reference yield: 44.0%

4-methoxy-6-(3',4'-dihydroxystyryl)-2-pyrone (13709-20-1) → hispidin (87888-40-2,555-55-5)

Guidance literature:

With sodium hydride; ethanethiol; In N,N-dimethyl-formamide; for 1h; Heating;

DOI:10.1055/s-2004-815491

Reference yield:

4-hydroxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one (2082-94-2) → hispidin (87888-40-2,555-55-5)

Guidance literature:

With CYP₂C₉ in rabbit liver microsomes; Enzymatic reaction;

DOI:10.3390/molecules191016656

upstream raw materials:

4-methoxy-6-(3',4'-dihydroxystyryl)-2-pyrone

4-methoxy-6-(3',4'-dihydroxystyryl)-2-pyrone

4-hydroxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one

Downstream raw materials:

4-methoxy-6-(2-(3,4-dimethoxyphenyl)ethenyl)-2H-pyran-2-one

Refernces

• 1、 Purtov, Konstantin V.,Petushkov, Valentin N.,Baranov, Mikhail S.,Mineev, Konstantin S.,Rodionova, Natalja S.,Kaskova, Zinaida M.,Tsarkova, Aleksandra S.,Petunin, Alexei I.,Bondar, Vladimir S.,Rodicheva, Emma K.,Medvedeva, Svetlana E.,Oba, Yuichi,Oba, Yumiko,Arseniev, Alexander S.,Lukyanov, Sergey,Gitelson, Josef I.,Yampolsky, Ilia V.. "The Chemical Basis of Fungal Bioluminescence". supporting information. p. 8124 - 8128. Retrieved 2015/07/07.
• 2、 Adam,Saha-Moller,Veit,Welke. "A convenient synthesis of hispidin from piperonal". . p. 1133 - 1134. Retrieved 2007/10/02.