Homo-orientin

Base Information

• Chemical Name: Homo-orientin
• CAS No.: 28608-75-5
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.383
• Hs Code.: 29389090
• NSC Number: 133101
• Wikidata: Q104194955
• Mol file: 28608-75-5.mol

Synonyms:8-C-beta-glucopyranosyl-3',4',5,7-tetrahydroxyflav-2-en-3-one;luteolin 8-C-beta-D-glucopyranoside;luteolin-8-c-glucoside;orientin;orientine

Chemical Property of Homo-orientin

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 3.63E-28mmHg at 25°C
• Melting Point: 260-285 °C
• Refractive Index: 1.767
• Boiling Point: 816.1 °C at 760 mmHg
• PKA: 6.24±0.40(Predicted)
• Flash Point: 289.1 °C
• PSA: 201.28000
• Density: 1.759 g/cm³
• LogP: -0.20270
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: 1 M NaOH: soluble1mg/mL, clear, yellow-orange
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 448.10056145
• Heavy Atom Count: 32
• Complexity: 729

Purity/Quality:

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

Orientin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O)O
• Description: Orientin is a flavone glycoside originally isolated from P. orientale that has diverse biological activities, including antioxidant, antibacterial, and anti-inflammatory properties. Orientin scavenges 2,2-diphenyl-1-picryl-hydrazyl (DPPH; ) radicals with an IC50 value of 316.21 μg/ml. It also decreases the cytopathic effects of parainfluenza type 3 virus with an IC50 value of 11.7 μg/ml and a cytotoxic concentration (CC50) value of 375 μg/ml in Hep-2 cells. Orientin (5-40 μM) inhibits LPS-induced barrier disruption, decreases the expression of toll-like receptor 4 (TLR4), phosphorylated p38, and NF-κB, and decreases TNF-α production and IL-6 secretion in a dose-dependent manner in human umbilical vein endothelial cells (HUVECs). It also prolongs survival in a mouse model of LPS-induced lethal endotoxemia when administered at a dose of 36 μg/animal 12 hours after LPS administration.
• Uses: Orientin is a flavone, a chemical flavonoid compound. Orientin have been investigated for its anti-oxidant, antihypertensive and antihyperlipidemic effects.

Technology Process of Homo-orientin

There total 16 articles about Homo-orientin 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: 100.0%

2-(3,4-bis-benzyloxyphenyl)-7-benzyloxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-hydroxy-4H-1-benzopyran-4-one (381686-07-3) → Luteolin-8-C-glucoside (7480-94-6,28608-75-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; at 20 ℃;

DOI:10.1016/S0008-6215(01)00192-6

Reference yield: 56.0%

C15H12O7 + UDP-glucose → isoorientin (4261-42-1) + Luteolin-8-C-glucoside (7480-94-6,28608-75-5)

Guidance literature:

With recombinant Oryza sativa C-glycosyltransferase; In ethanol; at 30 ℃; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.phytochem.2016.02.013

Reference yield: 50.0%

2″,6″-O-diacetylorientin (131507-99-8) → Luteolin-8-C-glucoside (7480-94-6,28608-75-5)

Guidance literature:

With hydrogenchloride; In methanol; for 1h; Heating;

DOI:10.1248/cpb.38.2277

upstream raw materials:

3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone

2″,6″-O-diacetylorientin

2-(3,4-bis-benzyloxyphenyl)-7-benzyloxy-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-hydroxy-4H-1-benzopyran-4-one

1‐(2‐(benzyloxy)‐4,6‐dihydroxyphenyl)ethan‐1‐one

Downstream raw materials:

orientin-2-O-β-D-glucopyranoside

orientin-2-O-β-D-galactopyranoside

isoorientin

D-glucose

Refernces

• 1、 Seikel,Bushnell. "-". . p. 1995. Retrieved 1959.
• 2、 He, Jun-Bin,Zhao, Peng,Hu, Zhi-Min,Liu, Shuang,Kuang, Yi,Zhang, Meng,Li, Bin,Yun, Cai-Hong,Qiao, Xue,Ye, Min. "Molecular and Structural Characterization of a Promiscuous C-Glycosyltransferase from Trollius chinensis". supporting information. p. 11513 - 11520. Retrieved 2019/07/16.
• 3、 Liu, Jiang-Yun,Li, Sheng-Yin,Feng, Jian-Yong,Sun, Yan,Cai, Jin-Na,Sun, Xiao-Fei,Yang, Shi-Lin. "Flavone C-glycosides from the flowers of Trollius chinensis and their anti-complementary activity". . p. 325 - 331. Retrieved 2013/06/27.