HOMOORIENTIN

Base Information

• Chemical Name: HOMOORIENTIN
• CAS No.: 4261-42-1
• Molecular Formula: C21H20O11
• Molecular Weight: 448.383
• Hs Code.: 29389090
• European Community (EC) Number: 610-045-3
• UNII: A37342TIX1
• DSSTox Substance ID: DTXSID50962609
• Nikkaji Number: J14.555F
• Wikipedia: Isoorientin
• Wikidata: Q3155592
• Metabolomics Workbench ID: 51105
• ChEMBL ID: CHEMBL239559
• Mol file: 4261-42-1.mol

Synonyms:Isoorientin(7CI,8CI);3',4',5,7-Tetrahydroxy-6-C-glucopyranosylflavone;Homoorientin;Lespecapitioside;Lespecapitoside;Luteolin 6-C-glucoside;Luteolin 6-C-b-D-glucopyranoside;Luteolin 6-C-b-D-glucoside;Luteolin 6-C-b-glucopyranoside;Lutonaretin;(1S)-1,5-anhydro-1-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-D-glucitol;

Chemical Property of HOMOORIENTIN

Chemical Property:

• Vapor Pressure: 2.9E-31mmHg at 25°C
• Melting Point: 245-246°C
• Refractive Index: 1.767
• Boiling Point: 856.7 °C at 760 mmHg
• PKA: 5.90±0.40(Predicted)
• Flash Point: 303.2 °C
• PSA: 201.28000
• Density: 1.759 g/cm³
• LogP: -0.20270
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble5mg/mL, clear, colorless to yellow
• 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% ^*data from raw suppliers

Homoorientin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• General Description: Homoorientin (also known as isoorientin) is a C-glycosidic flavonoid structurally related to luteolin, featuring a glucose moiety at the 6-position. While the provided abstract discusses the bioinspired oxidation of orientin and isoorientin using Salen complexes, it does not specifically elaborate on the properties, metabolism, or biological significance of homoorientin itself. Thus, no direct conclusions about homoorientin can be drawn from this study. **Return:** Null

Technology Process of HOMOORIENTIN

There total 26 articles about HOMOORIENTIN 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-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one (321133-86-2) → isoorientin (4261-42-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; at 20 ℃; for 4.5h;

DOI:10.1016/S0008-6215(00)00226-3

Reference yield: 60.0%

2'',6''-Di-O-acetylisoorientin (131507-98-7) → isoorientin (4261-42-1)

Guidance literature:

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

DOI:10.1248/cpb.38.2277

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

upstream raw materials:

luteolin 8-C-D-glucoside

2'',6''-Di-O-acetylisoorientin

2-(3,4-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one

3,4-dibenzyloxybenzaldehyde

Downstream raw materials:

Luteolin-8-C-glucoside

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one

Refernces

Bioinspired oxidation in cytochrome P450 of isomers orientin and isoorientin using Salen complexes

10.1002/rcm.8757

The study focused on the bioinspired oxidation of the flavonoids orientin and isoorientin, which are C-glycosidic flavonoids found in certain plant species, including Passiflora edulis var. flavicarpa. The aim was to evaluate and characterize the in vitro metabolism of these flavonoids by simulating phase I biotransformation reactions using Salen complexes as catalysts. The chemicals used in the study included m-chloroperbenzoic acid (m-CPBA) and iodozylbenzene (PhIO) as oxidants, and the Jacobsen catalyst or [Mn(3-MeOSalen)Cl] as catalysts. The [Mn(3-MeOSalen)Cl] catalyst was synthesized and characterized by spectrometric techniques. The study utilized UPLC-DAD and HPLC/MS/MS to monitor and analyze the oxidation reactions and products, which are crucial for understanding the potential pharmacological and toxicological properties of these compounds, thus aiding in the safe use of plant products containing orientin as a chemical marker.