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:

99%, ^*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
• Uses: Isoorientin is a flavonoid compound that can be isolated from the passion flower, and several other species of plants. Isoorientin has also shown to exert antioxidant, anti-nociceptive, anti-inflammat ory and gastroprotective activities in several studies. Reference Standard in the analysis of herbal medicinal products

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

• 1、 Pei, Jianjun,Sun, Qing,Zhao, Linguo,Shi, Hao,Tang, Feng,Cao, Fuliang. "Efficient Biotransformation of Luteolin to Isoorientin through Adjusting Induction Strategy, Controlling Acetic Acid, and Increasing UDP-Glucose Supply in Escherichia coli". . p. 331 - 340. Retrieved 2019.
• 2、 Grignon-Dubois, Micheline,De Montaudouin, Xavier,Rezzonico, Bernadette. "Flavonoid pattern inheritance in the allopolyploid Spartina anglica – Comparison with the parental species S. maritima and S. alterniflora". . . Retrieved 2020/03/27.