Patuletin

Base Information

• Chemical Name: Patuletin
• CAS No.: 519-96-0
• Molecular Formula: C16H12 O8
• Molecular Weight: 332.266
• Hs Code.: 2914509090
• European Community (EC) Number: 208-280-8
• UNII: 9BNM33N01N
• ChEMBL ID: CHEMBL465155
• DSSTox Substance ID: DTXSID20199864
• Metabolomics Workbench ID: 26069
• Nikkaji Number: J11.683A
• Wikidata: Q6626552
• Wikipedia: Patuletin
• Mol file: 519-96-0.mol

Synonyms:2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-chromen-4-one;patuletin

Chemical Property of Patuletin

Chemical Property:

• Vapor Pressure: 1.19E-19mmHg at 25°C
• Melting Point: 256 °C
• Boiling Point: 684.1°Cat760mmHg
• PKA: 6.29±0.40(Predicted)
• Flash Point: 258.8°C
• PSA: 140.59000
• Density: 1.73g/cm³
• LogP: 1.99660
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 332.05321734
• Heavy Atom Count: 24
• Complexity: 532

Purity/Quality:

99%, ^*data from raw suppliers

Patuletin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(C=C1O)OC(=C(C2=O)O)C3=CC(=C(C=C3)O)O)O
• Uses: Patuletin is an antioxidant flavonoid found in spinach leaves.

Technology Process of Patuletin

There total 19 articles about Patuletin 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: 74.0%

7-Benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3,5-dihydroxy-6-methoxy-chromen-4-one (188927-61-9) → patuletin (519-96-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; Ambient temperature;

DOI:10.1248/cpb.45.446

Reference yield:

patuletin 3-O-β-D-glucopyranosyl-(1->6)-<β-D-apiofuranosyl-(1->2)>-β-D-glucopyranoside → patuletin (519-96-0)

Guidance literature:

With hydrogenchloride; In methanol; water; at 100 ℃; for 1h;

DOI:10.1016/S0031-9422(00)94534-5

Reference yield:

1-(2,4-Bis-benzyloxy-3,6-dimethoxy-phenyl)-ethanone (3162-51-4) → patuletin (519-96-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / conc. HCl, acetic acid / 1 h / Ambient temperature

2: 83 percent / K₂CO₃, KI / acetone; dimethylformamide / Heating

3: 75 percent / AlBr₃, NaI / acetonitrile / 0.25 h / 0 °C

4: pyridine / 2 h / 70 - 80 °C

5: KOH / pyridine / 80 °C

6: 97 percent / conc. H₂SO₄, acetic acid / 1 h / 50 °C

7: 70 percent / dimethyldioxirane / acetone / 0 °C

8: 81 percent / K₂CO₃ / acetone / Heating

9: 97 percent / AlCl₃ / acetonitrile / 0.5 h / Ambient temperature

10: 96 percent / K₂CO₃ / methanol / 1.5 h / Heating

11: 74 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature

With pyridine; hydrogenchloride; potassium hydroxide; aluminium trichloride; aluminum tri-bromide; sulfuric acid; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; acetic acid; potassium iodide; sodium iodide; palladium on activated charcoal; In pyridine; methanol; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1248/cpb.45.446

upstream raw materials:

3,5,7,3',4'-pentahydroxy-6-methoxyflavone-3-O-β-D-glucopyranoside

3,5,7,3′,4′-pentahydroxy-6-methoxyflavone 7-O-β-D-glucopyranoside

7-Benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3,5-dihydroxy-6-methoxy-chromen-4-one

1-(2,4-Bis-benzyloxy-3,6-dimethoxy-phenyl)-ethanone

Downstream raw materials:

artemetin

3,3',4',7-tetra-O-cinnamoylpatuletin

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-(8-2H)-4H-1-benzopyran-4-one

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-6-methoxy-chromen-4-one

Refernces

• 1、 Lin, Long-Ze,Chen, Pei,Ozcan, Mustafa,Harnly, James M.. "Chromatographic profiles and identification of new phenolic components of Ginkgo biloba leaves and selected products". . p. 6671 - 6679. Retrieved 2008.
• 2、 Horie, Tokunaru,Shibata, Kenichi,Yamashita, Kazuyo,Kawamura, Yasuhiko,Tsukayama, Masao. "Studies of the selective O-alkylation and dealkylation of flavonoids. XXII. A convenient method for synthesizing 3,5,7-trihydroxy-6-methoxyflavones". . p. 446 - 451. Retrieved 2007/10/03.
• 3、 Barron, Denis,Ibrahim, Ragai K.. "OMBUIN 3-SULPHATE FROM FLAVERIA CHLORAEFOLIA". . p. 2362 - 2363. Retrieved 2007/10/02.