5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-

Base Information

• Chemical Name: 5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-
• CAS No.: 4670-05-7
• Molecular Formula: C29H24 O12
• Molecular Weight: 564.502
• Hs Code.: 29329990
• Wikidata: Q415677
• Pharos Ligand ID: XPUMTDZYTXHN
• ChEMBL ID: CHEMBL346119
• Mol file: 4670-05-7.mol

Synonyms:UNII-1IA46M0D13;CHEMBL346119;GTPL12464;HY-N0243;BDBM50487716;CS-5885;AC-34090;T3962;Q415677;(4az,7e,9z)-1-((2r,3r)-3,4-dihydro-3,5,7-trihydroxy-2h-chromen-2-yl)-3,4,5-trihydroxy-8-((2r,3r)-3,5,7-trihydroxychroman-2-yl)-6h-benzo[7]annulen-6-one

Chemical Property of 5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-

Chemical Property:

• Melting Point: 237-240 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 1003.9°Cat760mmHg
• PKA: 6.65±0.20(Predicted)
• Flash Point: 336.5°C
• PSA: 156.91000
• Density: 1.87g/cm³
• LogP: 3.09660
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 2
• Exact Mass: 564.12677620
• Heavy Atom Count: 41
• Complexity: 1260

Purity/Quality:

99% ^*data from raw suppliers

Theaflavin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)C5C(CC6=C(C=C(C=C6O5)O)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@@H]5[C@@H](CC6=C(C=C(C=C6O5)O)O)O)O)O
• Description: Theaflavins are a group of polyphenol pigments found in both black and oolong teas. They are obtained by the oxidation and dimerization of green tea catechins during the manufacture of black tea and oolong tea. Theaflavins contribute to the characteristic bright orange-red color of black tea. Theaflavins include theaflavin, theaflavin-3-gallate, theaflavin-3'-gallate and theaflavin-3,3'-digallate.Theaflavins are used to manage cholesterol and used to support the heart and digestive system. They could be used as protective agents against cardiovascular disease and cancer. It is also believed that they have a wide range of other pharmaceutical benefits, including antihypertensive, antioxidative and hypolipidemic activities. It is suggested that theaflavins have a potential to be developed as a safe and affordable topical microbicide for preventing sexual transmission of HIV.
• Uses: Theaflavin is a polyphenolic compound found in black tea. Theaflavin derivatives show anti-HIV-1 activity by targeting gp41. Theaflavin is a potent inhibitor of amyloid-β (Aβ) and α-synuclein (αS) fibrillogenesis. Theaflavin also shows potent anti-tumor and and antoxidant activities.

Technology Process of 5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-

There total 15 articles about 5H-Benzocyclohepten-5-one, 1,8-bis((2R,3R)-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy- 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: 70.0%

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) + epigallocatechin (970-73-0,1617-55-6,3371-27-5,13425-13-3,136892-45-0,970-74-1,98032-84-9) → theaflavin (4670-05-7)

Guidance literature:

With dihydrogen peroxide; In aq. phosphate buffer; acetone; for 0.0666667h; pH=6; Reagent/catalyst;

DOI:10.1016/j.tetlet.2014.07.092

Reference yield: 55.0%

(2R,3R)-5,7,5,7-tetra-O-(2-nitrobenzenesulfonyl)neotheaflavin (1203550-44-0) → neotheaflavin (4670-05-7,31701-93-6,36451-14-6,131486-05-0,137820-46-3)

Guidance literature:

With caesium carbonate; thiophenol; In N,N-dimethyl-formamide; acetonitrile; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0032-1318131

Reference yield: 39.0%

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) + epigallocatechin (970-73-0,1617-55-6,3371-27-5,13425-13-3,136892-45-0,970-74-1,98032-84-9) → theaflavin (4670-05-7) + theanaphthoquinone (302776-47-2)

Guidance literature:

With banana fruit flesh (Musa acuminata Colla cv. giant cavend..; In water; at 20 ℃; for 5h;

DOI:10.1039/b003510f

upstream raw materials:

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

epigallocatechin

GLUTATHIONE

1,2-diamino-benzene

Downstream raw materials:

theanaphthoquinone

Refernces

• 1、 Tanaka, Takashi,Mine, Chie,Kouno, Isao. "Structures of two new oxidation products of green tea polyphenols generated by model tea fermentation". . p. 8851 - 8856. Retrieved 2002.
• 2、 Matsuo, Yosuke,Oowatashi, Ryosuke,Saito, Yoshinori,Tanaka, Takashi. "Nonenzymatic Biomimetic Synthesis of Black Tea Pigment Theaflavins". . p. 2505 - 2508. Retrieved 2017/10/06.
• 3、 Asakawa, Tomohiro,Kawabe, Yusuke,Yoshida, Atsushi,Aihara, Yoshiyuki,Manabe, Tamiko,Hirose, Yoshitsugu,Sakurada, Asuka,Inai, Makoto,Hamashima, Yoshitaka,Furuta, Takumi,Wakimoto, Toshiyuki,Kan, Toshiyuki. "Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol". . p. 299 - 312. Retrieved 2016/05/09.