Hemiphloin

Base Information

• Chemical Name: Hemiphloin
• CAS No.: 3682-03-9
• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.4
• European Community (EC) Number: 803-508-8
• DSSTox Substance ID: DTXSID50958027
• Nikkaji Number: J145.279G
• Wikidata: Q82938531
• Mol file: 3682-03-9.mol

Synonyms:naringenin-6-C-glucoside

Chemical Property of Hemiphloin

Chemical Property:

• Vapor Pressure: 8.53E-29mmHg at 25°C
• Boiling Point: 824.6°Cat760mmHg
• PKA: 6.95±0.40(Predicted)
• Flash Point: 292.4°C
• PSA: 177.14000
• Density: 1.638g/cm³
• LogP: 0.02480
• Storage Temp.: ?20°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 434.12129689
• Heavy Atom Count: 31
• Complexity: 638

Purity/Quality:

(2S)-Naringenin6-C-β-D-Glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=C(C1=O)C(=C(C(=C2)O)C3C(C(C(C(O3)CO)O)O)O)O)C4=CC=C(C=C4)O
• Isomeric SMILES: C1[C@H](OC2=C(C1=O)C(=C(C(=C2)O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C4=CC=C(C=C4)O
• Uses: (2S)-Naringenin 6-C-β-D-Glucopyranoside is a naturally occurring Naringenin (N378950) derivative and exerts potent bone anabolic effects through mimicking oetrogen action on osteoblasts.

Technology Process of Hemiphloin

There total 3 articles about Hemiphloin 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: 74.5%

UDP-glucose (133-89-1) + 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → naringenin-5-O-glucoside (23711-00-4) + 6-(C-β-D-glucopyranosyl)naringenin (3682-03-9,71963-94-5,139626-87-2)

Guidance literature:

With C-glycosyltransferase from Mangifera indica; In methanol; at 40 ℃; for 12h; pH=6.6; Enzymatic reaction;

DOI:10.1002/chem.201600411

Reference yield: 22.0%

D-glucose (50-99-7) + 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on (480-41-1) → 6-(C-β-D-glucopyranosyl)naringenin (3682-03-9,71963-94-5,139626-87-2)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In water; acetonitrile; for 12h; regioselective reaction; Reflux;

DOI:10.1016/j.carres.2010.04.001

Reference yield:

→ 6-(C-β-D-glucopyranosyl)naringenin (3682-03-9,71963-94-5,139626-87-2)

Guidance literature:

racem.-Naringenin, 1. Acetobromglucose, Natriumjodid, Natriumbutylat enthalt. Butanol, 20grad, 2. saure Hydrolyse;

upstream raw materials:

D-glucose

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

UDP-glucose

Downstream raw materials:

6-(C-β-D-glucopyranosyl)-8-(C-β-D-xylopyranosyl)naringenin

Refernces

• 1、 Sato, Shingo,Koide, Tomoyuki. "Synthesis of vicenin-1 and 3, 6,8- and 8,6-di-C-β-d-(glucopyranosyl- xylopyranosyl)-4′,5,7-trihydroxyflavones using two direct C-glycosylations of naringenin and phloroacetophenone with unprotected d-glucose and d-xylose in aqueous solution as the key reactions". experimental part. p. 1825 - 1830. Retrieved 2010/10/18.