Picein

Base Information

• Chemical Name: Picein
• CAS No.: 530-14-3
• Molecular Formula: C14H18O7
• Molecular Weight: 298.293
• European Community (EC) Number: 208-473-7
• UNII: 2H3ACT49CQ
• DSSTox Substance ID: DTXSID201031535
• Nikkaji Number: J6.697D
• Wikipedia: Picein
• Wikidata: Q7190609
• Metabolomics Workbench ID: 68000
• ChEMBL ID: CHEMBL1512620
• Mol file: 530-14-3.mol

Synonyms:beta-glucopyrane-4-oxyacetophenone;picein

Chemical Property of Picein

Chemical Property:

• Appearance/Colour: pale yellow solid
• Melting Point: 195 °C
• Refractive Index: 1.6380 (estimate)
• Boiling Point: 562.6 °C at 760 mmHg
• PKA: 12.71±0.70(Predicted)
• Flash Point: 213.2 °C
• PSA: 116.45000
• Density: 1.433 g/cm³
• LogP: -0.93210
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Ethanol (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 298.10525291
• Heavy Atom Count: 21
• Complexity: 353

Purity/Quality:

≥98% ^*data from raw suppliers

4-Acetylphenyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: CC(=O)C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of Picein

There total 8 articles about Picein 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%

p-hydroxyacetophenone-4-O-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranoside (25876-45-3) → picein (530-14-3)

Guidance literature:

With water; triethylamine; In methanol; Ambient temperature;

DOI:10.1016/0031-9422(95)00219-7

Reference yield: 43.0%

→ picein (530-14-3)

Guidance literature:

With methanol; In dichloromethane; for 0.333333h;

With sodium methylate; In dichloromethane;

Reference yield:

4-Hydroxyacetophenone (99-93-4) → picein (530-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / KOH; triethylbenzylammonium chloride / CHCl₃; H₂O / Heating

2: 56 percent / 1M NaOMe / methanol

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; sodium methylate; In methanol; chloroform; water; 1: Koenigs-Knorr reaction;

DOI:10.1023/A:1013971214679

upstream raw materials:

UDP-glucose

4-Hydroxyacetophenone

p-hydroxyacetophenone-4-O-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

1-[4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-ethanone

3-Piperidin-1-yl-1-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propan-1-one; hydrochloride

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-(4-acetyl-phenoxy)-6-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Refernces

• 1、 Al Bittar, Sheiraz,Mora, Nathalie,Loonis, Michèle,Dangles, Olivier. "A simple synthesis of 3-deoxyanthocyanidins and their O-glucosides". . p. 4294 - 4302. Retrieved 2016/07/06.
• 2、 Hashimoto, Makoto,Takahashi, Miho. "Effective friedel-crafts acylations of O- and C-arylglycosides with triflic acid". scheme or table. p. 227 - 231. Retrieved 2009/09/06.