618-65-5

Basic information

• Product Name: HELICIN
• Synonyms: HELECIN;HELICIN;HELICIN HYDRATE;2-(BETA-D-GLUCOPYRANOSYLOXY)BENZALDEHYDE;2-FORMYLPHENYL BETA-D-GLUCOPYRANOSIDE;2'-FORMYLPHENYL-BETA-D-GLUCOPYRANOSIDE;2-(O-BETA-D-GLUCOPYRANOSYLOXY)BENZALDEHYDE;(2S,3R,4S,5S,6R)-4-(3,4,5-TRIHYDROXY-6-HYDROXYMETHYL-TETRAHYDRO-PYRAN-2-YLOXY)-BENZALDEHYDE
• CAS NO: 618-65-5
• Molecular Formula: C₁₃H₁₆O₇
• Molecular Weight: 284.26
• EINECS: 210-558-9
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);13C & 2H Sugars;Biochemistry;Glucose;Glycosides;Sugars;Carbohydrates & Derivatives
• Mol File: 618-65-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 178 °C(lit.)
• Boiling Point: 386.76°C (rough estimate)
• Flash Point: 212.6 °C
• Appearance: White to yellow/Crystalline Powder
• Density: 1.3514 (rough estimate)
• Refractive Index: -62 ° (C=0.8, H2O)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Methanol, Water
• PKA: 12.77±0.70(Predicted)
• Water Solubility: 16.39g/L(cold water)
• Merck: 14,4628
• BRN: 89596
• CAS DataBase Reference: HELICIN(CAS DataBase Reference)
• NIST Chemistry Reference: HELICIN(618-65-5)
• EPA Substance Registry System: HELICIN(618-65-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 618-65-5(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Helicin (cas# 618-65-5) is a compound useful in organic synthesis.

Definition

ChEBI: A beta-D-glucoside resultng from the oxidation of the benzylic hydroxy group of salicin to the corresponding aldehyde.

Upstream product

• 14581-83-0 helicin acetate 
• 53765-89-2 Acetic acid 4-acetoxy-5-chloro-2-(1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester 
• 90-02-8 salicylaldehyde 
• 112289-85-7 2-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)benzaldehyde 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 89-95-2 2-methyl-benzyl alcohol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 898283-68-6 2-((2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)oxy)benzaldehyde 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 102178-93-8 isonicotinic acid-(2-β-D-glucopyranosyloxy-benzylidenehydrazide) 
• 101575-68-2 5-(2-β-D-glucopyranosyloxy-benzylidene)-barbituric acid 
• 101575-67-1 5-(2-β-D-glucopyranosyloxy-benzylidene)-2-thio-barbituric acid 
• 618-67-7 (3-(2'-O-glucophenyl)-2-trans-propenoic acid) 
• 113861-01-1 5-(2-β-D-glucopyranosyloxy-benzylidene)-1-phenyl-barbituric acid 
• 530-36-9 2-amino-1,2-diphenylethanol 
• 111240-28-9 2-β-D-glucopyranosyloxy-benzaldehyde-(4-hydroxy-phenylimine) 
• 111063-93-5 2-β-D-glucopyranosyloxy-benzaldehyde-(4-methoxy-phenylimine) 
• 121708-03-0 4-(2-β-D-glucopyranosyloxy-benzylidenamino)-benzoic acid 
• 103649-76-9 4-(2-β-D-glucopyranosyloxy-benzylidenamino)-2-hydroxy-benzoic acid 
• 110330-39-7 2-(2-glucopyranosyloxy-phenyl)-quinoline-4-carboxylic acid 
• 114202-58-3 2-(2-β-D-glucopyranosyloxy-phenyl)-quinoline-4-carboxylic acid ethyl ester 
• 111443-02-8 N-(2-β-D-glucopyranosyloxy-benzylidene)-sulfanilic acid amide 
• 28146-37-4 4-(2-β-D-glucopyranosyloxy-benzylidenamino)-benzoic acid ethyl ester 

Relevant articles and documents

Structure and reactivity of glycosides: IV. Koenigs-Knorr synthesis of aryl β-D-glucopyranosides using phase-transfer catalysts

A series of acetylated aryl β-D-glucopyranosides were prepared in 12-63% yields from tetra-O-acetyl-α-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols. 2001 MAIK "Nauka/Interperiodica".

PHASE-TRANSFER-CATALYZED D-GLUCOSYLATION:SYNTHESIS OF BENZOYLATED ARYL β-D-GLUCOPYRANOSIDES AND β-D-GLUCOPYRANOSYL-SUBSTITUTED CINNAMATES

Phase-transfer-catalysed D-glucosylation of chelated phenolic aglucons and substituted cinnamic acids, using 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide, resulted in the stereospecific formation of benzoylated aryl β-D-glucopyranosides and substituted-β-D-glucopyranosyl cinnamates, respectively, in good yields.The results conclusively disproved an earlier report that the phase-transfer method requires a nonparticipating group at C-2 or C-6 in the carbohydrate moiety. 1,2,3,4,6-Penta-O-benzoyl-β-D-glucopyranose was obtained as a minor side-product in all of these reactions.The possible mechanism of the phase-transfer method is discussed.