Salicylaldehyde-beta-D-glucoside, 2-Formylphenyl bD-glucopyranoside

2-Formylphenyl bD-glucopyranoside is a phenolic compound that has been shown to have high resistance to transport. It has been shown to possess surface methodology and this property can be used for the delivery of compounds. 2-Formylphenyl bD-glucopyranoside has also been shown to inhibit plant enzyme activities such as detoxification enzymes and carbohydrate chemistry, which are important in the uptake of natural compounds. In addition, it is able to bind with amines and hydroxyl groups on cells, which may be due to its receptor cell properties. 2-Formylphenyl bD-glucopyranoside can be synthesized by reacting trifluoroacetic acid with an amine and a hydroxyl group in the presence of glycol ethers or natural compounds.

Helicin analytical standard provided with chromatographic purity, to be used as reference material for qualitative determination.

Helicin is a beta-D-glucoside resultng from the oxidation of the benzylic hydroxy group of salicin to the corresponding aldehyde. It has a role as a metabolite. It is a member of benzaldehydes, a beta-D-glucoside and a monosaccharide derivative. It derives from a salicylaldehyde and a salicin.

Title: Helicin

CAS Registry Number: 618-65-5

CAS Name: 2-(bD-Glucopyranosyloxy)benzaldehyde

Additional Names: salicylaldehyde bD-glucoside

Molecular Formula: C13H16O7

Molecular Weight: 284.26

Percent Composition: C 54.93%, H 5.67%, O 39.40%

Literature References: Prepn by the oxidation of salicin with dil nitric acid: Schiff, Ann. 154, 19 (1870); from salicylaldehyde + O-tetraacetyl-a-glucosidyl bromide: Robertson, Waters, J. Chem. Soc. 1930, 2729 . ORD and stereochemical studies: Tsuzuki et al., Bull. Chem. Soc. Jpn. 44, 526 (1971).

Properties: Needles with 0.75 mol H2O from H2O; mp 175-176? when dried at 100?. [a]D20 -60? (c = 1.4). One gram dissolves in 55 ml water; freely sol in hot water, alcohol. Forms compds with urea, thiourea, certain amino acids.

Melting point: mp 175-176? when dried at 100?

Optical Rotation: [a]D20 -60? (c = 1.4)

Derivative Type: Tetraacetate

Molecular Formula: C21H24O11

Molecular Weight: 452.41

Percent Composition: C 55.75%, H 5.35%, O 38.90%

Properties: Needles from alc, mp 142?. [a]D20 -37? (acetone).

Melting point: mp 142?

Optical Rotation: [a]D20 -37? (acetone)

NOTE: The same formula is ascribed to spirein, found in Spiraea camtschatica Pall. and in S. ulmaria L., Rosaceae. Emulsin hydrolyzes helicin and spirein, yielding D-glucose and salicylaldehyde.