Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo

Kabushiki Kaisha Hayashibara

Seibutsu Kagaku Kenkyujo

Masaru Yoneyama

Toshio Miyake

Shuzo Sakai

Takahiko Mandai

Yukio Suzuki

Kei Suzuki

Hajime Aga

Takashi Shibuya

Hiromi Hijiya

Satoshi Iritani

2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-gluco-pyranosyl-L-acorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.

Pharmaceutical composition containing

A separation system to prepare a high .alpha.-glycosyl-L-ascorbic acid content product involves the use of a specific anion-exchange membrane having a molecular weight cut-off in the range of about 100-1,000. The system readily separates .alpha.-glycosyl-L-ascorbic acid from L-ascorbic acid and other impurities and provides a relatively-high yield.

Separation system for preparing high .alpha.-glycosyl-L-ascorbic acid

A novel .alpha.-glycosyl quercetin, wherein at least equimolar D-glucose residues are attached to quercetin via the .alpha.-bond, has a satisfactory water-solubility, light tolerance and stability, and exerts the inherent activity of quercetin in vivo. The .alpha.-glycosyl quercetin is prepared by a process comprising subjecting a solution containing quercetin and an .alpha.-glucosyl saccharide to the action of a saccharide-transferring enzyme to form an .alpha.-glycosyl quercetin, and recoverying the resultant .alpha.-glycosyl quercetin. The .alpha.-glycosyl quercetin can be advantageously used in combination with other materials in food products, cosmetic compositions and pharmaceutical compositions as a highly-safe and natural vitamin P-enriched agent, yellow-color-imparting agent, antioxidant, deodorant, stabilizer, quality-improving agent, antiseptic, prophylactic agent, therapeutic agent and ultraviolet-absorbing agent.

.alpha.-glycosyl quercetin, and its preparation and uses

A novel panose-rich saccharide powder which contains 48-93 w/w % panose, d.s.b., together with other oligo-saccharides, and has a crystallinity of 19% or higher on x-ray powder diffraction analysis. The saccharide powder has a substantial non-hygroscopicity, as well as a satisfiable free-flowing ability and stability. Thus, the saccharide powder is advantageously used in food products, cosmetics and pharmaceuticals.

Saccharide in the form of powder, and its preparation and use

2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these characteristics, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-glucopyranosyl-L-acorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.

Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid, and its

Disclosed is an industrial-scale preparation of a high 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid content product with an improved purity, the preparation comprising subjecting a solution containing 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid and a saccharide derivative of L-ascorbic acid exhibiting a direct reducing activity to an oxidation treatment, subjecting the resultant mixture ti column chromatography using a strongly-acidic cation exchange resin, and recoverying the resultant high 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid content fraction. Thus, the preparatiobn has a great significance in the industrial field.

Process for preparing high 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid

Crystalline 2-O-.alpha.-d-glucopyranosyl-L-ascorbic acid, and its

2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these, characteristics crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.

A high .alpha.-glycosyl-L-ascorbic acid content product is prepared by subjecting an aqueous solution containing .alpha.-glycosylL-ascorbic acid together with L-ascorbic acid and/or a saccharide to electrodialysis wherein an anion-exchange membrane is used in order to allow the L-ascorbic acid to predominantly permeate the membrane and to separate the L-ascorbic acid from .alpha.-glycosyl-L-ascorbic acid, or in order to allow the .alpha.-glycosyl-L-ascorbic acid to predominantly permeate the membrane and to separate the .alpha.-glycosyl-L-ascorbic acid from the saccharide. Thus, a high .alpha.-glycosyl-L-ascorbic acid content product having a desirable stability and physiological activity is readily prepared.

Process for preparing high .alpha.-glycosyl-L-ascorbic acid, and

5-O-.alpha.-D-Glucopyranosyl-L-ascorbic acid is a novel derivative of L-ascorbic acid which has a direct reducing activity and a satisfiable stability, as well as being readily hydrolyzed in vivo to form L-ascorbic acid. The 5-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is prepared by allowing a saccharide-transferring enzyme together with or without .alpha.-glucosidase to a solution containing an a-glucosyl saccharide and L-ascorbic acid, and suitably used in food products, agents of anti-susceptive diseases and cosmetics containing thereof.

5-0-.alpha.-D-Glucopyranosyl-L-ascorbic acid, and its preparation and

5-O-.alpha.-D-Glucopyranosyl-L-ascorbic acid is a novel derivative of L-ascorbic acid which has a direct reducing activity and a satisfiable stability, as well as being readily hydrolyzed in vivo to form L-ascorbic acid. The 5-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is prepared by allowing a saccharide-transferring enzyme together with or without .alpha.-glucosidase to a solution containing an .alpha.-glucosyl saccharide and L-ascorbic acid, and suitably used in food products, agents of anti-susceptive diseases and cosmetics containing thereof.

5-O-.alpha.-D-glucopyranosyl-L-ascorbic acid

A novel glycoside, 4.sup.G -alpha-D-glucopyranosyl rutin, is formed by a saccharide-transferring enzyme and glucoamylase in a solution which contains rutin together with glucoamylase. The 4.sup.G -alpha-D-glucopyranosyl rutin formed in such a solution is purified with a synthetic macroreticular resin, and crystallization in an organic solvent yields a complex crystal with the organic solvent. 4.sup.G -Alpha-D-glucopyranosyl rutin exhibits the same molecular absorption coefficient as intact rutin, and is readily water-soluble, substantially tasteless and odorless, and readily hydrolyzable in vivo to exhibit physiological activities inherent to rutin. These render 4.sup.G -alpha-D-glucopyranosyl rutin very useful as a highly-safe, natural yellow coloring agent, antioxidant, stabilizer, quality-improving agent, preventive, remedy, uv-absorbent and deterioration-preventing agent in foods, beverages, tobaccos, cigarets, feeds, pet foods, pharmaceuticals, cosmetics and plastics.

4.sup.G -alpha-D-glucopyranosyl rutin, and its preparation and uses

Alpha-glycosyl rutin is formed at a high concentration by allowing a saccharide-transferring enzyme to act on a high-rutin content liquid in suspension or solution to effect saccharide-transfer reaction. The resultant alpha-glycosyl rutin is easily recovered from the reaction mixture by allowing it to contact with a synthetic macroreticular resin. Alpha-glycosyl rutin is superior in water-solubility, resistance to light and stability to intact rutin, as well as having the physiological activities as intact rutin has. Thus, alpha-glycosyl rutin is favorably usable as a yellow coloring agent, antioxidant, stabilizer, fading-preventing agent, quality-improving agent, preventive, remedy, uv-absorbent and deterioration-preventing agent in foods, beverages, tobaccos, cigarettes, feeds, pet foods, pharmaceuticals for susceptive diseases, cosmetics including skin-refining agent and skin-whitening agent, and plastics, in addition to the use in vitamin P-enriching agents.

Preparation and uses of alpha-glycosyl rutin

2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-glucopyranosyl-L-acorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.

Growing community of inventors

Okayama, Japan

Masaru Yoneyama