129499-78-1

Basic information

• Product Name: ASCORBYL GLUCOSIDE
• Synonyms: ASCORBYL GLUCOSIDE;L-Ascorbic acid, 2-O-.alpha.-D-glucopyranosyl-;AA-2G;ascorbic acid 2-O-glucoside;ASCORBYL GLUCOSIDE, ASCORBIC ACID-2- GLUCOSIDE;2-O-A-D-GLUCOPYRANOSYL-L-ASCORBIC ACID;L-Ascorbic acid 2-o-alpha-glucoside;Pyrido(1,2-A)indol-6(7H)-one, 8,9-dihydro-7-(hydroxy(5-methyl-1H-imidazol-4-yl)methyl)-10-propyl-, (R*,S*)-
• CAS NO: 129499-78-1
• Molecular Formula: C₁₂H₁₈O₁₁
• Molecular Weight: 338.26472
• Mol File: 129499-78-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 158-163℃
• Boiling Point: 717.451 °C at 760 mmHg
• Flash Point: 271.813 °C
• Appearance: White to Off-white/Powder
• Density: 1.835 g/cm³
• Vapor Pressure: 8.94E-24mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.38±0.10(Predicted)
• Water Solubility: Soluble in water. (879 g/L) at 25°C.
• CAS DataBase Reference: ASCORBYL GLUCOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ASCORBYL GLUCOSIDE(129499-78-1)
• EPA Substance Registry System: ASCORBYL GLUCOSIDE(129499-78-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 129499-78-1(Hazardous Substances Data)

Usage

Description

Ascorbyl glucoside is a natural active substance containing Vitamin C structure, but it is stable. Ascorbyl glucoside can effectively inhibit formation of melanin, dilute the skin color, reduce age spots and freckles pigmentation.Ascorbic Acid 2-Glucoside(AA-2G) was originally developed as a quasi-drug cosmetic product in Japan to lighten the overall tone of the skin and reduce the pigmentation in age spots and freckles. Further research has shown other dramatic benefits and today AA-2G is used all over the world-not only for whitening but also for brightening dull looking skin, reversing the effects of aging, and in sunscreen products for protection.

Uses

Different sources of media describe the Uses of 129499-78-1 differently. You can refer to the following data:
1. According to the manufacturer, ascorbyl glucoside functions as a time-release version of vitamin C (ascorbic acid), and therefore is more stable than traditional ascorbic acid. It is considered to have skin-lightening and anti-hyperpigmentation properties, thanks to an ability to suppress melanin production. Its skinbrightening capacities are attributed to an apparent ability to reduce pre-existing melanin levels (as in the case of freckles or age spots). Ascorbyl glucoside could also help promote collagen synthesis and help reduce skin inflammation. It is found in antiaging, anti-wrinkle, and sun care products.
2. 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid reduce the free radicals that result from UV irradiation of the skin, and significantly reduce cell damage and photo-aging. It also promotes collagen synthesis. It can function as an antioxidant.

General Description

Ascorbyl glucoside is a stable form of vitamin C combined with glucose. When properly formulated and absorbed into skin, it breaks down to ascorbic acid (pure vitamin C).2-O-a-D-Glucopyranosyl-L-ascorbic Acid is a useful cosmetic gel and skin cleanser. Once absorbed, its breakdown to vitamin C is gradual, creating what’s known as a reservoir effect within skin. This leads to longer-lasting benefits.

Biochem/physiol Actions

2-O-a-D-glucopyranosyl-L-ascorbic acid or ascorbyl glucoside functions as a skin whitener and radical scavenger in cosmetics. It is responsible for the bleaching action of bleaching cosmetics. This compound is activated in a manner identical to that of vitamin C. The enzyme present in the epidermal basal membrane, ascorbyl phosphatase, slowly converts 2-O-a-D-glucopyranosyl-L-ascorbic acid into vitamin C, thereby maintaining a high vitamin C level in skin throughout the day.

InChI:InChI=1/C12H18O11/c13-1-3(15)9-8(19)10(11(20)22-9)23-12-7(18)6(17)5(16)4(2-14)21-12/h3-7,9,12-18,20H,1-2H2/t3-,4+,5+,6-,7+,9+,12+/m0/s1

Synthetic route

ascorbic acid (50-81-7) + Sucrose (57-50-1) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
With Bifidobacterium longum sucrose phosphorylase In aq. buffer at 40℃; for 72h; pH=5.2; Catalytic behavior; pH-value; Reagent/catalyst; Temperature; Enzymatic reaction; regioselective reaction;	50%

ascorbic acid (50-81-7) + dextrin → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: ascorbic acid; dextrin With Geobacillus stearothermophilus Tc-62 cyclomaltodextrin glucanotransferase In water at 55℃; for 50h; pH=5.5; Enzymatic reaction; Stage #2: With glucoamylase GLUCZYM AF6 In water for 24h; pH=4.5; Catalytic behavior; Reagent/catalyst; Time; Enzymatic reaction;	39%

sodium ascorbate (134-03-2) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
rat intestinal (or rice seed) α-glucosidase, maltose, thiourea, 0.1 M acetate buffer, 3 h, 50 deg C, in the dark;	14%

sodium ascorbate (134-03-2) + alpha cyclodextrin (10016-20-3) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: sodium ascorbate; alpha cyclodextrin With cyclodextrin glucanotransferase from Thermoanaerobacter sp. In aq. acetate buffer at 40℃; for 24h; pH=4.0; Enzymatic reaction; Stage #2: With amyloglucosidase from Aspergillus niger In aq. acetate buffer at 60℃; for 2h; Enzymatic reaction; regioselective reaction;	0.27%

sodium ascorbate (134-03-2) + β‐cyclodextrin (7585-39-9) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: sodium ascorbate; β‐cyclodextrin With cyclodextrin glucanotransferase from Thermoanaerobacter sp. In aq. acetate buffer at 40℃; for 24h; pH=4.0; Enzymatic reaction; Stage #2: With amyloglucosidase from Aspergillus niger In aq. acetate buffer at 60℃; for 2h; Enzymatic reaction; regioselective reaction;	0.24%

sodium ascorbate (134-03-2) + cyclomaltooctaose (17465-86-0) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: sodium ascorbate; cyclomaltooctaose With cyclodextrin glucanotransferase from Thermoanaerobacter sp. In aq. acetate buffer at 40℃; for 24h; pH=4.0; Enzymatic reaction; Stage #2: With amyloglucosidase from Aspergillus niger In aq. acetate buffer at 60℃; for 2h; Enzymatic reaction; regioselective reaction;	0.21%

Maltose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 6363-53-7) + sodium ascorbate (134-03-2) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
With acetate buffer; rice seed α-glucosidase; thiourea at 50℃; for 5h;

alpha cyclodextrin (10016-20-3) + ascorbic acid (50-81-7) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
at 60℃; for 24h; cyclomaltodextrin glucanotransferase, pH 5.5;	250 g
With Thermoanaerobacter sp. cyclodextringlucanotransferase; thiourea In aq. buffer at 50℃; pH=4.5; Temperature; Darkness;

β‐cyclodextrin (7585-39-9) + ascorbic acid (50-81-7) → 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1)

Conditions	Yield
Stage #1: β‐cyclodextrin; ascorbic acid at 45℃; for 120h; pH=5.5; aq. acetate buffer; Darkness; Molecular sieve; Stage #2: With glucoamylase at 65℃; for 6h; pH=5.5; aq. acetate buffer;

2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) + stearic anhydride (638-08-4) → 2-O-α-D-glucopyranosyl-6-O-octadecanoyl-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 0.5h;	52.8%

lauric anhydride (645-66-9) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 6‐O‐dodecanoyl‐2‐O‐α‐D‐glucopyranosyl‐Lascorbicacid

Conditions	Yield
With poly(4-vinylpyridine) In N,N-dimethyl-formamide at 45℃; for 21h; regioselective reaction;	49.7%
With pyridine at 60℃; for 1h;	45.7%
With pyridine at 60℃;

palmitic anhydride (623-65-4) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2-O-α-D-glucopyranosyl-6-O-hexadecanoyl-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 0.5h;	49.5%

capric anhydride (2082-76-0) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2-O-α-D-glucopyranosyl-6-O-decanoyl-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 1h;	39.5%

vinyl laurate (2146-71-6) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 5-O-dodecanoyl-2-O-α-D-glucopyranosyl-L-ascorbic acid (1242146-27-5) + 2-O-(6'-O-dodecanoyl-α-D-glucopyranosyl)-L-ascorbic acid (1242146-28-6) + 6‐O‐dodecanoyl‐2‐O‐α‐D‐glucopyranosyl‐Lascorbicacid

Conditions	Yield
With Bacillus subtilis alkaline protease In 1,4-dioxane; water; N,N-dimethyl-formamide at 45℃; for 46h; Enzymatic reaction; regioselective reaction;	A n/a B n/a C 38.1%

vinyl octanoate (818-44-0) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 6‐O‐octanoyl‐2‐O‐α‐D‐glucopyranosyl‐L-ascorbic acid

Conditions	Yield
With pyridine; Bacillus subtilis protease at 45℃; for 18h;	37.2%

octanoic acid anhydride (623-66-5) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 6‐O‐octanoyl‐2‐O‐α‐D‐glucopyranosyl‐L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 1h;	30%
With pyridine at 60℃;

2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) + myristic anhydride (626-29-9) → 2-O-α-D-glucopyranosyl-6-O-tetradecanoyl-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 1h;	29.8%

2-ethylbutyric anhydride (54502-37-3) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 6-O-(2-ethylbutyryl)-2-O-α-D-glucopyranosyl-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 2h;	24.9%

n-hexanoic anhydride (2051-49-2) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2-O-α-D-glucopyranosyl-6-O-hexanoyl-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 1h;	24.6%
With pyridine at 60℃;

2-propylpentanoic anhydride (51660-44-7) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2‐O‐α‐D‐glucopyranosyl‐6‐O‐(2‐propylpentanoyl)‐L‐ascorbic acid

Conditions	Yield
With pyridine at 60℃;	21.4%

vinyl laurate (2146-71-6) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 5-O-dodecanoyl-2-O-α-D-glucopyranosyl-L-ascorbic acid (1242146-27-5) + 6‐O‐dodecanoyl‐2‐O‐α‐D‐glucopyranosyl‐Lascorbicacid

Conditions	Yield
With Bacillus subtilis alkaline protease In water; N,N-dimethyl-formamide at 45℃; for 54h;	A 5.5% B 20.4%

butanoic acid anhydride (106-31-0) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 6-O-butyryl-2-O-α-D-glucopyranosyl-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃; for 1h;	17.2%

2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) + 2-pentylheptanoic anhydride (577772-84-0) → 2-O-α-D-glucopyranosyl-6-O-(2-pentylheptanoyl)-L-ascorbic acid

Conditions	Yield
With pyridine at 60℃;	14.3%

palmitic anhydride (623-65-4) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → (S)-2-hydroxy-2-((R)-3-hydroxy-5-oxo-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2,5-dihydrofuran-2-yl)ethyl palmitate + ((2R,3S,4S,5R,6S)-6-((R)-5-((S)-1,2-dihydroxyethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl palmitate

Conditions	Yield
With pyridine at 60℃;	A 3.9% B 1.9%

vinyl n-butyrate (123-20-6) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 6-O-butyryl-2-O-α-D-glucopyranosyl-L-ascorbic acid

Conditions	Yield
With pyridine; Bacillus subtilis protease at 45℃; for 24h;

vinyl caproate (3050-69-9) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2-O-α-D-glucopyranosyl-6-O-hexanoyl-L-ascorbic acid

Conditions	Yield
With pyridine; Bacillus subtilis protease at 45℃; for 24h;

vinyl caprate (4704-31-8) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2-O-α-D-glucopyranosyl-6-O-decanoyl-L-ascorbic acid

Conditions	Yield
With pyridine; Bacillus subtilis protease at 45℃; for 24h;

vinyl laurate (2146-71-6) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 6‐O‐dodecanoyl‐2‐O‐α‐D‐glucopyranosyl‐Lascorbicacid

Conditions	Yield
With pyridine; Bacillus subtilis protease at 45℃; for 24h;

vinyl palmitate (693-38-9) + 2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2-O-α-D-glucopyranosyl-6-O-hexadecanoyl-L-ascorbic acid

Conditions	Yield
With pyridine; Bacillus subtilis protease at 45℃; for 24h;

2-O-α-D-glucopyranosyl L-ascorbate (129499-78-1) → 2-O-α-D-glucosyl-L-ascorbic acid, sodium salt

Conditions	Yield
With sodium hydroxide In methanol at 4℃; for 504h;	35 g

Upstream product

• 134-03-2 sodium ascorbate 
• 7585-39-9 β‐cyclodextrin 
• 50-81-7 ascorbic acid 
• 57-50-1 Sucrose 
• 10016-20-3 alpha cyclodextrin 
• 17465-86-0 cyclomaltooctaose 

Relevant articles and documents

L-Ascorbic acid α-glucoside formed by regioselective transglucosylation with rat intestinal and rice seed α-glucosidases: Its improved stability and structure determination

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Walking a Fine Line with Sucrose Phosphorylase: Efficient Single-Step Biocatalytic Production of l-Ascorbic Acid 2-Glucoside from Sucrose

The 2-O-α-d-glucoside of l-ascorbic acid (AA-2G) is a highly stabilized form of vitamin C, with important industrial applications in cosmetics, food, and pharmaceuticals. AA-2G is currently produced through biocatalytic glucosylation of l-ascorbic acid from starch-derived oligosaccharides. Sucrose would be an ideal substrate for AA-2G synthesis, but it lacks a suitable transglycosidase. We show here that in a narrow pH window (pH 4.8–6.0, with sharp optimum at pH 5.2), sucrose phosphorylases catalyzed the 2-O-α-glucosylation of l-ascorbic acid from sucrose with high efficiency and perfect site-selectivity. Optimized synthesis with the enzyme from Bifidobacterium longum at 40 °C gave a concentrated product (155 g L?1; 460 mm), from which pure AA-2G was readily recovered in ～50 % overall yield, thus providing the basis for advanced production. The peculiar pH dependence is suggested to arise from a “reverse-protonation” mechanism in which the catalytic base Glu232 on the glucosyl–enzyme intermediate must be protonated for attack on the anomeric carbon from the 2-hydroxyl of the ionized l-ascorbate substrate.

METHOD FOR PRODUCING 2-O- ALPHA-D-GLUCOSYL-L-ASCORBIC ACID ANHYDROUS CRYSTAL-CONTAINING POWDER

[Object] An object of the present invention is to provide a process for enabling the production of a particulate composition containing anhydrous crystalline ascorbic acid 2-glucoside that significantly, more hardly cakes, even when the production yield of ascorbic acid 2-glucoside does not reach 35% by weight. [Construction] The above object is solved by providing a process for producing a particulate composition containing anhydrous crystalline ascorbic acid 2-glucoside, which comprises allowing a CGTase to act on a solution containing either liquefied starch or dextrin and L-ascorbic acid and then allowing a glucoamylase to act on the resulting solution to obtain a solution with an ascorbic acid 2-glucoside production yield of at least 27%, purifying the obtained solution to increase the ascorbic acid 2-glucoside content to a level of over 86% by weight, precipitating anhydrous crystalline ascorbic acid 2-glucoside by a controlled cooling method or pseudo-controlled cooling method, collecting the precipitated anhydrous crystalline ascorbic acid 2-glucoside, and ageing and drying the collected anhydrous crystalline ascorbic acid 2-glucoside.