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Introduction
Ascorbic Acid 2-Glucoside (AA2G), a stabilized derivative of ascorbic acid (Vitamin C), has gained substantial attention due to its improved stability, prolonged shelf-life, and potent biological activity.
Ascorbic acid is a vital nutrient involved in various physiological processes, including collagen synthesis, antioxidant protection, and immune system modulation.
However, pure ascorbic acid is chemically unstable and prone to oxidation, especially in aqueous and light-exposed environments.
To overcome these limitations, AA2G was developed by attaching a glucose moiety to the 2-hydroxyl group of ascorbic acid.
Chemical Identity
CAS Number: 129499-78-1
Synonyms:
AA2G,Ascorbyl glucoside,2-O-α-D-Glucopyranosyl-L-ascorbic acid,Vitamin C glucoside
AA2G is particularly valuable in cosmetic, pharmaceutical, and food industries where oxidative stability and sustained release of Vitamin C are essential.
It enhances the effectiveness of Vitamin C-based formulations by preventing early degradation and ensuring a more prolonged biological impact after enzymatic activation.
This article provides a comprehensive overview of AA2G, covering its chemical properties, synthesis methods, mechanisms of action, applications, safety profile, and recent advancements.
IUPAC Name: (2R)-2-[(2R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyfuran-2(5H)-one
Molecular Formula: C12H18O11
Molecular Weight: 338.26 g/mol
Structure: AA2G consists of a glucose moiety bound via an alpha-glycosidic linkage to the second carbon of the ascorbic acid molecule.
This structure enhances its resistance to oxidation and makes it more stable in aqueous environments.
Chemical Class: Glycosylated antioxidant, Vitamin C derivative
Synthesis and Industrial Production
AA2G is synthesized primarily through an enzymatic reaction using glycosyltransferases.
These enzymes catalyze the transfer of a glucose moiety from activated donor molecules such as uridine diphosphate glucose (UDP-glucose) to ascorbic acid.
Enzymatic Synthesis:
Enzyme: Glucosyltransferase (α-glucosyltransferase)
Source: Bacillus stearothermophilus or other Bacillus spp.
Substrate: L-Ascorbic acid
Donor: UDP-Glucose
Buffer conditions: pH 6.0–7.5
Reaction temperature: 25–40°C
Reaction time: 6–24 hours
Process Optimization:
Substrate molar ratios are optimized for maximum yield
Immobilized enzyme reactors improve cost efficiency and reusability
Chemical Synthesis (Less common):
Involves activation of glucose and acid catalysis
Lower specificity and lower yields
Purification:
Ion-exchange chromatography to remove salts and impurities
Reverse-phase HPLC for purification
Freeze-drying or spray-drying for final product formulation
Industrial Production:
Bioreactors are employed at large scales with inline monitoring
Typically, AA2G is produced under GMP conditions for cosmetic and pharmaceutical use
Physicochemical Properties
Appearance: White to pale yellow crystalline powder
Solubility: Highly soluble in water (up to 50 mg/mL), sparingly soluble in ethanol
Melting Point: 158–160°C (with decomposition)
pH Stability: Stable between pH 5.0–7.0; degrades under extreme acidic (pH < 3) or basic (pH > 8) conditions
Thermal Stability: Retains 90% of original concentration after 4 weeks at 40°C
Light Sensitivity: Exhibits improved photostability compared to ascorbic acid
Hygroscopic Nature: AA2G is moderately hygroscopic and should be stored in moisture-proof containers
Partition Coefficient (logP): –2.1 (suggesting hydrophilic nature)
UV Absorption: λmax at 265 nm
These physicochemical properties allow AA2G to be easily incorporated into a wide range of water-based formulations without the instability associated with pure Vitamin C.
Mechanism of Action
AA2G functions as a prodrug of Vitamin C. After application, it is enzymatically hydrolyzed to release biologically active ascorbic acid.
This activation is mediated by α-glucosidase enzymes present in the skin, intestines, and other tissues.
Hydrolysis:
Catalyzed by endogenous α-glucosidase enzymes
Rate depends on tissue type and enzyme availability
Slow, sustained release ensures prolonged antioxidant effect
Biological Pathway:
After hydrolysis, ascorbic acid enters the cytoplasm where it participates in redox cycling
Supports hydroxylation reactions, particularly in collagen synthesis
Regenerates other antioxidants such as Vitamin E and glutathione
Prolonged Action:
Delayed release reduces oxidative burst, prolonging efficacy in tissues
Enhances dermal penetration due to increased water solubility and stability
Biological Activity
AA2G has been extensively studied for its biological efficacy, which closely mirrors that of Vitamin C due to its efficient enzymatic conversion.
Antioxidant Activity:
Neutralizes reactive oxygen species (ROS) and reactive nitrogen species (RNS)
Protects lipids, proteins, and DNA from oxidative damage
Maintains redox homeostasis in skin and internal tissues
Collagen Synthesis:
Stimulates proline and lysine hydroxylation in collagen chains
Promotes fibroblast proliferation and matrix formation
Enhances elasticity and reduces fine lines when applied topically
Melanogenesis Inhibition:
Inhibits tyrosinase, the rate-limiting enzyme in melanin synthesis
Reduces pigmentation in hyperpigmented areas
UV Protection:
Absorbs UVB light directly
Reduces formation of cyclobutane pyrimidine dimers (CPDs)
Protects against UV-induced erythema and inflammation
Anti-inflammatory Effects:
Reduces IL-1β, TNF-α, and IL-6 expression in keratinocytes
Modulates NF-κB pathway activity
SAFETY INFORMATION ABOUT ASCORBIC ACID 2-GLUCOSIDE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
