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N-Acetyl Glucosamine modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly.
N-Acetyl Glucosamine regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription.
N-Acetyl Glucosamine exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate.
CAS Number: 7512-17-6
Molecular Formula: C8H15NO6
Molecular Weight: 221.21
EINECS Number: 231-368-2
Synonyms: Marine Sweet, GreenNAG, Bio-NAG, DTXSID3045855, N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide, acetyl glucosamine, N-((2R,3R,4S,5R)-3,4,5,6-Tetrahydroxy-1-oxohexan-2-yl)acetamide, 2-Acetamido-2-deoxyglucose, D-Glucose, 2-(acetylamino)-2-deoxy-, 2 Acetamido 2 Deoxyglucose, N-ACETYL GLUCOSAMINE D-, 2 Acetamido 2 Deoxy D Glucose, DTXCID5032369, D-Glucose, 2-acetamido-2-deoxy-, Glucopyranose, 2-acetamido-2-deoxy-, V956696549, N acetylglucosamine, NSC-400525, NSC-524344, Glucosamine, Acetyl, N Acetyl Glucosamine, Glucosamine, N-acetyl, beta N Acetylglucosamine, RefChem:936033, GlyTouCan:G01864SU, N Acetyl beta D Glucosamine, CHEBI:59640, G01864SU, 231-368-2, 2-Acetylamino-2-deoxy-D-glucose, 7512-17-6, Acetylglucosamine, N-Acetyl Glucosamine, N-Acetylglucosamine, aldehydo-N-acetyl-D-glucosamine, MFCD00136044, N-Acetyl-D-glucosamine - plant source, NSC 524344, CCRIS 9357, acetyl-glucosamine, NCGC00159338-02, NCGC00159338-03, EINECS 231-368-2, MFCD00061615, UNII-V956696549, NSC 400525, N Acetyl D Glucosamine, Glucosamine, N-acetyl-, A1EJ0, SCHEMBL19900, MLS006011606, orb1302795, N-Acetyl-D-Glucosamine (NAG), CHEMBL4303483, N-ACETYLGLUCOSAMINE [MI], CHEBI:17411, HY-A0132R, N-ACETYLGLUCOSAMINE [DSC], N-Acetyl-D-glucosamine (Standard), HY-A0132, Tox21_111344, BBL033994, EBC-26229, N-ACETYLGLUCOSAMINE [USP-RS], N-ACETYLGLUCOSAMINE [WHO-DD], STK801800, AKOS005622647, DB00141, MA00834, MA10891, NCGC00159338-05, BP-13072, DS-18661, SMR002121580, SY046107, 2-Acetamido-2-deoxy-alpga-D-glucopyranose, CAS-7512-17-6, CS-0017447, T4514, A-1200, A-1202, AB01325684-02, EN300-7414561, F224637, GLUCOPYRANOSE, 2-ACETAMIDO-2-DEOXY-, D-, N-Acetyl-D-glucosamine-Agarose, saline suspension, BRD-K80653534-001-01-7, Q32030210, 1186B229-E28C-4CF9-8146-EC06A584F821, N-[(1R,2R,3S,4R)-1-formyl-2,3,4,5-tetrahydroxy-pentyl]acetamide, GLUCOSAMINE SULFATE POTASSIUM CHLORIDE IMPURITY A [ EP IMPURITY], 2-Acetamido-2-deoxy-D-glucose 2-Acetamido-2-deoxy-D-glucopyranose N-Acetyl-D-glucosamine N-[2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]acetamide D-GlcNAc, 27555-50-6, N-Acetyl-D-glucosaMine, 98.0%(LC&N;N-qcetyl-D-glucosamine;2-Acetamido-2-deoxy-alpga-D-glucopyranose;ACETYL-D-GLUCOSAMINE, N-;N-ACETYL-DELTA-GLUCOSAMINE;2-ACETAMIDO-2-DESOXY-D-GLUCOPYRANOSE, N-ACETYL-D-GLUCOSAMINE;2-AcetaMido-2-deoxy-D-glucopyranose, 98% 10GR;N-ACETYL-D-GLUCOSAMINE 80 MESH
N-Acetyl Glucosamine is the N-acetyl derivative of glucosamine.
N-Acetyl Glucosamine is an amide between glucosamine and acetic acid.
A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification.
N-Acetyl Glucosamine is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans.
N-Acetyl Glucosamine is also synthesized in the glycosylation pathway as uridine diphosphate (UDP-GlcNAc), which can then be released following degradation of glycosylated proteins.
D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s).
N-Acetyl Glucosamine is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease.
N-Acetyl Glucosamine is used as a substrate in sialic acid production, cosmetics and in drug development research.
N-Acetyl Glucosamine, also known as N-acetyl-D-glucosamine, NAG or GlcNAc, is an amino sugar derived from glucose and the N-acetylated form of glucosamine.
N-Acetyl Glucosamine has the molecular formula C8H15NO6, a molecular weight of 221.21 g/mol, and CAS number 7512-17-6.
N-Acetyl Glucosamine occurs naturally in biological systems and serves as an important structural component and metabolic building block in organisms.
N-Acetyl Glucosamine is a monosaccharide derivative containing multiple hydroxyl groups together with an acetamido functional group.
N-Acetyl Glucosamines IUPAC name is N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide, reflecting its carbohydrate structure and N-acetyl substitution.
The combination of several hydroxyl groups gives the molecule a strongly hydrophilic character and contributes to its compatibility with aqueous biological and cosmetic formulations.
N-Acetyl Glucosamine is closely related to glucosamine but has an acetyl group attached to the amino functionality.
This modification provides greater chemical stability than glucosamine in certain formulation conditions and has helped establish N-Acetyl Glucosamine as a useful ingredient in topical cosmetic products.
N-Acetyl Glucosamines stability and skin penetration characteristics have been specifically investigated in formulations designed to address visible pigmentation irregularities.
N-Acetyl Glucosamine is also a naturally occurring component of several important biological polymers and structures.
N-Acetyl Glucosamine is one of the two repeating sugar units that form hyaluronic acid, where it alternates with D-glucuronic acid in the polysaccharide chain.
Hyaluronic acid is involved in processes including tissue organization, wound repair, cell signaling and maintenance of extracellular matrix properties.
N-Acetyl Glucosamine is found throughout nature and participates in carbohydrate metabolism and the biosynthesis of structural biomolecules.
In microorganisms and other organisms, N-Acetyl Glucosamine can be incorporated into larger polysaccharides and glycoconjugates that contribute to cellular or structural functions.
This broad biological occurrence is one reason N-Acetyl Glucosamine is studied in biochemical, nutritional, pharmaceutical and cosmetic research.
N-Acetyl Glucosamine has attracted particular interest in skincare because of its effects on pathways associated with melanin production.
Research indicates that it can interfere with the glycosylation and maturation of tyrosinase, an enzyme involved in melanogenesis, providing a mechanism for reducing the appearance of hyperpigmentation.
Clinical research has reported that topical formulations containing 2% N-Acetyl Glucosamine reduced the appearance of facial hyperpigmentation over an eight-week treatment period.
N-Acetyl Glucosamine can penetrate the skin sufficiently to reach relevant epidermal structures, which supports its use as a topical cosmetic active.
In controlled research, N-Acetyl Glucosamine was evaluated both alone and together with niacinamide, with the combination producing greater improvement in some pigmentation measurements than the individual treatment context.
Its combination of water compatibility, formulation stability and skin tolerability has contributed to its use in modern cosmetic formulations.
N-Acetyl Glucosamine is being investigated for broader effects on skin biology and cellular processes.
Experimental studies have reported changes in pigmentation-related gene expression following topical exposure, while other glucosamine-related research has examined antioxidant and anti-inflammatory mechanisms.
These findings provide a basis for continued cosmetic research, although individual biological effects should be distinguished from clinically established cosmetic benefits.
N-Acetyl Glucosamine also has notable physicochemical characteristics that influence how it behaves in formulations and biological systems.
It is a highly polar, hydrophilic molecule with a molecular weight of 221.21 g/mol, multiple hydrogen-bond donors and acceptors, and a relatively high topological polar surface area.
Experimental data report substantial water solubility, although the exact solubility can vary with temperature, pH, crystal form and measurement conditions.
The molecule exists as a stereochemically defined amino-sugar derivative, with the naturally relevant D-configuration being particularly important in biological systems.
Its carbohydrate structure allows it to participate in enzyme-mediated glycosylation reactions and to serve as a precursor for activated sugar nucleotides such as UDP-N-acetylglucosamine.
This biochemical versatility explains why N-Acetyl Glucosamine occurs in pathways involving extracellular matrix formation, protein modification and structural polysaccharide synthesis.
N-Acetyl Glucosamine has also been investigated for its potential anti-inflammatory effects in biological and dermatological research.
N-Acetyl Glucosamines metabolic relationship with glycosaminoglycans and cellular glycosylation pathways provides several possible mechanisms through which it may influence inflammatory signaling.
These mechanisms have generated interest in its incorporation into formulations intended for maintaining the appearance and condition of stressed or sensitive skin, although the strength of evidence varies between specific applications.
Another area of research concerns the interaction between N-Acetyl Glucosamine and chondroitin-containing formulations.
Clinical research has evaluated oral combinations of N-acetyl glucosamine and chondroitin sulfate in adults with knee discomfort, including a randomized, double-blind, placebo-controlled study using 100 mg of N-acetyl glucosamine and 180 mg of chondroitin sulfate daily for 24 weeks.
Such studies provide evidence that N-acetyl glucosamine is being investigated as a nutritional ingredient for joint-related applications, but results from glucosamine research cannot automatically be transferred to every N-acetyl glucosamine formulation or dose.
Melting point: 211 °C (dec.) (lit.)
Alpha: 42° (c = 2, water, 2 hrs)
Vapor pressure: 8 Pa at 20 °C
Refractive index: +39.0 to +42.0° (C = 1, H2O)
Storage temp.: -20 °C
Solubility: Soluble in concentrated hydrochloric acid, sulfuric acid, phosphoric acid and formic acid. Insoluble in water, dilute acids, dilute alkalis, concentrated alkalis and organic solvents.
Form: Saline suspension
Boiling point: 636.4 ± 55.0 °C (Predicted)
Density: 1.54 g/cm3
pKa: 13.04 ± 0.20 (Predicted)
Color: White to off-white
Biological source: Crab (red)
Optical activity: Alpha type +75 → +41; Beta type -22 → +41.3
Water solubility: H2O: 50 mg/mL, colorless to faint yellow solution, clear to very slightly hazy
Sensitive: Hygroscopic
Merck: 14,4458
BRN: 1727589
Stability: Stable. Incompatible with strong oxidizing agents.
N-Acetyl Glucosamine is the D isomer of N-acetylglucosamine.
N-Acetyl Glucosamine has a role as a bacterial metabolite.
N-Acetyl Glucosamine is a N-acetylglucosamine and a N-acetyl-D-hexosamine.
N-Acetyl Glucosamine is a monosaccharide, derived from glucose and undergoes linear polymerization by (1,4)-β-linkages to form the polymer chitin.
N-Acetyl Glucosamine is also a component of heterogenous polysaccharides, such as murein and hyaluronic acid.
N-Acetyl Glucosamine exhibits anti-inflammatory properties and is considered as a potential drug in the treatment of osteoarthritis.
N-Acetyl Glucosamines antiarthritic mode of mechanism involves the suppression of IL-1β (Interleuken-1β)-induced NO (nitric oxide), cyclooxygenase-2 (COX-2), and IL-6 production by inhibition of expression of iNOS (inducible nitric oxide synthase) protein and mRNA.
N-Acetyl Glucosamine oligomer may have the ability to initiate factors for canine polymorphonuclear cells (PMN) in vivo.
It possesses wound healing and chemotactic activity.
N-Acetyl Glucosamine and its derivatives are usually employed in preparing dietary supplements and also used in therapeutic development.
N-Acetyl Glucosamine is also an important precursor in the biosynthesis of hyaluronic acid, because cells use UDP-N-acetylglucosamine as one of the two substrates required by hyaluronan synthase enzymes.
Through this metabolic pathway, N-acetylglucosamine contributes to the formation of hyaluronic acid in the extracellular matrix, including the epidermis.
This relationship has increased interest in N-Acetyl Glucosamine as a cosmetic ingredient associated with skin hydration, extracellular matrix maintenance and barrier-related functions.
N-Acetyl Glucosamine also occurs as a fundamental structural sugar in chitin, the polysaccharide found in the exoskeletons of crustaceans and insects and in the cell walls of many fungi.
N-Acetyl Glucosamine is also incorporated into bacterial peptidoglycan, where N-acetylglucosamine alternates with N-acetylmuramic acid to form an important component of bacterial cell walls.
Its presence in these structurally different biological materials demonstrates that N-Acetyl Glucosamine has functions extending far beyond its applications in cosmetics.
N-Acetyl Glucosamine is involved in protein glycosylation and cellular signaling through the hexosamine biosynthetic pathway.
The resulting UDP-GlcNAc can participate in O-GlcNAc modification of intracellular proteins, including regulatory proteins involved in transcription and cellular signaling.
Changes in cellular GlcNAc metabolism can therefore influence processes such as gene regulation, nutrient sensing and signal transduction.
N-Acetyl Glucosamine is closely connected with the formation and maintenance of the skin extracellular matrix, particularly through its relationship with hyaluronan metabolism.
Hyaluronan is continuously synthesized and degraded in the skin, and its molecular size influences its biological behavior and interactions with epidermal cells.
N-Acetyl Glucosamine forms part of the hyaluronan structure, its availability is linked to an important metabolic pathway involved in epidermal extracellular matrix homeostasis.
Research has also examined N-Acetyl Glucosamine in relation to skin barrier function and epidermal renewal.
The production of hyaluronan in keratinocytes is associated with processes involving epidermal organization, hydration and barrier maintenance, although the precise relationship between hyaluronan metabolism and keratinocyte proliferation remains complex.
This has encouraged investigation of N-acetylglucosamine-related compounds as cosmetic ingredients for supporting the appearance and condition of the skin barrier.
N-Acetyl Glucosamine can be produced from chitin-rich biological materials, making crustacean shells and fungal biomass important potential starting materials for industrial production.
Traditional manufacturing approaches can involve enzymatic or chemical conversion of chitin or chitosan into N-acetylglucosamine, while microbial and enzymatic production methods have also been investigated.
These production routes allow N-Acetyl Glucosamine to be supplied for applications in cosmetics, food, biotechnology and pharmaceutical research.
N-Acetyl Glucosamine is particularly interesting in cosmetic formulations because it combines a relatively small molecular structure with multiple hydroxyl groups and an acetamido group.
Its hydrophilic character allows it to be incorporated into aqueous formulations such as serums, gels, creams and lotions without requiring the highly lipophilic delivery systems used for oil-soluble actives.
N-Acetyl Glucosamines compatibility with other commonly used cosmetic ingredients has also supported research into combination formulations, including products containing niacinamide and other skin-active compounds.
Another important characteristic is that N-Acetyl Glucosamine is not simply a passive structural sugar, because its metabolic derivatives participate in cellular regulation.
UDP-GlcNAc availability reflects the integration of carbohydrate, amino-acid, fatty-acid and nucleotide metabolism and can influence protein O-GlcNAcylation.
Consequently, N-Acetyl Glucosamine is studied not only as a structural carbohydrate but also as part of broader metabolic and cellular signaling networks.
Uses Of N-Acetyl Glucosamine:
N-Acetyl Glucosamine is used in the identification and characterization of N-acetyl-beta-D-hexoaminidase.
N-Acetyl Glucosamine is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease.
Further, it is used as a substrate in sialic acid production, cosmetics and in drug development research.
N-Acetyl Glucosamine is a monosaccharide derivative of glucose.
It is released by the action of O-GlcNAcase, in mammalian systems from proteins that have been post-translationally modified with O-GlcNAc.
N-Acetyl Glucosamine enhances the proliferation and collagen expression of fibroblasts, reduces hyperpigmentation and is therefore considered a valuable ingredient in cosmetics for improving skin wrinkles and color.
Important substrate for the production of sialic acids.
Used in multiple other applications in drug development and food supplement, based on a newly described bio-wave model.
N-Acetyl Glucosamine is widely used in skincare formulations as a multifunctional cosmetic active, particularly in products designed for uneven skin tone and visible signs of aging.
N-Acetyl Glucosamine can be incorporated into creams, lotions, serums, moisturizers, masks and other topical preparations because of its water compatibility and formulation stability.
Its established cosmetic research profile has made it especially relevant to products targeting pigmentation, skin texture and overall skin appearance.
One of the best-documented cosmetic applications of N-Acetyl Glucosamine is the reduction of the appearance of facial hyperpigmentation.
A double-blind, placebo-controlled study found that topical 2% N-Acetyl Glucosamine reduced the appearance of facial hyperpigmentation after eight weeks of use.
N-Acetyl Glucosamine is therefore used in brightening products intended for dark spots, uneven pigmentation and other forms of visible discoloration.
N-Acetyl Glucosamine is also used in combination with niacinamide in cosmetic formulations for uneven pigmentation.
A randomized, double-blind clinical study evaluated a moisturizer containing 4% niacinamide and 2% N-Acetyl Glucosamine and reported reductions in detectable facial spots and pigmentation compared with the vehicle formulation.
This combination is therefore relevant to facial moisturizers, brightening creams and daily skincare products formulated for irregular pigmentation.
The ingredient is used in moisturizing and skin-conditioning products because topical N-Acetyl Glucosamine has been investigated for effects on stratum corneum hydration and exfoliation.
Clinical and laboratory research reported increased skin moisturization, reduced flakiness and normalization of stratum corneum desquamation following topical treatment with N-Acetyl Glucosamine.
These properties support its incorporation into products intended for dry, rough or unevenly textured skin.
N-Acetyl Glucosamine is also used in anti-aging skincare, including formulations targeting fine lines, wrinkles, skin texture and loss of visible smoothness.
Clinical research has evaluated products containing N-Acetyl Glucosamine in facial and neck formulations and reported improvements in several measured signs of skin aging.
This has led to its inclusion in firming creams, facial moisturizers, neck creams and décolletage treatments.
N-Acetyl Glucosamine is particularly suitable for neck and décolletage products where pigmentation and textural changes are common cosmetic concerns.
A 16-week clinical study evaluated a firming neck and décolletage cream containing N-Acetyl Glucosamine and reported improvements in texture-related aging parameters and measured skin brightness.
This supports its use in specialized products for areas that receive significant environmental exposure but are often treated differently from facial skin.
N-Acetyl Glucosamine is also used in formulations intended to support skin smoothness and epidermal renewal.
N-Acetyl Glucosamines effects on keratinocyte differentiation markers and stratum corneum desquamation have been investigated as a possible alternative approach to improving skin surface texture.
Consequently, it can be incorporated into exfoliating or smoothing skincare products without relying exclusively on conventional alpha-hydroxy acids.
Beyond cosmetics, N-Acetyl Glucosamine is used as a dietary supplement ingredient, particularly in products related to joint and connective-tissue health.
Its biological relationship with glycosaminoglycans and proteoglycans has encouraged investigation of oral N-Acetyl Glucosamine in joint-support formulations.
Clinical studies have evaluated N-Acetyl Glucosamine-containing supplements in people with knee discomfort and osteoarthritis-related symptoms, although the evidence depends on the particular formulation and study design.
N-Acetyl Glucosamine also has applications in the food and nutraceutical industries as a functional carbohydrate ingredient.
Research has investigated its incorporation into nutritional products and food systems, while its relationship with naturally occurring glycoproteins and glycosaminoglycans provides a biochemical basis for these applications.
Its relatively established production technology and availability from chitin-derived raw materials further support its use as a specialty nutritional ingredient.
An important industrial application is the use of N-Acetyl Glucosamine as a starting material for chitin-derived biomaterials and oligosaccharides.
It can be converted into chitin oligosaccharides and related carbohydrate materials that are being investigated for antimicrobial, antioxidant, anti-inflammatory, agricultural and biomedical applications.
This gives N-Acetyl Glucosamine relevance not only as a finished ingredient but also as a building block for higher-value functional materials.
N-Acetyl Glucosamine is also used as a research and biotechnology substrate for studying carbohydrate metabolism, glycosylation and microbial utilization of amino sugars.
Microorganisms can metabolize GlcNAc as a carbon or nitrogen source, and research has explored its conversion into useful biochemical products, including biofuel-related compounds.
These applications are particularly relevant to fermentation biotechnology and the valorization of chitin-rich biomass.
In industrial biotechnology, N-Acetyl Glucosamine can be produced from chitin-rich waste streams, including crustacean shells and fungal biomass.
Chemical hydrolysis, enzymatic conversion and microbial biotransformation have all been investigated as routes for converting chitin into purified N-Acetyl Glucosamine.
This creates opportunities for producing cosmetic, nutritional and pharmaceutical ingredients while adding value to otherwise underutilized biological waste materials.
Safety Profile Of N-Acetyl Glucosamine:
N-Acetyl Glucosamine is generally considered to have a relatively low hazard profile when handled and used under appropriate conditions.
Current aggregated GHS information reports that N-Acetyl Glucosamine does not meet the criteria for classification as a hazardous substance, with all reported ECHA notifications indicating no GHS hazard classification.
The Cosmetic Ingredient Review Expert Panel has also concluded that Acetyl Glucosamine is safe for cosmetic use under the assessed conditions when formulations are designed to be non-irritating.
The formal classification can nevertheless differ between individual commercial grades and suppliers.
For example, a recent Thermo Fisher SDS for N-Acetyl-D-glucosamine states that the product is not classified as hazardous under the applicable OSHA standard, while other supplier databases have historically reported irritation or other hazard classifications.
The SDS supplied with the specific grade should therefore be used as the primary reference for workplace handling and regulatory classification.
Dry N-Acetyl Glucosamine is a powdered material, making dust generation an important practical handling consideration even when the substance itself is not formally classified as hazardous.
The current Thermo Fisher SDS recommends adequate ventilation, appropriate personal protective equipment and avoidance of dust formation during handling.
These precautions are particularly relevant during weighing, transferring, grinding or industrial-scale mixing of the powdered material.
Eye contact with concentrated powder should be avoided during laboratory and manufacturing operations.
Although current CLP data do not classify N-Acetyl Glucosamine as an eye irritant, direct exposure to chemical powders can cause mechanical discomfort or irritation.
Safety glasses are therefore appropriate when handling the dry raw material, particularly where dust or accidental splashing of prepared solutions is possible.
Skin contact with concentrated material should likewise be minimized during routine handling.
The current European SDS does not identify a specific skin-hazard classification for N-Acetyl-D-glucosamine, while some older supplier information reported potential irritation.
Wearing suitable gloves and washing exposed skin with water are reasonable precautions for repeated occupational handling.
Inhalation exposure is primarily relevant when the substance is handled as a fine powder.
Accidental ingestion of N-Acetyl Glucosamine is not generally associated with significant acute toxicity at normal intended exposure levels.
N-Acetyl Glucosamine Procurement and Technical Support:
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Additional support can be provided regarding product specifications, available documentation, and the evaluation of suitable product options based on the intended application.
