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Acetyl Glucosamine
"Descrizione"
by Carnob (1983 pt)
2023-Aug-30 17:30

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Acetyl Glucosamine (N-Acetyl-alpha-D-glucosamine) is a chemical compound derived from glucosamine.

The name describes the structure of the molecule

  • "Acetyl". Refers to an acetyl group, which is a derivative of acetic acid. This group is often added to molecules to enhance their stability or functionality.
  • "Glucosamine". Is an amino sugar that's naturally found in the body, particularly in the cartilage of joints. It's known for its joint and skin-beneficial properties.

Description of raw materials used in production

  • Glucosamine - A substance found naturally in many body tissues, especially in the cartilage of joints.
  • Acetic Acid - An organic acid used to introduce the acetyl group.

Step-by-step summary of industrial chemical synthesis process

  • Preparation - Glucosamine is purified and readied for the reaction.
  • Acetylation - Glucosamine is reacted with acetic acid or one of its derivatives (like acetic anhydride) to introduce the acetyl group, forming acetyl glucosamine.
  • Purification - The reaction product is purified to remove impurities or unreacted compounds.
  • Quality Control - The acetyl glucosamine is tested to ensure it's pure and meets desired specifications.

It appears in the form of a white powder. 

What it is for and where

Medical

Supplements. Acetyl Glucosamine is sometimes used in joint health supplements, though it's different from the glucosamine often employed for this purpose.

Research. Explored for its potential benefits in treating skin conditions and promoting skin health (1).

Cosmetics

Skin conditioning agent. It is the mainstay of topical skin treatment as it has the function of restoring, increasing or improving skin tolerance to external factors, including melanocyte tolerance. The most important function of the conditioning agent is to prevent skin dehydration, but the subject is rather complex and involves emollients and humectants that can be added in the formulation (2)

Commercial Applications

Cosmetics. Used in skincare products for its hydrating properties and as a skin barrier-improving ingredient.

Anti-Aging Products. Included in formulas aiming to reduce the appearance of fine lines and wrinkles.

Brightening Products. Utilized in products aiming to diminish the appearance of dark spots and even out skin tone.



  • Molecular Formula  C8H15NO6
  • Molecular Weight  221.21 g/mol
  • CAS  10036-64-3   7512-17-6
  • UNII    T13TI5GH3D
  • EC Number   233-115-1
  • DTXSID20905442
  • Nikkaji    J149.690E

Synonyms:

N-Acetyl-alpha-D-glucosamine

2-(Acetylamino)-2-deoxy-A-D-glucopyranose

References_____________________________________________________________________

(1) Bissett DL, Robinson LR, Raleigh PS, Miyamoto K, Hakozaki T, Li J, Kelm GR. Reduction in the appearance of facial hyperpigmentation by topical N-acetyl glucosamine. J Cosmet Dermatol. 2007 Mar;6(1):20-6. doi: 10.1111/j.1473-2165.2007.00295.x. PMID: 17348991.

Abstract. Glucosamine has been reported to inhibit melanin production in melanocyte culture. It thus has a potential to reduce hyperpigmentation via topical use. Due to stability limitations of glucosamine, we chose to clinically evaluate the stable derivative N-acetyl glucosamine (NAG). Based on in vitro Franz cell testing, NAG is a good skin penetrant. In an 8-week, double-blind, placebo-controlled, left-right randomized, split-face clinical test, topical 2% NAG reduced the appearance of facial hyperpigmentation. In a second clinical study involving the topical combination of 2% NAG with 4% niacinamide, an agent previously shown to be clinically active, the effect on hyperpigmentation was greater. Both of these agents are well tolerated by the skin. This high tolerance coupled with relative ease of formulation and stability in solution make NAG, especially in combination with niacinamide, a suitable cosmetic ingredient for use in skin care products dealing with issues of skin hyperpigmentation.

(2) Bissett DL. Glucosamine: an ingredient with skin and other benefits. J Cosmet Dermatol. 2006 Dec;5(4):309-15. doi: 10.1111/j.1473-2165.2006.00277.x. 

Abstract. Both glucosamine and its derivative N-acetyl glucosamine are amino-monosaccharides that serve key biochemical functions on their own and as substrate precursors for the biosynthesis of polymers such as glycosaminoglycans (e.g., hyaluronic acid) and for the production of proteoglycans. Glucosamine has an excellent safety profile and has been shown to provide benefits in several clinical disorders. Glucosamine compounds have been reported to have several beneficial effects on the skin or skin cells. Because of its stimulation of hyaluronic acid synthesis, glucosamine has been shown to accelerate wound healing, improve skin hydration, and decrease wrinkles. In addition, as an inhibitor of tyrosinase activation, it inhibits melanin production and is useful in treatment of disorders of hyperpigmentation. Mechanistically, glucosamine also has both anti-inflammatory and chondroprotective effects. Clinical trials have shown benefit in using oral glucosamine supplementation to improve symptoms and slow the progression of osteoarthritis in humans. Glucosamine has also been used to prevent and treat osteoarthritis in animals. Based on other observations, glucosamine has been suggested for additional clinical uses, including treatment of inflammatory bowel disease, migraine headaches, and viral infections. The current clinical uses for topical and oral glucosamine compounds and the mechanistic rationale for these uses are reviewed here.

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