4-O-[2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl]-beta-D-glucopyranuronic acid

Base Information

• Chemical Name: 4-O-[2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl]-beta-D-glucopyranuronic acid
• CAS No.: 9004-61-9
• Molecular Formula: (C14H21NO11)n
• Molecular Weight: 403.31
• Hs Code.: 3004909090
• UNII: ARD3DLZ5K3
• DSSTox Substance ID: DTXSID201145699
• Wikidata: Q76414588
• Mol file: 9004-61-9.mol

Synonyms:4-O-[2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl]-beta-D-glucopyranuronic acid;139626-60-1;GlcNAc(b1-4)b-GlcA;ARD3DLZ5K3;CHEBI:150712;DTXSID201145699;beta-D-GlcpNAc-(1->4)-beta-D-GlcpA;2-acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->4)-beta-D-gluco-hexopyranuronic acid;4-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-beta-D-glucopyranuronic acid;beta-D-Glucopyranuronic acid, 4-O-[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-;WURCS=2.0/2,2,1/[a2122A-1b_1-5][a2122h-1b_1-5_2*NCC/3=O]/1-2/a4-b1;(2S,3S,4R,5R,6R)-3-[(2S,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid

Chemical Property of 4-O-[2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl]-beta-D-glucopyranuronic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.666
• Boiling Point: 1274.4oC at 760 mmHg
• Flash Point: 724.5oC
• PSA: 399.71000
• Density: 1.78 g/cm3
• LogP: -8.49480
• Storage Temp.: −20°C
• Solubility.: H2O: 5 mg/mL, clear, colorless
• Water Solubility.: Soluble in water.
• XLogP3: -4.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 397.12202517
• Heavy Atom Count: 27
• Complexity: 546

Purity/Quality:

98%, ^*data from raw suppliers

Hyaluronic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: B
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2C(C(C(OC2C(=O)O)O)O)O)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2C(=O)O)O)O)O)CO)O)O
• Uses: Hyaluronic acid is a naturally derived, non - immunogenic, non - adhesive glycosaminoglycan that plays a prominent role in various wound - healing processes, as it as it is naturally angiogenic when degraded to small fragments. Hyaluronic acid promotes early inflammation which is critical for initiating wound healing, but then moderates later stages of the process, allowing matrix stabilization and reduction of long term inflammation. Hyaluronic acid is a main source for pharmaceutical, medical and cosmetic application. Synovitis agent (veterinary). hyaluronic acid is a glycosaminoglycan component. Hyaluronic acid occurs naturally in the dermis. It is thought to play a critical role in healthy skin by controlling the physical and biochemical characteristics of epidermal cells. It also regulates general skin activity, such as water content, elasticity, and the distribution of nutrients. Its water-absorption abilities and large molecular structure allow the epidermis to achieve greater suppleness, proper plasticity, and turgor. Hyaluronic acid is a natural moisturizer with excellent water-binding capabilities. In a solution of 2 percent hyaluronic acid and 98 percent water, the hyaluronic acid holds the water so tightly that it appears to create a gel. However, it is a true liquid in that it can be diluted and will exhibit a liquid’s normal viscous flow properties. When applied to the skin, hyaluronic acid forms a viscoelastic film in a manner similar to the way it holds water in the intercellular matrix of dermal connective tissues. This performance and behavior suggests that hyaluronic acid makes an ideal moisturizer base, allowing for the delivery of other agents to the skin. Manufacturers claim that the use of hyaluronic acid in cosmetics results in the need for much lower levels of lubricants and emollients in a formulation, thereby providing an essentially greaseless product. Furthermore, its ability to retain water gives immediate smoothness to rough skin surfaces and significantly improves skin appearance. For the benefits of hyaluronic acid to be realized in a cosmetic, the product needs to be applied on a regular basis as it is broken down in skin within 24 to 48 hours of application. note, this is not the case with hyaluronic acid injections as the technology used is different.

Technology Process of 4-O-[2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl]-beta-D-glucopyranuronic acid

There total 5 articles about 4-O-[2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl]-beta-D-glucopyranuronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

2-methyl-[1,2-di-deoxy-3-O-(sodium β-D-glucopyranosyluronate)-α-D-glucopyrano]-[2,1,d]-2-oxazoline → hyaluronic acid (9004-61-9)

Guidance literature:

With Carbonate buffer; ovine testicular hyaluronidase; In water-d2; at 30 ℃; for 36h; pH=7.1;

DOI:10.1021/ja017104+

Reference yield:

hyaluronic acid, sodium salt → hyaluronic acid (9004-61-9)

Guidance literature:

With Amberlyte IR 120, H(+)-form resin; In water;

Reference yield:

sodium hyaluronate (9067-32-7) → hyaluronic acid (9004-61-9)

Guidance literature:

upstream raw materials:

sodium hyaluronate

Downstream raw materials:

2-deoxy-2-amino glucose

D-glucuronic acid

sodium hyaluronate

Refernces

• 1、 -. "COMPOSITION COMPRISING HYALURONIC ACID AND/OR ITS SALTS FOR TREATMENT OF ATOPIC DERMATITIS". Page/Page column 8; 10. . Retrieved 2008/12/06.
• 2、 -. "PHARMACEUTICAL FORMULATIONS". Page/Page column 17. . Retrieved 2010/02/15.