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Hyaluronic acid (hyaluronan; hyaluronate; HA) is an anionic, nonsulfated glycosaminoglycan distributed widely throughout connective, epithelial, and neural tissues. As one of the chief components of the extracellular matrix, it contributes significantly to cell proliferation and migration, and also may be involved in the progression of some malignant tumors
Physicochemical Properties
| Molecular Formula | C28H44N2O23 |
| Molecular Weight | 5000-130000 |
| Exact Mass | 776.233 |
| CAS # | 9004-61-9 |
| Related CAS # | Hyaluronic acid sodium;9067-32-7 |
| PubChem CID | 24728612 |
| Appearance | White to off-white solid powder |
| Density | 1.8±0.1 g/cm3 |
| Boiling Point | 1274.4±65.0 °C at 760 mmHg |
| Flash Point | 724.5±34.3 °C |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.666 |
| LogP | -6.62 |
| Hydrogen Bond Donor Count | 14 |
| Hydrogen Bond Acceptor Count | 23 |
| Rotatable Bond Count | 12 |
| Heavy Atom Count | 53 |
| Complexity | 1300 |
| Defined Atom Stereocenter Count | 16 |
| SMILES | CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](OC1O)CO)O)O[C@H]2[C@@H]([C@H]([C@@H](C(O2)C(=O)O)O[C@H]3[C@@H](C([C@@H]([C@H](O3)CO)O)O[C@@H]4[C@@H]([C@H](C([C@H](O4)C(=O)O)O)O)O)NC(=O)C)O)O |
| InChi Key | KIUKXJAPPMFGSW-YXBJCWEESA-N |
| InChi Code | InChI=1S/C28H44N2O23/c1-5(33)29-9-18(11(35)7(3-31)47-25(9)46)49-28-17(41)15(39)20(22(53-28)24(44)45)51-26-10(30-6(2)34)19(12(36)8(4-32)48-26)50-27-16(40)13(37)14(38)21(52-27)23(42)43/h7-22,25-28,31-32,35-41,46H,3-4H2,1-2H3,(H,29,33)(H,30,34)(H,42,43)(H,44,45)/t7-,8-,9-,10-,11-,12-,13+,14?,15-,16-,17-,18-,19?,20+,21+,22?,25?,26+,27+,28-/m1/s1 |
| Chemical Name | (2S,4S,5R,6S)-6-[(2S,3R,5S,6R)-3-acetamido-2-[(3S,4R,5R,6R)-6-[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid |
| Synonyms | Hyaluronan; Hyaluronate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Endogenous Metabolite |
| ln Vitro | Hyaluronic acid (HA) is frequently utilized in cosmetic medicine because of its capacity to attach to a significant number of water molecules. Tissue hydration and resistance to mechanical injury are both enhanced by it. The processes of wound healing, ovulation, fertilization, signal transduction, and tumor physiology are all significantly impacted by HA. Rheumatoid arthritis and osteoarthritis are two joint conditions that are treated with HA. High molecular weight hyaluronic acid functions as a strong barrier to the inflammatory process, lessens the chemotaxis and migration of inflammatory cells, and guards against the damaging effects of free radicals. Because of its ability to lubricate the corneal endothelium, HA is utilized in ophthalmology. It is also used in cosmetic dermatology to increase tissue hydration and cellular resilience to mechanical damage, all while having minimal negative effects. Numerous studies have demonstrated its function in liver disorders, medications, and tumor indicators [1]. The growth and metastasis of cancer are significantly influenced by hyaluronic acid. In addition to promoting cell proliferation, adhesion, migration, and invasion, HA and HA fragment-tumor cell interactions can also induce angiogenesis, lymphangiogenesis, the epithelial-mesenchymal transition, stem cell-like properties, and resistance to chemotherapy and radiation in digestive tract tumors. therapeutic qualities[2]. |
| ln Vivo | Numerous studies on animals have shown the benefits of intra-articular hyaluronic acid administration. Studies on HA reveal that it can increase the synthesis of cartilage matrix, stop it from degrading, lessen inflammation, trigger the production of endogenous HA, and enhance the cartilage's suppleness and moisture content [1]. Fresh wounds can heal more quickly when polymer HA formulations are applied topically. They can also be utilized to treat chronic wounds and aid in the healing of venous leg ulcers [3]. |
| Enzyme Assay | Hyaluronic acid (hyaluronan, HA) is a linear polysaccharide formed from disaccharide units containing N-acetyl-D-glucosamine and glucuronic acid. It has a high molecular mass, usually in the order of millions of Daltons, and interesting viscoelastic properties influenced by its polymeric and polyelectrolyte characteristics. HA is present in almost all biological fluids and tissues. In clinical medicine, it is used as a diagnostic marker for many diseases including cancer, rheumatoid arthritis and liver pathologies, as well as for supplementation of impaired synovial fluid in arthritic patients by means of intra-articular injections. It is also used in certain ophthalmological and otological surgeries and cosmetic regeneration and reconstruction of soft tissue[3]. |
| Cell Assay | Hyaluronan (HA), an extracellular and peri-cellular glycosaminoglycan with a large molecular weight, plays an important role in cancer growth and metastasis. The correlation between HA accumulation and tumor progression has been shown in various digestive cancers. HA and HA fragment-tumor cell interaction could activate the downstream signaling pathways, promoting cell proliferation, adhesion, migration and invasion, and inducing angiogenesis, lymphangiogenesis, epithelial-mesenchymal transition, stem cell-like property, and chemoradioresistance in digestive cancers.[2] |
| References |
[1]. Physiochemical properties and application of hyaluronic acid: a systematic review. J Cosmet Dermatol. 2016 Dec;15(4):520-526. [2]. Hyaluronic acid in digestive cancers. J Cancer Res Clin Oncol. 2017 Jan;143(1):1-16. [3]. Hyaluronic acid: a natural biopolymer with a broad range of biomedical and industrial applications. Biotechnol Lett. 2007 Jan;29(1):17-25. |
Solubility Data
| Solubility (In Vitro) |
H2O : ~14.29 mg/mL DMSO : ~1 mg/mL) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 9.09 mg/mL (Infinity mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.) |