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

HCID 9844971
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Basic information

CAS
139626-60-1
Standard SMILES
CC(=O)N[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2C(=O)O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChIKey
LJKKEBYAXYCTNF-GIXQJHCPSA-N
Molecular formula
C14H23NO12
Average molar mass
397.33 g/mol
Monoisotopic mass
397.12202517

Overview

Beta-D-GlcpNAc-(1->4)-beta-D-GlcpA is an amino disaccharide consisting of 2-acetamido-beta-D-glucopyranose and beta-D-glucopyranuronic acid residues joined in sequence by a (14)-glycosidic bond. It is a member of acetamides, an amino disaccharide and a monocarboxylic acid. It is functionally related to a N-acetyl-beta-D-glucosamine and a beta-D-glucuronic acid.

Names & identifiers

Preferred name
4-O-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)-beta-D-glucopyranuronic acid
IUPAC
(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
English name
Hyaluronic acid
Molecular formula
C14H22NNaO11
Molecular weight
403.31

Names & synonyms

DTXSID201145699139626-60-14-O-[2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl]-beta-D-glucopyranuronic acid4-O-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)-beta-D-glucopyranuronic acidRefChem:935798GlyTouCan:G42361UODTXCID201577282G42361UO4-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-beta-D-glucopyranuronic acidGlcNAc(b1-4)b-GlcAARD3DLZ5K3CHEBI:150712
Show more names
HYALURONIC ACID SODIUMHyaluronic acid powderHyaluronate Acidacid hyaluronicHYALURONIC ACID (SODIUM HYALURONATE)aluronic acid、HAhyaluronic acid fillerSodium Hyaluronate MMWHyaluronic acid, bovine vitreous humorMucoitin
beta-D-GlcpNAc-(1->4)-beta-D-GlcpA2-acetamido-2-deoxy-beta-D-gluco-hexopyranosyl-(1->4)-beta-D-gluco-hexopyranuronic acid4-O-[2-(Acetylamino)-2-deoxy-I(2)-D-glucopyranosyl]-I(2)-D-glucopyranuronic acidbeta-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

Properties

Computed structural propertiesFilling in

XLogP
-4.5
Topological polar surface area
215 Ų
Hydrogen bond donors
8
Hydrogen bond acceptors
12
Rotatable bonds
5
Heavy atoms
27
Formal charge
0
Complexity
546

Experimental & physicochemical properties

Physical DescriptionSolid

Physicochemical properties

storage temp.
20 °C · −20°C
solubility
2 O: · H2O: 5 mg/mL, clear, colorless
form
Lyophilized Powder
color
White
Odor
Odorless
optical activity
-70 · -70~-80
Water Solubility
Soluble in water.
Major Application
3 D · 3D bioprintingtissue engineering (Hydrogels)
Cosmetics Ingredients Functions
SKIN CONDITIONINGANTISTATICMOISTURISINGHUMECTANT
Cosmetic Ingredient Review (CIR)
Hyaluronic acid (9004-61-9)
InChIKey
MAKUBRYLFHZREJ-IUPJJCKZNA-M
SMILES
[C@@H]1(O[C@H]2[C@H](O)[C@H]([C@H](O)O[C@@H]2C(=O)[O-])O)O[C@H](CO)[C@@H](O)C[C@H]1NC(=O)C.[Na+] |&1:0,2,3,5,6,9,15,18,21,r|

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
3-10
wgk
3
tsca
TSCA listed
rtecs
MT7250000
hazard_code
B
safety_code
22-24/25
Hazardous Substances Data
9004-61-9(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular
Applications · 3 items

UsesHyaluronic 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.

UsesSynovitis agent (veterinary).

Useshyaluronic 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.

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Database identifiers

CAS
139626-60-1、9004-61-9
PubChem CID
9844971
DTXSID
DTXSID201145699
ChEBI
CHEBI:150712
UNII
ARD3DLZ5K3
LogP
-6.623 · -6.623 (est)
CAS DataBase Reference
9004 · 9004-61-9
EWG's Food Scores
1 · 1
FDA UNII
HYALURONIC ACID (NON-ANIMAL STABILIZED) (B7SG5YV2SI)HYALURONIC ACID (S270N0TRQY)
NCI Drug Dictionary
hyaluronic acid
ATC code
3 AX05,M09AX01,R01AX09,S01KA01,S01KA51 · D03AX05,M09AX01,R01AX09,S01KA01,S01KA51
EPA Substance Registry System
Hyaluronic acid (9004-61-9)
UNSPSC Code
51202002 · 51202002
NACRES
23 · NA.23
Hazard Codes
B
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
RTECS
7250000 · MT7250000
F
3 · 3-10
TSCA
TSCA listed
Hazardous Substances Data
9004 · 9004-61-9(Hazardous Substances Data)

Upstream & downstream products

Upstream raw materials

A PRONASE APR3 (c-ANCA) ELISA
Additional notes · 2 items

Definitionhyaluronic acid: A glycosaminoglycan(mucopolysaccharide) that ispart of the matrix of connective tissue.Hyaluronic acid binds cells togetherand helps to lubricate joints.It may play a role in the migration ofcells at wounds; this activity ceaseswhen hyaluronidase breaks downhyaluronic acid.

DefinitionChEBI: A mucopolysaccharide composed of N-acetylglucosamine and glucuronic acid subunits. It is found in the connective tissues of vertebrates.