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A8625

N-Acetyl-D-glucosamine

≥99% (HPLC)

Synonym(s):

2-Acetamido-2-deoxy-D-glucose, D-GlcNAc

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About This Item

Empirical Formula (Hill Notation):
C8H15NO6
CAS Number:
7512-17-6
Molecular Weight:
221.21
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24891348
EC Number:
231-368-2
Beilstein/REAXYS Number:
1727589
MDL number:
MFCD00061615

Key Documents

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Product Name

N-Acetyl-D-glucosamine, ≥99% (HPLC)

InChI key

OVRNDRQMDRJTHS-RTRLPJTCSA-N

InChI

1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1

SMILES string

CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

biological source

crab (red)

assay

≥99% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

mp

211 °C (dec.) (lit.)

solubility

H2O: 50 mg/mL, clear to very slightly hazy (colorless to faint yellow solution)

storage temp.

−20°C

Quality Level

200

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This Item
A4106A32861079
N-Acetyl-D-glucosamine ≥99% (HPLC)

Sigma-Aldrich

A8625

N-Acetyl-D-glucosamine

N-Acetyl-D-glucosamine ≥95% (HPLC)

Sigma-Aldrich

A4106

N-Acetyl-D-glucosamine

N-Acetyl-D-glucosamine suitable for cell culture, BioReagent

Sigma-Aldrich

A3286

N-Acetyl-D-glucosamine

N-Acetyl-D-glucosamine An acceptor substrate for galactosyltransferases. Inhibits the lectin WGA and β-N-acetylhexosaminidase (Ki = 430 µM). When added to a medium, it improves the recovery of Haemophilus influenza from sputum.

Millipore

1079

N-Acetyl-D-glucosamine

technique(s)

HPLC: suitable

technique(s)

-

technique(s)

cell culture | mammalian: suitable

technique(s)

-

biological source

crab (red)

biological source

-

biological source

-

biological source

-

assay

≥99% (HPLC)

assay

≥95% (HPLC)

assay

≥95% (HPLC)

assay

≥98% (HPLC)

solubility

H2O: 50 mg/mL, clear to very slightly hazy (colorless to faint yellow solution)

solubility

water: 50 mg/mL, clear to cloudy, colorless to faintly yellow

solubility

-

solubility

water: 10 mg/mL

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

form

powder

form

powder

form

powder

form

powder

Application

N-Acetyl-D-glucosamine has been used:
  • as sugar for competitive inhibition in lectin histochemistry
  • as a component in Barbour-Stonner-Kelly (BSK) medium for cultivating Borrelia burgdorferi spirochetes strains
  • as a component of binding buffer to suspend Streptococcus pneumoniae strains for inhibition assay to examine the specificity of M-ficolin binding to S. pneumoniae strains

Biochem/physiol Actions

N-acetylglucosamine (GlcNAc) is mainly used in the food, cosmetics, and pharmaceutical industries.

General description

N-acetylglucosamine (GlcNAc) is the acetylated derivative of glucosamine (GlcN). It is an important component of proteoglycans, glycoproteins, glycosaminoglycans (GAGs), and other building units found in connective tissue.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000514883
0000514883
0000503973
0000503972
0000503972

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Kwang-Hyup Lee et al.
Tissue & cell, 48(4), 361-369 (2016-05-29)
The morphological characteristics and glycoconjugate composition of the vomeronasal organ (VNO) of the horse was investigated using histological, immunohistochemical, and lectin histochemical methods. The VNO is bilaterally located at the base of the nasal septum, has a tubular structure surrounded
Bingwu Yu et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 228, 159-165 (2013-01-09)
Strong (1)H-(1)H coupling can significantly reduce the accuracy of (1)J(CH) measured from frequency differences in coupled HSQC spectra. Although accurate (1)J(CH) values can be extracted from spectral simulation, it would be more convenient if the same accurate (1)J(CH) values can
Yasuhito Onodera et al.
The Journal of clinical investigation, 124(1), 367-384 (2013-12-10)
There is a considerable resurgence of interest in the role of aerobic glycolysis in cancer; however, increased glycolysis is frequently viewed as a consequence of oncogenic events that drive malignant cell growth and survival. Here we provide evidence that increased
Colette Cywes-Bentley et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(24), E2209-E2218 (2013-05-30)
Microbial capsular antigens are effective vaccines but are chemically and immunologically diverse, resulting in a major barrier to their use against multiple pathogens. A β-(1→6)-linked poly-N-acetyl-d-glucosamine (PNAG) surface capsule is synthesized by four proteins encoded in genetic loci designated intercellular
Lucy G Weaver et al.
Carbohydrate research, 371, 68-76 (2013-03-26)
Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the
View All Related Papers

Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. What is the physicochemical method or principle used to determine optical rotation in this product, could you confirm that the product is released with polarimetry?

    1 answer

    1. The method of analysis for this product is considered proprietary, however details and conditions are published in the Certificate of Analysis. See the link below for a sample CofA.
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/A8625-5G0000185218.pdf

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