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HomeProduct name listMURAMIC ACID

MURAMIC ACID

Synonym(s):2-Amino-3-O-(1-carboxyethyl)-2-deoxy-D-glucose

  • CAS NO.:1114-41-6
  • Empirical Formula: C9H17NO7
  • Molecular Weight: 251.23
  • MDL number: MFCD00213428
  • EINECS: 214-214-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-23 13:36:13
MURAMIC ACID Structural

What is MURAMIC ACID?

Chemical properties

White Solid

The Uses of MURAMIC ACID

Amino sugar found (as the N-acetyl derivative) in peptidoglycan, the main skeletal component of the bacterial cell wall. The N-acetyl derivative of muramic acid is an amino sugar that constitutes the peptidoglycan bacterial cell wall of Gram negative and Gram positive bacteria. Muramic acid is used as a chemical marker for the detection of bacterial contamination.

The Uses of MURAMIC ACID

Amino sugar found (as the N-acetyl derivative) in peptidoglycan, the main skeletal component of the bacterial cell wall. The N-acetyl derivative of muramic acid is an amino sugar that constitutes the peptidoglycan bacterial cell wall of Gram negative and Gram positive bacteria. Muramic acid is used as a chemical marker for the detection of bacterial contamination.

What are the applications of Application

Muramic acid is a component in many Gram-positive bacterial cell wall

General Description

Muramic acid is a marker for Gram-positive bacteria.

Purification Methods

Muramic acid crystallises from H2O or aqueous EtOH as the monohydrate which loses H2O at 80o in vacuo over P2O5. It sometimes contains some NaCl. It has been purified by dissolving 3.2g in MeOH (75mL), filtering from some insoluble material, concentrating to ~10mL and refrigerating. The colourless crystals are washed with absolute MeOH. This process does not remove NaCl; to do so, the product is recrystallised from an equal weight of H2O to give a low recovery yield of very pure acid (0.12g). On paper chromatography 0.26_g give one ninhydrin positive spot after development with 75% phenol (RF 0.51) or with sec-BuOH/HCO2H/H2O (7:1:2) (RF 0.30). [Matsushima & Park Biochemical Preparations 10 109 1963, J Org Chem 27 3581 1962.] The acid has also been purified by dissolving 990mg in 50% aqueous EtOH (2mL), cooling, collecting the colourless needles on a sintered glass funnel and drying over P2O5 at 80o/0.1mm to give the anhydrous acid. [Lambert & Zilliken Chem Ber 93 2915 1960.] Alternatively the acid is dissolved in a small volume of H2O, neutralised to pH 7 with ion-exchange resin beads (IR4B in OH-form), filtered, evaporated and dried. The residue is recrystallised from 90% EtOH (v/v) and dried as above for 24hours. [Strange & Kent Biochem J 71 333 1959.] The N-acetyl derivative (NAMA, R-2-(acetylamino)-3-O -(1-carboxyethyl)-2-deoxy-D-glucose, R -2(2 -acetylamino-2-deoxy -D-glucose -3-yloxy)-propionic acid) [10597-89-4], M 292.3, has m ~125o (dec) and [] 20D +41.2o after 24hours (c 1.5, H2O), pKEst ~ 3.6. [Watanabe & Saito J Bacteriol 144 428 1980, Beilstein 4 IV 2029.]

Properties of MURAMIC ACID

Melting point: 140-150 °C (dec.)
Boiling point: 592.0±50.0 °C(Predicted)
alpha  D25 +103° (c = 0.26 in water) (Matsushima, Park); D22 +146° (6 minutes) +116° (31 hrs) (c = 0.57 in water) (Osawa, Jeanloz)
Density  1.448±0.06 g/cm3(Predicted)
Flash point: 14℃
storage temp.  -20°C
solubility  Methanol (Slightly), Water (Slightly)
form  Solid
pka 3.18±0.10(Predicted)
color  White to Light Brown
Merck  13,6328
BRN  1713780
Stability: Hygroscopic
CAS DataBase Reference 1114-41-6(CAS DataBase Reference)

Safety information for MURAMIC ACID

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for MURAMIC ACID

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