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
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) |
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
New Products
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