MURAMIC ACID Chemical Properties

Melting point:

140-150 °C (dec.)

alpha 

D25 +103° (c = 0.26 in water) (Matsushima, Park); D22 +146° (6 minutes) +116° (31 hrs) (c = 0.57 in water) (Osawa, Jeanloz)

Boiling point:

592.0±50.0 °C(Predicted)

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

Safety Statements 

22-24/25

WGK Germany 

1

F 

3-10

HS Code 

2932990090

MSDS

• Language:English Provider:SigmaAldrich

MURAMIC ACID Usage And Synthesis

Chemical Properties

White Solid

Uses

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.

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.]

MURAMIC ACID(1114-41-6)Related Product Information

• AC-MURAMIC ACID
• BENZYL N-ACETYL-4,6-O-BENZYLIDENEMURAMIC ACID
• MURAMIC ACID
• AC-ALPHA-BENZYL-4,6-O-BENZYLIDENE-MURAMIC ACID
• BENZYL N-ACETYL-4,6-O-BENZYLIDENE-A-D-MURAMIC ACID, METHYL ESTER,BENZYL N-ACETYL-4,6-O-BENZYLIDENE-ALPHA-D-MURAMIC ACID, METHYL ESTER
• N-ACETYL ALPHA-MURAMIC ACID
• 2-[[7-(ACETYLAMINO)-6-(BENZYLOXY)-2-PHENYLPERHYDROPYRANO[3,2-D][1,3]DIOXIN-8-YL]OXY]PROPANOIC ACID
• 2-Acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-2-D-glucose Methyl Ester
• 2-ACETAMIDO-4-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSL)-1,6-DI-O-N-ACETYL-ALPHA-D-MURAMIC ACID
• Benzyl N-Acetyl-6-O-benzyl-α-D-muramic Acid, Methyl Ester
• ALPHA-BENZYL-4,6-O-BENZYLIDENE-MURAMIC ACID
• BENZYL N-ACETYL-6-O-BENZYL-ALPHA-D-MURAMIC ACID, METHYL ESTER,BENZYL N-ACETYL-6-O-BENZYL-A-D-MURAMIC ACID, METHYL ESTER
• 2-Acetamido-4-O-(2-acetamido-2-deoxy--D-glucopyranosl)-1,6-di-O-N-acetyl-a-D-muramic Acid
• Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid, Methyl Ester
• N-Acetyl-4-O-[2-(acetylamino)-2-deoxy-b-D-glucopyranosyl]-muramic Acid,N-Acetyl-4-O-[2-(acetylamino)-2-deoxy--D-glucopyranosyl]-muramic Acid
• MURAMIC ACID, (+)-(P)
• BENZYL N-ACETYL-6-O-BENZYL-A-D-MURAMIC ACID, METH
• Benzyl 4-O-(2-Acetamido-2-deoxy-3,4,6-Tri-O-acetyl--D-glucopyranosl)-N-acetyl-a-D-muramic Acid, Methyl Ester