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MedKoo Cat#: 534819 | Name: Muramic acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Muramic acid is a bioactive chemical.

Chemical Structure

Muramic acid
Muramic acid
CAS#484-57-1

Theoretical Analysis

MedKoo Cat#: 534819

Name: Muramic acid

CAS#: 484-57-1

Chemical Formula: C9H17NO7

Exact Mass: 251.1005

Molecular Weight: 251.24

Elemental Analysis: C, 43.03; H, 6.82; N, 5.58; O, 44.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Muramic acid
IUPAC/Chemical Name
D-Glucopyranose, 2-amino-3-O-(1-carboxyethyl)-2-deoxy-, (R)-
InChi Key
MSFSPUZXLOGKHJ-WMDYQWKBSA-N
InChi Code
InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3?,4-,5-,6-,7-,9-/m1/s1
SMILES Code
O[C@H]1[C@H](N)[C@H]([C@@H]([C@@H](CO)O1)O)OC(C(O)=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 251.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jana M, Ghosh A, Santra A, Kar RK, Misra AK, Bhunia A. Synthesis of novel muramic acid derivatives and their interaction with lysozyme: Action of lysozyme revisited. J Colloid Interface Sci. 2017 Jul 15;498:395-404. doi: 10.1016/j.jcis.2017.03.060. Epub 2017 Mar 16. PMID: 28343137. 2: Vollmer W, Massidda O, Tomasz A. The Cell Wall of Streptococcus pneumoniae. Microbiol Spectr. 2019 May;7(3). doi: 10.1128/microbiolspec.GPP3-0018-2018. PMID: 31172911. 3: Davidson ME, Schaeffer J, Clark ML, Magzamen S, Brooks EJ, Keefe TJ, Bradford M, Roman-Muniz N, Mehaffy J, Dooley G, Poole JA, Mitloehner FM, Reed S, Schenker MB, Reynolds SJ. Personal exposure of dairy workers to dust, endotoxin, muramic acid, ergosterol, and ammonia on large-scale dairies in the high plains Western United States. J Occup Environ Hyg. 2018 Mar;15(3):182-193. doi: 10.1080/15459624.2017.1403610. PMID: 29157144. 4: Poole JA, Dooley GP, Saito R, Burrell AM, Bailey KL, Romberger DJ, Mehaffy J, Reynolds SJ. Muramic acid, endotoxin, 3-hydroxy fatty acids, and ergosterol content explain monocyte and epithelial cell inflammatory responses to agricultural dusts. J Toxicol Environ Health A. 2010;73(10):684-700. doi: 10.1080/15287390903578539. PMID: 20391112; PMCID: PMC2856089. 5: King JD, White DC. Muramic acid as a measure of microbial biomass in estuarine and marine samples. Appl Environ Microbiol. 1977 Apr;33(4):777-83. PMID: 869528; PMCID: PMC170766. 6: Mayer C, Kluj RM, Mühleck M, Walter A, Unsleber S, Hottmann I, Borisova M. Bacteria's different ways to recycle their own cell wall. Int J Med Microbiol. 2019 Nov;309(7):151326. doi: 10.1016/j.ijmm.2019.06.006. Epub 2019 Jul 4. PMID: 31296364. 7: Coullon H, Rifflet A, Wheeler R, Janoir C, Boneca IG, Candela T. N-Deacetylases required for muramic-δ-lactam production are involved in Clostridium difficile sporulation, germination, and heat resistance. J Biol Chem. 2018 Nov 23;293(47):18040-18054. doi: 10.1074/jbc.RA118.004273. Epub 2018 Sep 28. PMID: 30266804; PMCID: PMC6254358. 8: Lehtonen L, Eerola E, Toivanen P. Muramic acid in human peripheral blood leucocytes in different age groups. Eur J Clin Invest. 1997 Sep;27(9):791-2. doi: 10.1046/j.1365-2362.1997.1950732.x. PMID: 9352253. 9: Christensson B, Gilbart J, Fox A, Morgan SL. Mass spectrometric quantitation of muramic acid, a bacterial cell wall component, in septic synovial fluids. Arthritis Rheum. 1989 Oct;32(10):1268-72. doi: 10.1002/anr.1780321012. PMID: 2679561. 10: Kozar MP, Krahmer MT, Fox A, Gray BM. Failure To detect muramic acid in normal rat tissues but detection in cerebrospinal fluids from patients with Pneumococcal meningitis. Infect Immun. 2000 Aug;68(8):4688-98. doi: 10.1128/iai.68.8.4688-4698.2000. PMID: 10899874; PMCID: PMC98412. 11: Norbäck D, Hashim JH, Markowicz P, Cai GH, Hashim Z, Ali F, Larsson L. Endotoxin, ergosterol, muramic acid and fungal DNA in dust from schools in Johor Bahru, Malaysia--Associations with rhinitis and sick building syndrome (SBS) in junior high school students. Sci Total Environ. 2016 Mar 1;545-546:95-103. doi: 10.1016/j.scitotenv.2015.12.072. Epub 2015 Dec 31. PMID: 26745297. 12: Liang C, Zhang X, Wei L, He H, Higbee AJ, Balser TC. Investigation of the molecular ion structure for aldononitrile acetate derivatized muramic acid. J Microbiol Methods. 2011 Aug;86(2):224-30. doi: 10.1016/j.mimet.2011.05.007. Epub 2011 May 19. PMID: 21621564. 13: van Strien RT, Engel R, Holst O, Bufe A, Eder W, Waser M, Braun-Fahrländer C, Riedler J, Nowak D, von Mutius E; ALEX Study Team. Microbial exposure of rural school children, as assessed by levels of N-acetyl-muramic acid in mattress dust, and its association with respiratory health. J Allergy Clin Immunol. 2004 May;113(5):860-7. doi: 10.1016/j.jaci.2004.01.783. PMID: 15131567. 14: Di Filippo P, Pomata D, Riccardi C, Buiarelli F, Uccelletti D, Zanni E. Muramic and dipicolinic acids in atmospheric particulate matter as biomarkers of bacteria and bacterial spores. Anal Bioanal Chem. 2017 Feb;409(6):1657-1666. doi: 10.1007/s00216-016-0111-y. Epub 2016 Dec 7. PMID: 27928607. 15: Liang C, Read HW, Balser TC. GC-based detection of aldononitrile acetate derivatized glucosamine and muramic acid for microbial residue determination in soil. J Vis Exp. 2012 May 19;(63):e3767. doi: 10.3791/3767. PMID: 22643738; PMCID: PMC3466959. 16: Mayer VMT, Hottmann I, Figl R, Altmann F, Mayer C, Schäffer C. Peptidoglycan-type analysis of the N-acetylmuramic acid auxotrophic oral pathogen Tannerella forsythia and reclassification of the peptidoglycan-type of Porphyromonas gingivalis. BMC Microbiol. 2019 Sep 2;19(1):200. doi: 10.1186/s12866-019-1575-7. PMID: 31477019; PMCID: PMC6721243. 17: Moynihan PJ, Cadby IT, Veerapen N, Jankute M, Crosatti M, Mukamolova GV, Lovering AL, Besra GS. The hydrolase LpqI primes mycobacterial peptidoglycan recycling. Nat Commun. 2019 Jun 14;10(1):2647. doi: 10.1038/s41467-019-10586-2. PMID: 31201321; PMCID: PMC6572805. 18: Lehtonen L, Kortekangas P, Oksman P, Eerola E, Aro H, Toivanen A. Synovial fluid muramic acid in acute inflammatory arthritis. Br J Rheumatol. 1994 Dec;33(12):1127-30. doi: 10.1093/rheumatology/33.12.1127. PMID: 8000740. 19: Black GE, Fox A, Fox K, Snyder AP, Smith PB. Electrospray tandem mass spectrometry for analysis of native muramic acid in whole bacterial cell hydrolysates. Anal Chem. 1994 Dec 1;66(23):4171-6. doi: 10.1021/ac00095a010. PMID: 7847623. 20: Liang C, Read HW, Balser TC. Reliability of muramic acid as a bacterial biomarker is influenced by methodological artifacts from streptomycin. Microb Ecol. 2009 Apr;57(3):494-500. doi: 10.1007/s00248-008-9406-7. Epub 2008 Jun 28. PMID: 18587610.