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MedKoo Cat#: 145091 | Name: MAPA

Description:

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

MAPA is a synthesis of various 2-methylaminopyidine amides from 2-bromopyridine via the catalytic Goldberg reaction using CuI and 1,10-phenanthroline. This, along with catalyst loading between 0.5-3 mol%, provided high yields and scalability for multigram-scale reactions. Additionally, a modification of the method enabled the synthesis of 2-N-substituted aminopyridines from secondary N-alkyl(aryl)formamides and 2-bromopyridine, providing a versatile route to these compounds with high yields through in situ cleavage of intermediate aminopyridine formamides.

Chemical Structure

MAPA
MAPA
CAS#16648-44-5

Theoretical Analysis

MedKoo Cat#: 145091

Name: MAPA

CAS#: 16648-44-5

Chemical Formula: C11H12O3

Exact Mass: 192.0786

Molecular Weight: 192.21

Elemental Analysis: C, 68.74; H, 6.29; O, 24.97

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
MAPA;
IUPAC/Chemical Name
methyl 3-oxo-2-phenylbutanoate
InChi Key
CYSACHQWYQYLIG-UHFFFAOYSA-N
InChi Code
1S/C11H12O3/c1-8(12)10(11(13)14-2)9-6-4-3-5-7-9/h3-7,10H,1-2H3
SMILES Code
COC(=O)C(C(C)=O)C1=CC=CC=C1
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 192.21 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: Inge P, Orchard JJ, Purdue R, Orchard JW. Exercise after pregnancy. Aust J Gen Pract. 2022 Mar;51(3):117-121. doi: 10.31128/AJGP-09-21-6181. PMID: 35224572. 2: Comins DL. Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction. Molecules. 2022 Mar 11;27(6):1833. doi: 10.3390/molecules27061833. PMID: 35335206; PMCID: PMC8952803. 3: Gonçalves MT, Squaiella-Baptistão CC, Pidde G, Lopes PH, da Silva Nunes I, Tambourgi DV. P-MAPA, a Fungi-Derived Immunomodulatory Compound, Induces a Proinflammatory Response in a Human Whole Blood Model. Mediators Inflamm. 2020 Nov 24;2020:8831389. doi: 10.1155/2020/8831389. PMID: 33299378; PMCID: PMC7707968. 4: Jia W, Yang D. Study effect of MAPA-VIP on control of allergic asthma pathophysiology. Postepy Dermatol Alergol. 2023 Aug;40(4):548-553. doi: 10.5114/ada.2023.129458. Epub 2023 Sep 1. PMID: 37692278; PMCID: PMC10485757. 5: Maino GB, Parma-Benfenati S, Maino G, Maino GN, Benfenati LP, Roncati M. MAPA-cision: A New Regenerative Technique for Periodontally Facilitated Orthodontic Treatment. A Case Series. Int J Periodontics Restorative Dent. 2021 Jan-Feb;41(1):23-30. doi: 10.11607/prd.5238. PMID: 33528446. 6: Collins AJ, Pastora AB, Smith TJ, O'Toole GA. MapA, a Second Large RTX Adhesin Conserved across the Pseudomonads, Contributes to Biofilm Formation by Pseudomonas fluorescens. J Bacteriol. 2020 Aug 25;202(18):e00277-20. doi: 10.1128/JB.00277-20. PMID: 32631946; PMCID: PMC7925077. 7: Silveira HS, Lupi LA, Romagnoli GG, Kaneno R, da Silva Nunes I, Fávaro WJ, de Almeida Chuffa LG. P-MAPA activates TLR2 and TLR4 signaling while its combination with IL-12 stimulates CD4+ and CD8+ effector T cells in ovarian cancer. Life Sci. 2020 Aug 1;254:117786. doi: 10.1016/j.lfs.2020.117786. Epub 2020 May 18. PMID: 32433918. 8: Cheraghifard M, Taghizadeh G, Akbarfahimi M, Eakman AM, Hosseini SH, Azad A. Psychometric properties of Meaningful Activity Participation Assessment (MAPA) in chronic stroke survivors. Top Stroke Rehabil. 2021 Sep;28(6):422-431. doi: 10.1080/10749357.2020.1834275. Epub 2020 Oct 20. PMID: 33078689. 9: Nam S, Eakman AM, Bae S, Hong I. Item-Level Psychometrics of the Meaningful Activity Participation Assessment (MAPA) Scale. Int J Aging Hum Dev. 2023 Dec;97(4):496-512. doi: 10.1177/00914150221143956. Epub 2022 Dec 22. PMID: 36560911. 10: Le Bizec B. Brazilian Ministry of Agriculture, Livestock and Food Supply (MAPA): strategies to tackle chemical food safety issues. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(4):481. doi: 10.1080/19440049.2012.662768. Epub 2012 Mar 9. PMID: 22435874. 11: Lima MC, Azevedo EAN, de Morais CNL, de Sousa LIO, Carvalho BM, da Silva IN, Franca RFO. The P-MAPA Immunomodulator Partially Prevents Apoptosis Induced by Zika Virus Infection in THP-1 Cells. Curr Pharm Biotechnol. 2021;22(4):514-522. doi: 10.2174/1389201021666200602140005. PMID: 32484769. 12: Camafort M, Alcocer L, Coca A, Lopez-Lopez JP, López-Jaramillo P, Ponte- Negretti CI, Sebba-Barroso W, Valdéz O, Wyss F. Latin-American Ambulatory Blood Pressure Registry (MAPA-LATAM): An urgent need. Rev Clin Esp (Barc). 2021 Nov;221(9):547-552. doi: 10.1016/j.rceng.2021.02.004. Epub 2021 Sep 9. PMID: 34509417. 13: Lupi LA, Delella FK, Cucielo MS, Romagnoli GG, Kaneno R, Nunes IDS, Domeniconi RF, Martinez M, Martinez FE, Fávaro WJ, Chuffa LGA. P-MAPA and Interleukin-12 Reduce Cell Migration/Invasion and Attenuate the Toll-Like Receptor-Mediated Inflammatory Response in Ovarian Cancer SKOV-3 Cells: A Preliminary Study. Molecules. 2019 Dec 18;25(1):5. doi: 10.3390/molecules25010005. PMID: 31861351; PMCID: PMC6982916. 14: Júnior LAL, Cucielo MS, Domeniconi RF, Dos Santos LD, Silveira HS, da Silva Nunes I, Martinez M, Martinez FE, Fávaro WJ, Chuffa LGA. P-MAPA and IL-12 Differentially Regulate Proteins Associated with Ovarian Cancer Progression: A Proteomic Study. ACS Omega. 2019 Dec 11;4(26):21761-21777. doi: 10.1021/acsomega.9b02512. PMID: 31891054; PMCID: PMC6933580. 15: Socca EAR, Reis SK, Genaro SC, Leite SK, Reis IB, Bockëlmann PK, Durán N, Fávaro WJ. P-mapa, a promisor immunomodulator against tumor cells of colonic tissues: An investigation of the action mechanism over the TLR4 signaling pathway. Life Sci. 2020 Feb 1;242:117185. doi: 10.1016/j.lfs.2019.117185. Epub 2019 Dec 18. PMID: 31862453. 16: Wall C, Byrnes J, Botha L, Roe J. Acute sport-related knee injuries. Aust J Gen Pract. 2023 Nov;52(11):761-766. doi: 10.31128/AJGP-04-23-6785. PMID: 37935146. 17: Yeh YC, Park D, Yang SY, Kuo CC. Developing and validating the Taiwan version of the meaningful activity participation assessment (T-MAPA) with Rasch analysis. BMC Geriatr. 2023 Mar 22;23(1):159. doi: 10.1186/s12877-023-03839-9. PMID: 36949379; PMCID: PMC10032021. 18: Silva JCS, Lins CRB, Lacerda SS, Ramos REM, Araújo HDA, Melo-Junior MR, Alves LC, Brayner FA, Nunes IS, Melo FL, Carvalho BM. In vitro and in vivo effects of P-MAPA immunomodulator on schistosomiasis. Acta Trop. 2021 Jun;218:105909. doi: 10.1016/j.actatropica.2021.105909. Epub 2021 Mar 28. PMID: 33789153. 19: Malik S, De I, Singh M, Galanakis CM, Alamri AS, Yadav JK. Isolation and characterisation of milk-derived amyloid-like protein aggregates (MAPA) from cottage cheese. Food Chem. 2022 Mar 30;373(Pt B):131486. doi: 10.1016/j.foodchem.2021.131486. Epub 2021 Oct 28. PMID: 34800818. 20: de Almeida Chuffa LG, de Moura Ferreira G, Lupi LA, da Silva Nunes I, Fávaro WJ. P-MAPA immunotherapy potentiates the effect of cisplatin on serous ovarian carcinoma through targeting TLR4 signaling. J Ovarian Res. 2018 Jan 17;11(1):8. doi: 10.1186/s13048-018-0380-5. PMID: 29343281; PMCID: PMC5773141.