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MedKoo Cat#: 584672 | Name: Mammeisin

Description:

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

Mammeisin is a constituent of Mammea americana.

Chemical Structure

Mammeisin
Mammeisin
CAS#18483-64-2

Theoretical Analysis

MedKoo Cat#: 584672

Name: Mammeisin

CAS#: 18483-64-2

Chemical Formula: C25H26O5

Exact Mass: 406.1780

Molecular Weight: 406.48

Elemental Analysis: C, 73.87; H, 6.45; O, 19.68

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
Mammeisin
IUPAC/Chemical Name
5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(3-methyl-1-oxobutyl)-4-phenyl-2H-1-benzopyran-2-one
InChi Key
JIFOADIANOIMSK-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H26O5/c1-14(2)10-11-17-23(28)22(19(26)12-15(3)4)24(29)21-18(13-20(27)30-25(17)21)16-8-6-5-7-9-16/h5-10,13,15,28-29H,11-12H2,1-4H3
SMILES Code
O=C1C=C(C2=CC=CC=C2)C3=C(O)C(C(CC(C)C)=O)=C(O)C(C/C=C(C)\C)=C3O1
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 406.48 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: da Cunha MG, Ramos-Junior ES, Franchin M, Taira TM, Beutler JA, Franco GCN, Ikegaki M, de Alencar SM, Fukada SY, Rosalen PL. Effects of Cinnamoyloxy-mammeisin from Geopropolis on Osteoclast Differentiation and Porphyromonas gingivalis-Induced Periodontitis. J Nat Prod. 2017 Jun 23;80(6):1893-1899. doi: 10.1021/acs.jnatprod.7b00194. Epub 2017 Jun 1. PubMed PMID: 28570825. 2: Franchin M, Rosalen PL, da Cunha MG, Silva RL, Colón DF, Bassi GS, de Alencar SM, Ikegaki M, Alves-Filho JC, Cunha FQ, Beutler JA, Cunha TM. Cinnamoyloxy-mammeisin Isolated from Geopropolis Attenuates Inflammatory Process by Inhibiting Cytokine Production: Involvement of MAPK, AP-1, and NF-κB. J Nat Prod. 2016 Jul 22;79(7):1828-33. doi: 10.1021/acs.jnatprod.6b00263. Epub 2016 Jul 1. PubMed PMID: 27367493. 3: Leuna JM, Sop SK, Makota S, Njanja E, Ebelle TC, Azebaze AG, Ngameni E, Nassi A. Voltammetric behavior of Mammeisin (MA) at a glassy carbon electrode and its interaction with Bovine Serum Albumin (BSA). Bioelectrochemistry. 2018 Feb;119:20-25. doi: 10.1016/j.bioelechem.2017.08.008. Epub 2017 Sep 7. PubMed PMID: 28889056. 4: Finnegan RA, Merkel KE. Constituents of Mammea americana L. IX. Oxidation of mammein and mammeisin. J Pharm Sci. 1972 Oct;61(10):1603-8. PubMed PMID: 5072407. 5: da Cunha MG, Rosalen PL, Franchin M, de Alencar SM, Ikegaki M, Ransom T, Beutler JA. Antiproliferative Constituents of Geopropolis from the Bee Melipona scutellaris. Planta Med. 2016 Feb;82(3):190-4. doi: 10.1055/s-0035-1558142. Epub 2015 Nov 6. PubMed PMID: 26544117; PubMed Central PMCID: PMC4792278. 6: Kunesch G, Hildesheim R, Polonsky J. [On the biogenetic origin of the isovaleryl group of mammeisin (4-phenyl coumarin)]. C R Acad Sci Hebd Seances Acad Sci D. 1969 Apr 21;268(16):2143-5. French. PubMed PMID: 4980355. 7: da Cunha MG, Franco GC, Franchin M, Beutler JA, de Alencar SM, Ikegaki M, Rosalen PL. Prediction of pharmacokinetic and toxicological parameters of a 4-phenylcoumarin isolated from geopropolis: In silico and in vitro approaches. Toxicol Lett. 2016 Nov 30;263:6-10. doi: 10.1016/j.toxlet.2016.10.010. Epub 2016 Oct 20. PubMed PMID: 27773722. 8: Dongmo AB, Azebaze AG, Nguelefack TB, Ouahouo BM, Sontia B, Meyer M, Nkengfack AE, Kamanyi A, Vierling W. Vasodilator effect of the extracts and some coumarins from the stem bark of Mammea africana (Guttiferae). J Ethnopharmacol. 2007 May 4;111(2):329-34. Epub 2006 Dec 1. PubMed PMID: 17204384.

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