Mammeisin

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

MedKoo CAT#: 584672

CAS#: 18483-64-2

Description: Mammeisin is a constituent of Mammea americana.


Chemical Structure

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Mammeisin
CAS# 18483-64-2

Theoretical Analysis

MedKoo Cat#: 584672
Name: Mammeisin
CAS#: 18483-64-2
Chemical Formula: C25H26O5
Exact Mass: 406.178
Molecular Weight: 406.478
Elemental Analysis: C, 73.87; H, 6.45; O, 19.68

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

Preparing Stock Solutions

The following data is based on the product molecular weight 406.478 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

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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.