Synonym
6-Geranylnaringenin; Mimulone; Propolin J; BonannioneA; Bonannione-A; Bonannione A
IUPAC/Chemical Name
(2S)-6-[(2E)-3,7-Dimethylocta-2,6-dienyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
InChi Key
XYIQIBWIEGCVQY-RWHUQTJRSA-N
InChi Code
InChI=1S/C25H28O5/c1-15(2)5-4-6-16(3)7-12-19-20(27)13-23-24(25(19)29)21(28)14-22(30-23)17-8-10-18(26)11-9-17/h5,7-11,13,22,26-27,29H,4,6,12,14H2,1-3H3/b16-7+/t22-/m0/s1
SMILES Code
O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=C1C(O)=C(C/C=C(C)/CC/C=C(C)\C)C(O)=C3
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
408.49
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.
| 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: Zhang LB, Lei C, Gao LX, Li JY, Li J, Hou AJ. Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata. Nat Prod Bioprospect. 2016 Feb;6(1):25-30. doi: 10.1007/s13659-015-0082-2. Epub 2016 Jan 20. PubMed PMID: 26791751; PubMed Central PMCID: PMC4749519.
2: Inui S, Shimamura Y, Masuda S, Shirafuji K, Moli RT, Kumazawa S. A new prenylflavonoid isolated from propolis collected in the Solomon Islands. Biosci Biotechnol Biochem. 2012;76(5):1038-40. PubMed PMID: 22738984.
3: Yoder BJ, Cao S, Norris A, Miller JS, Ratovoson F, Razafitsalama J, Andriantsiferana R, Rasamison VE, Kingston DG. Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest. J Nat Prod. 2007 Mar;70(3):342-6. Epub 2007 Feb 28. PubMed PMID: 17326683; PubMed Central PMCID: PMC2614403.
4: Murphy BT, Cao S, Norris A, Miller JS, Ratovoson F, Andriantsiferana R, Rasamison VE, Kingston DG. Cytotoxic flavanones of Schizolaena hystrix from the Madagascar rainforest. J Nat Prod. 2005 Mar;68(3):417-9. PubMed PMID: 15787448.
5: Wang Y, Tan W, Li WZ, Li Y. A facile synthetic approach to prenylated flavanones: first total syntheses of (+/-)-bonannione A and (+/-)-sophoraflavanone A. J Nat Prod. 2001 Feb;64(2):196-9. PubMed PMID: 11429999.
