Synonym
Emericellin; Variecoxanthone B
IUPAC/Chemical Name
8-hydroxy-1-(hydroxymethyl)-3-methyl-2-(3-methylbut-2-enoxy)-5-(3-methylbut-2-enyl)xanthen-9-one
InChi Key
JZHBEPYIKRDWBE-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H28O5/c1-14(2)6-7-17-8-9-19(27)22-23(28)21-18(13-26)24(29-11-10-15(3)4)16(5)12-20(21)30-25(17)22/h6,8-10,12,26-27H,7,11,13H2,1-5H3
SMILES Code
O=C1C2=C(OC3=C1C(O)=CC=C3C/C=C(C)\C)C=C(C)C(OC/C=C(C)/C)=C2CO
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
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: Pang XJ, Zhang SB, Xian PJ, Wu X, Yang DF, Fu HY, Yang XL. Emericellins A and B: Two sesquiterpenoids with an unprecedented tricyclo[4,4,2,1]hendecane scaffold from the liquid cultures of endophytic fungus Emericella sp. XL 029. Fitoterapia. 2018 Nov;131:55-58. doi: 10.1016/j.fitote.2018.10.022. Epub 2018 Oct 22. PubMed PMID: 30352295.
2: Inoue N, Wakana D, Takeda H, Yaguchi T, Hosoe T. Production of an emericellin and its analogues as fungal biological responses for Shimbu-to extract. J Nat Med. 2018 Jan;72(1):357-363. doi: 10.1007/s11418-017-1156-8. Epub 2017 Nov 29. PubMed PMID: 29188416.
3: Yin WB, Reinke AW, Szilágyi M, Emri T, Chiang YM, Keating AE, Pócsi I, Wang CCC, Keller NP. bZIP transcription factors affecting secondary metabolism, sexual development and stress responses in Aspergillus nidulans. Microbiology. 2013 Jan;159(Pt 1):77-88. doi: 10.1099/mic.0.063370-0. Epub 2012 Nov 15. PubMed PMID: 23154967; PubMed Central PMCID: PMC3542729.
4: Simpson TJ. Genetic and biosynthetic studies of the fungal prenylated xanthone shamixanthone and related metabolites in Aspergillus spp. revisited. Chembiochem. 2012 Jul 23;13(11):1680-8. doi: 10.1002/cbic.201200014. Epub 2012 Jun 22. PubMed PMID: 22730213.
5: Sanchez JF, Entwistle R, Hung JH, Yaegashi J, Jain S, Chiang YM, Wang CC, Oakley BR. Genome-based deletion analysis reveals the prenyl xanthone biosynthesis pathway in Aspergillus nidulans. J Am Chem Soc. 2011 Mar 23;133(11):4010-7. doi: 10.1021/ja1096682. Epub 2011 Feb 25. PubMed PMID: 21351751; PubMed Central PMCID: PMC3119361.
6: Márquez-Fernández O, Trigos A, Ramos-Balderas JL, Viniegra-González G, Deising HB, Aguirre J. Phosphopantetheinyl transferase CfwA/NpgA is required for Aspergillus nidulans secondary metabolism and asexual development. Eukaryot Cell. 2007 Apr;6(4):710-20. Epub 2007 Feb 2. PubMed PMID: 17277172; PubMed Central PMCID: PMC1865657.
7: Lu P, Zhang A, Dennis LM, Dahl-Roshak AM, Xia YQ, Arison B, An Z, Tkacz JS. A gene (pks2) encoding a putative 6-methylsalicylic acid synthase from Glarea lozoyensis. Mol Genet Genomics. 2005 Apr;273(2):207-16. Epub 2005 Mar 31. PubMed PMID: 15800788.
