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MedKoo Cat#: 585320 | Name: Asperlin

Description:

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

Asperlin is a marine-derived natural product with antifungal and anti-inflammatory activities in vitro.

Chemical Structure

Asperlin
Asperlin
CAS#30387-51-0

Theoretical Analysis

MedKoo Cat#: 585320

Name: Asperlin

CAS#: 30387-51-0

Chemical Formula: C10H12O5

Exact Mass: 212.0685

Molecular Weight: 212.20

Elemental Analysis: C, 56.60; H, 5.70; O, 37.70

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
Asperlin; U 13933; U 13,933; U-13933; U-13,933; U13933; U13,933
IUPAC/Chemical Name
[(2R,3S)-2-[(2S,3R)-3-methyloxiran-2-yl]-6-oxo-2,3-dihydropyran-3-yl] acetate'
InChi Key
SPKNARKFCOPTSY-XWPZMVOTSA-N
InChi Code
InChI=1S/C10H12O5/c1-5-9(13-5)10-7(14-6(2)11)3-4-8(12)15-10/h3-5,7,9-10H,1-2H3/t5-,7+,9+,10-/m1/s1
SMILES Code
CC(O[C@@H](C=C1)[C@H]([C@H]2O[C@@H]2C)OC1=O)=O
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 212.20 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: Zhou Y, Chen R, Liu D, Wu C, Guo P, Lin W. Asperlin Inhibits LPS-Evoked Foam Cell Formation and Prevents Atherosclerosis in ApoE(-/-) Mice. Mar Drugs. 2017 Nov 14;15(11). pii: E358. doi: 10.3390/md15110358. PubMed PMID: 29135917; PubMed Central PMCID: PMC5706047. 2: Wu C, Zhou Y, Qi G, Liu D, Cao X, Yu J, Zhang R, Lin W, Guo P. Asperlin Stimulates Energy Expenditure and Modulates Gut Microbiota in HFD-Fed Mice. Mar Drugs. 2019 Jan 9;17(1). pii: E38. doi: 10.3390/md17010038. PubMed PMID: 30634484; PubMed Central PMCID: PMC6356881. 3: He L, Nan MH, Oh HC, Kim YH, Jang JH, Erikson RL, Ahn JS, Kim BY. Asperlin induces G₂/M arrest through ROS generation and ATM pathway in human cervical carcinoma cells. Biochem Biophys Res Commun. 2011 Jun 10;409(3):489-93. doi: 10.1016/j.bbrc.2011.05.032. Epub 2011 May 12. PubMed PMID: 21600879. 4: Lee DS, Jeong GS, Li B, Lee SU, Oh H, Kim YC. Asperlin from the marine-derived fungus Aspergillus sp. SF-5044 exerts anti-inflammatory effects through heme oxygenase-1 expression in murine macrophages. J Pharmacol Sci. 2011;116(3):283-95. Epub 2011 Jun 25. PubMed PMID: 21705844. 5: Grau MF, Entwistle R, Chiang YM, Ahuja M, Oakley CE, Akashi T, Wang CCC, Todd RB, Oakley BR. Hybrid Transcription Factor Engineering Activates the Silent Secondary Metabolite Gene Cluster for (+)-Asperlin in Aspergillus nidulans. ACS Chem Biol. 2018 Nov 16;13(11):3193-3205. doi: 10.1021/acschembio.8b00679. Epub 2018 Oct 29. PubMed PMID: 30339758; PubMed Central PMCID: PMC6546424. 6: Abou-Mansour E, Débieux JL, Ramírez-Suero M, Bénard-Gellon M, Magnin-Robert M, Spagnolo A, Chong J, Farine S, Bertsch C, L'Haridon F, Serrano M, Fontaine F, Rego C, Larignon P. Phytotoxic metabolites from Neofusicoccum parvum, a pathogen of Botryosphaeria dieback of grapevine. Phytochemistry. 2015 Jul;115:207-15. doi: 10.1016/j.phytochem.2015.01.012. Epub 2015 Mar 5. PubMed PMID: 25747381. 7: Tanabe M, Hamasaki T, Thomas D, Johnson L. Biosynthesis studies with carbon-13. Asperlin. J Am Chem Soc. 1971 Jan 13;93(1):273-4. PubMed PMID: 5538864. 8: Akita H. [Natural products syntheses based on the biotransformation using biocatalyst]. Yakugaku Zasshi. 2011 Feb;131(2):269-84. Review. Japanese. PubMed PMID: 21297373. 9: Horie H, Akaike H, Kato K, Akita H. Nucleophilic addition to 2,3-disubstituted butanal derivatives and their application to natural product synthesis. Chem Pharm Bull (Tokyo). 2010 Oct;58(10):1411-8. PubMed PMID: 20930415. 10: Tjota MY, Sperling AI. Distinct dendritic cell subsets actively induce Th2 polarization. Curr Opin Immunol. 2014 Dec;31:44-50. doi: 10.1016/j.coi.2014.09.006. Epub 2014 Oct 4. Review. PubMed PMID: 25290173; PubMed Central PMCID: PMC4737705. 11: Glatt H, Jung R, Oesch F. Bacterial mutagenicity investigation of epoxides: drugs, drug metabolites, steroids and pesticides. Mutat Res. 1983 Oct;111(2):99-118. PubMed PMID: 6355833. 12: Tjota MY, Hrusch CL, Blaine KM, Williams JW, Barrett NA, Sperling AI. Signaling through FcRγ-associated receptors on dendritic cells drives IL-33-dependent TH2-type responses. J Allergy Clin Immunol. 2014 Sep;134(3):706-713.e8. doi: 10.1016/j.jaci.2014.06.013. Epub 2014 Jul 31. PubMed PMID: 25088053; PubMed Central PMCID: PMC4149927. 13: Edelblum KL, Singh G, Odenwald MA, Lingaraju A, El Bissati K, McLeod R, Sperling AI, Turner JR. γδ Intraepithelial Lymphocyte Migration Limits Transepithelial Pathogen Invasion and Systemic Disease in Mice. Gastroenterology. 2015 Jun;148(7):1417-26. doi: 10.1053/j.gastro.2015.02.053. Epub 2015 Mar 4. PubMed PMID: 25747597; PubMed Central PMCID: PMC4685713. 14: Hrusch CL, Stein MM, Gozdz J, Holbreich M, von Mutius E, Vercelli D, Ober C, Sperling AI. T-cell phenotypes are associated with serum IgE levels in Amish and Hutterite children. J Allergy Clin Immunol. 2019 Nov;144(5):1391-1401.e10. doi: 10.1016/j.jaci.2019.07.034. Epub 2019 Aug 8. PubMed PMID: 31401285; PubMed Central PMCID: PMC6842432. 15: Sperling AI, Bluestone JA. ICOS costimulation: It's not just for TH2 cells anymore. Nat Immunol. 2001 Jul;2(7):573-4. PubMed PMID: 11429535. 16: Sperling AJ, Lu Zl, Manis FR, Seidenberg MS. Selective magnocellular deficits in dyslexia: a "phantom contour" study. Neuropsychologia. 2003;41(10):1422-9. PubMed PMID: 12757913. 17: Sperling AI, Sedy JR, Manjunath N, Kupfer A, Ardman B, Burkhardt JK. TCR signaling induces selective exclusion of CD43 from the T cell-antigen-presenting cell contact site. J Immunol. 1998 Dec 15;161(12):6459-62. PubMed PMID: 9862667.