MedKoo Cat#: 146224 | Name: Islandicin

Description:

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

Islandicin is an anthraquinone compound naturally found in certain lichen and fungal species. It exhibits antimicrobial, antifungal, and potential anticancer activities, making it a compound of interest in pharmaceutical and natural product research. The mechanism of action is believed to involve intercalation into DNA, inhibition of key enzymes, and disruption of microbial cell functions. Its ability to interfere with cellular replication and oxidative processes contributes to its biological effects and potential therapeutic applications.

Chemical Structure

Islandicin
Islandicin
CAS#476-56-2

Theoretical Analysis

MedKoo Cat#: 146224

Name: Islandicin

CAS#: 476-56-2

Chemical Formula: C15H10O5

Exact Mass: 270.0528

Molecular Weight: 270.24

Elemental Analysis: C, 66.67; H, 3.73; O, 29.60

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
Islandicin;
IUPAC/Chemical Name
1,4,5-trihydroxy-2-methylanthracene-9,10-dione
InChi Key
FHFHNVHRVKQQHN-UHFFFAOYSA-N
InChi Code
1S/C15H10O5/c1-6-5-9(17)11-12(13(6)18)14(19)7-3-2-4-8(16)10(7)15(11)20/h2-5,16-18H,1H3
SMILES Code
CC1=CC(O)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 270.24 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: Lin LC, Chou CJ, Kuo YC. Cytotoxic principles from Ventilago leiocarpa. J Nat Prod. 2001 May;64(5):674-6. doi: 10.1021/np000569d. PMID: 11374975. 2: Paulick RC, Casey ML, Hillenbrand DF, Whitlock HW Jr. Letter: A 13C nuclear magnetic resonance study of the biosynthesis of islandicin from 13CH313CO2Na. J Am Chem Soc. 1975 Sep 3;97(18):5303-5. doi: 10.1021/ja00851a060. PMID: 1165367. 3: Liberman DF, Schaefer FL, Fink RC, Ramgopal M, Ghosh AC, Mulcahy R. Mutagenicity of islandicin and chrysophanol in the Salmonella/microsome system. Appl Environ Microbiol. 1980 Sep;40(3):476-9. doi: 10.1128/aem.40.3.476-479.1980. PMID: 6999990; PMCID: PMC291608. 4: Ghosh AC, Manmade A, Kobbe B, Townsend JM, Demain AL. Production of luteoskyrin and isolation of a new metabolite, pibasterol, from Penicillium islandicum Sopp. Appl Environ Microbiol. 1978 Mar;35(3):563-6. doi: 10.1128/aem.35.3.563-566.1978. PMID: 565188; PMCID: PMC242880. 5: Bouras N, Strelkov SE. Influence of carbon source on growth and mycotoxin production by isolates of Pyrenophora tritici-repentis from wheat. Can J Microbiol. 2010 Oct;56(10):874-84. doi: 10.1139/w10-073. PMID: 20962911. 6: Jung ME, Lowe JA. Synthetic approaches to adriamycin involving Diels-Alder reactions of photochemically generated bisketenes. Total synthesis of islandicin and digitopurpone. J Org Chem. 1977 Jul 8;42(14):2371-3. doi: 10.1021/jo00434a005. PMID: 874615. 7: Le Pogam P, Boustie J. Xanthones of Lichen Source: A 2016 Update. Molecules. 2016 Mar 2;21(3):294. doi: 10.3390/molecules21030294. PMID: 26950106; PMCID: PMC6273661. 8: Kitchawalit S, Kanokmedhakul K, Kanokmedhakul S, Soytong K. A new benzyl ester and ergosterol derivatives from the fungus Gymnoascus reessii. Nat Prod Res. 2014;28(14):1045-51. doi: 10.1080/14786419.2014.903478. Epub 2014 Apr 7. PMID: 24708569. 9: Mahrosh HS, Mustafa G. An in silico approach to target RNA-dependent RNA polymerase of COVID-19 with naturally occurring phytochemicals. Environ Dev Sustain. 2021;23(11):16674-16687. doi: 10.1007/s10668-021-01373-5. Epub 2021 Apr 3. PMID: 33841038; PMCID: PMC8018901. 10: Tikkanen L, Matsushima T, Natori S. Mutagenicity of anthraquinones in the Salmonella preincubation test. Mutat Res. 1983 Mar;116(3-4):297-304. doi: 10.1016/0165-1218(83)90067-8. PMID: 6339896. 11: Stark AA, Townsend JM, Wogan GN, Demain AL, Manmade A, Ghosh AC. Mutagenicity and antibacterial activity of mycotoxins produced by Penicillium islandicum Sopp and Penicillium rugulosum. J Environ Pathol Toxicol. 1978 Nov- Dec;2(2):313-24. PMID: 368283. 12: Dong Y, Ding W, Sun C, Ji X, Ling C, Zhou Z, Chen Z, Chen X, Ju J. Julichrome Monomers from Marine Gastropod Mollusk-Associated Streptomyces and Stereochemical Revision of Julichromes Q3 ⋅ 5 and Q3 ⋅ 3. Chem Biodivers. 2020 Apr;17(4):e2000057. doi: 10.1002/cbdv.202000057. Epub 2020 Mar 12. PMID: 32091654. 13: Bouras N, Kim YM, Strelkov SE. Influence of water activity and temperature on growth and mycotoxin production by isolates of Pyrenophora tritici-repentis from wheat. Int J Food Microbiol. 2009 May 31;131(2-3):251-5. doi: 10.1016/j.ijfoodmicro.2009.02.001. Epub 2009 Feb 6. PMID: 19268381. 14: Mori H, Yoshimi N, Iwata H, Tanaka T, Kawai K, Sankawa U. Additional survey on genotoxicity of natural anthraquinones in the hepatocyte primary culture/DNA repair assay. J Toxicol Sci. 1988 Aug;13(3):161-6. doi: 10.2131/jts.13.161. PMID: 3193483. 15: Degli Esposti M, Ghelli A, Crimi M, Baracca A, Solaini G, Tron T, Meyer A. Cytochrome b of fish mitochondria is strongly resistant to funiculosin, a powerful inhibitor of respiration. Arch Biochem Biophys. 1992 May 15;295(1):198-204. doi: 10.1016/0003-9861(92)90506-r. PMID: 1315503. 16: Huang KX, Iwakami N, Fujii I, Ebizuka Y, Sankawa U. Transformations of Penicillium islandicum and Penicillium frequentans that produce anthraquinone- related compounds. Curr Genet. 1995 Nov;28(6):580-4. doi: 10.1007/BF00518172. PMID: 8593690. 17: Kunz WS, Konstantinov AA. Effect of b-c1-site inhibitors on the midpoint potentials of mitochondrial cytochromes b. FEBS Lett. 1983 May 8;155(2):237-40. doi: 10.1016/0014-5793(82)80611-x. PMID: 6303845. 18: Ksenzenko M, Konstantinov AA, Khomutov GB, Tikhonov AN, Ruuge EK. Effect of electron transfer inhibitors on superoxide generation in the cytochrome bc1 site of the mitochondrial respiratory chain. FEBS Lett. 1983 May 2;155(1):19-24. doi: 10.1016/0014-5793(83)80200-2. PMID: 6301880. 19: Tsai AL, Kauten R, Palmer G. The interaction of yeast Complex III with some respiratory inhibitors. Biochim Biophys Acta. 1985 Mar 13;806(3):418-26. doi: 10.1016/0005-2728(85)90249-x. PMID: 2982396. 20: Rich PR, Jeal AE, Madgwick SA, Moody AJ. Inhibitor effects on redox-linked protonations of the b haems of the mitochondrial bc1 complex. Biochim Biophys Acta. 1990 Jul 17;1018(1):29-40. doi: 10.1016/0005-2728(90)90106-e. PMID: 2165418.