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MedKoo Cat#: 582044 | Name: Dechlorogriseofulvin
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Description:

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

Dechlorogriseofulvin is a major photoproduct of Griseofulvin.

Chemical Structure

Dechlorogriseofulvin
Dechlorogriseofulvin
CAS#3680-32-8

Theoretical Analysis

MedKoo Cat#: 582044

Name: Dechlorogriseofulvin

CAS#: 3680-32-8

Chemical Formula: C17H18O6

Exact Mass: 318.1100

Molecular Weight: 318.32

Elemental Analysis: C, 64.14; H, 5.70; O, 30.16

Price and Availability

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1mg USD 285.00 Back order
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Synonym
Dechlorogriseofulvin; 7-Dechlorogriseofulvin; griseofulvin impurity B [EP impurity]
IUPAC/Chemical Name
(2S,6'R)-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
InChi Key
QPCYNIYZPDJCMB-XLFHBGCDSA-N
InChi Code
InChI=1S/C17H18O6/c1-9-5-10(18)6-14(22-4)17(9)16(19)15-12(21-3)7-11(20-2)8-13(15)23-17/h6-9H,5H2,1-4H3/t9-,17+/m1/s1
SMILES Code
O=C1[C@]2(OC3=CC(OC)=CC(OC)=C31)[C@@H](CC(C=C2OC)=O)C
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 318.32 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: Knowles SL, Raja HA, Wright AJ, Lee AML, Caesar LK, Cech NB, Mead ME, Steenwyk JL, Ries LNA, Goldman GH, Rokas A, Oberlies NH. Mapping the Fungal Battlefield: Using in situ Chemistry and Deletion Mutants to Monitor Interspecific Chemical Interactions Between Fungi. Front Microbiol. 2019 Feb 19;10:285. doi: 10.3389/fmicb.2019.00285. eCollection 2019. PubMed PMID: 30837981; PubMed Central PMCID: PMC6389630. 2: Ribeiro AI, Costa ES, Thomasi SS, Brandão DFR, Vieira PC, Fernandes JB, Forim MR, Ferreira AG, Pascholati SF, Gusmão LFP, da Silva MFDGF. Biological and Chemical Control of Sclerotinia sclerotiorum using Stachybotrys levispora and Its Secondary Metabolite Griseofulvin. J Agric Food Chem. 2018 Jul 25;66(29):7627-7632. doi: 10.1021/acs.jafc.7b04197. Epub 2018 Jul 10. PubMed PMID: 29944364. 3: Ali T, Inagaki M, Chai HB, Wieboldt T, Rapplye C, Rakotondraibe LH. Halogenated Compounds from Directed Fermentation of Penicillium concentricum, an Endophytic Fungus of the Liverwort Trichocolea tomentella. J Nat Prod. 2017 May 26;80(5):1397-1403. doi: 10.1021/acs.jnatprod.6b01069. Epub 2017 Apr 14. PubMed PMID: 28409637. 4: Brooks WC, Paguigan ND, Raja HA, Moy FJ, Cech NB, Pearce CJ, Oberlies NH. qNMR for profiling the production of fungal secondary metabolites. Magn Reson Chem. 2017 Jul;55(7):670-676. doi: 10.1002/mrc.4571. Epub 2017 Feb 5. PubMed PMID: 28024162; PubMed Central PMCID: PMC5459663. 5: Wubshet SG, Nyberg NT, Tejesvi MV, Pirttilä AM, Kajula M, Mattila S, Staerk D. Targeting high-performance liquid chromatography-high-resolution mass spectrometry-solid-phase extraction-nuclear magnetic resonance analysis with high-resolution radical scavenging profiles-Bioactive secondary metabolites from the endophytic fungus Penicillium namyslowskii. J Chromatogr A. 2013 Aug 9;1302:34-9. doi: 10.1016/j.chroma.2013.05.032. Epub 2013 May 22. PubMed PMID: 23827469. 6: Zhao JH, Zhang YL, Wang LW, Wang JY, Zhang CL. Bioactive secondary metabolites from Nigrospora sp. LLGLM003, an endophytic fungus of the medicinal plant Moringa oleifera Lam. World J Microbiol Biotechnol. 2012 May;28(5):2107-12. doi: 10.1007/s11274-012-1015-4. Epub 2012 Feb 12. PubMed PMID: 22806033. 7: Shang Z, Li XM, Li CS, Wang BG. Diverse secondary metabolites produced by marine-derived fungus Nigrospora sp. MA75 on various culture media. Chem Biodivers. 2012 Jul;9(7):1338-48. doi: 10.1002/cbdv.201100216. PubMed PMID: 22782879. 8: Hazalin NA, Ramasamy K, Lim SM, Cole AL, Majeed AB. Induction of apoptosis against cancer cell lines by four ascomycetes (endophytes) from Malaysian rainforest. Phytomedicine. 2012 May 15;19(7):609-17. doi: 10.1016/j.phymed.2012.01.007. Epub 2012 Mar 6. PubMed PMID: 22397996. 9: Xia X, Li Q, Li J, Shao C, Zhang J, Zhang Y, Liu X, Lin Y, Liu C, She Z. Two new derivatives of griseofulvin from the mangrove endophytic fungus Nigrospora sp. (strain No. 1403) from Kandelia candel (L.) Druce. Planta Med. 2011 Oct;77(15):1735-8. doi: 10.1055/s-0030-1271040. Epub 2011 Apr 21. PubMed PMID: 21512970. 10: Morimura T, Hashiba M, Kameda H, Takami M, Takahama H, Ohshige M, Sugawara F. Identification of macrolide antibiotic-binding Human_p8 protein. J Antibiot (Tokyo). 2008 May;61(5):291-6. doi: 10.1038/ja.2008.41. PubMed PMID: 18653994. 11: Nicoletti R, Lopez-Gresa MP, Manzo E, Carella A, Ciavatta ML. Production and fungitoxic activity of Sch 642305, a secondary metabolite of Penicillium canescens. Mycopathologia. 2007 May;163(5):295-301. Epub 2007 Apr 12. PubMed PMID: 17429757. 12: Xue C, Li T, Deng Z, Fu H, Lin W. Janthinolide A-B, two new 2,5-piperazinedione derivatives from the endophytic Penicillium janthinellum isolated from the soft coral Dendronephthya sp. Pharmazie. 2006 Dec;61(12):1041-4. PubMed PMID: 17283665. 13: Wang L, Zhou HB, Frisvad JC, Samson RA. Penicillium persicinum, a new griseofulvin, chrysogine and roquefortine C producing species from Qinghai Province, China. Antonie Van Leeuwenhoek. 2004 Aug;86(2):173-9. PubMed PMID: 15280651. 14: Jadulco R, Edrada RA, Ebel R, Berg A, Schaumann K, Wray V, Steube K, Proksch P. New communesin derivatives from the fungus Penicillium sp. derived from the Mediterranean sponge Axinella verrucosa. J Nat Prod. 2004 Jan;67(1):78-81. PubMed PMID: 14738391. 15: Jarvis BB, Zhou Y, Jiang J, Wang S, Sorenson WG, Hintikka EL, Nikulin M, Parikka P, Etzel RA, Dearborn DG. Toxigenic molds in water-damaged buildings: dechlorogriseofulvins from Memnoniella echinata. J Nat Prod. 1996 Jun;59(6):553-4. PubMed PMID: 8786360. 16: Cole RJ, Kirksey JW, Holaday CE. Detection of griseofulvin and dechlorogriseofulvin by thin-layer chromatography and gas-liquid chromatography. Appl Microbiol. 1970 Jan;19(1):106-8. PubMed PMID: 5415206; PubMed Central PMCID: PMC376619.