Viridicatol | CAS#14484-44-7 | antimicrobial

MedKoo Cat#: 585382 | Name: Viridicatol

Description:

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

Viridicatol is a fungal metabolite that has been found in various Penicillium species as well as Phoma with antimicrobial properties.

Chemical Structure

Viridicatol

CAS#14484-44-7

Theoretical Analysis

MedKoo Cat#: 585382

Name: Viridicatol

CAS#: 14484-44-7

Chemical Formula: C15H11NO3

Exact Mass: 253.0739

Molecular Weight: 253.26

Elemental Analysis: C, 71.14; H, 4.38; N, 5.53; O, 18.95

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

Viridicatol

IUPAC/Chemical Name

3-hydroxy-4-(3-hydroxyphenyl)-1H-quinolin-2-one

InChi Key

QIJIOTTYIGBOQA-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H11NO3/c17-10-5-3-4-9(8-10)13-11-6-1-2-7-12(11)16-15(19)14(13)18/h1-8,17-18H,(H,16,19)

SMILES Code

O=C1NC2=C(C=CC=C2)C(C3=CC=CC(O)=C3)=C1O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 253.26 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: Tangella Y, Manasa KL, Krishna NH, Sridhar B, Kamal A, Nagendra Babu B. Regioselective Ring Expansion of Isatins with In Situ Generated α-Aryldiazomethanes: Direct Access to Viridicatin Alkaloids. Org Lett. 2018 Jun 15;20(12):3639-3642. doi: 10.1021/acs.orglett.8b01417. Epub 2018 Jun 6. PubMed PMID: 29874092. 2: Mamedov VA, Mamedova VL, Kadyrova SF, Galimullina VR, Khikmatova GZ, Korshin DE, Gubaidullin AT, Krivolapov DB, Rizvanov IK, Bazanova OB, Sinyashin OG, Latypov SK. Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel-Crafts Alkylation Strategy. J Org Chem. 2018 Nov 2;83(21):13132-13145. doi: 10.1021/acs.joc.8b01871. Epub 2018 Oct 17. PubMed PMID: 30272451. 3: Bu YY, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M. Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp. J Antibiot (Tokyo). 2016 Jan;69(1):57-61. doi: 10.1038/ja.2015.82. Epub 2015 Aug 5. PubMed PMID: 26243556. 4: Luckner M. [On the synthesis of quinoline alkaloids in plants. 2. Fermentativ conversion of the penicillin alkaloids cyclopenin and cyclopenol to viridicatin and viridicatol]. Eur J Biochem. 1967 Jul;2(1):74-8. German. PubMed PMID: 6079765. 5: Fremlin LJ, Piggott AM, Lacey E, Capon RJ. Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor. J Nat Prod. 2009 Apr;72(4):666-70. doi: 10.1021/np800777f. PubMed PMID: 19245260. 6: BIRKINSHAW JH, LUCKNER M, MOHAMMED YS, MOTHES K, STICKINGS CE. STUDIES IN THE BIOCHEMISTRY OF MICRO-ORGANISMS. 114. VIRIDICATOL AND CYCLOPENOL, METABOLITES OF PENICILLIUM VIRIDICATUM WESTLING AND PENICILLIUM CYCLOPIUM WESTLING. Biochem J. 1963 Nov;89:196-202. PubMed PMID: 14084602; PubMed Central PMCID: PMC1202346. 7: Ma YM, Qiao K, Kong Y, Li MY, Guo LX, Miao Z, Fan C. A new isoquinolone alkaloid from an endophytic fungus R22 of Nerium indicum. Nat Prod Res. 2017 Apr;31(8):951-958. doi: 10.1080/14786419.2016.1258556. Epub 2016 Dec 2. PubMed PMID: 27910702. 8: Sohn JH, Lee YR, Lee DS, Kim YC, Oh H. PTP1B inhibitory secondary metabolites from marine-derived fungal strains Penicillium spp. and Eurotium sp. J Microbiol Biotechnol. 2013 Sep 28;23(9):1206-11. PubMed PMID: 23770564. 9: Mousa WK, Schwan A, Davidson J, Strange P, Liu H, Zhou T, Auzanneau FI, Raizada MN. An endophytic fungus isolated from finger millet (Eleusine coracana) produces anti-fungal natural products. Front Microbiol. 2015 Oct 21;6:1157. doi: 10.3389/fmicb.2015.01157. eCollection 2015. PubMed PMID: 26539183; PubMed Central PMCID: PMC4612689. 10: Li J, Wang J, Jiang CS, Li G, Guo YW. (+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza. J Asian Nat Prod Res. 2014;16(5):542-8. doi: 10.1080/10286020.2014.911290. Epub 2014 Apr 29. PubMed PMID: 24773150. 11: Tao YW, Wang Y. 3-Hy-droxy-4-(3-hy-droxy-phen-yl)-2-quinolone monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2011 Aug 1;67(Pt 8):o2195-6. doi: 10.1107/S160053681102945X. Epub 2011 Jul 30. PubMed PMID: 22091203; PubMed Central PMCID: PMC3213626. 12: Kozlovskiĭ AG, Zhelifonova VP, Adanin VM, Antipova TV, Shnyreva AV, Viktorov AN. [The biosynthesis of low-molecular-weight nitrogen-containing secondary metabolite-alkaloids by the resident strains of Penicillium chrysogenum and Penicillium expansum isolated on the board of the Mir space station ]. Mikrobiologiia. 2002 Nov-Dec;71(6):773-7. Russian. PubMed PMID: 12526198. 13: Sonjak S, Frisvad JC, Gunde-Cimerman N. Comparison of secondary metabolite production by Penicillium crustosum strains, isolated from Arctic and other various ecological niches. FEMS Microbiol Ecol. 2005 Jun 1;53(1):51-60. Epub 2004 Dec 22. PubMed PMID: 16329929. 14: Frisvad JC, Samson RA, Rassing BR, van der Horst MI, van Rijn FT, Stark J. Penicillium discolor, a new species from cheese, nuts and vegetables. Antonie Van Leeuwenhoek. 1997 Aug;72(2):119-26. PubMed PMID: 9298190.