Actiphenol | CAS#526-02-3 | Antiviral bacterial metabolite

MedKoo Cat#: 464015 | Name: Actiphenol

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Description:

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

Actiphenol is a bacterial metabolite that has been found in Streptomyces and has antiviral activity. It is active against coxsackievirus B3 and influenza A virus. Actiphenol potentiates the antifungal activity of miconazole against C. albicans in a disc assay.

Chemical Structure

Actiphenol

CAS#526-02-3

Theoretical Analysis

MedKoo Cat#: 464015

Name: Actiphenol

CAS#: 526-02-3

Chemical Formula: C15H17NO4

Exact Mass: 275.1158

Molecular Weight: 275.30

Elemental Analysis: C, 65.44; H, 6.22; N, 5.09; O, 23.25

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks
5mg	USD 1,350.00	2 Weeks

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Related CAS #

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Synonym

Actiphenol; Actinophenol; NSC 58413; NSC58413; NSC-58413;

IUPAC/Chemical Name

4-(2-(2-hydroxy-3,5-dimethylphenyl)-2-oxoethyl)piperidine-2,6-dione

InChi Key

YTLMIHBTPWTPEV-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H17NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h3-4,10,20H,5-7H2,1-2H3,(H,16,18,19)

SMILES Code

O=C1NC(CC(C1)CC(C2=C(C(C)=CC(C)=C2)O)=O)=O

Appearance

Solid powder

Purity

>95% (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

>2 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

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 275.30 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: Yin M, Yan Y, Lohman JR, Huang SX, Ma M, Zhao GR, Xu LH, Xiang W, Shen B. Cycloheximide and actiphenol production in Streptomyces sp. YIM56141 governed by single biosynthetic machinery featuring an acyltransferase-less type I polyketide synthase. Org Lett. 2014 Jun 6;16(11):3072-5. doi: 10.1021/ol501179w. Epub 2014 May 9. PMID: 24815182; PMCID: PMC4051428. 2: Hu JQ, Zhang A, Wang H, Niu L, Wang QX, Zhu LL, Li YZ, Wu C. Discovery and Biosynthesis of Glycosylated Cycloheximide from a Millipede-Associated Actinomycete. J Nat Prod. 2023 Feb 24;86(2):340-345. doi: 10.1021/acs.jnatprod.2c00951. Epub 2023 Jan 24. PMID: 36693198. 3: Bobek J, Filipová E, Bergman N, Čihák M, Petříček M, Lara AC, Kristufek V, Megyes M, Wurzer T, Chroňáková A, Petříčková K. Polyenic Antibiotics and Other Antifungal Compounds Produced by Hemolytic Streptomyces Species. Int J Mol Sci. 2022 Nov 30;23(23):15045. doi: 10.3390/ijms232315045. PMID: 36499372; PMCID: PMC9740855. 4: Spízek J, Málek I, Suchý J, Vondrácek M, Vanĕk Z. Metabolites of Streptomyces noursei. V. Relation of the production of cycloheximide and actiphenol to the production of fungicidin. Folia Microbiol (Praha). 1965 Sep;10(5):263-6. doi: 10.1007/BF02871023. PMID: 5855299. 5: Wardecki T, Brötz E, De Ford C, von Loewenich FD, Rebets Y, Tokovenko B, Luzhetskyy A, Merfort I. Endophytic Streptomyces in the traditional medicinal plant Arnica montana L.: secondary metabolites and biological activity. Antonie Van Leeuwenhoek. 2015 Aug;108(2):391-402. doi: 10.1007/s10482-015-0492-5. Epub 2015 Jun 4. PMID: 26036671. 6: Sun D, Sun W, Yu Y, Li Z, Deng Z, Lin S. A new glutarimide derivative from marine sponge-derived Streptomyces anulatus S71. Nat Prod Res. 2014;28(19):1602-6. doi: 10.1080/14786419.2014.928877. Epub 2014 Jun 20. PMID: 24949797. 7: Shah AM, Shakeel-U-Rehman, Hussain A, Mushtaq S, Rather MA, Shah A, Ahmad Z, Khan IA, Bhat KA, Hassan QP. Antimicrobial investigation of selected soil actinomycetes isolated from unexplored regions of Kashmir Himalayas, India. Microb Pathog. 2017 Sep;110:93-99. doi: 10.1016/j.micpath.2017.06.017. Epub 2017 Jun 22. PMID: 28647504. 8: Fotso S, Mahmud T, Zabriskie TM, Santosa DA, Proteau PJ. Rearranged and unrearranged angucyclinones from Indonesian Streptomyces spp. J Antibiot (Tokyo). 2008 Jul;61(7):449-56. doi: 10.1038/ja.2008.61. PMID: 18776657. 9: Human ZR, Moon K, Bae M, de Beer ZW, Cha S, Wingfield MJ, Slippers B, Oh DC, Venter SN. Antifungal Streptomyces spp. Associated with the Infructescences of Protea spp. in South Africa. Front Microbiol. 2016 Nov 2;7:1657. doi: 10.3389/fmicb.2016.01657. PMID: 27853450; PMCID: PMC5090004. 10: Nur Azura AB, Yusoff M, Tan GY, Jegadeesh R, Appleton DR, Vikineswary S. Streptomyces sanglieri which colonised and enhanced the growth of Elaeis guineensis Jacq. seedlings was antagonistic to Ganoderma boninense in in vitro studies. J Ind Microbiol Biotechnol. 2016 Apr;43(4):485-93. doi: 10.1007/s10295-015-1724-4. Epub 2015 Dec 31. PMID: 26721619. 11: Schrey SD, Erkenbrack E, Früh E, Fengler S, Hommel K, Horlacher N, Schulz D, Ecke M, Kulik A, Fiedler HP, Hampp R, Tarkka MT. Production of fungal and bacterial growth modulating secondary metabolites is widespread among mycorrhiza-associated streptomycetes. BMC Microbiol. 2012 Aug 2;12:164. doi: 10.1186/1471-2180-12-164. PMID: 22852578; PMCID: PMC3487804. 12: Fukuda T, Matsumoto A, Takahashi Y, Tomoda H, Omura S. Phenatic acids A and B, new potentiators of antifungal miconazole activity produced by Streptomyces sp. K03-0132. J Antibiot (Tokyo). 2005 Apr;58(4):252-9. doi: 10.1038/ja.2005.29. Erratum in: J Antibiot (Tokyo). 2006 Dec;59(12):C-2. PMID: 15981411.

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ACT-660602