Viridiol | CAS#23820-80-6 | phytotoxic

MedKoo Cat#: 585383 | Name: Viridiol

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Description:

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

Viridiol is a fungal steroid that demonstrates phytotoxic activity.

Chemical Structure

Viridiol

CAS#23820-80-6

Theoretical Analysis

MedKoo Cat#: 585383

Name: Viridiol

CAS#: 23820-80-6

Chemical Formula: C20H18O6

Exact Mass: 354.1103

Molecular Weight: 354.36

Elemental Analysis: C, 67.79; H, 5.12; O, 27.09

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 500.00	2 Weeks

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Related CAS #

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Synonym

Viridiol

IUPAC/Chemical Name

(1R,16R,17S,18S)-16,18-dihydroxy-17-methoxy-1-methyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11-dione

InChi Key

JZAFRYPNQHUUMQ-HUYLIWGRSA-N

InChi Code

InChI=1S/C20H18O6/c1-20-11-5-3-8-9(4-6-12(8)21)13(11)16(23)17-14(20)10(7-26-17)15(22)18(25-2)19(20)24/h3,5,7,15,18-19,22,24H,4,6H2,1-2H3/t15-,18-,19-,20-/m1/s1

SMILES Code

O=C1C(C=CC([C@@]2(C)[C@H](O)[C@H](OC)[C@H](O)C3=COC4=C23)=C5C4=O)=C5CC1

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 354.36 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: Bansal R, Sahoo SA, Barvkar VT, Srivastava AK, Mukherjee PK. Trichoderma virens exerts herbicidal effect on Arabidopsis thaliana via modulation of amino acid metabolism. Plant Sci. 2023 Jul;332:111702. doi: 10.1016/j.plantsci.2023.111702. Epub 2023 Apr 7. PMID: 37030329. 2: Bansal R, Pachauri S, Gururajaiah D, Sherkhane PD, Khan Z, Gupta S, Banerjee K, Kumar A, Mukherjee PK. Dual role of a dedicated GAPDH in the biosynthesis of volatile and non-volatile metabolites- novel insights into the regulation of secondary metabolism in Trichoderma virens. Microbiol Res. 2021 Dec;253:126862. doi: 10.1016/j.micres.2021.126862. Epub 2021 Sep 9. PMID: 34563853. 3: Elfstrand M, Chen J, Cleary M, Halecker S, Ihrmark K, Karlsson M, Davydenko K, Stenlid J, Stadler M, Durling MB. Comparative analyses of the Hymenoscyphus fraxineus and Hymenoscyphus albidus genomes reveals potentially adaptive differences in secondary metabolite and transposable element repertoires. BMC Genomics. 2021 Jul 4;22(1):503. doi: 10.1186/s12864-021-07837-2. PMID: 34217229; PMCID: PMC8254937. 4: Pakora GA, Mann S, Kone D, Buisson D. Bioconversion of antifungal viridin to phytotoxin viridiol by environmental non-viridin producing microorganisms. Bioorg Chem. 2021 Jul;112:104959. doi: 10.1016/j.bioorg.2021.104959. Epub 2021 May 1. PMID: 33971564. 5: Pachauri S, Sherkhane PD, Kumar V, Mukherjee PK. Whole Genome Sequencing Reveals Major Deletions in the Genome of M7, a Gamma Ray-Induced Mutant of Trichoderma virens That Is Repressed in Conidiation, Secondary Metabolism, and Mycoparasitism. Front Microbiol. 2020 Jun 12;11:1030. doi: 10.3389/fmicb.2020.01030. PMID: 32595612; PMCID: PMC7303927. 6: Sinno M, Bézier A, Vinale F, Giron D, Laudonia S, Garonna AP, Pennacchio F. Symbiosis disruption in the olive fruit fly, Bactrocera oleae (Rossi), as a potential tool for sustainable control. Pest Manag Sci. 2020 Sep;76(9):3199-3207. doi: 10.1002/ps.5875. Epub 2020 May 26. PMID: 32358914. 7: Masi M, Di Lecce R, Tuzi A, Linaldeddu BT, Montecchio L, Maddau L, Evidente A. Hyfraxinic Acid, a Phytotoxic Tetrasubstituted Octanoic Acid, Produced by the Ash (Fraxinus excelsior L.) Pathogen Hymenoscyphus fraxineus Together with Viridiol and Some of Its Analogues. J Agric Food Chem. 2019 Dec 11;67(49):13617-13623. doi: 10.1021/acs.jafc.9b06055. Epub 2019 Nov 25. PMID: 31661270. 8: Ji Y, Xin Z, He H, Gao S. Total Synthesis of Viridin and Viridiol. J Am Chem Soc. 2019 Oct 16;141(41):16208-16212. doi: 10.1021/jacs.9b08577. Epub 2019 Oct 3. PMID: 31554399. 9: Mukherjee PK, Mehetre ST, Sherkhane PD, Muthukathan G, Ghosh A, Kotasthane AS, Khare N, Rathod P, Sharma KK, Nath R, Tewari AK, Bhattacharyya S, Arya M, Pathak D, Wasnikar AR, Tiwari RKS, Saxena DR. A Novel Seed-Dressing Formulation Based on an Improved Mutant Strain of Trichoderma virens, and Its Field Evaluation. Front Microbiol. 2019 Aug 30;10:1910. doi: 10.3389/fmicb.2019.01910. PMID: 31543866; PMCID: PMC6730527. 10: Kocaturk NM, Akkoc Y, Kig C, Bayraktar O, Gozuacik D, Kutlu O. Autophagy as a molecular target for cancer treatment. Eur J Pharm Sci. 2019 Jun 15;134:116-137. doi: 10.1016/j.ejps.2019.04.011. Epub 2019 Apr 11. PMID: 30981885. 11: Del Bel M, Abela AR, Ng JD, Guerrero CA. Enantioselective Chemical Syntheses of the Furanosteroids (-)-Viridin and (-)-Viridiol. J Am Chem Soc. 2017 May 24;139(20):6819-6822. doi: 10.1021/jacs.7b02829. Epub 2017 May 12. PMID: 28463562. 12: Cleary MR, Andersson PF, Broberg A, Elfstrand M, Daniel G, Stenlid J. Genotypes of Fraxinus excelsior with different susceptibility to the ash dieback pathogen Hymenoscyphus pseudoalbidus and their response to the phytotoxin viridiol - a metabolomic and microscopic study. Phytochemistry. 2014 Jun;102:115-25. doi: 10.1016/j.phytochem.2014.03.005. Epub 2014 Apr 4. PMID: 24709032. 13: Halecker S, Surup F, Kuhnert E, Mohr KI, Brock NL, Dickschat JS, Junker C, Schulz B, Stadler M. Hymenosetin, a 3-decalinoyltetramic acid antibiotic from cultures of the ash dieback pathogen, Hymenoscyphus pseudoalbidus. Phytochemistry. 2014 Apr;100:86-91. doi: 10.1016/j.phytochem.2014.01.018. Epub 2014 Feb 12. PMID: 24529574. 14: Crutcher FK, Parich A, Schuhmacher R, Mukherjee PK, Zeilinger S, Kenerley CM. A putative terpene cyclase, vir4, is responsible for the biosynthesis of volatile terpene compounds in the biocontrol fungus Trichoderma virens. Fungal Genet Biol. 2013 Jul;56:67-77. doi: 10.1016/j.fgb.2013.05.003. Epub 2013 May 22. PMID: 23707931. 15: Andersson PF, Broberg A, Lundberg D. The furan-osteroid viridiol. Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 2;69(Pt 4):o467-8. doi: 10.1107/S1600536813005606. PMID: 23634026; PMCID: PMC3629508. 16: Andersson PF, Bengtsson S, Cleary M, Stenlid J, Broberg A. Viridin-like steroids from Hymenoscyphus pseudoalbidus. Phytochemistry. 2013 Feb;86:195-200. doi: 10.1016/j.phytochem.2012.09.012. Epub 2012 Oct 22. PMID: 23098903. 17: Andersson PF, Bengtsson S, Stenlid J, Broberg A. B-norsteroids from Hymenoscyphus pseudoalbidus. Molecules. 2012 Jun 25;17(7):7769-81. doi: 10.3390/molecules17077769. PMID: 22732888; PMCID: PMC6268255. 18: Cao S, Ross L, Tamayo G, Clardy J. Asterogynins: secondary metabolites from a Costa Rican endophytic fungus. Org Lett. 2010 Oct 15;12(20):4661-3. doi: 10.1021/ol101972g. PMID: 20839869; PMCID: PMC2951720. 19: Phuwapraisirisan P, Rangsan J, Siripong P, Tip-Pyang S. 9-epi-Viridiol, a novel cytotoxic furanosteroid from soil fungus Trichoderma virens. Nat Prod Res. 2006 Dec;20(14):1321-5. doi: 10.1080/14786410601101969. PMID: 17393658. 20: Mukherjee M, Horwitz BA, Sherkhane PD, Hadar R, Mukherjee PK. A secondary metabolite biosynthesis cluster in Trichoderma virens: evidence from analysis of genes underexpressed in a mutant defective in morphogenesis and antibiotic production. Curr Genet. 2006 Sep;50(3):193-202. doi: 10.1007/s00294-006-0075-0. Epub 2006 Jun 28. PMID: 16804721.