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

MedKoo CAT#: 585383

CAS#: 23820-80-6

Description: Viridiol is a fungal steroid that demonstrates phytotoxic activity.

Chemical Structure

CAS# 23820-80-6

Theoretical Analysis

MedKoo Cat#: 585383
Name: Viridiol
CAS#: 23820-80-6
Chemical Formula: C20H18O6
Exact Mass: 354.1103
Molecular Weight: 354.358
Elemental Analysis: C, 67.79; H, 5.12; O, 27.09

Price and Availability

Size Price Availability Quantity
1.0mg USD 357.0 2 Weeks
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Synonym: Viridiol

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


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

Preparing Stock Solutions

The following data is based on the product molecular weight 354.358 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

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1: 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. Review. PubMed PMID: 30981885.

2: 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. PubMed PMID: 28463562.

3: 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. PubMed PMID: 31554399.

4: Jones RW, Hancock JG. Conversion of viridin to viridiol by viridin-producing fungi. Can J Microbiol. 1987 Nov;33(11):963-6. PubMed PMID: 3447692.

5: 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. PubMed PMID: 24709032.

6: 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. Print 2013 Apr 1. PubMed PMID: 23634026; PubMed Central PMCID: PMC3629508.

7: Wipf P, Kerekes AD. Structure reassignment of the fungal metabolite TAEMC161 as the phytotoxin viridiol. J Nat Prod. 2003 May;66(5):716-8. PubMed PMID: 12762817.

8: 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. eCollection 2019. PubMed PMID: 31543866; PubMed Central PMCID: PMC6730527.

9: 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. PubMed PMID: 17393658.

10: 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. PubMed PMID: 23098903.

11: 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. PubMed PMID: 31661270.

12: 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. PubMed PMID: 23707931.

13: 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. PubMed PMID: 20839869; PubMed Central PMCID: PMC2951720.

14: 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. PubMed PMID: 22732888; PubMed Central PMCID: PMC6268255.

15: 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. PubMed PMID: 24529574.

16: 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. Epub 2006 Jun 28. PubMed PMID: 16804721.