Zinniol | CAS#17811-28-8 | biochemical

MedKoo Cat#: 146198 | Name: Zinniol

Description:

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

Zinniol is a phenolic compound produced by certain fungi and plants, notably associated with pathogenic fungi like Alternaria species. It acts as a phytotoxin, disrupting plant cell function by inducing oxidative stress and interfering with mitochondrial activity. Zinniol's mechanism involves the generation of reactive oxygen species (ROS), leading to membrane damage and cell death in host tissues. While primarily studied in the context of plant pathology, understanding zinniol's action has potential applications in developing disease-resistant crops and studying oxidative stress mechanisms.

Chemical Structure

Zinniol

CAS#17811-28-8

Theoretical Analysis

MedKoo Cat#: 146198

Name: Zinniol

CAS#: 17811-28-8

Chemical Formula: C15H22O4

Exact Mass: 266.1518

Molecular Weight: 266.34

Elemental Analysis: C, 67.65; H, 8.33; O, 24.03

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Zinniol;

IUPAC/Chemical Name

(3-methoxy-4-methyl-5-((3-methylbut-2-en-1-yl)oxy)-1,2-phenylene)dimethanol

InChi Key

DUMQPTRUYCCSEZ-UHFFFAOYSA-N

InChi Code

1S/C15H22O4/c1-10(2)5-6-19-14-7-12(8-16)13(9-17)15(18-4)11(14)3/h5,7,16-17H,6,8-9H2,1-4H3

SMILES Code

COC1=C(CO)C(CO)=CC(OCC=C(C)C)=C1C

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 266.34 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: Gamboa-Angulo MM, Escalante-Erosa F, García-Sosa K, Alejos-González F, Delgado-Lamas G, Peña-Rodríguez LM. Natural zinniol derivatives from Alternaria tagetica. Isolation, synthesis, and structure-activity correlation. J Agric Food Chem. 2002 Feb 27;50(5):1053-8. doi: 10.1021/jf010641t. PMID: 11853479. 2: Moreno-Escobar J, Puc-Carrillo A, Cáceres-Farfán M, Peña-Rodríguez LM, Gamboa-Angulo MM. Two new zinniol-related phytotoxins from Alternaria solani. Nat Prod Res. 2005 Sep;19(6):603-7. doi: 10.1080/14786410410001729159. PMID: 16010827. 3: Thuleau P, Graziana A, Rossignol M, Kauss H, Auriol P, Ranjeva R. Binding of the phytotoxin zinniol stimulates the entry of calcium into plant protoplasts. Proc Natl Acad Sci U S A. 1988 Aug;85(16):5932-5. doi: 10.1073/pnas.85.16.5932. PMID: 16593970; PMCID: PMC281879. 4: Meena M, Gupta SK, Swapnil P, Zehra A, Dubey MK, Upadhyay RS. Alternaria Toxins: Potential Virulence Factors and Genes Related to Pathogenesis. Front Microbiol. 2017 Aug 8;8:1451. doi: 10.3389/fmicb.2017.01451. PMID: 28848500; PMCID: PMC5550700. 5: Montillet JL, Rossignol M, Auriol P. Radioimmunoassay of the phytotoxic compound zinniol. J Immunoassay. 1987;8(1):11-27. doi: 10.1080/01971528708063052. PMID: 3558826. 6: Meena M, Samal S. Alternaria host-specific (HSTs) toxins: An overview of chemical characterization, target sites, regulation and their toxic effects. Toxicol Rep. 2019 Jul 17;6:745-758. doi: 10.1016/j.toxrep.2019.06.021. Erratum in: Toxicol Rep. 2020 Dec 22;8:28-29. doi: 10.1016/j.toxrep.2020.12.007. PMID: 31406682; PMCID: PMC6684332. 7: Masi M, Di Lecce R, Maddau L, Marsico G, Superchi S, Evidente A. Argyrotoxins A-C, a trisubstituted dihydroisobenzofuranone, a tetrasubstituted 2-hydroxyethylbenzamide and a tetrasubstitutedphenyl trisubstitutedbutyl ether produced by Alternaria argyroxiphii, the causal agent of leaf spot on African mahogany trees (Khaya senegalensis). Phytochemistry. 2021 Nov;191:112921. doi: 10.1016/j.phytochem.2021.112921. Epub 2021 Aug 21. PMID: 34425462. 8: Gamboa-Angulo MM, Alejos-González F, Escalante-Erosa F, García-Sosa K, Delgado-Lamas G, Peña-Rodríguez LM. Novel dimeric metabolites from Alternaria tagetica. J Nat Prod. 2000 Aug;63(8):1117-20. doi: 10.1021/np990422q. PMID: 10978208. 9: Wang T, Tang C, Xiao M, Cao Z, He M, Qi J, Li Y, Li X. Effect of Air Drying on the Metabolic Profile of Fresh Wild and Artificial Cordyceps sinensis. Foods. 2023 Dec 21;13(1):48. doi: 10.3390/foods13010048. PMID: 38201076; PMCID: PMC10778509. 10: Lecomte M, Hamama L, Voisine L, Gatto J, Hélesbeux JJ, Séraphin D, Peña- Rodriguez LM, Richomme P, Boedo C, Yovanopoulos C, Gyomlai M, Briard M, Simoneau P, Poupard P, Berruyer R. Partial resistance of carrot to Alternaria dauci correlates with in vitro cultured carrot cell resistance to fungal exudates. PLoS One. 2014 Jul 1;9(7):e101008. doi: 10.1371/journal.pone.0101008. PMID: 24983469; PMCID: PMC4077726. 11: Liu Z, Xia G, Chen S, Liu Y, Li H, She Z. Eurothiocin A and B, sulfur- containing benzofurans from a soft coral-derived fungus Eurotium rubrum SH-823. Mar Drugs. 2014 Jun 20;12(6):3669-80. doi: 10.3390/md12063669. PMID: 24955555; PMCID: PMC4071596. 12: Ai HL, Zhang LM, Chen YP, Zi SH, Xiang H, Zhao DK, Shen Y. Two new compounds from an endophytic fungus Alternaria solani. J Asian Nat Prod Res. 2012;14(12):1144-8. doi: 10.1080/10286020.2012.733701. Epub 2012 Oct 29. PMID: 23106531. 13: Yang XL, Zhang S, Hu QB, Luo DQ, Zhang Y. Phthalide derivatives with antifungal activities against the plant pathogens isolated from the liquid culture of Pestalotiopsis photiniae. J Antibiot (Tokyo). 2011 Nov;64(11):723-7. doi: 10.1038/ja.2011.82. Epub 2011 Sep 14. PMID: 21915132. 14: Horiuchi M, Ohnishi K, Iwase N, Nakajima Y, Tounai K, Yamashita M, Yamada Y. A novel isoindoline, porritoxin sulfonic acid, from Alternaria porri and the structure-phytotoxicity correlation of its related compounds. Biosci Biotechnol Biochem. 2003 Jul;67(7):1580-3. doi: 10.1271/bbb.67.1580. PMID: 12913305. 15: Berestetskiĭ AO, Iuzikhin OS, Katkova AS, Dobrodumov AV, Sivogrivov DE, Kolombet LV. [Isolation, identification, and characteristics of the phytotoxin produced by the fungus Alternaria cirsinoxia]. Prikl Biokhim Mikrobiol. 2010 Jan-Feb;46(1):84-8. Russian. PMID: 20198923. 16: Gamboa-Angulo MM, García-Sosa K, Alejos-González F, Escalante-Erosa F, Delgado-Lamas G, Peña-Rodríguez LM. Tagetolone and tagetenolone: two phytotoxic polyketides from Alternaria tagetica. J Agric Food Chem. 2001 Mar;49(3):1228-32. doi: 10.1021/jf000872k. PMID: 11312841.