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Details

Stereochemistry ACHIRAL
Molecular Formula C15H22O4
Molecular Weight 266.3328
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZINNIOL

SMILES

COC1=C(C)C(OCC=C(C)C)=CC(CO)=C1CO

InChI

InChIKey=DUMQPTRUYCCSEZ-UHFFFAOYSA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C15H22O4
Molecular Weight 266.3328
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12913305 | https://www.ncbi.nlm.nih.gov/pubmed/16593970 | https://www.ncbi.nlm.nih.gov/pubmed/28848500

Zinniol is a non-host selective phytotoxin which was originally isolated from culture filtrates of Alternaria zinnia, and then from those of A. dauci. This toxin induces several symptoms on zinnia and carrot and also inhibits seed germination of various plants. Zinniol has been shown to produce necrosis on leaves of susceptible marigold (Tagetes erecta) plants, probably through calcium regulation. The phytotoxin binds to carrot protoplasts and isolated membranes in a saturable and reversible manner. Receptor occupancy stimulates the entry of calcium into protoplasts. Zinniol can partially reverse the effects and binding of the calcium-channel blockers Desmethoxy-verapamil and bepridil. Selected cell lines that are insensitive to Zinniol lose part of their binding capacity and sensitivity to the action of the agonist-like compound but are still able to bind calcium-channel blockers.

Originator

Sources: Canadian Journal of Botany (1967), 45, (11), 2087-90.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Alternaria Toxins: Potential Virulence Factors and Genes Related to Pathogenesis.
2017

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Certified seeds of T. erecta L. Were used for activity evaluation. Five-day-old cell cultures were transferred to liquid MS medium without growth regulators at a final density of 250,000 cells/ml and allowed to recover for 12 h (Wang et al. 1996). After this period, flasks were treated with different concentrations of the various phytotoxic fractions (Zinniol) and incubated at 25C for 48 h. Cell viability was determined with Evan’s blue
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:50:54 GMT 2023
Edited
by admin
on Fri Dec 15 19:50:54 GMT 2023
Record UNII
2XM821R13R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZINNIOL
Common Name English
3-METHOXY-4-METHYL-5-(3-METHYL-2-BUTENYLOXY)-1,2-BENZENEDIMETHANOL
Systematic Name English
NSC-125427
Code English
Code System Code Type Description
NSC
125427
Created by admin on Fri Dec 15 19:50:54 GMT 2023 , Edited by admin on Fri Dec 15 19:50:54 GMT 2023
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PUBCHEM
87317
Created by admin on Fri Dec 15 19:50:54 GMT 2023 , Edited by admin on Fri Dec 15 19:50:54 GMT 2023
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CAS
17811-28-8
Created by admin on Fri Dec 15 19:50:54 GMT 2023 , Edited by admin on Fri Dec 15 19:50:54 GMT 2023
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MESH
C051798
Created by admin on Fri Dec 15 19:50:54 GMT 2023 , Edited by admin on Fri Dec 15 19:50:54 GMT 2023
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FDA UNII
2XM821R13R
Created by admin on Fri Dec 15 19:50:54 GMT 2023 , Edited by admin on Fri Dec 15 19:50:54 GMT 2023
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EPA CompTox
DTXSID10170425
Created by admin on Fri Dec 15 19:50:54 GMT 2023 , Edited by admin on Fri Dec 15 19:50:54 GMT 2023
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