22944-03-2

Basic information

• Product Name: Siccayne
• Synonyms: Siccayne;2-(3-Methyl-3-buten-1-ynyl)hydroquinone;2-(3-Methyl-3-butene-1-ynyl)-1,4-benzenediol
• CAS NO: 22944-03-2
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 0
• Mol File: 22944-03-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 342.4°Cat760mmHg
• Flash Point: 169.3°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 3.82E-05mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: Siccayne(CAS DataBase Reference)
• NIST Chemistry Reference: Siccayne(22944-03-2)
• EPA Substance Registry System: Siccayne(22944-03-2)

Safety Data

• Hazardous Substances Data: 22944-03-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H10O2/c1-8(2)3-4-9-7-10(12)5-6-11(9)13/h5-7,12-13H,1H2,2H3

Upstream product

• 121007-19-0 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid 
• 1138-41-6 4-hydroxy-3-prenylbenzoic acid 
• 107743-98-6 4-methoxy-3-(3'-methyl-2'-butenyl)-benzoic acid 
• 131136-47-5 2-Bromo-1,4-bis(methoxymethoxy)benzene 
• 78-80-8 2-methylbut-1-en-3-yne 
• 123-08-0 4-hydroxy-benzaldehyde 
• 60032-63-5 4-hydroxy-3-iodo-benzaldehyde 
• 496881-71-1 2-iodohydroquinone diacetate 
• 66416-73-7 p-hydroxy-o-iodoaniline 
• 3958-83-6 2-iodocyclohexa-2,5-diene-1,4-dione 
• 22944-04-3 siccayne diacetate 
• 131136-49-7 4-<2,5-Bis(methoxymethyloxy)phenyl>-2-methyl-1-buten-3-yne 
• 121007-17-8 4-hydroxy-3-(3-methylbut-3-en-1-yn-1-yl)benzaldehyde 
• 106-51-4 p-benzoquinone 

Relevant articles and documents

Biosynthesis of Biscognienyne B Involving a Cytochrome P450-Dependent Alkynylation

The alkyne is a biologically significant moiety found in many natural products and a versatile functional group widely used in modern chemistry. Recent studies have revealed the biosynthesis of acetylenic bonds in fatty acids and amino acids. However, the

Synthesis and structure - Phytotoxicity relationships of acetylenic phenols and chromene metabolites, and their analogues, from the grapevine pathogen Eutypa lata

Eutypa lata, the fungus responsible for dying-arm disease in grapevines, produces a number of structurally related secondary metabolites, of which eutypine (1) has been implicated as the principal phytotoxin. However, analysis of an E. lata strain from California known to be pathogenic to grapevines showed that eutypine was not present, suggesting that other metabolites could be phytotoxic. Investigation of the relative phytotoxicities of individual metabolites has been limited by insufficient material and lack of a reliable bioassay. Metabolites of particular interest and their precursors were therefore synthesized, and a rapid, quantitative bioassay via topical application of individual compounds to disks of grape leaves and measurement of chlorophyll loss was developed to provide a relative measure of tissue damage. The recently reported metabolite eulatachromene (2) was found to have phytotoxicity greater than that of eutypine (1). The cyclization product, 5-formyl-2-methylvinyl[1]benzofuran (3), also showed significant activity, whereas the reduction product, eutypinol (4), was inactive, as was the quinol, siccayne (5). These results indicate that before strains of Eutypa are incriminated as pathogenic they must be analyzed for the presence or absence of specific constituents for which the phytotoxicity has been unequivocally established.

Total synthesis of siccayne

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