33580-05-1

Basic information

• Product Name: fucoserratene,(3E,5E)-1,3,5-octatriene,(E,Z)-1,3,5-octatriene
• Synonyms: fucoserratene,(3E,5E)-1,3,5-octatriene,(E,Z)-1,3,5-octatriene;(3E,5Z)-Octa-1,3,5-triene;Fucoserratene
• CAS NO: 33580-05-1
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.18
• Mol File: 33580-05-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 138.8°Cat760mmHg
• Flash Point: 21.5°C
• Appearance: /
• Density: 0.756g/cm³
• Vapor Pressure: 8.24mmHg at 25°C
• Refractive Index: 1.457
• CAS DataBase Reference: fucoserratene,(3E,5E)-1,3,5-octatriene,(E,Z)-1,3,5-octatriene(CAS DataBase Reference)
• NIST Chemistry Reference: fucoserratene,(3E,5E)-1,3,5-octatriene,(E,Z)-1,3,5-octatriene(33580-05-1)
• EPA Substance Registry System: fucoserratene,(3E,5E)-1,3,5-octatriene,(E,Z)-1,3,5-octatriene(33580-05-1)

Safety Data

• Hazardous Substances Data: 33580-05-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12/c1-3-5-7-8-6-4-2/h3,5-8H,1,4H2,2H3/b7-5+,8-6-

Upstream product

• 55136-51-1 1,3-cis-octadien-5-yne 
• 55136-50-0 1,3-trans-octadien-5-yne 
• 4313-02-4 trans,cis-2,4-heptadienal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 20432-40-0 (E)-penta-2,4-dienal 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 6108-61-8 cis,cis-2,4-Hexadien 
• 56039-54-4 cis-1-Z-propenyl-2-methylcyclopropane 
• 21651-12-7 (E)-2,4-pentadienoic acid 
• 4949-20-6 (E)-2,4-pentadien-1-ol 
• 10420-90-3 1,3-hexadien-5-yne 
• 103197-98-4 (E)-hept-2-en-4-yn-1-ol 
• 34501-81-0 hept-2t-en-4-ynal 
• 114515-45-6 (E,Z)-hexa-1,3-dienyloxirane 

Downstream Products

• 29837-20-5 dictyopterene D 
• 29837-20-5 (+/-)-dictyopterene 
• 34048-44-7 Ectocarpene 
• 288-13-1 NH-pyrazole 
• 69508-34-5 3-<(E,Z)-1,3-hexadienyl>-5-vinyl-1-pyrazoline 

Relevant articles and documents

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The preparation and electrocyclic ring-opening of cyclobutenes: Stereocontrolled approaches to substituted conjugated dienes and trienes

Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alkadienals exclusively, and the process is exploited in transforming cis-3-cyclobutene-1,2-dimethanol 1 into a variety of naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates. Desymmetrisation of 1 with Pseudomonas fluorescens lipase gives access to both enantiomers of 3-oxabicyclo[3.2.0]hept-6-en-2-one 4, for use in stereocontrolled routes to 6-oxygenated (2Z,4E)-alkadienals.

Stereospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae

Giffordene (=(2Z,4Z,6E,8Z)-2,4,6,8-undecatetraene; 9f) and five stereoisomers are new C11H16 hydrocarbons from the marine brown alga Giffordia mitchellae.Their synthesis is based on non-stereoselective Wittig reactions of (E)-2-alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting (E/Z)-pairs.The uniform enynes (>98percent purity) are then stereospecifically reduced to (Z)-alkenes with Zn(Cu/Ag) in aq.MeOH at r.t. 13C- and 1H-NMR data of the new tetraenes are presented.Biosynthetically, giffordene (9f) originates from dodeca-3,6,9-trienoic acid via an unstable (3Z,5Z,8Z)-1,3,5,8-undecatetraene followed by a thermally allowed antarafacial 1,7-sigmatropic hydrogen shift to the (2Z,4Z,6E,8Z)-isomer 9f.