8066-07-7

Basic information

• Product Name: [1S-[1alpha(2Z,4E),4alpha,6alpha]]-5-(4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-methylpenta-2,4-dienal
• Synonyms: [1S-[1alpha(2Z,4E),4alpha,6alpha]]-5-(4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-methylpenta-2,4-dienal;2-cis,4-trans-Xanthoxin;C13453
• CAS NO: 8066-07-7
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33338
• EINECS: 232-513-2
• Mol File: 8066-07-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 371.1°Cat760mmHg
• Flash Point: 132.6°C
• Appearance: /
• Density: 1.151g/cm³
• CAS DataBase Reference: [1S-[1alpha(2Z,4E),4alpha,6alpha]]-5-(4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-methylpenta-2,4-dienal(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-[1alpha(2Z,4E),4alpha,6alpha]]-5-(4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-methylpenta-2,4-dienal(8066-07-7)
• EPA Substance Registry System: [1S-[1alpha(2Z,4E),4alpha,6alpha]]-5-(4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-methylpenta-2,4-dienal(8066-07-7)

Safety Data

• Hazardous Substances Data: 8066-07-7(Hazardous Substances Data)

Usage

Uses

Xanthoxin is a growth inhibitor in plants.

Upstream product

• 26927-07-1 9-cis-violaxanthin 
• 69350-47-6 (1R,3S,6S)-6-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-1,5,5-trimethyl-7-oxa-bicyclo[4.1.0]heptan-3-ol 
• 10153-97-6 (15E,9'Z)-neoxanthin 
• 69297-03-6 (1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester 
• 130320-96-6 (-)-(1R,3S,6R)-6-ethynyl-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol 
• 214335-71-4 (-)-[(S)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-enyl]methanol 
• 439859-70-8 (-)-(1S,4S,6R)-4-(tert-butyldimethylsilyloxy)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde 
• 439859-71-9 (-)-[(1R,4S,6R)-4-(tert-butyldimethylsilyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]heptan-1-yl]methanol 
• 23069-07-0 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol 
• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 51318-62-8 ethyl 4-bromo-3-methylcrotonate 
• 122346-85-4 (-)-(1S,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-carbaldehyd 
• 122346-75-2 (+)-(1R,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-methanol 
• 122346-88-7 (2Z,4E)-3-Methyl-5-((1S,6R)-2,2,6-trimethyl-4-oxo-7-oxa-bicyclo[4.1.0]hept-1-yl)-penta-2,4-dienoic acid methyl ester 

Downstream Products

• 142204-43-1 (9'Z)-15,15'-Didehydroneoxanthin 
• 142204-43-1 15,15'-Didehydroneoxanthin 

Relevant articles and documents

Stereocontrolled syntheses of carotenoid oxidative metabolites, (-)-loliolide, (-)-xanthoxin, and their stereoisomers

We achieved the stereocontrolled syntheses of (-)-loliolide, (-)-xanthoxin, and their stereoisomers from (+)- or (-)-3-alkoxy-6-hydroxymethyl-1,1,5-trimethylcyclohexene through the corresponding syn and anti-epoxides, respectively, which were obtained by utilizing the highly diastereoselective Sharpless asymmetric epoxidation or mCPBA oxidation.

Convenient Syntheses of Optically Active Abscisic Acid and Xanthoxin

The Reformatzky reaction of 3-(bromomethyl)crotonate with an optically active epoxycyclohexane aldehyde derivative (3), followed by dehydration, gave the chiral dienoic acid (6) stereospecifically.The product was derived to optically active abscisic acid (1) and xanthoxin (2) successfully.

CAROTENOID METABOLISM AND THE BIOSYNTHESIS OF ABSCISIC ACID

The conversion of all-trans-violaxanthin to 9'-cis-neoxanthin was shown to occur in fluridone-treated etiolated Lycopersicon and Phaseolus seedlings, following exposure to light.The results of deuterium oxide labelling experiments supported this precursor/product relationship, and provided further evidence for the origin of abscisic acid.Several apo-carotenoids, putative by-products of abscisic acid biosynthesis, were synthesised by chemical oxidation but were not detected in plant extracts.In vitro, lipoxygenase cleaved neoxanthin and violaxanthin down to small (/=C13) fragments.It may be that in vivo any apo-carotenoids formed by the specific cleavage of 9'-cis-neoxanthin, during abscisic acid biosynthesis, are rapidly metabolized by lipoxygenase or similar enzymes.