249647-14-1

Basic information

• Product Name: (2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enal
• Synonyms: 5-Hydroxyconiferaldehyde
• CAS NO: 249647-14-1
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.184
• Mol File: 249647-14-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 415.2°C at 760 mmHg
• Flash Point: 169.8°C
• Density: 1.306g/cm³
• Vapor Pressure: 1.74E-07mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: (2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enal(249647-14-1)
• EPA Substance Registry System: (2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enal(249647-14-1)

Safety Data

• Hazardous Substances Data: 249647-14-1(Hazardous Substances Data)

Upstream product

• 4055-72-5 5-Hydroxyeugenol 
• 71186-63-5 2-allyloxy-3-methoxy-phenol 
• 87-66-1 2-hydroxyresorcinol 
• 65841-02-3 3,4-diacetoxy-5-methoxybenzaldehyde 
• 314728-26-2 1-(3-methoxy-4,5-dihydroxy-phenol)propene 
• 934-00-9 3-methocycatechol 
• 340010-10-8 (E)-3-methoxy-5-(3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate 

Relevant articles and documents

DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids

Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization-ring-closing-metathesis strategy.

Total synthesis of six natural products of benzodioxane neolignans

(±)-Eusiderin E, (±)-Eusiderin F, (±)-Eusiderin K, (±)-Eusiderin J, (±)-Eusiderin M and (±)-Eusiderin G were first synthesized from pyrogallol, in which the Claisen Rearrangement was used to afford two important C6-C3 units.

Chemical syntheses of caffeoyl and 5-OH coniferyl aldehydes and alcohols and determination of lignin o-methyltransferase activities in dicot and monocot species

To investigate the substrate preferences of O-methyltransferases in the monolignol biosynthetic pathways, caffeoyl and 5-hydroxy coniferyl aldehydes were synthesized by a new procedure involving a Wittig reaction with the corresponding hydroxybenzaldehydes. The same procedure can also be used to synthesize caffeoyl and 5-hydroxyconiferyl alcohols. Relative O-methyltransferase activities against these substrates were determined using crude extracts and recombinant caffeic acid O-methyltransferase from alfalfa (Medicago sativa), and crude extracts from the model legume. Medicago truncatula, tobacco, wheat and tall fescue. Extracts from all these species catalyzed methylation of the various monolignol aldehydes and alcohols more effectively than the corresponding hydroxycinnamic acids.