821775-38-6

Basic information

• Product Name: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)
• Synonyms: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)
• CAS NO: 821775-38-6
• Molecular Formula: C12H12O3
• Molecular Weight: 0
• Product Categories: METHYL
• Mol File: 821775-38-6.mol
• Article Data: 34

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)(821775-38-6)
• EPA Substance Registry System: 2-Propenal,3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-,(2E)-(9CI)(821775-38-6)

Safety Data

• Hazardous Substances Data: 821775-38-6(Hazardous Substances Data)

Usage

Physical Appearance

Colorless to pale yellow liquid

Uses

Flavoring agent
Fragrance ingredient in consumer products
Production of dyes
Production of pharmaceuticals
Production of other chemical compounds

Classification

Aldehyde

Toxicity

Considered to have low toxicity

Handling Precautions

Should be handled with caution due to its irritant properties

Upstream product

• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 108-05-4 vinyl acetate 
• 120-57-0 piperonal 
• 120-58-1 isosafrole 
• 6329-73-3 1-benzo[1,3]dioxol-5-yl-ethanol 
• 68-12-2 N,N-dimethyl-formamide 
• 7031-03-0 3-(benzo[d][1,3]dioxol-5-yl)propan-1-ol 
• 94-62-2 Piperine 
• 4043-71-4 isosafrole 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 64-19-7 acetic acid 
• 495-76-1 piperonol 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 121-44-8 triethylamine 

Downstream Products

• 1020270-20-5 (S)-3-(2-chlorophenyl)-4-nitrobutanal 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 52826-25-2 3-benzo[1,3]dioxol-5-yl-acrylaldehyde-(N-phenyl oxime ) 

Relevant articles and documents

Dramatic Effect of γ-Heteroatom Dienolate Substituents on Counterion Assisted Asymmetric Anionic Amino-Cope Reaction Cascades

We report a dramatic effect on product outcomes of the lithium ion enabled amino-Cope-like anionic asymmetric cascade when different γ-dienolate heteroatom substituents are employed. For dienolates with azide, thiomethyl, and trifluoromethylthiol substituents, a Mannich/amino-Cope/cyclization cascade ensues to form chiral cyclohexenone products with two new stereocenters in an anti-relationship. For fluoride-substituted nucleophiles, a Mannich/amino-Cope cascade proceeds to afford chiral acyclic products with two new stereocenters in a syn-relationship. Bromide- and chloride-substituted nucleophiles appear to proceed via the same pathway as the fluoride albeit with the added twist of a 3-exo-trig cyclization to yield chiral cyclopropane products with three stereocenters. When this same class of nucleophiles is substituted with a γ-nitro group, the Mannich-initiated cascade is now diverted to a β-lactam product instead of the amino-Cope pathway. These anionic asymmetric cascades are solvent- and counterion-dependent, with a lithium counterion being essential in combination with etheral solvents such as MTBE and CPME. By altering the geometry of the imine double bond from E to Z, the configurations at the R1 and X stereocenters are flipped. Mechanistic, computational, substituent, and counterion studies suggest that these cascades proceed via a common Mannich-product intermediate, which then proceeds via either a chair (X = N3, SMe, or SCF3) or boat-like (X = F, Cl, or Br) transition state to afford amino-Cope-like products or β-lactam in the case of X = NO2.

Co-Oxidative Transformation of Piperine to Piperonal and 3,4-Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus

The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOXPsa1) of the basidiomycete Pleurotus sapidus was identified to convert piperine, the abundant pungent principle of black pepper (Piper nigrum), to piperonal and a second volatile product, 3,4-methylenedioxycinnamaldehyde, with a vanilla-like odor through an alkene cleavage. The reaction principle was co-oxidation, as proven by its dependence on the presence of linoleic or α-linolenic acid, common substrates of lipoxygenases. Optimization of the reaction conditions (substrate concentrations, reaction temperature and time) led to a 24-fold and 15-fold increase of the piperonal and 3,4-methylenedioxycinnamaldehyde concentration using the recombinant enzyme. Monokaryotic strains showed different concentrations of and ratios between the two reaction products.

Compound with piperine skeleton structure as well as preparation and application thereof

The invention discloses a compound with a piperine skeleton structure as well as preparation and application of the compound, wherein the structural formulas of the compound are shown as a formula I-1and a formula I-2; in the formulas, R1 is hydrogen, halogen, nitryl or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, C1-C5 straight-chain or branched-chain alkyl and C1-C5 alkoxy; R2 is hydrogen, halogen, nitro or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, phenyl, aryl and aromatic heterocyclic group, or substituted or unsubstituted C1-C5 straight-chain or branched-chain alkyl, or substituted or unsubstituted C1-C5 alkoxy, or substituted or unsubstituted C6-C30 aryl, fused ring and fused heterocyclic ring. As a chitinase inhibitor, the compound provided by the invention has the advantages of high activity, good broad spectrum and easiness in synthesis, and shows excellent insecticidal ability and insecticidal spectrum.