4313-02-4

Basic information

• Product Name: 2,4-heptadienal,(E,Z)-2,4-heptadienal
• Synonyms: 2,4-heptadienal,(E,Z)-2,4-heptadienal
• CAS NO: 4313-02-4
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.1537
• Mol File: 4313-02-4.mol

Chemical Properties

• Boiling Point: 129.2 °C at 760 mmHg
• Flash Point: 28.8 °C
• Appearance: /
• Density: 0.824 g/cm³
• Vapor Pressure: 10.3mmHg at 25°C
• Refractive Index: 1.432
• CAS DataBase Reference: 2,4-heptadienal,(E,Z)-2,4-heptadienal(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-heptadienal,(E,Z)-2,4-heptadienal(4313-02-4)
• EPA Substance Registry System: 2,4-heptadienal,(E,Z)-2,4-heptadienal(4313-02-4)

Safety Data

• Hazardous Substances Data: 4313-02-4(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2,4-Heptadienal,(E,Z)-2,4-heptadienal is used as a flavor and fragrance compound for its aromatic properties. The (E)-2,4-heptadienal isomer contributes a fruity, floral, and green leafy note, while the (Z)-2,4-heptadienal isomer adds a pungent and grassy odor to the final product. These compounds are important in creating realistic and appealing scents in various applications.
Used in Food Industry:
2,4-Heptadienal,(E,Z)-2,4-heptadienal is used as a flavor enhancer in the food industry. The (E)-2,4-heptadienal isomer provides a fruity, floral, and green leafy taste, while the (Z)-2,4-heptadienal isomer offers a more pungent and grassy flavor. These compounds are used to enhance the natural taste of fruits and vegetables, as well as to create new and unique flavor profiles in food products.
Used in Perfumery:
2,4-Heptadienal,(E,Z)-2,4-heptadienal is used as a base note in perfumery. The (E)-2,4-heptadienal isomer contributes a fruity, floral, and green leafy scent, while the (Z)-2,4-heptadienal isomer provides a more pungent and grassy aroma. These compounds are used to create complex and long-lasting fragrances in perfumes and other scented products.

InChI:InChI=1/C7H10O/c1-2-3-4-5-6-7-8/h4-6H,2-3H2,1H3/b5-4+

Upstream product

• 1576-95-0 cis-2-penten-1-ol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 6107-37-5 ethylzinc bromide 
• 131947-32-5 (2E,4E)-1-Iodo-hepta-2,4-diene 
• 70979-88-3 (2E,4Z)-hepta-2,4-dien-1-ol 

Downstream Products

• 33580-05-1 1,3-trans,5-cis-octatriene 

Relevant articles and documents

Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms

α,β,γ,δ-Unsaturated aldehydes have gained increasing attention since 2,4-decadienal and 2,4,7-decatrienal were isolated from the diatom Thalassiosira rotula and characterized as cell antiproliferative metabolites. Structurally related α,β,γ,δ-unsaturated aldehydes were found in this alga as well as in other diatom species. We present a short and universal synthesis of this compound class along with a structure-activity study of the potential to inhibit sea urchin egg cleavage. Pd0- or CoII-mediated cross coupling of 5-iodo-penta-2,4-dienal with organo-zincates allows the fast and flexible synthesis of numerous aldehydes from this universal precursor. The stereochemistry of the double bond system of the precursor was preserved during the coupling. Bioassays showed that the polarity of the side chain is important for antiproliferative activity with 2,4-decadienal as the most active compound tested compared to the shorter-chain aliphatic homologues and to ω-oxo acids with conjugated double systems. In contrast, the double bond geometry has no influence on biological activity. The α,β-unsaturated 2E-decenal was also highly active, while activity diminished in the case of saturated aldehydes of similar chain length. 1-Decanol, 2-decanone and decanoic acid were not active.

Straightforward preparation of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal

A concise synthesis of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-1-ol was converted to ethyl-(2E,4Z)-2,4-heptadienoate by reaction with activated MnO2 and (carboethoxymethylene)triphenylphosphorane in the presence of benzoic acid as a catalyst. Ethyl-(2E,4Z)-2,4-hep-tadienoate was converted to (2E,4Z)-2,4-heptadien-1-ol with LiAlH4. The alcohol was partially oxidized to (2E,4Z)-2,4-heptadienal with MnO2. The title compounds are male-specific, antennally active volatile compounds from the Saltcedar leaf beetle, Diorhabda elongata Brulle (Coleoptera: Chrysomelidae) and have potential use in the biological control of the invasive weed saltcedar (Tamarix spp).

(2E)-4,4-dimethoxy-2-butenal in the synthesis of conjugated dienes and dienals

Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)-and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds

A Novel and General Route to 1-Iodo-2,4(E,E)-dienes via Pentadienyl Dithiocarbamate

The title compounds were prepared from pentadienyl dithiocarbamate via S-methylathion and by use of the iodide an unsymmetric, all-trans-conjugated pentaene was synthesized.

HIGHLY STEREOCONTOROLLED SYNTHESIS OF (2E,4Z)-DIENIC ESTERS BY ALUMINA CATALYST

Thermal treatment of β-allenic esters (2) with alumina catalyst in aprotic solvents yielded (2E,4Z)-dienoic esters (3) in 57-87percent yields with 91-100percent stereoselectivity.