4313-03-5

Basic information

• Product Name: trans,trans-2,4-Heptadienal
• Synonyms: TRANS-2,TRANS-4-HEPTADIEN-1-AL;TRANS-2-TRANS-4-HEPTADIENAL;TRANS,TRANS-2,4-HEPTADIEN-1-AL;TRANS,TRANS-2,4-HEPTADIENAL;(2E,4E)-2,4-Heptadienal;(E)-2,(E)-4- heptadienal;(E,E)-2,4-Heptadien-1-al;(E,E)-2,4-Heptadienal
• CAS NO: 4313-03-5
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.15
• EINECS: 224-328-0
• Product Categories: API intermediates;aldehyde Flavor;Aldehydes;C7;Carbonyl Compounds;C7Volatiles/ Semivolatiles;E-L;Alpha Sort
• Mol File: 4313-03-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 84.5 °C
• Boiling Point: 84-84.5 °C(lit.)
• Flash Point: 150 °F
• Appearance: /
• Density: 0.881 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.04mmHg at 25°C
• Refractive Index: n20/D 1.534(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility: INSOLUBLE
• BRN: 1699244
• CAS DataBase Reference: trans,trans-2,4-Heptadienal(CAS DataBase Reference)
• NIST Chemistry Reference: trans,trans-2,4-Heptadienal(4313-03-5)
• EPA Substance Registry System: trans,trans-2,4-Heptadienal(4313-03-5)

Safety Data

• Hazard Codes: T,Xi
• Statements: 22-24-38
• Safety Statements: 36/37-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 10-23
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4313-03-5(Hazardous Substances Data)

Usage

Description

trans,trans-2,4-Heptadienal is an organic compound that plays a crucial role in preventing the development of off-flavors in auto-oxidizing fats and oils. It can be synthesized through a series of chemical reactions, including reduction with LiAlH4 of the dienoic acid prepared by the Doebner synthesis, followed by oxidation with MnO2 of the resulting dienol to the corresponding dienal. The method of Marshall and Whiting is also used for its preparation.

Uses

Used in Food Industry:
trans,trans-2,4-Heptadienal is used as a flavor enhancer and preservative for fats and oils in the food industry. It helps maintain the quality and taste of these products by retarding or preventing the development of off-flavors caused by auto-oxidation. This ensures a longer shelf life and improved consumer experience for food products containing fats and oils.

Synthesis

By reduction with LiAlH4 of the dienoic acid prepared by the Doebner synthesis, followed by oxidation with MnO2 of the resulting dienol to the corresponding dienol; by the method of Marshall and Whiting.

InChI:InChI=1/C7H10O/c1-2-3-4-5-6-7-8/h3-7H,2H2,1H3/b4-3-,6-5-

Upstream product

• 65518-46-9 (2E,4E)-hepta-2,4-dienoic acid 
• 123-38-6 propionaldehyde 
• 18937-78-5 methyl 2-heptynoate 
• 693-02-7 hex-1-yne 
• 56424-97-6 (2E,4E)-methyl hepta-2,4-dienoate 
• 189068-20-0 (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 
• 1576-87-0 trans-2-pentenal 
• 81981-06-8 Hepta-3,4-dienoic acid methyl ester 
• 39924-42-0 (2E,4Z)-hepta-2,4-dienoic acid methyl ester 
• 102299-04-7 cis-4-<<(4-methoxyphenyl)methoxy>methyl>-2-cyclobutene-1-methanol 
• 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 

Downstream Products

• 57018-53-8 (E,E,E)-2,4,6-nonatrienal 
• 84000-59-9 Fecapentaene-12 
• 84000-59-9 3-<(1E,3E,7E,9E)-1,3,5,7,9-dodecapentaenyloxy>-1,2-propanediol 
• 89229-67-4 (2E,4E)-hepta-2,4-dien-1-yltriphenyl phosphonium bromide 
• 134824-33-2 2,3,6-Trimethyl-5-(2,4-heptadienyl)-1,4-benzoquinone 
• 134824-29-6 2,3-Dimethyl-5-(2,4-heptadienyl)-1,4-benzoquinone 
• 120696-90-4 (3E,5Z)-2-benzyl-3,5-heptadienal dimethylhydrazone 

Relevant articles and documents

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Iron-catalyzed aerobic oxidation of allylic alcohols: The issue of C=C bond isomerization

An aerobic oxidation of allylic alcohols using Fe(NO3) 3·9H2O/TEMPO/NaCl as catalysts under atmospheric pressure of oxygen at room temperature was developed. This eco-friendly and mild protocol provides a convenient pathway to the synthesis of stereodefined α,β-unsaturated enals or enones with the retention of the C-C double-bond configuration.

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.