(2E,4E)-Cinnamylideneacetic acid

Name: (2E,4E)-Cinnamylideneacetic acid
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CAS No. 28010-12-0
Cat. No. CS-0166761
Molecule weight174.20
Purity≥96%
MDL No.None

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(2E,4E)-Cinnamylideneacetic acid|CS-0166761

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General Information

CAS No. 28010-12-0
Cat. No. CS-0166761
Purity ≥96%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₀O₂
Molecular Weight 174.20
Synonym(s) (2E,4E)-Cinnamalacetic acid; (E,E)-Cinnamylideneacetic Acid
SMILES O=C(O)/C=C/C=C/C1=CC=CC=C1

Description

This conjugated diene acid features a rigid, planar structure enabling efficient π-electron delocalization. The (2E,4E)-stereochemistry enhances geometric stability and facilitates controlled Michael additions. Its electrophilic β-carbon supports nucleophilic functionalization in synthetic transformations.

Application

(2E,4E)-Cinnamylideneacetic acid serves as a versatile dienophile in Diels-Alder reactions and functions as a key building block for conjugated enone systems. Its defined (2E,4E) stereochemistry ensures reproducible cycloaddition outcomes, while the acetic acid moiety enables direct derivatization or salt formation for improved solubility and purification. The compound exhibits good bench stability and is compatible with standard synthetic workflows, facilitating access to complex heterocyclic scaffolds and natural product analogs.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 37.3
LogP 2.3406
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Olefins

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(2E,4E)-Cinnamylideneacetic acid

CAS No. 28010-12-0

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