Allylbenzene is a colorless flammable oil. Essential oils derived from allylbenzene are collectively known as allylbenzenes. Many allylbenzenes have well documented medicinal actions. For example, eugenol is commonly used for dental pain relief. The medicinal actions of allylbenzene itself are poorly documented.

Allylbenzene and propenylbenzene are nearly identical chemically, with the only difference being the location of the double carbon bond on the tail.

propenylbenzene allylbenzene
propenylbenzene.png allylbenzene.png


Rats metabolize allylbenzene to 1'-hydroxyallylbenzene which is speculated to able to rearrange to yield cinnamyl alcohol which is further metabolized. This rearrange mechanism is proposed by Ozwald and Peele to account for the appearance of "propenyl type" metabolites from allylbenzene compounds.[1] However, there is no evidence to support this theory of rearrangement. It's possible that cinnamyl alcohol is a direct metabolite of allylbenzene, and doesn't form from 1'-hydroxyallylbenzene.

Allylbenzene and 1'-hydroxyallylbenzene yield basic ninhydrin-positive metabolites.[1]

It is proposed by Ozwald and Peele, that allylbenzene is first oxidized on the benzylic carbon to form 1'-hydroxyallylbenzene, which is further oxidized to form phenyl vinyl ketone, which condenses with the secondary amines piperidine and dimethylamine to form tertiary aminopropiophenones (Mannich bases).[1] It's important to note that this theory has not been proven to occur in humans.

Chemical Properties

CAS No: 300-57-2
PubChem CID: 9309
Molecular Weight: 118.1757 [g/mol]
Molecular Formula: C9H10
XLogP3: 3.2
Melting point: -40 C
Boiling point: 156 C
IUPAC Name: prop-2-enylbenzene
InChI: InChI=1S/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-5,7-8H,1,6H2
Canonical SMILES: C=CCC1=CC=CC=C1

Metabolism of naturally occurring propenylbenzene derivatives. III. Allylbenzene, propenyl benzene, and related metabolic products. Peele JD Jr, Oswald EO. PMID: 870079
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