Benzyl cinnamate

Basic Info

Common NameBenzyl cinnamate(F02869)
2D Structure
Description

Benzyl cinnamate is included in the Chemical Group (CG) 23 for flavouring substances. The flavours included in this group have all been detected in plant materials, fruits or in processed foods; however, the reports of their distribution vary greatly. Some are widely distributed (e.g. benzyl alcohol, benzaldehyde, vanillin, salicylaldehyde, benzoic acid, benzyl acetate, methyl benzoate, ethyl salicylate, and methyl salicylate) while for others there appears only a single reference to their occurrence in food (e.g. benzyl phenylacetate and isobutyl salicylate).

FRCD IDF02869
CAS Number103-41-3
PubChem CID5273469
FormulaC16H14O2
IUPAC Name

benzyl (E)-3-phenylprop-2-enoate

InChI Key

NGHOLYJTSCBCGC-VAWYXSNFSA-N

InChI

InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11+

Canonical SMILES

C1=CC=C(C=C1)COC(=O)C=CC2=CC=CC=C2

Isomeric SMILES

C1=CC=C(C=C1)COC(=O)/C=C/C2=CC=CC=C2

Synonyms
        
            BENZYL CINNAMATE
        
            Cinnamein
        
            103-41-3
        
            Benzylcinnamoate
        
            Benzyl 3-phenylpropenoate
        
            Benzylcinnamate
        
            Benzyl-3-phenylpropenoate
        
            Benzyl gamma-phenylacrylate
        
            Cinnamic acid, benzyl ester
        
            UNII-V67O3RO97U
Classifies
                

                  
                    Predicted: Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
SubclassCinnamic acid esters
Intermediate Tree NodesNot available
Direct ParentCinnamic acid esters
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsCinnamic acid ester - Benzyloxycarbonyl - Styrene - Fatty acid ester - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Carbonyl group - Organic oxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Properties

Property NameProperty Value
Molecular Weight238.286
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Complexity271
Monoisotopic Mass238.099
Exact Mass238.099
XLogP3.8
Formal Charge0
Heavy Atom Count18
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9837
Human Intestinal AbsorptionHIA+0.9971
Caco-2 PermeabilityCaco2+0.8763
P-glycoprotein SubstrateNon-substrate0.7742
P-glycoprotein InhibitorNon-inhibitor0.8539
Non-inhibitor0.7598
Renal Organic Cation TransporterNon-inhibitor0.7642
Distribution
Subcellular localizationMitochondria0.5764
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7861
CYP450 2D6 SubstrateNon-substrate0.9397
CYP450 3A4 SubstrateNon-substrate0.7457
CYP450 1A2 InhibitorInhibitor0.8862
CYP450 2C9 InhibitorNon-inhibitor0.7181
CYP450 2D6 InhibitorNon-inhibitor0.9271
CYP450 2C19 InhibitorInhibitor0.6044
CYP450 3A4 InhibitorNon-inhibitor0.9594
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.7876
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9456
Non-inhibitor0.9568
AMES ToxicityNon AMES toxic0.8441
CarcinogensNon-carcinogens0.5979
Fish ToxicityHigh FHMT0.9756
Tetrahymena Pyriformis ToxicityHigh TPT0.9998
Honey Bee ToxicityHigh HBT0.7900
BiodegradationReady biodegradable0.6130
Acute Oral ToxicityIII0.8495
Carcinogenicity (Three-class)Non-required0.6683
Model Value Unit
Absorption
Aqueous solubility-3.8228LogS
Caco-2 Permeability1.7597LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8021LD50, mol/kg
Fish Toxicity-0.3963pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.8084pIGC50, ug/L

References

TitleJournalDatePubmed ID
Propolis specimens from different locations of central Italy: chemical profiling and gas chromatography-mass spectrometry (GC-MS) quantitative analysis of the allergenic esters benzyl cinnamate and benzyl salicylate.J Agric Food Chem2011 Jan 1221126078

Targets

Target Details

Peroxisome proliferator-activated receptor gamma

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]