methyl cinnamate (CHEBI:6857)

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ChEBI Name	methyl cinnamate

ChEBI ID	CHEBI:6857

Definition	A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	eMolecules:30520770

Download	Molfile XML SDF

Wikipedia	License
Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2–6% fresh weight yield in the leaf and twigs. Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry. It is known to attract males of various orchid bees, such as Aglae caerulea.
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Formula

C10H10O2

Net Charge

Average Mass

162.188

Monoisotopic Mass

162.06808

InChI

InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3

InChIKey

CCRCUPLGCSFEDV-UHFFFAOYSA-N

SMILES

[H]C(=CC1=CC=CC=C1)C(=O)OC

Metabolite of Species	Details
Ocimum (NCBI:txid39173)	See: DOI
Tricholoma matsutake (NCBI:txid40145)	Found in fruit body (BTO:0000487). See: PubMed
Zanthoxylum armatum (NCBI:txid67938)	See: PubMed

Roles Classification
Biological Role(s):	flavouring agent A food additive that is used to added improve the taste or odour of a food. insect attractant A chemical that attracts insects. volatile oil component Any plant metabolite that is found naturally as a component of a volatile oil.

Application(s):	flavouring agent A food additive that is used to added improve the taste or odour of a food. fragrance A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. anti-inflammatory agent Any compound that has anti-inflammatory effects.

ChEBI Ontology
Outgoing	methyl cinnamate (CHEBI:6857) has role anti-inflammatory agent (CHEBI:67079) methyl cinnamate (CHEBI:6857) has role flavouring agent (CHEBI:35617) methyl cinnamate (CHEBI:6857) has role fragrance (CHEBI:48318) methyl cinnamate (CHEBI:6857) has role insect attractant (CHEBI:24850) methyl cinnamate (CHEBI:6857) has role volatile oil component (CHEBI:27311) methyl cinnamate (CHEBI:6857) is a alkyl cinnamate (CHEBI:17958) methyl cinnamate (CHEBI:6857) is a methyl ester (CHEBI:25248)

Incoming	methyl cis-cinnamate (CHEBI:194139) is a methyl cinnamate (CHEBI:6857) methyl trans-cinnamate (CHEBI:194138) is a methyl cinnamate (CHEBI:6857)

IUPAC Name

methyl 3-phenylprop-2-enoate

Synonyms	Sources
3-phenyl-2-propenoic acid methyl ester	ChEBI
3-phenylacrylic acid methyl ester	ChEBI
cinnamic acid methyl ester	ChemIDplus
cinnamic acid, methyl ester	ChemIDplus
FEMA 2698	ChemIDplus
methyl 3-phenyl-2-propenoate	ChemIDplus
methyl 3-phenylacrylate	ChemIDplus
methyl 3-phenylpropenoate	ChemIDplus
methyl cinnamylate	ChemIDplus
methyl ester of cinnamic acid	NIST Chemistry WebBook

Citations

Last Modified

29 November 2022