<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:56 UTC</creation_date>
  <update_date>2019-11-26 03:05:55 UTC</update_date>
  <accession>FDB012001</accession>
  <name>Methyl cinnamate</name>
  <description>Occurs in essential oils e.g. from Ocimum and Alpinia subspecies Also present in various fruits, e.g. guava, feijoa, strawberry. Flavouring agent

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 found in many foods, some of which are chinese cinnamon, fruits, herbs and spices, and sweet basil.</description>
  <synonyms>
    <synonym>2-propenoic acid, 3-phenyl-, methyl ester, (2E)-</synonym>
    <synonym>2-Propenoic acid, 3-phenyl-, methyl ester, (E)-</synonym>
    <synonym>3-Phenyl-methyl ester(2e)-2-propenoic acid</synonym>
    <synonym>3-Phenyl-methyl ester(e)-2-propenoic acid</synonym>
    <synonym>Cinnamic acid, methyl ester, (e)-</synonym>
    <synonym>Cinnamic acid,methyl ester (trans)</synonym>
    <synonym>FEMA 2698</synonym>
    <synonym>Methyl (2E)-3-phenyl-2-propenoate</synonym>
    <synonym>Methyl (2E)-3-phenylacrylate</synonym>
    <synonym>Methyl (e)-cinnamate</synonym>
    <synonym>Methyl cinnamate, (e)</synonym>
    <synonym>Methyl ester(e)-cinnamic acid</synonym>
    <synonym>Methyl trans-cinnamate</synonym>
    <synonym>Trans-methyl cinnamate</synonym>
  </synonyms>
  <chemical_formula>C10H10O2</chemical_formula>
  <average_molecular_weight>162.1852</average_molecular_weight>
  <monisotopic_moleculate_weight>162.068079564</monisotopic_moleculate_weight>
  <iupac_name>methyl (2Z)-3-phenylprop-2-enoate</iupac_name>
  <traditional_iupac>methyl (2Z)-3-phenylprop-2-enoate</traditional_iupac>
  <cas_registry_number>103-26-4</cas_registry_number>
  <smiles>COC(=O)\C=C/C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-</inchi>
  <inchikey>CCRCUPLGCSFEDV-FPLPWBNLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.</description>
    <direct_parent>Cinnamic acid esters</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Cinnamic acid esters</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl esters</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cinnamic acid ester</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl ester</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.20e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 36°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>2.52</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-6.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>methyl (2Z)-3-phenylprop-2-enoate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>162.1852</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>162.068079564</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC(=O)\C=C/C1=CC=CC=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H10O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>CCRCUPLGCSFEDV-FPLPWBNLSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>26.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>47.83</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>17.51</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>156968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2807114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2807115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2807116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2898291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2898292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2898293</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB33833</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32c8c5e8&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Ceylon cinnamon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cinnamomum verum</name_scientific>
      <ncbi_taxonomy_id>128608</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chinese cinnamon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cinnamomum aromaticum</name_scientific>
      <ncbi_taxonomy_id>119260</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cumin</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cuminum cyminum</name_scientific>
      <ncbi_taxonomy_id>52462</ncbi_taxonomy_id>
      <average_value>13.8</average_value>
      <max_value>13.8</max_value>
      <min_value>13.8</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Fruits</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Guava</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Psidium guajava</name_scientific>
      <ncbi_taxonomy_id>120290</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Pepper (Spice)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Piper nigrum</name_scientific>
      <ncbi_taxonomy_id>13216</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Peppermint</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Mentha X piperita</name_scientific>
      <ncbi_taxonomy_id>34256</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Safflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carthamus tinctorius</name_scientific>
      <ncbi_taxonomy_id>4222</ncbi_taxonomy_id>
      <average_value>0.008</average_value>
      <max_value>0.008</max_value>
      <min_value>0.008</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</ncbi_taxonomy_id>
      <average_value>140.05</average_value>
      <max_value>140.05</max_value>
      <min_value>140.05</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Sweet bay</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Laurus nobilis</name_scientific>
      <ncbi_taxonomy_id>85223</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>balsam</name>
    </flavor>
    <flavor>
      <name>cherry</name>
    </flavor>
    <flavor>
      <name>cinnamon</name>
    </flavor>
    <flavor>
      <name>strawberry</name>
    </flavor>
    <flavor>
      <name>sweet</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Insecticide</name>
      <id>1040</id>
      <definition>Strictly, a substance intended to kill members of the class Insecta.  In common usage, any substance used for preventing, destroying, repelling or controlling insects.</definition>
    </health_effect>
    <health_effect>
      <name>Name</name>
      <id>936</id>
      <definition>A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.</definition>
    </health_effect>
    <health_effect>
      <name>Nematicide</name>
      <id>1141</id>
      <definition>A substance used to destroy pests of the phylum Nematoda (roundworms).</definition>
    </health_effect>
    <health_effect>
      <name>Perfumery</name>
      <id>1206</id>
      <definition>A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.</definition>
    </health_effect>
    <health_effect>
      <name>Pesticide</name>
      <id>1210</id>
      <definition>Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.</definition>
    </health_effect>
  </health_effects>
</compound>
