<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:29 UTC</creation_date>
  <update_date>2025-11-19 00:49:59 UTC</update_date>
  <accession>FDB014827</accession>
  <name>Cinnzeylanine</name>
  <description>Constituent of Cinnamomum zeylanicum (cinnamon) and Cinnamomum cassia (Chinese cinnamon). Cinnzeylanine is found in chinese cinnamon, ceylon cinnamon, and herbs and spices.</description>
  <synonyms>
    <synonym>Cinnzeylanine</synonym>
    <synonym>Ryanodol; 3-Deoxy, 10-Ac</synonym>
  </synonyms>
  <chemical_formula>C22H34O8</chemical_formula>
  <average_molecular_weight>426.5006</average_molecular_weight>
  <monisotopic_moleculate_weight>426.225368064</monisotopic_moleculate_weight>
  <iupac_name>6,9,11,13,14-pentahydroxy-3,7,10-trimethyl-11-(propan-2-yl)-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-2-yl acetate</iupac_name>
  <traditional_iupac>6,9,11,13,14-pentahydroxy-11-isopropyl-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-2-yl acetate</traditional_iupac>
  <cas_registry_number>62203-47-8</cas_registry_number>
  <smiles>CC(C)C1(O)CC2(O)C3(C)CC4(O)OC5(C(OC(C)=O)C(C)CCC35O)C2(O)C14C</smiles>
  <inchi>InChI=1S/C22H34O8/c1-11(2)17(24)10-19(26)15(5)9-20(27)16(17,6)22(19,28)21(30-20)14(29-13(4)23)12(3)7-8-18(15,21)25/h11-12,14,24-28H,7-10H2,1-6H3</inchi>
  <inchikey>DFYFOAFKHRTQLA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.</description>
    <direct_parent>Diterpenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Oxepanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Oxepane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Ryanodane diterpenoid</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.36e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 265-267°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>6,9,11,13,14-pentahydroxy-3,7,10-trimethyl-11-(propan-2-yl)-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-2-yl acetate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>426.5006</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>426.225368064</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)C1(O)CC2(O)C3(C)CC4(O)OC5(C(OC(C)=O)C(C)CCC35O)C2(O)C14C</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C22H34O8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C22H34O8/c1-11(2)17(24)10-19(26)15(5)9-20(27)16(17,6)22(19,28)21(30-20)14(29-13(4)23)12(3)7-8-18(15,21)25/h11-12,14,24-28H,7-10H2,1-6H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>DFYFOAFKHRTQLA-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>136.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>102.66</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>43.73</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>5</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>26501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>133758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>141492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>133177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2448770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2448771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2448772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2486649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2486650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2486651</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB36011</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:0x000055ce3334e728&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>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
