<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:00 UTC</creation_date>
  <update_date>2025-11-18 23:00:59 UTC</update_date>
  <accession>FDB006135</accession>
  <name>1-Menthyl-beta-D-glucoside</name>
  <description>1-menthyl-beta-d-glucoside, also known as (-)-menthyl o-β-glucopyranoside, is a member of the class of compounds known as terpene glycosides. Terpene glycosides are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Thus, 1-menthyl-beta-d-glucoside is considered to be an isoprenoid lipid molecule. 1-menthyl-beta-d-glucoside is soluble (in water) and a very weakly acidic compound (based on its pKa). 1-menthyl-beta-d-glucoside can be found in peppermint, which makes 1-menthyl-beta-d-glucoside a potential biomarker for the consumption of this food product. </description>
  <synonyms>
  </synonyms>
  <chemical_formula>C16H30O6</chemical_formula>
  <average_molecular_weight>318.4058</average_molecular_weight>
  <monisotopic_moleculate_weight>318.204238692</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>(-)-menthyl β-D-glucoside</traditional_iupac>
  <cas_registry_number>52528-10-6</cas_registry_number>
  <smiles>CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C16H30O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h8-20H,4-7H2,1-3H3/t9-,10+,11-,12-,13-,14+,15-,16-/m1/s1</inchi>
  <inchikey>GZSDZJZIZBGBON-NZZARTGWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.</description>
    <direct_parent>Terpene glycosides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Terpene glycosides</sub_class>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Menthane monoterpenoids</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monoterpenoid</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>P-menthane monoterpenoid</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Terpene glycoside</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>Menthane monoterpenoids</external_descriptor>
      <external_descriptor>beta-D-glucoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.22e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.89</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>12.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}oxane-3,4,5-triol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>318.4058</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>318.204238692</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H30O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H30O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h8-20H,4-7H2,1-3H3/t9-,10+,11-,12-,13-,14+,15-,16-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>GZSDZJZIZBGBON-NZZARTGWSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>99.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>79.86</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>34.44</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</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>18249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>42819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>168080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>64887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>64888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>64889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2663230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2663231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2663232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3014878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3014879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3014880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>112998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>112999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>113017</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0032368</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <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>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
