<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:31 UTC</creation_date>
  <update_date>2019-11-26 03:10:52 UTC</update_date>
  <accession>FDB014885</accession>
  <name>Picrocrocin</name>
  <description>Isolated from saffron (stamens of Crocus sativus). Food colour and flavouring ingredient

During the drying process picrocrocin liberates the aglycone (HTCC, C10H16O2) due to the action of the enzyme glucosidase. The aglycone is then transformed to safranal by dehydration. Picrocrocin is a degradation product of the carotenoid zeaxanthin.[citation needed]; Picrocrocin is a glycoside formed from glucose and safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste and is the chemical most responsible for the taste of saffron.; ; It is believed that picrocrocin is a degradation product of the carotenoid zeaxanthin .; Picrocrocin is a monoterpene glycoside precursor of safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste and is the chemical most responsible for the taste of saffron.</description>
  <synonyms>
    <synonym>Picrocrocin</synonym>
    <synonym>Saffronbitter</synonym>
    <synonym>Safranbitter</synonym>
  </synonyms>
  <chemical_formula>C16H26O7</chemical_formula>
  <average_molecular_weight>330.3734</average_molecular_weight>
  <monisotopic_moleculate_weight>330.167853186</monisotopic_moleculate_weight>
  <iupac_name>2,6,6-trimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde</iupac_name>
  <traditional_iupac>2,6,6-trimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde</traditional_iupac>
  <cas_registry_number>138-55-6</cas_registry_number>
  <smiles>CC1=C(C=O)C(C)(C)CC(C1)OC1OC(CO)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3</inchi>
  <inchikey>WMHJCSAICLADIN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</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>Aldehyde</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a glucoside</external_descriptor>
      <external_descriptor>an apocarotenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.04e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 156°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.75</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>2,6,6-trimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>330.3734</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>330.167853186</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC1=C(C=O)C(C)(C)CC(C1)OC1OC(CO)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H26O7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>WMHJCSAICLADIN-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>116.45</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>81.18</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>34.26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</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::MsMs</type>
      <spectrum_id>75345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134975</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB05796</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>Herbs and Spices</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Saffron</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Crocus sativus</name_scientific>
      <ncbi_taxonomy_id>82528</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>bitter</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
