<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:52 UTC</creation_date>
  <update_date>2019-11-26 02:56:03 UTC</update_date>
  <accession>FDB001176</accession>
  <name>Isodulcitol</name>
  <description>Constituent of many glycosides in plants. Quercetin (main constituent of lemon flavin) and Naringin (from grapefruit-canning wastes) have been used as sources

A methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides.; Rhamnose (Rham) is a naturally-occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally-occurring sugars are in D-form. Exceptions are the methyl pentoses L-fucose and L-rhamnose and the pentose L-arabinose.; Rhamnose is a component of the outer cell membrane of acid-fast bacteria in the Mycobacterium genus, which includes the organsism that causes tuberculosis. Isodulcitol is found in many foods, some of which are tarragon, sweet basil, garden cress, and coconut.</description>
  <synonyms>
    <synonym>6-Deoxy-L-mannopyranose</synonym>
    <synonym>6-Deoxy-L-mannose</synonym>
    <synonym>6-Deoxy-L(+)-mannose</synonym>
    <synonym>6-Deoxy-mannose</synonym>
    <synonym>6-Deoxyhexopyranose</synonym>
    <synonym>6-Deoxyhexose</synonym>
    <synonym>6-Deoxymannose</synonym>
    <synonym>Isodulcit</synonym>
    <synonym>Isodulcitol</synonym>
    <synonym>L-(+)-Rhamnose</synonym>
    <synonym>L-(+)-Rhamnose 1-hydrate</synonym>
    <synonym>L-(+)-Rhamnose hydrate = 6-deoxy-L-mannose monohydrate</synonym>
    <synonym>L-(+)-Rhamnose monohydrate</synonym>
    <synonym>L-Rha</synonym>
    <synonym>L-Rhamnopyranose</synonym>
    <synonym>L-Rhamnose</synonym>
    <synonym>L-Rhamnose for biochemistry</synonym>
    <synonym>L-Rhamnose monohydrate</synonym>
    <synonym>L(+)-Rhamnose</synonym>
    <synonym>L(+)-Rhamnose monohydrate</synonym>
    <synonym>Locaose</synonym>
    <synonym>Lokaose</synonym>
    <synonym>Mono(6-deoxy-b-L-mannopyranosyl) ester</synonym>
    <synonym>Mono(6-deoxy-beta-L-mannopyranosyl) ester</synonym>
    <synonym>P-(6-Deoxy-b-L-mannopyranosyl) ester</synonym>
    <synonym>P-(6-Deoxy-beta-L-mannopyranosyl) ester</synonym>
    <synonym>Rhamnopyranose</synonym>
    <synonym>Rhamnosemonohydrate</synonym>
    <synonym>UDP-Rhamnose</synonym>
    <synonym>Uridine 5-pyroate</synonym>
    <synonym>Uridine diate rhamnose</synonym>
  </synonyms>
  <chemical_formula>C18H36O15</chemical_formula>
  <average_molecular_weight>492.4694</average_molecular_weight>
  <monisotopic_moleculate_weight>492.205420482</monisotopic_moleculate_weight>
  <iupac_name>2,3,4,5-tetrahydroxyhexanal; 5-(1-hydroxyethyl)oxolane-2,3,4-triol; 6-methyloxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>5-(1-hydroxyethyl)oxolane-2,3,4-triol; 6-methyloxane-2,3,4,5-tetrol; L(+)-rhamnose</traditional_iupac>
  <cas_registry_number>3615-41-6</cas_registry_number>
  <smiles>CC(O)C(O)C(O)C(O)C=O.CC(O)C1OC(O)C(O)C1O.CC1OC(O)C(O)C(O)C1O</smiles>
  <inchi>InChI=1S/3C6H12O5/c1-2(7)5-3(8)4(9)6(10)11-5;1-2-3(7)4(8)5(9)6(10)11-2;1-3(8)5(10)6(11)4(9)2-7/h2*2-10H,1H3;2-6,8-11H,1H3</inchi>
  <inchikey>LSOFIIQFGYOXNZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.</description>
    <direct_parent>Medium-chain aldehydes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <molecular_framework/>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain aldehyde</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.27e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 93-95° (hydrate)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>12.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2,3,4,5-tetrahydroxyhexanal; 5-(1-hydroxyethyl)oxolane-2,3,4-triol; 6-methyloxane-2,3,4,5-tetrol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>492.4694</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>492.205420482</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(O)C(O)C(O)C(O)C=O.CC(O)C1OC(O)C(O)C1O.CC1OC(O)C(O)C(O)C1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H36O15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/3C6H12O5/c1-2(7)5-3(8)4(9)6(10)11-5;1-2-3(7)4(8)5(9)6(10)11-2;1-3(8)5(10)6(11)4(9)2-7/h2*2-10H,1H3;2-6,8-11H,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>LSOFIIQFGYOXNZ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>97.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>35.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>15.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</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>
  </spectra>
  <hmdb_id>HMDB00849</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>16055</chebi_id>
  <biocyc_id/>
  <het_id>1CB8</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce317a8460&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a82a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a80f0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7e70&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7cb8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7b00&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7948&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7740&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7588&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7380&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a7178&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a6f98&gt;</reference>
    <reference>#&lt;Reference:0x000055ce317a6de0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Arabica coffee</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Coffea arabica</name_scientific>
      <ncbi_taxonomy_id>13443</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Asparagus</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Asparagus officinalis</name_scientific>
      <ncbi_taxonomy_id>4686</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Capers</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capparis spinosa</name_scientific>
      <ncbi_taxonomy_id>65558</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Caraway</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carum carvi</name_scientific>
      <ncbi_taxonomy_id>48032</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota ssp. sativus</name_scientific>
      <ncbi_taxonomy_id>79200</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cashew nut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anacardium occidentale</name_scientific>
      <ncbi_taxonomy_id>171929</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cocoa bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Theobroma cacao</name_scientific>
      <ncbi_taxonomy_id>3641</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Coconut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cocos nucifera</name_scientific>
      <ncbi_taxonomy_id>13894</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common buckwheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Fagopyrum esculentum</name_scientific>
      <ncbi_taxonomy_id>3617</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Date</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phoenix dactylifera</name_scientific>
      <ncbi_taxonomy_id>42345</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European plum</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus domestica</name_scientific>
      <ncbi_taxonomy_id>3758</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ficus carica</name_scientific>
      <ncbi_taxonomy_id>3494</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Flaxseed</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Linum usitatissimum</name_scientific>
      <ncbi_taxonomy_id>4006</ncbi_taxonomy_id>
      <average_value>1149.5</average_value>
      <max_value>1149.5</max_value>
      <min_value>1149.5</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>French plantain</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Musa X paradisiaca</name_scientific>
      <ncbi_taxonomy_id>89151</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden cress</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepidium sativum</name_scientific>
      <ncbi_taxonomy_id>33125</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden onion</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium cepa</name_scientific>
      <ncbi_taxonomy_id>4679</ncbi_taxonomy_id>
    </food>
    <food>
      <name>German camomile</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Matricaria recutita</name_scientific>
      <ncbi_taxonomy_id>127986</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Grape wine</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.0</average_value>
      <max_value>0.0</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </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>Horseradish tree</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Moringa oleifera</name_scientific>
      <ncbi_taxonomy_id>3735</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mung bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Vigna radiata</name_scientific>
      <ncbi_taxonomy_id>157791</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Okra</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Abelmoschus esculentus</name_scientific>
      <ncbi_taxonomy_id>455045</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Olive</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Olea europaea</name_scientific>
      <ncbi_taxonomy_id>4146</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Peach</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Prunus persica</name_scientific>
      <ncbi_taxonomy_id>3760</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum tuberosum</name_scientific>
      <ncbi_taxonomy_id>4113</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Roselle</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hibiscus sabdariffa</name_scientific>
      <ncbi_taxonomy_id>183260</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sea-buckthornberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hippophae rhamnoides</name_scientific>
      <ncbi_taxonomy_id>193516</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soft-necked garlic</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium sativum L. var. sativum</name_scientific>
      <ncbi_taxonomy_id>4682</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sunflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Helianthus annuus</name_scientific>
      <ncbi_taxonomy_id>4232</ncbi_taxonomy_id>
    </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>
    </food>
    <food>
      <name>Tarragon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Artemisia dracunculus</name_scientific>
      <ncbi_taxonomy_id>72341</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota</name_scientific>
      <ncbi_taxonomy_id>4039</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>odorless</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
