<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:11:15 UTC</creation_date>
  <update_date>2026-09-18 18:06:28 UTC</update_date>
  <accession>FDB014420</accession>
  <name>Crocetin</name>
  <description>Crocetin is a natural carotenoid dicarboxylic acid that is found in the crocus flower and Gardenia jasminoides (fruits). </description>
  <synonyms>
    <synonym>2,6,11,15-Tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioic acid</synonym>
    <synonym>8,8'-Diapo-8,8'-carotenedioic acid</synonym>
    <synonym>a-Crocetin</synonym>
    <synonym>Gardenidin?</synonym>
    <synonym>Nyctanthin</synonym>
  </synonyms>
  <chemical_formula>C20H24O4</chemical_formula>
  <average_molecular_weight>328.4022</average_molecular_weight>
  <monisotopic_moleculate_weight>328.167459256</monisotopic_moleculate_weight>
  <iupac_name>(2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid</iupac_name>
  <traditional_iupac>(2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid</traditional_iupac>
  <cas_registry_number>27876-94-4</cas_registry_number>
  <smiles>C\C(\C=C\C=C(/C)C(O)=O)=C\C=C\C=C(/C)\C=C\C=C(\C)C(O)=O</smiles>
  <inchi>InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9-,16-10+,17-13+,18-14-</inchi>
  <inchikey>PANKHBYNKQNAHN-AWVVJTJESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.</description>
    <direct_parent>Acyclic 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 acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic diterpenoid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.58e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.65</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>328.4022</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>328.167459256</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C\C(\C=C\C=C(/C)C(O)=O)=C\C=C\C=C(/C)\C=C\C=C(\C)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H24O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9-,16-10+,17-13+,18-14-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>PANKHBYNKQNAHN-AWVVJTJESA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>74.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>103.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>38.37</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-2</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>24760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>44186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>159174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2382449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2382450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2382451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2579859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2579860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2579861</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB0035098</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>Cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea var. capitata</name_scientific>
      <ncbi_taxonomy_id>3716</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>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>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>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
    <food>
      <name>White cabbage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Brassica oleracea L. var. capitata L. f. alba DC.</name_scientific>
      <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>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Acetyl-coenzyme A synthetase, chloroplastic/glyoxysomal</name>
      <uniprot_id>B9DGD6</uniprot_id>
      <uniprot_name>ACS_ARATH</uniprot_name>
      <gene_name>ACS</gene_name>
    </enzyme>
    <enzyme>
      <name>ATP-binding cassette sub-family C member 2</name>
      <uniprot_id>Q92887</uniprot_id>
      <uniprot_name/>
      <gene_name>ABCC2</gene_name>
    </enzyme>
    <enzyme>
      <name>Cytochrome P450 2A6</name>
      <uniprot_id>P11509</uniprot_id>
      <uniprot_name>CP2A6_HUMAN</uniprot_name>
      <gene_name>CYP2A6</gene_name>
    </enzyme>
    <enzyme>
      <name>D-lactate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q86WU2</uniprot_id>
      <uniprot_name/>
      <gene_name>LDHD</gene_name>
    </enzyme>
    <enzyme>
      <name>Delta-aminolevulinic acid dehydratase, chloroplastic</name>
      <uniprot_id>P24493</uniprot_id>
      <uniprot_name>HEM2_SPIOL</uniprot_name>
      <gene_name>HEMB</gene_name>
    </enzyme>
    <enzyme>
      <name>DNA topoisomerase 2-binding protein 1</name>
      <uniprot_id>Q92547</uniprot_id>
      <uniprot_name>TOPB1_HUMAN</uniprot_name>
      <gene_name>TOPBP1</gene_name>
    </enzyme>
    <enzyme>
      <name>DNA-directed RNA polymerase I subunit RPA34</name>
      <uniprot_id>O15446</uniprot_id>
      <uniprot_name>RPA34_HUMAN</uniprot_name>
      <gene_name>POLR1G</gene_name>
    </enzyme>
    <enzyme>
      <name>Focal adhesion kinase 1</name>
      <uniprot_id>Q05397</uniprot_id>
      <uniprot_name/>
      <gene_name>PTK2</gene_name>
    </enzyme>
    <enzyme>
      <name>Glutathione peroxidase 1</name>
      <uniprot_id>P07203</uniprot_id>
      <uniprot_name/>
      <gene_name>GPX1</gene_name>
    </enzyme>
    <enzyme>
      <name>Inhibitor of nuclear factor kappa-B kinase subunit alpha</name>
      <uniprot_id>O15111</uniprot_id>
      <uniprot_name/>
      <gene_name>CHUK</gene_name>
    </enzyme>
    <enzyme>
      <name>Inhibitor of nuclear factor kappa-B kinase subunit beta</name>
      <uniprot_id>O14920</uniprot_id>
      <uniprot_name/>
      <gene_name>IKBKB</gene_name>
    </enzyme>
    <enzyme>
      <name>Isoflavone reductase homolog A622</name>
      <uniprot_id>P52579</uniprot_id>
      <uniprot_name>IFRH_TOBAC</uniprot_name>
      <gene_name>A622</gene_name>
    </enzyme>
    <enzyme>
      <name>NAD(P)H:quinone oxidoreductase</name>
      <uniprot_id>Q8H9D2</uniprot_id>
      <uniprot_name>NQR_SOLTU</uniprot_name>
      <gene_name/>
    </enzyme>
    <enzyme>
      <name>Nucleoside diphosphate phosphatase ENTPD5</name>
      <uniprot_id>O75356</uniprot_id>
      <uniprot_name>ENTP5_HUMAN</uniprot_name>
      <gene_name>ENTPD5</gene_name>
    </enzyme>
    <enzyme>
      <name>PTEN upstream open reading frame MP31</name>
      <uniprot_id>C0HLV8</uniprot_id>
      <uniprot_name>MP31_HUMAN</uniprot_name>
      <gene_name>MLDHR</gene_name>
    </enzyme>
    <enzyme>
      <name>RAC-alpha serine/threonine-protein kinase</name>
      <uniprot_id>P31749</uniprot_id>
      <uniprot_name/>
      <gene_name/>
    </enzyme>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Analgesic</name>
      <id>56</id>
      <definition>An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti carcinogenic</name>
      <id>161</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti convulsant</name>
      <id>204</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti depressant</name>
      <id>223</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti hyperlipidemic</name>
      <id>348</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti hypertensive</name>
      <id>352</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti hypoxic</name>
      <id>358</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti lipogenic</name>
      <id>405</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti nociceptive</name>
      <id>484</id>
      <definition>A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.</definition>
    </health_effect>
    <health_effect>
      <name>Anti peroxidative</name>
      <id>520</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti thrombotic</name>
      <id>650</id>
      <definition>Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-angiogenic</name>
      <id>115</id>
      <definition>An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-apoptotic</name>
      <id>125</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-atherosclerotic</name>
      <id>138</id>
      <definition>A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-cancer</name>
      <id>159</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-diabetic</name>
      <id>228</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-fatigue</name>
      <id>274</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-mutagenic</name>
      <id>451</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-oxidant</name>
      <id>502</id>
      <definition>A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.</definition>
    </health_effect>
    <health_effect>
      <name>Anti-proliferative</name>
      <id>548</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Anti-viral</name>
      <id>689</id>
      <definition>A substance that destroys or inhibits replication of viruses.</definition>
    </health_effect>
    <health_effect>
      <name>Antitumor</name>
      <id>672</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Antitumor promoter</name>
      <id>673</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Anxiolytic</name>
      <id>698</id>
      <definition>Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.</definition>
    </health_effect>
    <health_effect>
      <name>Bronchodilator</name>
      <id>736</id>
      <definition>An agent that causes an increase in the expansion of a bronchus or bronchial tubes.</definition>
    </health_effect>
    <health_effect>
      <name>Cancer preventive</name>
      <id>754</id>
      <definition>A substance that inhibits or prevents the proliferation of neoplasms.</definition>
    </health_effect>
    <health_effect>
      <name>Cardioprotective</name>
      <id>769</id>
      <definition>A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.</definition>
    </health_effect>
    <health_effect>
      <name>Choleretic</name>
      <id>801</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Colorant</name>
      <id>826</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Genotoxic</name>
      <id>950</id>
      <definition>A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.</definition>
    </health_effect>
    <health_effect>
      <name>Hepatoprotective</name>
      <id>981</id>
      <definition>Any compound that is able to prevent damage to the liver.</definition>
    </health_effect>
    <health_effect>
      <name>Hepatotoxic</name>
      <id>984</id>
      <definition>A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.</definition>
    </health_effect>
    <health_effect>
      <name>Hypocholesterolemic</name>
      <id>1016</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Hypolipidemic</name>
      <id>1020</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Immunomodulator</name>
      <id>1031</id>
      <definition>Biologically active substance whose activity affects or plays a role in the functioning of the immune system.</definition>
    </health_effect>
    <health_effect>
      <name>Inhibitor</name>
      <id>1432</id>
      <definition>A substance that diminishes the rate of a chemical reaction.</definition>
    </health_effect>
    <health_effect>
      <name>Lipolytic</name>
      <id>1074</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Memory enhancer</name>
      <id>1098</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Nephroprotective</name>
      <id>1147</id>
      <definition>Any protective agent that is able to prevent damage to the kidney.</definition>
    </health_effect>
    <health_effect>
      <name>Neuroprotective</name>
      <id>1158</id>
      <definition>Any compound that can be used for the treatment of neurodegenerative disorders.</definition>
    </health_effect>
    <health_effect>
      <name>Teratogenic</name>
      <id>1347</id>
      <definition>A role played by a chemical compound  in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.</definition>
    </health_effect>
    <health_effect>
      <name>Toxic</name>
      <id>1371</id>
      <definition>A role played by the molecular entity or part thereof which causes the development of a pathological process.</definition>
    </health_effect>
    <health_effect>
      <name>Vasoprotective</name>
      <id>1416</id>
      <definition/>
    </health_effect>
  </health_effects>
</compound>
