<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:59:53 UTC</creation_date>
  <update_date>2026-04-03 01:07:03 UTC</update_date>
  <accession/>
  <common_name>Retinal</common_name>
  <class>SmallMolecule</class>
  <description>Retinal is an organic compound with the formula $\text{C}_{20}\text{H}_{28}\text{O}$ and an average molecular weight of 284.44 g/mol. Retinal belongs to the retinoids, a subclass of prenol lipids within the organic compounds.

In biological contexts, the compound serves as a chromophore (PMC12361693). Industrially, it is utilized as a softener and conditioner (PMC12361693). Retinal is associated with 12 recorded sources. Within the category of electrical and electronic equipment, it is found in amplifiers, antennas, coils, electric hearing aids, loudspeakers, and three additional sources. In the sector of household cleaning and consumer products, it is identified in tobacco product cases and non-electric simulated smoking devices. Furthermore, it is found in floors within building and construction, as well as in the preparation of vinegar within food, food processing and cookware.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>11-cis-Retinaldehyde</synonym>
    <synonym>9-cis-Retinal</synonym>
    <synonym>all-trans-retinal</synonym>
  </synonyms>
  <chemical_formula>C20H28O</chemical_formula>
  <average_molecular_weight>284.4357</average_molecular_weight>
  <monisotopic_moleculate_weight>284.214015518</monisotopic_moleculate_weight>
  <iupac_name>(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal</iupac_name>
  <traditional_iupac>13-cis retinal</traditional_iupac>
  <cas_registry_number>116-31-4</cas_registry_number>
  <smiles>C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O</smiles>
  <inchi>InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+</inchi>
  <inchikey>NCYCYZXNIZJOKI-OVSJKPMPSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Retinoids</sub_class>
    <direct_parent>Retinoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Enals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Enal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Retinoid skeleton</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Retinoids</descriptor>
      <descriptor>retinal</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0000074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin A Deficiency</name>
      <smpdb_id>SMP0000336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin A Deficiency</name>
      <smpdb_id>SMP0125788</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>284.4357</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>284.214015518</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H28O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NCYCYZXNIZJOKI-OVSJKPMPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7270d54b18&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>638015</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>1041</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
