Record Information
Version1.0
Creation date2018-05-02 12:13:02 UTC
Update date2018-05-04 14:23:50 UTC
FoodComEx IDPC001183
FoodDB RecordFDB021828
Chemical Information
NameEnterodiol
DescriptionEnterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye and wheat), seeds, nuts, legumes and vegetables. (PMID: 12270221, J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.) [HMDB]. Enterodiol is a biomarker for the consumption of soy beans and other soy products.
CAS Number80226-00-2
Structure
Thumb
Synonyms
SynonymSource
(-)-EnterodiolHMDB
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
[R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediolHMDB
Arbo 9HMDB
Chemical FormulaC18H22O4
IUPAC name2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
InChI IdentifierInChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2
InChI KeyDWONJCNDULPHLV-UHFFFAOYSA-N
Isomeric SMILESOCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC=CC(O)=C1
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassDibenzylbutanediol lignans
Direct ParentDibenzylbutanediol lignans
Alternative Parents
Substituents
  • Dibenzylbutanediol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity Available1 to 2 mg
Delivery Time2 weeks
Storage Formpowder
Storage Conditions4°C
StabilityNot Available
Purityunknown
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Augustin ScalbertInternational Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372scalberta@iarc.fr
Commercial Vendors
AKSci 9828AL