Record Information
Version1.0
Creation date2010-04-08 22:08:38 UTC
Update date2020-09-17 15:41:00 UTC
Primary IDFDB009572
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-3 and trans-2-Hexenyl propionate
DescriptionLeucopelargonidin, also known as goratensidin, belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions. Leucopelargonidin (CAS: 520-17-2) is a colourless chemical compound belonging to the family of leucoanthocyanidins. Leucopelargonidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Leucopelargonidin can be found in a number of food items such as narrowleaf cattail, pepper (C. pubescens), macadamia nut (M. tetraphylla), and abiyuch, which makes leucopelargonidin a potential biomarker for the consumption of these food products (FooDB). Leucopelargonidin can also be found in Albizia lebbeck (East Indian walnut), in the fruit of Anacardium occidentale (cashew), in the fruit of Areca catechu (Areca nut), in the fruit of Hydnocarpus wightiana (Hindi Chaulmoogra), in the rhizome of Rumex hymenosepalus (Arizona dock), in Zea Mays (corn), and in Ziziphus jujuba (Chinese date) (Wikipedia). Leucopelargonidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucoanthocyanidins are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.
CAS Number98919-66-5
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.84 g/LALOGPS
logP0.62ALOGPS
logP1.18ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.08ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.23 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O6
IUPAC name(2R,3S,4S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
InChI IdentifierInChI=1S/C15H14O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,13-20H/t13-,14-,15+/m0/s1
InChI KeyFSVMLWOLZHGCQX-SOUVJXGZSA-N
Isomeric SMILESO[C@H]1[C@@H](O)C2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C=C1
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
Classification
Description Belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentLeucoanthocyanidins
Alternative Parents
Substituents
  • Leucoanthocyanidin-skeleton
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 4-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • 1,2-diol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MScis-3 and trans-2-Hexenyl propionate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0970000000-3e60660dfaca3137796cSpectrum
Predicted GC-MScis-3 and trans-2-Hexenyl propionate, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-2100069000-3ce0116528533bd0d171Spectrum
Predicted GC-MScis-3 and trans-2-Hexenyl propionate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-8b627d02db62b9f1f86c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-0950000000-2b74806e03f640f7e7962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-4900000000-59f4d5454c4db4612e0c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-6d8231aab24727e61b962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1970000000-922a65848e2bfc3f14812016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-5910000000-09cf6f8f89aea7db38a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-2d980c515d025d58a6fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0920000000-c778de7956c2638ac4b92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvu-3910000000-a7264b9a10375865f13c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-4a887fee01b47595208a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0910000000-788fd5f61f426f40a4622021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-181b5d47afc5e25b536c2021-09-23View Spectrum
NMRNot Available
ChemSpider ID389080
ChEMBL IDNot Available
KEGG Compound IDC03648
Pubchem Compound ID440073
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32322
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID1664
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference