Record Information
Version1.0
Creation date2010-04-08 22:05:23 UTC
Update date2015-07-20 21:45:54 UTC
Primary IDFDB002470
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameC.I. Natural Red 20
DescriptionRed dye component of alkanet root extract used for colouring sausage casings, margarine, confectionery and wine. This extract, formerly FEMA 2016, has been removed from the FEMA GRAS list. Not permitted in Germany. Japan approved
CAS Number517-88-4
Structure
Thumb
Synonyms
SynonymSource
Alkanet extractHMDB
Alkanet extract (van)biospider
Alkanna redHMDB
Alkanna red (van)biospider
AlkanninHMDB
Alkannin (van)biospider
Anchusa acidHMDB
Anchusa acid (van)biospider
AnchusinHMDB
Anchusin (van)biospider
C.I. 75530db_source
C.I. Natural red 20db_source
C.I. Natural Red 20 (VAN)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.19ALOGPS
logP3.01ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.6ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.82 m³·mol⁻¹ChemAxon
Polarizability29.8 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H16O5
IUPAC name5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
InChI IdentifierInChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
InChI KeyInChIKey=NEZONWMXZKDMKF-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC(O)C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O
Average Molecular Weight288
Monoisotopic Molecular Weight288
Classification
DescriptionThis compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aromatic monoterpenoid
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • Aryl ketone
  • Quinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.66%; H 5.59%; O 27.75%DFC
Melting PointMp 116-117° (149°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20Hg -157 (C6H6)DFC
Spectroscopic UV Data563 (e 5900) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ml-9280000000-b0844b9158a9ed8540c0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01yc-9400800000-80ea5d873c7acc0809bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-075012fc8e371dc2176eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fy9-3690000000-91f11e32821de969fc96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9230000000-192f49a494c02eaf64b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-d06cd6d33d99ce2f26d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2790000000-649136aee6eabbfaaf17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2900000000-bbd3966288658c0b712fView in MoNA
ChemSpider ID5019
ChEMBL IDNot Available
KEGG Compound IDC10292
Pubchem Compound ID5208
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30579
CRC / DFC (Dictionary of Food Compounds) IDCLZ50-C:CLZ55-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002787
HET 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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference