Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2020-02-24 19:10:08 UTC
Primary IDFDB000497
Secondary Accession Numbers
  • FDB000786
Chemical Information
FooDB NameBetanin
DescriptionRed pigment from beetroot, Beta vulgaris variety rubra and other Centrospermae. It is used as a food dye Betanin is a betalain pigment, together with isobetanin, probetanin, and neobetanin. Other pigments contained in beet are indicaxanthin and vulgaxanthins.; Betanin, or Beetroot Red, is a red glycosidic food dye obtained from beets; its aglycone, obtained by hydrolyzing away the glucose molecule, is betanidin. As a food additive, its E number is E162. Betanin degrades when subjected to light, heat, and oxygen; therefore, it is used in frozen products, products with short shelf life, or products sold in dry state. Betanin can survive pasteurization when in products with high sugar content. Its sensitivity to oxygen is highest in products with high content of water and/or containing metal cations (eg. iron and copper); antioxidants like ascorbic acid and sequestrants can slow this process down, together with suitable packaging. In dry form betanin is stable in presence of oxygen. Betanin is found in many foods, some of which are pepper (c. frutescens), parsley, swamp cabbage, and pigeon pea.
CAS Number7659-95-2
Structure
Thumb
Synonyms
SynonymSource
(3E)-4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-oneChEBI
gamma-IononChEBI
g-IononGenerator
Γ-iononGenerator
g-IononeGenerator
Γ-iononeGenerator
(3E)-4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-oneHMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-oneHMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one, 9ciHMDB
4-(2-Methylene-6,6-dimethylcyclohexyl)-3-buten-2-oneHMDB
FEMA 3175HMDB
gamma-LononeHMDB
Laquo gammaraquo -iononeHMDB
BetanineHMDB
e162HMDB
PhytolaccaninHMDB
Betalain pigmentsMeSH, HMDB
2-Carboxy-1-[2-(2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene)ethylidene]-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-6-olic acidGenerator
Betanindb_source
E162db_source
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP0.21ALOGPS
logP-5.4ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area249.38 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity149.71 m³·mol⁻¹ChemAxon
Polarizability52.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H26N2O13
IUPAC name(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate
InChI IdentifierInChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)
InChI KeyDHHFDKNIEVKVKS-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(O)C=C3C(CC(C([O-])=O)\[N+]3=C/C=C3\CC(NC(=C3)C(O)=O)C(O)=O)=C2)C(O)C(O)C1O
Average Molecular Weight550.4688
Monoisotopic Molecular Weight550.143488928
Classification
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ionone derivative
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.37%; H 4.76%; N 5.09%; O 37.78%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06sr-6811590000-46636eb43361f2098849JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3300029000-a3df643de601301006f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0100090000-e8d3751464fed113038dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-1200090000-eb6a0bd055cce9bc0ccfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9801010000-69f46043e141b0e01333JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1300090000-f163fd5bba6112945538JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-5700090000-6bc84bfc087b6e018e8cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-e4f97d60e300bc9b176bJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08540
Pubchem Compound ID91559
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID708
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBCX92-K:BCX94-M
EAFUS IDNot Available
Dr. Duke IDBETANINE|BETANIN
BIGG IDNot Available
KNApSAcK IDC00001584
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBetanin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 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.DUKE
anti peroxidantDUKE
heme-sparingDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).