Showing Compound Betanin (FDB000497)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:35 UTC

Update date

2020-02-24 19:10:08 UTC

Primary ID

FDB000497

Secondary Accession Numbers

FDB000786

Chemical Information

FooDB Name

Betanin

Description

Red 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 Number

7659-95-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Betanine	HMDB
e162	HMDB
Phytolaccanin	HMDB
Betalain pigments	MeSH, 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 acid	Generator
Betanin	db_source
E162	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
logP	0.21	ALOGPS
logP	-5.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	249.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	149.71 m³·mol⁻¹	ChemAxon
Polarizability	52.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C24H26N2O13

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 Identifier

InChI=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 Key

DHHFDKNIEVKVKS-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(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 Weight

550.4688

Monoisotopic Molecular Weight

550.143488928

Classification

Description

Belongs to the class of organic compounds known as betacyanins and derivatives. These are organic compounds containing a glycoside of indolium-2-carboxylic acid attached, with the nitrogen ring of the indolium ring attached to an ethylpyridine-2,6-dicarboxylic acid derivative. Betacyanins are red nitrogenous pigments found in certain plants, such as beetroots.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Betalains

Sub Class

Betacyanins and derivatives

Direct Parent

Betacyanins and derivatives

Alternative Parents

Substituents

Betacyanin
Phenolic glycoside
Hexose monosaccharide
Indolecarboxylic acid
Indolecarboxylic acid derivative
O-glycosyl compound
Glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Tetrahydropyridine
Oxane
Monosaccharide
Benzenoid
Hydropyridine
Amino acid
Carboxylic acid salt
Secondary alcohol
Amino acid or derivatives
Shiff base
Acetal
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Enamine
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Polyol
Amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organic salt
Carbonyl group
Alcohol
Organic zwitterion
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Primary alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 52.37%; H 4.76%; N 5.09%; O 37.78%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Betanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06sr-6811590000-46636eb43361f2098849	Spectrum
Predicted GC-MS	Betanin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-3300029000-a3df643de601301006f4	Spectrum
Predicted GC-MS	Betanin, "Betanin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betanin, TMS_2_19, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0100090000-e8d3751464fed113038d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-1200090000-eb6a0bd055cce9bc0ccf	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ow-9801010000-69f46043e141b0e01333	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1300090000-f163fd5bba6112945538	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-5700090000-6bc84bfc087b6e018e8c	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9200000000-e4f97d60e300bc9b176b	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0003090000-12c41fae6fb421dfc9fb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-1709270000-ac3f053be7f6646a8ea4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0109110000-8cab56ea03fccc586da6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zms-0105190000-337da834c51fdb43b82f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-059e-0109550000-b3f8eafba5be1f7b8754	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fbi-2319210000-2eebd8f8d7eec66cd5ed	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C08540

Pubchem Compound ID

91559

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

708

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BCX92-K:BCX94-M

EAFUS ID

Not Available

Dr. Duke ID

BETANINE|BETANIN

BIGG ID

Not Available

KNApSAcK ID

C00001584

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Betanin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti peroxidant		An agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.	DUKE
Heme-sparing		An agent that conserves heme, a vital molecule for oxygen transport and energy production, by reducing its breakdown. It plays a biological role in maintaining cellular energy and preventing damage. Therapeutically, heme-sparing agents have applications in treating porphyrias and other disorders involving heme deficiency, with key medical uses including managing anemia and preventing tissue damage.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	DUKE
Pigment	26130	A biological coloring agent, playing a role in skin and eye protection. Therapeutically, pigments are used in photodynamic therapy and skin camouflage. Medically, they are used to treat conditions like vitiligo, albinism, and skin discoloration, as well as in diagnostic imaging and wound healing applications.	DUKE