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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H26N2O13
Molecular Weight 550.4688
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BETANIN

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C=C2O)N(\C=C\C4=CC(=N[C@@H](C4)C(O)=O)C(O)=O)[C@@H](C3)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=CTMLKIKAUFEMLE-FTNGGYTGSA-N
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/h1-3,6-7,12,14,17-20,24,27-31H,4-5,8H2,(H,32,33)(H,34,35)(H,36,37)/b2-1+/t12-,14-,17+,18+,19-,20+,24+/m0/s1

HIDE SMILES / InChI
Betanin (betanidin-5-O-beta-glucoside, Beetroot Red) is a red glycosidic food dye obtained from beets. Betanin is the most common betacyanin in the plant kingdom. According to the regulation on food additives betanin is permitted quantum satis as a natural red food colorant (E162). Moreover, betanin is used as colorant in cosmetics and pharmaceuticals. Recently, potential health benefits of betalains and betalain-rich foods (e.g. red beet, Opuntia sp.) have been discussed. Betanin is a scavenger of reactive oxygen species and exhibits gene-regulatory activity partly via nuclear factor (erythroid-derived 2)-like 2-(Nrf2) dependent signaling pathways. Betanin may induce phase II enzymes and antioxidant defense mechanisms. Furthermore, betanin possibly prevents LDL oxidation and DNA damage. Potential blood pressure lowering effects of red beet seem to be mainly mediated by dietary nitrate rather than by betanin per se.

Originator

Sources: Doctorate Dissertation, Eidgenossischen Techn. Hochschule. Zurich (1918), 1-64.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

500 mL of a commercial red beet juice containing 362.7 mg of betalains
Route of Administration: Oral
The cancer cell proliferation inhibitory activity of all natural pigments isolated was evaluated by using the MTT colorimetric assay. The tumor cell lines AGS, HCT-116, MCF-7, NCI-H460, and SF-268 used were maintained in our laboratory at Michigan State University. The cell lines were maintained as adherent cell cultures in RPMI-1640 medium supplemented with 10% FBS, 10 units of penicillin, and 105 mkg/mL streptomycin at 37 C under 5% CO2 in a humidified incubator. The cells were harvested and counted by using a hemacytometer, and the appropriate number of cells (4000-8000 cells/mL) was transferred into 96 well plates and incubated for 24 h prior to the treatment. Betanin and cyanidin-3-O-glucoside were dissolved in water separately and diluted with RPMI-1640 medium to the desired concentrations of 12.5, 25, 50, 100, and 200 mkg/mL. The test compounds were exposed to cells for 48 h. Adriamycin (doxorubicin), dissolved in 0.1% DMSO, was used as the positive control.
Name Type Language
BETANIN
Common Name English
2,6-PYRIDINEDICARBOXYLIC ACID, 4-(2-(2-CARBOXY-5-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-6-HYDROXY-1H-INDOL-1-YL)ETHENYL)-2,3-DIHYDRO-, (S-(R*,R*))-
Common Name English
BETANIDIN 5-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
BETANIN [MI]
Common Name English
E-162BETANIN
Common Name English
BEETROOT RED
INCI  
Official Name English
INS-162BETANIN
Common Name English
INS NO.162BETANIN
Common Name English
NSC-170989
Code English
(S-(R*,R*-(E,E)))-2-CARBOXY-1-((2,6-DICARBOXY-2,3-DIHYDRO-4(1H)-PYRIDINYLIDENE ETHYLIDENE)-5-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-6-HYDROXY-1H-INDOLIUM HYDROXIDE, INNER SALT
Common Name English
PHYTOLACCANIN
Common Name English
BETANINE
Common Name English
BEETROOT RED [INCI]
Common Name English
(S-(R*,R*))-4-(2-(2-CARBOXY-5-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-6-HYDROXY-1H-INDOL-1-YL)VINYL)-2,3-DIHYDROPYRIDINE-2,6-DICARBOXYLIC ACID
Common Name English
(15S)-BETANIN
Common Name English
Classification Tree Code System Code
JECFA EVALUATION E-162
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
CODEX ALIMENTARIUS (GSFA) E-162
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
Code System Code Type Description
NSC
170989
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
231-628-5
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY
FDA UNII
5YJC992ZP6
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY
WIKIPEDIA
BETANIN
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY
CAS
78693-88-6
Created by admin on Sat Dec 16 20:01:27 GMT 2023 , Edited by admin on Sat Dec 16 20:01:27 GMT 2023
SUPERSEDED
CAS
7659-95-2
Created by admin on Sat Dec 16 20:01:27 GMT 2023 , Edited by admin on Sat Dec 16 20:01:27 GMT 2023
PRIMARY
MERCK INDEX
m11800
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY
PUBCHEM
6540685
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID50999950
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY
CAS
209056-04-2
Created by admin on Sat Dec 16 20:01:27 GMT 2023 , Edited by admin on Sat Dec 16 20:01:27 GMT 2023
ALTERNATIVE
SMS_ID
100000130109
Created by admin on Sat Dec 16 20:01:28 GMT 2023 , Edited by admin on Sat Dec 16 20:01:28 GMT 2023
PRIMARY