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betanin

Names

[ CAS No. ]:
7659-95-2

[ Name ]:
betanin

[Synonym ]:
(s-(r*,r*))--dihydro-6-hydroxy-1h-indol-1-yl)ethenyl)-3-dihydro
(Red Beet extract diluted with Dextrin)
Phytolaccanin
(2S)-4-{2-[(2S)-2-Carboxy-5-(β-D-glucopyranosyloxy)-6-hydroxy-2,3-dihydro-1H-indol-1-yl]vinyl}-2,3-dihydro-2,6-pyridinedicarboxylic acid
Beetroot Red
EINECS 231-628-5
2,6-Pyridinedicarboxylic acid, 4-[2-[(2S)-2-carboxy-5-(β-D-glucopyranosyloxy)-2,3-dihydro-6-hydroxy-1H-indol-1-yl]ethenyl]-2,3-dihydro-, (2S)-
Betanin (Red Beet extract diluted with Dextrin)

Biological Activity

[Description]:

Betanin has potent antioxidant and anti-inflammatory effect, that could inhibit peroxynitrite (ONOO-), with an IC50 of 19.2 μM. Betanin is a red glycoside obtained from beets that can be used as colorant.

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Metabolic Disease
Natural Products >> Saccharides and Glycosides

[Target]

IC50: 19.2 μM (ONOO-)[1].


[In Vitro]

Betanin is a representative constituent of red beetroot betacyanins, could inhibit peroxynitrite (ONOO-), with an IC50 of 19.2 μM[1]. Betanin also has anti-inflammatory, anti-proliferative effects, nephroprotective activity, cardioprotective activity, strong, antioxidant and angiotensin converting enzyme (ACE) inhibitory activity[2]. Another study is also indicated the protective effect of Betanin against high glucose induced rat renal epithelial cell fibrosis and matrix accumulation, major features of diabetic nephropathy (DN)[2].

[In Vivo]

Betanin can inhibit the fructose-induced diabetic cardiac fibrosis and paraquat induced acute kidney toxicity[2]. The co-administration of Betanin (20 mg/kg b.w.) to diabetic rats prevent significantly the raise of glucose level and also reverse the levels of insulin compared with untreated diabetic rats. Interestingly diabetic rats treated with Betanin (20 mg/kg b.w.) and glibenclamide portray the significant changes in the body weight compared to diabetic control. HbA1c levels significantly increases in diabetic rats and when treated with Betanin as well as glibenclamide. Treatment with Betanin as well as glibenlamide to STZ-NA induces diabetic rat’s elicit significant decreases in those levels when compared with diabetic control rats[3].

[Animal admin]

Rats[3] Healthy adult Male albino Wistar strain (Rattus norvegicus, 90-120 days of age) are used in the current study. After the successful induction of experimental diabetes, the rats are divided into four groups each comprising a minimum of six rats a total of 30 rats (18 diabetic surviving rats, 12 normal rats). Betanin is administered via oral intubation to the experimental rats using a gavage needle daily for a period of 30 days. Group 1: Normal Control rats. Group 2: Rats treated with Betanin (20 mg/kg b.w.) alone. Group 3: Diabetic Control rats. Group 4: Rats treated with STZ-NA by i.p. and Betanin (20 mg/kg b.w.). Group 5: Rats treated with STZ-NA by i.p. and glibenclamide (600 μg/kg b.w.)[3].

[References]

[1]. Sakihama Y, et al. Beetroot betalain inhibits peroxynitrite-mediated tyrosine nitration and DNA strand cleavage. Free Radic Res. 2012 Jan;46(1):93-9.

[2]. Sutariya B, et al. Betanin, isolated from fruits of Opuntia elatior Mill attenuates renal fibrosis in diabetic rats through regulating oxidative stress and TGF-β pathway. J Ethnopharmacol. 2017 Feb 23;198:432-443.

[3]. Indumathi D, et al. Betanin exhibits significant potential as an antihyperglycemic and attenuating the glycoprotein components in streptozotocin-nicotinamide-induced experimental rats. Toxicol Mech Methods. 2018 Sep;28(7):547-554.


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Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
983.5±75.0 °C at 760 mmHg

[ Molecular Formula ]:
C24H26N2O13

[ Molecular Weight ]:
550.469

[ Flash Point ]:
548.6±37.1 °C

[ Exact Mass ]:
550.143494

[ PSA ]:
249.38000

[ LogP ]:
-4.49

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.740

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
US7968100
CHEMICAL NAME :
2,6-Pyridinedicarboxylic acid, 4-(2-(2-carboxy-5-(beta-D-glucopyranosyloxy)-2,3-dihy dro-6- hydroxy-1H-indol-1-yl)ethenyl)-2,3-dihydro-, (S-(R*,R*))-
CAS REGISTRY NUMBER :
7659-95-2
LAST UPDATED :
199112
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C24-H26-N2-O13
MOLECULAR WEIGHT :
550.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
17200 gm/L
REFERENCE :
CYTOAN Cytologia. (Japan Pub. Trading Co. (USA), 1255 Howard St., San Francisco, CA 94103) V.1- 1929- Volume(issue)/page/year: 55,203,1990

Safety Information

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
2261.0

[ RTECS ]:
US7968100

[ Hazard Class ]:
6.1

[ HS Code ]:
3203001990

Customs

[ HS Code ]: 3203001990


Related Compounds

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