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Merck

R5143

Rutin hydrate

≥94% (HPLC), powder

Synonym(s):

Quercetin-3-rutinoside hydrate, Vitamin P hydrate

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About This Item

Empirical Formula (Hill Notation):
C27H30O16 · xH2O
CAS Number:
207671-50-9
Molecular Weight:
610.52 (anhydrous basis)
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24899379
EC Number:
205-814-1
Beilstein/REAXYS Number:
75455
MDL number:
MFCD01319140

Product Name

Rutin hydrate, ≥94% (HPLC), powder

InChI key

PGHSKTKIQIBATG-ZAAWVBGYSA-N

InChI

1S/C27H30O16.H2O/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9;/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3;1H2/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-;/m0./s1

SMILES string

[H]O[H].O[C@H]1[C@H](OC[C@H]([C@H]2O)O[C@@H](OC(C3=O)=C(C4=CC=C(O)C(O)=C4)OC5=C3C(O)=CC(O)=C5)[C@H](O)[C@H]2O)O[C@H]([C@@H]([C@H]1O)O)C

assay

≥94% (HPLC)

form

powder

color

yellow to green

mp

195 °C (dec.) (lit.)

solubility

pyridine: 50 mg/mL
DMSO: soluble
aqueous base: soluble

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

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Biochem/physiol Actions

A polyphenolic flavonoid that acts as an antioxidant and NO scavenger. It can attenuate peroxide production in glial cells by acting as a free radical scavenger and protect renal cells from oxidative injury. Inclusion of rutin in the diet of rats significantly reduced the appearance of single-strand breaks in nuclear DNA caused by hepatocarcinogens aflatoxin B1 and N-nitrosodiumethylamine. This protection from DNA damage was found to be due to a reduction in the induction of repair enzymes polymerase, DNA polymerase β and DNA ligase. Since DNA damage and inefficient repair are thought to initiate the process of carcinogenesis, effects of rutin on these functions suggests a protective role of this flavonoid against carcinogenesis induced by chemical carcinogens.

Application

Rutin hydrate has been used:
  • as an inhibitory compound against Skeletonema costatum
  • to analyze the phenolic component and antioxidant activity of nettle
  • to assess the flavonoid content in Propolis

General description

Rutin hydrate has radioprotective and antiplatelet activity. Rutin reduces hepatic and blood cholesterol levels.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN1808
BCCL7880
BCCJ3238
BCCH1908
BCCG8099

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In-vitro evaluation of rutin and rutin hydrate as potential radiation countermeasure agents
Ojha H, et al.
International Journal of Radiation Research, 14(1), 9-9 (2016)
S A van Acker et al.
Biochemical and biophysical research communications, 214(3), 755-759 (1995-09-25)
Flavonoids are a group of naturally occurring compounds used, e.g., in the treatment of vascular endothelial damage. They are known to be excellent scavengers of oxygen free radicals. Since the nitric oxide radical (.NO) probably plays a role in this
R P Webster et al.
Cancer letters, 109(1-2), 185-191 (1996-12-03)
Administration of hepatocarcinogens aflatoxin B1 and N-nitrosodimethylamine to rats caused single-strand breaks in nuclear DNA. Inclusion in the diet of rutin, a naturally occurring phenolic flavonoid glycoside, significantly reduced the appearance of such breaks. The protection against DNA damage was
Phenolic compounds analysis of root, stalk, and leaves of nettle
Otles S and Yalcin B
TheScientificWorldJournal, 2012 (2012)
E A Mazzio et al.
Planta medica, 64(7), 603-606 (1998-11-12)
Glial cell monoamine oxidase (MAO) activity has been implicated as a contributor to oxidative neuronal damage associated with various neurodegenerative diseases. The attenuation of MAO activity may provide protection against oxidative neurodegeneration. In this investigation, the presence of MAO-B in
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