Rutin - ≥95% , CAS No.153-18-4

CAS: 153-18-4 Cat. No.: R189033 Formula: C₂₇H₃₀O₁₆ Molecular Weight: 610.52 EC Number: 205-814-1 PubChem CID: 5280805

GRADE & PURITY ≥95%

Synonyms

Ilixanthin | Rutinic acid | Rutinoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl | 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- | Rutoside [INN] |

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Rutin (Quercetin 3-O-rutinoside) belongs to the flavonoid group of natural products with blood-brain barrier permeability. Rutin has a wide range of biological activities including antioxidant, anti-inflammatory, anti-tumor, hypoglycemic, neuroprotective, anti-bacterial, anti-aging and so on.

Specifications

Synonyms

Ilixanthin | Rutinic acid | Rutinoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl | 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- | Rutoside [INN] |

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Antioxidant and free radical scavenger (EC 50 = 12 μM). Active in vivo.

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

Pubchem Sid

504763315

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504763315

Canonical Smiles

CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

InChIKey

IKGXIBQEEMLURG-NVPNHPEKSA-N

INCHI

1S/C27H30O16/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/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1

Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

Alternate CAS

207671-50-9；250249-75-3

PubChem CID

5280805

Molecular Weight

610.52

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-3-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-3-O-glycosides
• Alternative Parents: 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones O-glycosyl compounds Chromones Disaccharides Catechols Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Oxanes Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Secondary alcohols Acetals Polyols Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-3-o-glycoside - Hydroxyflavonoid - Flavone - 3'-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - O-glycosyl compound - Glycosyl compound - Disaccharide - Chromone - 1-benzopyran - Benzopyran - Catechol - 1-hydroxy-2-unsubstituted benzenoid - Phenol - 1-hydroxy-4-unsubstituted benzenoid - Pyranone - Monocyclic benzene moiety - Benzenoid - Pyran - Oxane - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Acetal - Polyol - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
• External Descriptors: flavonols

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (1 Activities)

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F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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XDH Tclin Xanthine dehydrogenase (1038 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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AKR1B1 Tclin Aldose reductase (1404 Activities)

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LDHA Tchem L-lactate dehydrogenase A chain (1573 Activities)

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KCNA5 Tclin Voltage-gated potassium channel subunit Kv1.5 (1353 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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BCHE Tclin Butyrylcholinesterase (7174 Activities)

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ALB Tchem Serum albumin (2651 Activities)

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GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

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FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)

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CFTR Tclin Cystic fibrosis transmembrane conductance regulator (2075 Activities)

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EPHX2 Tchem Epoxide hydratase (3844 Activities)

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BACE1 Tchem Beta-secretase 1 (15641 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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K562 (73714 Activities)

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N9 (414 Activities)

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Raji (5516 Activities)

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SK-MEL-2 (46422 Activities)

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SK-OV-3 (52876 Activities)

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U-251 (51189 Activities)

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A549 (127892 Activities)

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HepG2 (196354 Activities)

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Monocyte (474 Activities)

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KB (17409 Activities)

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BT-549 (31254 Activities)

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ACP1 Tchem Low molecular weight phosphotyrosine protein phosphatase (1161 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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KDM1A Tchem Lysine-specific histone demethylase 1 (3916 Activities)

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AKR1B10 Tchem Aldo-keto reductase family 1 member B10 (300 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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NMUR2 Tchem Neuromedin-U receptor 2 (383 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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SLCO2B1 Tchem Solute carrier organic anion transporter family member 2B1 (580 Activities)

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NFKB2 Tchem Nuclear factor NF-kappa-B complex (2307 Activities)

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CYCS Tchem Cytochrome c (68 Activities)

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HEK-293T (167025 Activities)

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Associated Targets(non-human)

NA Neuraminidase (1107 Activities)

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blaZ Beta-lactamase (285 Activities)

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Alpha-chymotrypsin (819 Activities)

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Trypsin (394 Activities)

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DPP4 Dipeptidyl peptidase IV (11 Activities)

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Abcc1 Multidrug resistance-associated protein 1 (42 Activities)

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PREP Prolyl endopeptidase (14 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Nannizzia gypsea (2039 Activities)

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Paraphyton cookei (39 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Ralstonia solanacearum (520 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Salmonella typhimurium (15756 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Streptococcus pyogenes (16140 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Entamoeba histolytica (2676 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Candida parapsilosis (8521 Activities)

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Trichophyton rubrum (3646 Activities)

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Leishmania amazonensis (3813 Activities)

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Leishmania donovani (89745 Activities)

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Trypanosoma cruzi (99888 Activities)

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Giardia intestinalis (1290 Activities)

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Human gammaherpesvirus 4 (1538 Activities)

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Meloidogyne incognita (862 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Dengue virus (413 Activities)

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Trypanosoma brucei rhodesiense (7991 Activities)

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Trichophyton tonsurans (138 Activities)

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Epidermophyton floccosum (561 Activities)

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3T3-L1 (3664 Activities)

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MDCK (10148 Activities)

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PC-12 (7051 Activities)

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RAW264.7 (28094 Activities)

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C6 (2371 Activities)

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BV-2 (3710 Activities)

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L929 (3802 Activities)

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Trichophyton violaceum (39 Activities)

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Genome polyprotein (620 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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nanH Sialidase (337 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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BCHE Cholinesterase (8742 Activities)

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Trichophyton mentagrophytes (4846 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 610.500 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 6
• Exact Mass: 610.153 Da
• Monoisotopic Mass: 610.153 Da
• Topological Polar Surface Area: 266.000 Ų
• Heavy Atom Count: 43
• Formal Charge: 0
• Complexity: 1020.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 153-18-4, the molecular formula is C27H30O16, and the molecular weight is 610.52 g/mol. InChIKey IKGXIBQEEMLURG-NVPNHPEKSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.