Linarin - 10mM in DMSO , CAS No.480-36-4

CAS: 480-36-4 Cat. No.: L424170 Molecular Weight: 592.54

GRADE & PURITY 10mM in DMSO

Synonyms

Bis(L-arginin)-2-oxoglutarat | 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE | SCHEMBL1155704 | LINARIGENIN-GLUCOSIDE | Linarin | 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

Bis(L-arginin)-2-oxoglutarat | 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE | SCHEMBL1155704 | LINARIGENIN-GLUCOSIDE | Linarin | 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Pubchem Sid: 528775569
• Canonical Smiles: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• IUPAC Name: 5-hydroxy-2-(4-methoxyphenyl)-7-[(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: YFVGIJBUXMQFOF-PJOVQGMDSA-N
• INCHI: 1S/C28H32O14/c1-11-21(31)23(33)25(35)27(39-11)38-10-19-22(32)24(34)26(36)28(42-19)40-14-7-15(29)20-16(30)9-17(41-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-9,11,19,21-29,31-36H,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27+,28+/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=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• Molecular Weight: 592.54
• Reaxy-Rn: 25451328
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25451328&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-7-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-7-O-glycosides
• Alternative Parents: 4'-O-methylated flavonoids 5-hydroxyflavonoids Flavones Phenolic glycosides O-glycosyl compounds Chromones Disaccharides Phenoxy compounds Anisoles Methoxybenzenes 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Pyranones and derivatives Alkyl aryl ethers Oxanes Vinylogous acids Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Acetals Polyols Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-7-o-glycoside - 4p-methoxyflavonoid-skeleton - 5-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Phenolic glycoside - Chromone - Disaccharide - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Pyranone - Alkyl aryl ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Pyran - Benzenoid - Oxane - Monocyclic benzene moiety - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Polyol - Organoheterocyclic compound - Acetal - Oxacycle - Ether - Organooxygen compound - Hydrocarbon derivative - Alcohol - Organic oxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
• External Descriptors: Not available

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)

TYR Tclin Tyrosinase (717 Activities)

Discover Target: TYR

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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XDH Tclin Xanthine dehydrogenase (1038 Activities)

Discover Target: XDH

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GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

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Associated Targets(non-human)

Bacteria (550 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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PC-12 (7051 Activities)

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RAW264.7 (28094 Activities)

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HT-22 (3261 Activities)

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Akt1 RAC-alpha serine/threonine-protein kinase (147 Activities)

Discover Target: Akt1

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 260 °C
• Molecular Weight: 592.500 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 592.179 Da
• Monoisotopic Mass: 592.179 Da
• Topological Polar Surface Area: 214.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 955.000
• 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

References

1. Yang Huang, Ying Feng, Guangyun Tang, Minyi Li, Tingting Zhang, Marianne Fillet, Jacques Crommen, Zhengjin Jiang.  (2017)  Development and validation of a fast SFC method for the analysis of flavonoids in plant extracts.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:28347593] [10.1016/j.jpba.2017.03.012]

2. Yuqian Zhang, Shenghan Gao, Shengnan Xia, Haiyan Yang, Xinyu Bao, Qingxiu Zhang, Yun Xu.  (2024)  Linarin ameliorates ischemia-reperfusion injury by the inhibition of endoplasmic reticulum stress targeting AKR1B1.  BRAIN RESEARCH BULLETIN,      [PMID:38181967] [10.1016/j.brainresbull.2024.110868]