Eriocitrin - analytical standard, ≥98%(HPLC) , CAS No.13463-28-0

CAS: 13463-28-0 Cat. No.: E117960 Molecular Weight: 596.53 Beilstein Registry Number: 1304401 EC Number: 236-668-7

GRADE & PURITY Analytical standard, ≥98%(HPLC)

Synonyms

(S)-7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-4H-benzopyran-4-one | OMQADRGFMLGFJF-MNPJBKLOSA-N | 4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyran

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(S)-7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3, 4-dihydroxyphenyl)-2, 3-dihydro-5-hydroxy-4H-benzopyran-4-one | OMQADRGFMLGFJF-MNPJBKLOSA-N | 4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyran

Specifications & Purity

analytical standard, ≥98%(HPLC)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Analytical standard

Purity

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O
• IUPAC Name: (2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-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]oxy-2,3-dihydrochromen-4-one
• InChIKey: OMQADRGFMLGFJF-MNPJBKLOSA-N
• INCHI: 1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,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=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O
• WGK Germany: 3
• Molecular Weight: 596.53
• Beilstein: 1304401
• Reaxy-Rn: 37812840
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37812840&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: 5-hydroxyflavonoids Flavanones 4'-hydroxyflavonoids 3'-hydroxyflavonoids Phenolic glycosides Chromones Disaccharides O-glycosyl compounds Aryl alkyl ketones Catechols 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Oxanes Vinylogous acids Secondary alcohols Polyols Oxacyclic compounds Acetals Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-7-o-glycoside - 3'-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - Flavanone - Hydroxyflavonoid - Flavan - Phenolic glycoside - Chromone - Disaccharide - Glycosyl compound - O-glycosyl compound - Chromane - Benzopyran - 1-benzopyran - Catechol - Aryl alkyl ketone - Aryl ketone - 1-hydroxy-4-unsubstituted benzenoid - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Oxane - Vinylogous acid - Ketone - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Ether - Acetal - Polyol - Organooxygen compound - Alcohol - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - 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: flavanones

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 (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HL (112 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

DPP4 Dipeptidyl peptidase IV (11 Activities)

Discover Target: DPP4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Chlamydia pneumoniae (241 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 596.500 g/mol
• XLogP3: -1.400
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 596.174 Da
• Monoisotopic Mass: 596.174 Da
• Topological Polar Surface Area: 245.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 924.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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. Liu Xiaojuan, Zhao Chenning, Gong Qin, Wang Yue, Cao Jinping, Li Xian, Grierson Donald, Sun Chongde.  (2020)  Characterization of a caffeoyl-CoA O-methyltransferase-like enzyme involved in biosynthesis of polymethoxylated flavones in Citrus reticulata.  JOURNAL OF EXPERIMENTAL BOTANY,  71  (10): (3066-3079).  [PMID:32182355] [10.1093/jxb/eraa083]

2. Xiaojuan Liu, Yue Wang, Yezhi Chen, Shuting Xu, Qin Gong, Chenning Zhao, Jinping Cao, Chongde Sun.  (2020)  Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the In Vitro Cytotoxicity of Its Methylated Products.  MOLECULES,  25  (4): (858).  [PMID:32075249] [10.3390/molecules25040858]

3. Junlei Liu, Huarong Huang, Zebin Huang, Yuran Ma, Lanyue Zhang, Yan He, Dongli Li, Wenfeng Liu, Susan Goodin, Kun Zhang, Xi Zheng.  (2019)  Eriocitrin in combination with resveratrol ameliorates LPS-induced inflammation in RAW264.7 cells and relieves TPA-induced mouse ear edema.  Journal of Functional Foods,      [PMID:] [10.1016/j.jff.2019.03.008]

4. Yue Wang, Jing Qian, Jinping Cao, Dengliang Wang, Chunrong Liu, Rongxi Yang, Xian Li, Chongde Sun.  (2017)  Antioxidant Capacity, Anticancer Ability and Flavonoids Composition of 35 Citrus (Citrus reticulata Blanco) Varieties.  MOLECULES,  22  (7): (1114).  [PMID:28678176] [10.3390/molecules22071114]

5. Lu Wang, Qinqin Wang, Kai Sheng, Gaiping Li, Baoxian Ye.  (2016)  A new graphene nanocomposite modified electrode as efficient voltammetric sensor for determination of eriocitrin.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2016.11.061]

6. Xue Wang, Zhipeng Su, Xiang Li, Jiaxu Chen, Gaoyang Li, Yang Shan, Zhaoping Pan, Fuhua Fu.  (2024)  Targeted/untargeted metabolomics and antioxidant properties distinguish Citrus reticulata ‘Chachi’ from Citrus reticulata Blanco.  FOOD CHEMISTRY,      [PMID:39241684] [10.1016/j.foodchem.2024.140806]

7. Yating Lu, Dong Li, Li Li, Tarun Belwal, Yanqun Xu, Xingyu Lin, Zhenhua Duan, Zisheng Luo.  (2020)  Effects of elevated CO2 on pigment metabolism of postharvest mandarin fruit for degreening.  FOOD CHEMISTRY,      [PMID:32126463] [10.1016/j.foodchem.2020.126462]