Poncirin - analytical standard, ≥95% , CAS No.14941-08-3

CAS: 14941-08-3 Cat. No.: P114052 Formula: C₂₈H₃₄O₁₄ Molecular Weight: 594.56 Beilstein Registry Number: 74301 EC Number: 239-020-1

GRADE & PURITY Analytical standard, ≥95%

Synonyms

(S)-7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-BENZOPYRAN-4-ONE | 2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine | 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydrox

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Poncirin (with other flavonoids of the bitter orange) was tested as a control agent for mosquito infestation, and was found to be larvacidal, to repel females from egg-laying on treated water, and to repel insects from biting topically treated human volunteers.

Specifications

Synonyms

(S)-7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-BENZOPYRAN-4-ONE | 2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine | 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydrox

Specifications & Purity

analytical standard, ≥95%

Biochemical and Physiological Mechanisms

Poncirin is isolated from Poncirus trifoliata with anti-inflammory activites. Poncirin significantly reduces mechanical hyperalgesia and allodynia in Complete Freund’s Adjuvant (CFA)-induced inflammatory pain models.

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

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

Grade

Analytical standard

Purity

≥95%

Names and Identifiers

Pubchem Sid

528772155

Canonical Smiles

CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)OC)O)CO)O)O)O)O)O

IUPAC Name

(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one

InChIKey

NLAWPKPYBMEWIR-SKYQDXIQSA-N

INCHI

1S/C28H34O14/c1-11-21(32)23(34)25(36)27(38-11)42-26-24(35)22(33)19(10-29)41-28(26)39-14-7-15(30)20-16(31)9-17(40-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-30,32-36H,9-10H2,1-2H3/t11-,17-,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)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)OC)O)CO)O)O)O)O)O

WGK Germany

3

Molecular Weight

594.56

Beilstein

74301

Reaxy-Rn

55296504

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=55296504&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 Flavanones Phenolic glycosides O-glycosyl compounds Chromones Disaccharides Phenoxy compounds Anisoles Aryl alkyl ketones Methoxybenzenes 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Oxanes Vinylogous acids Secondary alcohols Oxacyclic compounds Acetals Polyols Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-7-o-glycoside - 4p-methoxyflavonoid-skeleton - Hydroxyflavonoid - 5-hydroxyflavonoid - Flavanone - Flavan - Phenolic glycoside - O-glycosyl compound - Glycosyl compound - Disaccharide - Chromone - Chromane - Benzopyran - 1-benzopyran - Phenoxy compound - Phenol ether - Anisole - Aryl ketone - Aryl alkyl ketone - Methoxybenzene - 1-hydroxy-4-unsubstituted benzenoid - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Oxane - Vinylogous acid - Secondary alcohol - Ketone - Polyol - Ether - Organoheterocyclic compound - Oxacycle - Acetal - Primary alcohol - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Alcohol - Organooxygen 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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Molecular Weight: 594.600 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 594.195 Da
• Monoisotopic Mass: 594.195 Da
• Topological Polar Surface Area: 214.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 900.000
• 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