Aloesin - ≥98% , CAS No.30861-27-9

CAS: 30861-27-9 Cat. No.: A329617 Molecular Weight: 394.37

GRADE & PURITY ≥98%

Synonyms

2-acetonyl-7-hydroxy-5-methyl-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one | SCHEMBL6936841 | ALOESIN [MI] | AC-34460 | 8-beta-D-glucopyranosyl-7-hydroxy-5-methyl-2-(2-oxopropyl)-4H-1-benzopyran-4-one | C08994 |

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Aloesin is a C-glycosylated chromone compound that has shown competitive inhibitory activity of tyrosinase, an enzyme responsible for catalyzing phenol oxidation in plants. Derivatives of aloesin have been observed to exhibit free radical scavenging and anti-inflammatory activity, and this compound has also been reported to modulate the formation of melanin (melanogenesis).

Specifications

Synonyms

2-acetonyl-7-hydroxy-5-methyl-8-[(2S, 3R, 4R, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one | SCHEMBL6936841 | ALOESIN [MI] | AC-34460 | 8-beta-D-glucopyranosyl-7-hydroxy-5-methyl-2-(2-oxopropyl)-4H-1-benzopyran-4-one | C08994 |

Specifications & Purity

≥98%

Source

Aloesp.

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504757479
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757479
• Canonical Smiles: CC1=CC(=C(C2=C1C(=O)C=C(O2)CC(=O)C)C3C(C(C(C(O3)CO)O)O)O)O
• IUPAC Name: 7-hydroxy-5-methyl-2-(2-oxopropyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• InChIKey: HKIKAXXIWJHWLY-ZIIYPAMZSA-N
• INCHI: 1S/C19H22O9/c1-7-3-10(22)14(19-17(26)16(25)15(24)12(6-20)28-19)18-13(7)11(23)5-9(27-18)4-8(2)21/h3,5,12,15-17,19-20,22,24-26H,4,6H2,1-2H3/t12-,15-,16+,17-,19+/m1/s1
• Isomeric SMILES: CC1=CC(=C(C2=C1C(=O)C=C(O2)CC(=O)C)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• Molecular Weight: 394.37
• Reaxy-Rn: 25669692
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25669692&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: Hexoses Chromones C-glycosyl compounds Pyranones and derivatives 1-hydroxy-2-unsubstituted benzenoids Oxanes Heteroaromatic compounds Secondary alcohols Ketones Polyols Oxacyclic compounds Dialkyl ethers Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenolic glycoside - Hexose monosaccharide - C-glycosyl compound - Chromone - Benzopyran - 1-benzopyran - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Benzenoid - Pyran - Monosaccharide - Oxane - Heteroaromatic compound - Secondary alcohol - Ketone - Oxacycle - Dialkyl ether - Ether - Organoheterocyclic compound - Polyol - Alcohol - Organic oxide - Hydrocarbon derivative - Primary alcohol - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• External Descriptors: chromones

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

• Solubility: Soluble in DMSO, and 100% ethanol.
• Sensitivity: light sensitive
• Refractive Index: n20D1.64 (Predicted)
• Boil Point(°C): 628.04° C at 760 mmHg (Predicted)
• Melt Point(°C): 272.85° C (Predicted)
• Molecular Weight: 394.400 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 394.126 Da
• Monoisotopic Mass: 394.126 Da
• Topological Polar Surface Area: 154.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 647.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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