4261-42-1

Basic information

• Product Name: HOMOORIENTIN
• Synonyms: 2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one;6-(β-D-Glucopyranosyl)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one;2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one;2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]chromone;Isoorientin/HoMoorientin;lespecapittoside;HoMoorientin, froM PolygonuM orientale;IsoorientinI
• CAS NO: 4261-42-1
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.38
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Tetra-substituted Flavones
• Mol File: 4261-42-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 245-246°C
• Boiling Point: 856.7 °C at 760 mmHg
• Flash Point: 303.2 °C
• Appearance: yellow/
• Density: 1.759 g/cm³
• Vapor Pressure: 2.9E-31mmHg at 25°C
• Refractive Index: 1.767
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble5mg/mL, clear, colorless to yellow
• PKA: 5.90±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: HOMOORIENTIN(CAS DataBase Reference)
• NIST Chemistry Reference: HOMOORIENTIN(4261-42-1)
• EPA Substance Registry System: HOMOORIENTIN(4261-42-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4261-42-1(Hazardous Substances Data)

Usage

Description

HOMOORIENTIN, also known as Isoorientin, is a flavonoid compound that can be isolated from various plant sources, including the passion flower. It is a flavone C-glycoside consisting of luteolin with a beta-D-glucosyl residue at the 6-position. HOMOORIENTIN exhibits a pale yellow solid appearance and has been found to possess antioxidant, anti-nociceptive, anti-inflammatory, and gastroprotective activities.

Uses

Used in Pharmaceutical Applications:
HOMOORIENTIN is used as a reference standard in the analysis of herbal medicinal products. It is produced and qualified by HWI Pharma Services GmbH, with the exact content determined by quantitative NMR, which can be found on the certificate.
Used in Antioxidant Applications:
HOMOORIENTIN is used as an antioxidant agent due to its ability to neutralize free radicals and protect cells from oxidative stress, which can lead to various diseases and aging.
Used in Pain Management:
HOMOORIENTIN is used as an anti-nociceptive agent, helping to alleviate pain by inhibiting the transmission of pain signals in the body.
Used in Anti-Inflammatory Applications:
HOMOORIENTIN is used as an anti-inflammatory agent, reducing inflammation and associated symptoms by modulating the immune system and inhibiting the production of inflammatory mediators.
Used in Gastroprotective Applications:
HOMOORIENTIN is used as a gastroprotective agent, protecting the stomach lining from damage and promoting healing in cases of gastric ulcers or other gastrointestinal issues.

Biochem/physiol Actions

C-glycosyl flavone with anti-inflammatory, antimicrobial and antioxidant properties. Induces antioxidant response through PI3K singaling.

InChI:InChI=1/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1

Upstream product

• 1163725-44-7 luteolin 8-C-D-glucoside 
• 131507-98-7 2'',6''-Di-O-acetylisoorientin 
• 321133-86-2 2-(3,4-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 39548-86-2 1‐(2‐(benzyloxy)‐4,6‐dihydroxyphenyl)ethan‐1‐one 
• 115623-29-5 2-benzyloxy-4,6-bis(methoxymethyloxy)acetophenone 
• 321133-81-7 2-benzyloxy-6-hydroxy-4-(2-methylbenzyloxy)acetophenone 
• 321133-82-8 6-benzyloxy-2-hydroxy-4-(2-methylbenzyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone 
• 321133-84-0 6-hydroxy-2,4-bis(2-methylbenzyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone 
• 321133-83-9 6-benzyloxy-2,4-bis(2-methylbenzyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone 
• 321133-85-1 3,4-dibenzyloxy-6'-hydroxy-2',4'-bis(2-methylbenzyloxy)-3'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone 
• 7480-94-6 Luteolin-8-C-glucoside 

Downstream Products

• 7480-94-6 Luteolin-8-C-glucoside 
• 1163725-44-7 luteolin 8-C-D-glucoside 

Relevant articles and documents

Gallates of isoorientin and (2S)-1,2-propanediol glucoside from the leaves of Schoepfia jasminodora

From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Schoepfia jasminodora collected from Okinawa Island, two new galloyl esters and 15 known compounds were isolated. The structures of the new compounds were elucidated by spectroscopic anal

Acylated flavone 8-C-glucosides from the flowers of Trollius chinensis

Ten new flavone 8-C-glucosides, trollichinensides A–J, with the substitution of various acyls at C-2″ C-3″ or C-6″ of the glucose moiety, together with thirteen known ones were isolated from the flowers of Trollius chinensis. Spectroscopic analyses including NMR and HRESIMS resulted in the establishment of the structures of these constituents and electronic circular dichroism (ECD) experiment was employed for the determination of the absolute configuration of the glucose residue in these molecules.

C-Glycosyl Flavones from Two Eastern Siberian Species of Silene

Flavonoids from Silene aprica Turcz. and S. samojedorum (Sambuk) Oxelman (Caryophyllaceae) growing in Baikal region were studied for the first time. A total of 14 compounds including three new compounds 1–3 were isolated. Their structures were established using UV, IR, and NMR spectroscopy and mass spectrometry. Apigenin-6-C-(2″-O-α-L-arabinopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside A, 1) and apigenin-6-C-(2″-O-β-D-glucopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside B, 2) were observed in S. aprica; 1 and luteolin-6-C-(2″-O-α-L-arabinopyranosyl-6″-O-acetyl)-β-D-glucopyranoside (sileneside C, 3), in S. samojedorum.