38953-85-4

Basic information

• Product Name: ISOVITEXIN
• Synonyms: SAPOMARETOM;SAPONARETIN;APIGENIN-6-C-GLUCOSIDE;HOMOVITEXIN;6-C-Glucosylapigenin;C01714;Apigenin 6-C-β-D-glucoside;Isovitexin, froM Crataegus pinnatifida
• CAS NO: 38953-85-4
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.38
• Mol File: 38953-85-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 257-258 °C
• Boiling Point: 807 °C at 760 mmHg
• Flash Point: 287.1 °C
• Appearance: /
• Density: 1.686g/cm³
• Vapor Pressure: 1.68E-27mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: ?20°C
• PKA: 5.93±0.40(Predicted)
• BRN: 66651
• CAS DataBase Reference: ISOVITEXIN(CAS DataBase Reference)
• NIST Chemistry Reference: ISOVITEXIN(38953-85-4)
• EPA Substance Registry System: ISOVITEXIN(38953-85-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 38953-85-4(Hazardous Substances Data)

Usage

Description

Isovitexin, a flavone belonging to the flavonoid class, is a naturally occurring compound with significant antiradical activities and potential health benefits. It is derived from various plant sources and has been studied for its positive effects on atherosclerosis, osteoporosis, and certain cancers.

Uses

Used in Pharmaceutical Research:
Isovitexin is used as a research compound for its potential therapeutic applications in the treatment of atherosclerosis, osteoporosis, and certain cancers. Its antiradical properties make it a promising candidate for pharmaceutical development.
Used in Nutritional Studies:
Isovitexin is used as a biomarker in the study of plant-based biochemicals and their nutritional benefits. It helps researchers understand the role of flavonoids in human health and their potential use in the development of functional foods and supplements.
Used in Enzyme Inhibition Studies:
Isovitexin has been used in research to assess collagenase inhibitors from Viola yedoensis, a plant species. This application helps in understanding the potential of Isovitexin in the development of treatments for conditions related to excessive collagenase activity.
Used in Antioxidant and Enzyme Inhibition Research:
Isovitexin has been utilized in studies investigating the inhibitory activity of Gentiana lutea extracts on the enzyme myeloperoxidase (MPO) and their antioxidant properties. This research contributes to the understanding of the potential use of Isovitexin in the development of antioxidant therapies and treatments for conditions associated with MPO overactivity.
General Information:
Isovitexin is produced and qualified by HWI Pharma Services GmbH, with its exact content determined by quantitative NMR, as detailed on the certificate. It is a yellow powder with chemical properties that make it suitable for various research and pharmaceutical applications.

Biochem/physiol Actions

Phytochemical found in medicinal herbs. Antioxidant.

InChI:InChI=1/C21H20O10/c22-6-13-17(26)19(28)20(29)21(31-13)14-11(24)5-12-15(18(14)27)16(25)10(7-30-12)8-1-3-9(23)4-2-8/h1-5,7,13,17,19-24,26-29H,6H2/t13-,17-,19+,20-,21+/m1/s1

Upstream product

• 1173925-23-9 isovitexin 2-O-sulfate 
• 10515-29-4 5,7,4'-trihydroxy-6-C-(β-D-glucopyranosyl)flavone peracetate 
• 29774-67-2 vitexin 
• 60767-80-8 5,7,4'-trihydroxyflavone 6-C-(2''-O-β-D-glucopyranosyl-β-D-glucopyranoside) 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 

Downstream Products

• 1233717-60-6 C₂₈H₂₄O₁₃S 
• 1233717-59-3 C₂₈H₂₄O₁₀ 
• 1173925-23-9 isovitexin 2-O-sulfate 
• 866737-00-0 chafuroside B 
• 3681-93-4 vitexin 
• 29774-67-2 vitexin 
• 20197-48-2 5,7-dimethoxy-2-(4-methoxyphenyl)-8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 6991-11-3 2'',3'',4'',6''-tetra-O-acetyl-4',5,7-tri-O-methylisovitexin 

Relevant articles and documents

Flavonoid pattern inheritance in the allopolyploid Spartina anglica – Comparison with the parental species S. maritima and S. alterniflora

The invasive species Spartina anglica arose in Europe by a cross between the Afro-European species S. maritima (native, paternal ancestor) and the introduced North American S. alterniflora (invasive, maternal ancestor). Aqueous methanolic extracts were prepared from plant tissue for chemotaxonomical comparison between the three species and determination of the phenolic pattern inheritance in S. anglica. A total of 20 phenolic compounds were detected in the aerial tissues of S. anglica and S. alterniflora, but only seven in S. maritima. They were isolated from their respective crude extracts, and their structures were determined according to spectroscopic data analysis and chemical evidence. They all belong to the flavonoid class, with 13 of them identified as C-glycoflavonoid and seven as O-glycoflavonoid. All these products were detected for the first time from S. anglica, fourteen of them for the first time from S. alterniflora, and three of them for the first time from S. maritima. The individual concentrations in the three species were determined by quantitative HPLC. The two parental species were found to differ markedly in their foliar phenolic fingerprint, whereas that of S. anglica showed a clear maternal dominance. Eight of the fourteen major compounds identified were of maternal origin among which, six were over-expressed, only three were from paternal origin but under-regulated, while two originated from the two parents. As far as we know, this work represents the first exhaustive report of the phenolic fingerprints of S. alterniflora and S. anglica and of the phenolic pattern inheritance in S. anglica. The similarity in the phenolic chemistry of the introduced and invasive S. alterniflora to its progeny could play a role in the physiological vigour and invasion success of S. anglica. This work provide a foundation for further studies, considering the reported biological activities of C-glycosidic flavonoids and tricin derivatives, and the lack of knowledge of the ecological chemistry of the genus Spartina.

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.

Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins

The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus.