isosakuranetin
angophorol
 
Notes:
None found
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      Product(s):
      480-43-3 Isosakuranetin 98.5%
      Isosakuranetin isolated from the fruits of Citrus aurantium L. antifungal; cytotoxic;
       
       
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CAS Number: 480-43-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 207-551-8
FDA UNII: U02X7TF8UA
Nikkaji Web: J12.391I
MDL: MFCD00017313
XlogP3-AA: 2.70 (est)
Molecular Weight: 286.28358000
Formula: C16 H14 O5
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 539.20 °C. @ 760.00 mm Hg (est)
Flash Point: 402.00 °F. TCC ( 205.60 °C. ) (est)
logP (o/w): 3.840 (est)
Soluble in:
 water, 109.2 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Alfa Biotechnology
For experimental / research use only.
Isosakuranetin 98%
BOC Sciences
For experimental / research use only.
Isosakuranetin 98.5%
Odor: characteristic
Use: Isosakuranetin isolated from the fruits of Citrus aurantium L. antifungal; cytotoxic;
Coompo
For experimental / research use only.
isoSakuranetin from Plants ≥96%
Odor: characteristic
Use: Isosakuranetin (ISK) is a plant exudate with known cytotoxic and fungicide properties. When tested on wheat root segments at a concentration of 70µM it inhibited K+ dependent H+ extrusion and net uptake of K+, while leaving the membrane potential (PD) unaltered. Fusicoccin (FC) + ISK treatment resulted in a slight membrane depolarization, while ISK alone did not alter O2 consumption or alternative oxidase activity. ISK did not increase the pyruvate content in incubated root tissues or inhibit Fe2+ uptake. The observed drop in K+ net uptake depended on a decrease in K+ influx into the cell, leading to the suggestion that ISK may act on wheat root segments as an inhibitor of K+ permeation. The lack of proton leakage and membrane disruption by ISK made this compound a weak candidate as a phytoalexin, and suggesting a major role as an allelopathic molecule. Isosakuranetin produced significant decrease in blood pressure.
ExtraSynthese
For experimental / research use only.
isoSakuranetin (HPLC) ≥99%
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for isosakuranetin usage levels up to:
 not for fragrance use.
 
Recommendation for isosakuranetin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 160481
National Institute of Allergy and Infectious Diseases: Data
 (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Chemidplus: 0000480433
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References:
 (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 160481
Pubchem (sid): 135116440
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C05334
HMDB (The Human Metabolome Database): Search
FooDB: FDB000610
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 orange fruit
Search Trop  Picture
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Synonyms:
 angophorol
4H-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (2S)-
4H-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (S)-
(S)-2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone
(S)-2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
(2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one
(2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
(2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
(2S)-5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one
5,7-dihydroxy-4'-methoxyflavanone
4'-methyl naringenin
4'-methylnaringenin
 naringenin 4'-methyl ether
isosakutanetin
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Articles:
PubMed: Isosakuranetin-5-O-rutinoside: a new flavanone with antidepressant activity isolated from Salvia elegans Vahl.
PubMed: Stereospecific pharmacokinetics of racemic homoeriodictyol, isosakuranetin, and taxifolin in rats and their disposition in fruit.
PubMed: Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo.
PubMed: Stereospecific high-performance liquid chromatographic assay of isosakuranetin in rat urine.
PubMed: A naturally occurring naringenin derivative exerts potent bone anabolic effects by mimicking oestrogen action on osteoblasts.
PubMed: [Notes on the identification of atsinoside with isosakuranetin-7-rutinoside didymium].
PubMed: [Synthesis of poncirin, an isosakuranetin-7-beta-neohesperidoside from Poncirus trifoliata Raf].
PubMed: [Structure clarification and synthesis of didymin, an isosakuranetin-7-beta-rutinoside from Monarda didyma L].
PubMed: Inhibition of the human neutrophil oxidative metabolism by Baccharis dracunculifolia DC (Asteraceae) is influenced by seasonality and the ratio of caffeic acid to other phenolic compounds.
PubMed: Drying effect on flavonoid composition and antioxidant activity of immature kumquat.
PubMed: Effects of an ethanol extract of Brazilian green propolis on human cytochrome P450 enzyme activities in vitro.
PubMed: [Study on chemical constituents of Artemisia sphaerocephala].
PubMed: Absorption, metabolism, and excretion of fermented orange juice (poly)phenols in rats.
PubMed: [Phenolic derivatives from Wisteria sinensis sweet caulis].
PubMed: Effect of Siam weed extract and its bioactive component scutellarein tetramethyl ether on anti-inflammatory activity through NF-κB pathway.
PubMed: Inhibitory activity of benzophenones from Anemarrhena asphodeloides on pancreatic lipase.
PubMed: Polyphenolic profile as a useful tool to identify the wood used in wine aging.
PubMed: Seasonality Role on the Phenolics from Cultivated Baccharis dracunculifolia.
PubMed: Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.
PubMed: Antihypertensive effects of flavonoids isolated from brazilian green propolis in spontaneously hypertensive rats.
PubMed: Kaurane-type diterpenoids from Chromoleana odorata, their X-ray diffraction studies and potent α-glucosidase inhibition of 16-kauren-19-oic acid.
PubMed: [Aromatic constituents of Heteroplexis micocephal and their bioactivities].
PubMed: Stereoisomeric separation of some flavanones using highly succinate-substituted α-cyclosophoro-octadecaoses as chiral additives in capillary electrophoresis.
PubMed: Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis.
PubMed: Phenolic compounds in cherry ( Prunus avium ) heartwood with a view to their use in cooperage.
PubMed: Modulation of Akt, JNK, and p38 activation is involved in citrus flavonoid-mediated cytoprotection of PC12 cells challenged by hydrogen peroxide.
PubMed: Spray-dried propolis extract, II: prenylated components of green propolis.
PubMed: A validated reverse-phase HPLC analytical method for the quantification of phenolic compounds in Baccharis dracunculifolia.
PubMed: Enantiomeric separation of some flavanones using shinorhizobial linear octasaccharides in CE.
PubMed: Effects of propolis crude hydroalcoholic extract on chromosomal aberrations induced by doxorubicin in rats.
PubMed: Some flavonoids and DHEA-S prevent the cis-effect of expanded CTG repeats in a stable PC12 cell transformant.
PubMed: Antimycobacterial activity and cytotoxicity of flavonoids from the flowers of Chromolaena odorata.
PubMed: Methoxylated flavonols and flavanones from Eupatorium odoratum.
PubMed: Antimicrobial activity of the extract and isolated compounds from Baccharis dracunculifolia D. C. (Asteraceae).
PubMed: A reliable quantitative method for the analysis of phenolic compounds in Brazilian propolis by reverse phase high performance liquid chromatography.
PubMed: [Studies on flavonoid constituents from herbs of Artemisia ordosica II].
PubMed: Effect of Baccharis dracunculifolia D.C. (Asteraceae) extracts and its isolated compounds on macrophage activation.
PubMed: Enantioseparation of some chiral flavanones using microbial cyclic beta-(1-->3),(1-->6)-glucans as novel chiral additives in capillary electrophoresis.
PubMed: Flavanone metabolism in healthy and tumor-bearing rats.
PubMed: Separation of some chiral flavonoids by microbial cyclosophoraoses and their sulfated derivatives in micellar electrokinetic chromatography.
PubMed: In-vitro trypanocidal activity evaluation of crude extract and isolated compounds from Baccharis dracunculifolia D.C. (Asteraceae).
PubMed: Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils.
PubMed: Antioxidative bioavailability of artepillin C in Brazilian propolis.
PubMed: Separation of some chiral flavanones by micellar electrokinetic chromatography.
PubMed: Flavonoids as inhibitors or enhancers of the cytotoxicity of tumor necrosis factor-alpha in L-929 tumor cells.
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