EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

sakuranetin
(S)-4',5-dihydroxy-7-methoxyflavone

Supplier Sponsors

Name:(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
CAS Number: 2957-21-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:220-980-5
FDA UNII: 3O38P61299
Nikkaji Web:J7.652J
Beilstein Number:0092466
MDL:MFCD00075651
XlogP3-AA:2.70 (est)
Molecular Weight:286.28358000
Formula:C16 H14 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge 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
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 152.00 °C. @ 760.00 mm Hg
Boiling Point: 555.90 °C. @ 760.00 mm Hg (est)
Flash Point: 414.00 °F. TCC ( 212.40 °C. ) (est)
logP (o/w): 3.370 (est)
Soluble in:
 water, 109.2 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Sakuranetin 98%
BOC Sciences
For experimental / research use only.
Sakuranetin
Coompo
For experimental / research use only.
Sakuranetin from Plants ≥96%
Sigma-Aldrich
For experimental / research use only.
Sakuranetin
analytical standard
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for sakuranetin usage levels up to:
 not for fragrance use.
 
Recommendation for sakuranetin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :73571
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
Chemidplus:0002957213
 
References:
 (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):73571
Pubchem (sid):135033686
 
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):C09833
HMDB (The Human Metabolome Database):HMDB30090
FooDB:FDB001472
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 carrot fruit
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 currant black currant leaf
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 juglans spp.
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 polymnia fruticosa
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 prunus spp
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 rice
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 walnut black walnut fruit
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Synonyms:
4H-1-benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (2S)-
4H-1-benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (S)- (9CI)
(2S)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
(S)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
(S)-(-)-4',5-dihydroxy-7-methoxyflavanone
(S)-4',5-dihydroxy-7-methoxyflavanone
(S)-4',5-dihydroxy-7-methoxyflavone
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-chromen-4-one
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-one
7-O-methylnaringenin
 naringenin 7-O-methyl ether
(-)-(S)-sakuranetin
(2S)-sakuranetin
 

Articles:

PubMed:Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus.
PubMed:Structural crystalline characterization of sakuranetin--an antimicrobial flavanone from twigs of Baccharis retusa (Asteraceae).
PubMed:The potential bioproduction of the pharmaceutical agent sakuranetin, a flavonoid phytoalexin in rice.
PubMed:Purification and identification of naringenin 7-O-methyltransferase, a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice.
PubMed:A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia.
PubMed:A flavanone from Baccharis retusa (Asteraceae) prevents elastase-induced emphysema in mice by regulating NF-κB, oxidative stress and metalloproteinases.
PubMed:Transcriptomic analysis of UV-treated rice leaves reveals UV-induced phytoalexin biosynthetic pathways and their regulatory networks in rice.
PubMed:Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli.
PubMed:Sakuranetin induces adipogenesis of 3T3-L1 cells through enhanced expression of PPARgamma2.
PubMed:Flavonone treatment reverses airway inflammation and remodelling in an asthma murine model.
PubMed:Ethanol extract and isolated constituents from artemisia dracunculus inhibit esophageal squamous cell carcinoma and induce apoptotic cell death.
PubMed:Antimicrobial activity of UV-induced phenylamides from rice leaves.
PubMed:A methyltransferase for synthesis of the flavanone phytoalexin sakuranetin in rice leaves.
PubMed:Stereospecific analysis of sakuranetin by high-performance liquid chromatography: pharmacokinetic and botanical applications.
PubMed:Naringenin 7-O-methyltransferase involved in the biosynthesis of the flavanone phytoalexin sakuranetin from rice (Oryza sativa L.).
PubMed:Multiple phytohormones and phytoalexins are involved in disease resistance to Magnaporthe oryzae invaded from roots in rice.
PubMed:Effects of chemopreventive natural products on non-homologous end-joining DNA double-strand break repair.
PubMed:In vitro antileishmanial and antitrypanosomal activities of flavanones from Baccharis retusa DC. (Asteraceae).
PubMed:[Derivations from asebotin to sakuranetin and from phlorizin to naringenin].
PubMed:Biosynthesis of phytoalexins and regulatory mechanisms of it in rice.
PubMed:[Chemical constituents contained in Populus tomentosa].
PubMed:Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.
PubMed:Transcriptome Analysis of Early Responsive Genes in Rice during Magnaporthe oryzae Infection.
PubMed:OsJAR1 contributes mainly to biosynthesis of the stress-induced jasmonoyl-isoleucine involved in defense responses in rice.
PubMed:Measurement of the influence of flavonoids on DNA repair kinetics using the comet assay.
PubMed:In vitro evaluation of flavonoids from Eriodictyon californicum for antagonist activity against the bitterness receptor hTAS2R31.
PubMed:Prunus yedoensis bark inhibits lipopolysaccharide-induced inflammatory cytokine synthesis by IκBα degradation and MAPK activation in macrophages.
PubMed:Evaluation of estrogen receptor Beta binding of pruni cortex and its constituents.
PubMed:Biflavonoids from Caper (Capparis spinosa L.) fruits and their effects in inhibiting NF-kappa B activation.
PubMed:Transport mechanisms of flavanone aglycones across Caco-2 cell monolayers and artificial PAMPA membranes.
PubMed:Identification of rice Allene Oxide Cyclase mutants and the function of jasmonate for defence against Magnaporthe oryzae.
PubMed:Three flavonoids targeting the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: crystal structure characterization with enzymatic inhibition assay.
PubMed:Thymus mastichina: chemical constituents and their anti-cancer activity.
PubMed:Production of 7-O-methyl aromadendrin, a medicinally valuable flavonoid, in Escherichia coli.
PubMed:A convenient method for simultaneous quantification of multiple phytohormones and metabolites: application in study of rice-bacterium interaction.
PubMed:Spasmolytic effects of Scrophularia nodosa extract on isolated rabbit intestine.
PubMed:Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts.
PubMed:Investigation of the extraction process and phytochemical composition of preparations of Dodonaea viscosa (L.) Jacq.
PubMed:Qualitative variation of anti-diabetic compounds in different tarragon (Artemisia dracunculus L.) cytotypes.
PubMed:Effects of naturally occurring dihydroflavonols from Inula viscosa on inflammation and enzymes involved in the arachidonic acid metabolism.
PubMed:Methionine-induced phytoalexin production in rice leaves.
PubMed:Phytoalexin production by amino acid conjugates of jasmonic acid through induction of naringenin-7-O-methyltransferase, a key enzyme on phytoalexin biosynthesis in rice (Oryza sativa L.).
PubMed:Reversal of multidrug resitance by natural substances from plants.
PubMed:Smooth muscle relaxing compounds from Dodonaea viscosa.
PubMed:Coronatine elicits phytoalexin production in rice leaves (Oryza sativa L.) in the same manner as jasmonic acid.
PubMed:Antifungal activity of Heterothalamus alienus metabolites.
PubMed:Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth.
PubMed:O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans.
PubMed:Differential expression of defense/stress-related marker proteins in leaves of a unique rice blast lesion mimic mutant (blm).
PubMed:The rice (Oryza sativa) blast lesion mimic mutant, blm, may confer resistance to blast pathogens by triggering multiple defense-associated signaling pathways.
PubMed:[Studies on chemical constitutes of Phellinus igniarius].
PubMed:Effects of selected flavonoids and carotenoids on drug accumulation and apoptosis induction in multidrug-resistant colon cancer cells expressing MDR1/LRP.
PubMed:Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli.
PubMed:Allergy-preventive flavonoids from Xanthorrhoea hastilis.
PubMed:Isolation and molecular characterization of a Spotted leaf 18 mutant by modified activation-tagging in rice.
PubMed:Anti-inflammatory activity of flavonoids from Populus davidiana.
PubMed:Antimycobacterial agents from selected Mexican medicinal plants.
PubMed:Methoxylated flavonols and flavanones from Eupatorium odoratum.
PubMed:Enantioseparation of some chiral flavanones using microbial cyclic beta-(1-->3),(1-->6)-glucans as novel chiral additives in capillary electrophoresis.
PubMed:Separation of some chiral flavonoids by microbial cyclosophoraoses and their sulfated derivatives in micellar electrokinetic chromatography.
PubMed:Cyclohexanoid protoflavanones from the stem-bark and roots of Ongokea gore.
PubMed:Induced volatiles in elicitor-treated and rice blast fungus-inoculated rice leaves.
PubMed:Anti-inflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata.
PubMed:A C-glucosylflavone from leaves of Piper lhotzkyanum.
PubMed:Phenolic compounds from Eucalyptus maculata.
PubMed:Synthesis of 7-methoxyapigeninidin and its fungicidal activity against Gloeocercospora sorghi.
PubMed:Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
PubMed:Isolation of potential cancer chemopreventive agents from Eriodictyon californicum.
PubMed:[Flavonoids of Artemisia campestris, ssp. glutinosa].
 
Notes:
major rice phytoalexin. Sakuranetin is a flavanone, a type of flavonoid. It can be found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae.
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