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sinensetin
5,6,7,3',4'-pentamethoxyflavone

Supplier Sponsors

Name:2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxychromen-4-one
CAS Number: 2306-27-6Picture of molecule3D/inchi
FDA UNII: 240LNZ51AT
Nikkaji Web:J94.519F
Beilstein Number:345748
MDL:MFCD00017421
XlogP3-AA:3.00 (est)
Molecular Weight:372.37380000
Formula:C20 H20 O7
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
Boiling Point: 547.00 to 548.00 °C. @ 760.00 mm Hg (est)
Flash Point: 465.00 °F. TCC ( 240.60 °C. ) (est)
logP (o/w): 2.634 (est)
Soluble in:
 water, 24.04 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Sinensetin 98%
BOC Sciences
For experimental / research use only.
Sinensetin >98%
Odor: characteristic
Use: Sinensetin is a natural flavonoid compound isolated from the fruit of Citrus aurantium L. Sinensetin exhibits the anti-inflammatory, antimutagenic and anticancer activities. antimutagenic, anticancer, anti-inflammatory
Coompo
For experimental / research use only.
Sinensetin from Plants ≥98%
Odor: characteristic
Use: Sinensetin exhibits anti-fungal, anti-histamine activity; induce cell differentiation, inhibition of linoleic acid oxidation, inhibition of white blood cells in the human zona protein Interleukin -1-induced expression of tissue factor.
ExtraSynthese
For experimental / research use only.
Sinensetin (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Sinensetin
Sigma-Aldrich
For experimental / research use only.
Sinensetin
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 sinensetin usage levels up to:
 not for fragrance use.
 
Recommendation for sinensetin 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 :145659
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxychromen-4-one
Chemidplus:0002306276
 
References:
 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxychromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):145659
Pubchem (sid):135104143
 
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):C10186
HMDB (The Human Metabolome Database):HMDB36633
FooDB:FDB015552
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
 citrus oils
Search PMC Picture
 mandarin pericarp
Search Trop Picture
 orange fruit
Search Trop Picture
 orange fruit juice
Search Trop Picture
 orange pericarp
Search Trop Picture
 orange plant
Search Trop Picture
 rosemary plant
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-
2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one
2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxychromen-4-one
5,6,7,3',4'-pentamethoxyflavone
 

Articles:

PubMed:Chemical fingerprint and metabolic profile analysis of Citrus reticulate 'Chachi' decoction by HPLC-PDA-IT-MS(n) and HPLC-Quadrupole-Orbitrap-MS method.
J-Stage:Sinensetin Attenuates LPS-Induced Inflammation by Regulating the Protein Level of I?B-a
PubMed:Orthosiphol A from the aerial parts of Orthosiphon aristatus is putatively responsible for hypoglycemic effect via alpha-glucosidase inhibition.
PubMed:Preparation and characterization of nano liposomes of Orthosiphon stamineus ethanolic extract in soybean phospholipids.
PubMed:Sonochemical effects on 14 flavonoids common in citrus: relation to stability.
PubMed:6-demethoxynobiletin, a nobiletin-analog citrus flavonoid, enhances extracellular signal-regulated kinase phosphorylation in PC12D cells.
PubMed:Identification of sinensetin metabolites in rat urine by an isotope-labeling method and ultrahigh-performance liquid chromatography-electrospray ionization mass spectrometry.
PubMed:Potent activity of nobiletin-rich Citrus reticulata peel extract to facilitate cAMP/PKA/ERK/CREB signaling associated with learning and memory in cultured hippocampal neurons: identification of the substances responsible for the pharmacological action.
PubMed:Chemical markers of shiikuwasha juice adulterated with calamondin juice.
PubMed:Potent α-glucosidase and α-amylase inhibitory activities of standardized 50% ethanolic extracts and sinensetin from Orthosiphon stamineus Benth as anti-diabetic mechanism.
PubMed:A simple isocratic HPLC method for the simultaneous determination of sinensetin, eupatorin, and 3'-hydroxy-5,6,7,4'-tetramethoxyflavone in Orthosiphon stamineus extracts.
PubMed:In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: identifying sinensetin as a novel antiangiogenesis agent.
PubMed:Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation.
PubMed:Sinensetin attenuates LPS-induced inflammation by regulating the protein level of IκB-α.
PubMed:Effects of sinensetin on lipid metabolism in mature 3T3-L1 adipocytes.
PubMed:[Effects of sinensetin on proliferation and apoptosis of human gastric cancer AGS cells].
PubMed:Molecular structures of citrus flavonoids determine their effects on lipid metabolism in HepG2 cells by primarily suppressing apoB secretion.
PubMed:In vitro effects of active constituents and extracts of Orthosiphon stamineus on the activities of three major human cDNA-expressed cytochrome P450 enzymes.
PubMed:Evaluation of the genotoxicity of Orthosiphon stamineus aqueous extract.
PubMed:HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves.
PubMed:Isolation of adenosine, iso-sinensetin and dimethylguanosine with antioxidant and HIV-1 protease inhibiting activities from fruiting bodies of Cordyceps militaris.
PubMed:Induction of apoptosis in human cervical carcinoma HeLa cells by polymethoxylated flavone-rich Citrus grandis Osbeck (Dangyuja) leaf extract.
PubMed:Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand.
PubMed:Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook.
PubMed:Suppression of bacterial cell-cell signalling, biofilm formation and type III secretion system by citrus flavonoids.
PubMed:CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells.
PubMed:UPLC/Q-TOFMS/MS as a powerful technique for rapid identification of polymethoxylated flavones in Fructus aurantii.
PubMed:Evaluation of the anti-pyretic potential of Orthosiphon stamineus Benth standardized extract.
PubMed:Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts.
PubMed:Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.
PubMed:Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques.
PubMed:Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.
PubMed:Characterization of polymethoxylated flavones in Fructus aurantii by liquid chromatography with atmospheric pressure chemical ionization combined with tandem mass spectrometry.
PubMed:Determination of polymethoxylated flavones in peels of selected Jamaican and Mexican citrus (Citrus spp.) cultivars by high-performance liquid chromatography.
PubMed:Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China.
PubMed:Liquid chromatography/mass spectrometry and liquid chromatography/nuclear magnetic resonance as complementary analytical techniques for unambiguous identification of polymethoxylated flavones in residues from molecular distillation of orange peel oils (Citrus sinensis).
PubMed:Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities.
PubMed:Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection.
PubMed:Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora.
PubMed:Effect of extraction method on the concentrations of selected bioactive compounds in mandarin juice.
PubMed:Reversal of P-glycoprotein-mediated multidrug resistance by 5,6,7,3',4'-pentamethoxyflavone (Sinensetin).
PubMed:Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels.
PubMed:Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones.
PubMed:Immunotoxicity of a standardized citrus polymethoxylated flavone extract.
PubMed:Inhibitors of 15-lipoxygenase from orange peel.
PubMed:Constituents of the Vietnamese medicinal plant Orthosiphon stamineus.
PubMed:Inhibition of metallopeptidases by flavonoids and related compounds.
PubMed:A citrus flavonoid, nobiletin, suppresses production and gene expression of matrix metalloproteinase 9/gelatinase B in rabbit synovial fibroblasts.
PubMed:Antimutagenic activity of polymethoxyflavonoids from Citrus aurantium.
PubMed:Simultaneous separation of flavanone glycosides and polymethoxylated flavones in citrus juices using liquid chromatography.
PubMed:Lipophilic flavonoids from Orthosiphon spicatus prevent oxidative inactivation of 15-lipoxygenase.
PubMed:C18 solid-phase isolation and high-performance liquid chromatography/ultraviolet diode array determination of fully methoxylated flavones in citrus juices.
PubMed:Flavones in citrus exhibit antiadhesive action on platelets.
PubMed:Flavonoids from Chenopodium botrys.
PubMed:Quantitation of polymethoxylated flavones in orange juice by high-performance liquid chromatography.
 
Notes:
isolated from citrus fruit; exhibit antiadhesive action on platelets. Found in orange peel and other plant sources
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