sinensetin
5,6,7,3',4'-pentamethoxyflavone
Identification
| Name | sinensetin |
| IUPAC | 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxychromen-4-one |
| CAS Number | 2306-27-6 |
| FDA UNII | 240LNZ51AT |
| Molecular Formula | C20 H20 O7 |
| Molecular Weight | 372.37380000 |
| MDL Number | MFCD00017421 |
| Nikkaji Number | J94.519F |
| Beilstein | 345748 |
Regulatory
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 |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
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Potential Uses
Natural Occurrence
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
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.