pinostrobin
4H-1-benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-methoxy-2-phenyl-, (S)-
Identification
| Name | pinostrobin |
| IUPAC | (2S)-5-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one |
| CAS Number | 480-37-5 |
| EINECS | 207-548-1 |
| FDA UNII | SZD9LZS694 |
| Molecular Formula | C16 H14 O4 |
| Molecular Weight | 270.28438000 |
| MDL Number | MFCD06858342 |
| Nikkaji Number | J196.197G |
| Beilstein | 270230 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 494.00 to 495.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 372.00 °F. TCC ( 188.80 °C. ) (est) |
| logP (o/w) | 3.591 (est) |
| Soluble in | water, 52.42 mg/L @ 25 °C (est) |
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 pinostrobin usage levels up to | not for fragrance use. |
| Recommendation for pinostrobin 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-dihydro-5-hydroxy-7-methoxy-2-phenyl-, (2S)-
4H-1-
benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-methoxy-2-phenyl-, (S)-
(S)-2,3-
dihydro-5-hydroxy-7-methoxy-2-phenyl-4-benzopyrone
(S)-2,3-
dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one
(2S)-5-
hydroxy-7-methoxy-2-phenyl-2,3-dihydro-4H-chromen-4-one
(S)-5-
hydroxy-7-methoxy-2-phenyl-2,3-dihydro-4H-chromen-4-one
(2S)-5-
hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
5-
hydroxy-7-methoxyflavanone
pinocembrin-7-methyl ether
pinocembrin-7-methylether
(-)-
pinostrobin
PubMed:
Anti-staphylococcal activity of C-methyl flavanones from propolis of Australian stingless bees (Tetragonula carbonaria) and fruit resins of Corymbia torelliana (Myrtaceae).
PubMed:
Pinostrobin and Cajanus lactone isolated from Cajanus cajan (L.) leaves inhibits TNF-α and IL-1β production: In vitro and in vivo experimentation.
PubMed:
Probing the interaction of a therapeutic flavonoid, pinostrobin with human serum albumin: multiple spectroscopic and molecular modeling investigations.
PubMed:
Flavonoids from the leaves of Carya cathayensis Sarg. inhibit vascular endothelial growth factor-induced angiogenesis.
PubMed:
Variation in contents of main active components and antioxidant activity in leaves of different pigeon pea cultivars during growth.
PubMed:
Quantification of three chiral flavonoids with reported bioactivity in selected licensed Canadian natural health products and US marketed dietary supplements.
PubMed:
The antiproliferative effect of pinostrobin on human umbilical vein endothelial cells (HUVEC).
PubMed:
Evaluation of biological activities of Alpinia mutica Roxb. and its chemical constituents.
PubMed:
Rational discovery of dengue type 2 non-competitive inhibitors.
PubMed:
Stereospecific analytical method development and preliminary in vivo pharmacokinetic characterization of pinostrobin in the rat.
PubMed:
HPLC determination of the major active flavonoids and GC-MS analysis of volatile components of Dysphania graveolens (Amaranthaceae).
PubMed:
Protective effects of pinostrobin on β-amyloid-induced neurotoxicity in PC12 cells.
PubMed:
Cytotoxicity and antimicrobial activity of the methanol extract and compounds from Polygonum limbatum.
PubMed:
[Chemical constituents of Carya cathayensis and their antitumor bioactivity].
PubMed:
Antitumor constituents from the leaves of Carya cathayensis.
PubMed:
A new hydrochalcone from Miliusa sinensis.
PubMed:
¹H-NMR simultaneous identification of health-relevant compounds in propolis extracts.
PubMed:
Determination of pinostrobin in rat plasma by LC-MS/MS: application to pharmacokinetics.
PubMed:
The methanolic extract of Boesenbergia rotunda (L.) Mansf. and its major compound pinostrobin induces anti-ulcerogenic property in vivo: possible involvement of indirect antioxidant action.
PubMed:
Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition.
PubMed:
[Determination of 5-hydroxy-7-methoxyflavan in Daemonorops draco by HPLC].
PubMed:
Phytochemical and cytotoxic investigations of Alpinia mutica rhizomes.
PubMed:
[Chemical constituents from seeds of Alpinia katsumadai, inhibition on NF-kappaB activation and anti-tumor effect].
PubMed:
Activity investigation of pinostrobin towards herpes simplex virus-1 as determined by atomic force microscopy.
PubMed:
Chemical composition of the SFE-CO extracts from Cajanus cajan (L.) Huth and their antimicrobial activity in vitro and in vivo.
PubMed:
Pinostrobin from Cajanus cajan (L.) Millsp. inhibits sodium channel-activated depolarization of mouse brain synaptoneurosomes.
PubMed:
Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents.
PubMed:
Ethnobotanical survey and cytotoxicity testing of plants of South-western Nigeria used to treat cancer, with isolation of cytotoxic constituents from Cajanus cajan Millsp. leaves.
PubMed:
Bioactivity of flavonoids isolated from Lychnophora markgravii against Leishmania amazonensis amastigotes.
PubMed:
Pinostrobin from Boesenbergia pandurata is an inhibitor of Ca2+-signal-mediated cell-cycle regulation in the yeast Saccharomyces cerevisiae.
PubMed:
Antioxidant activities of extracts and main components of Pigeonpea [Cajanus cajan (L.) Millsp.] leaves.
PubMed:
[Studies on chemical constituents and antibacterial activity from n-butanol extract of Sarcandra glabra].
PubMed:
Negative ion 'chip-based' nanospray tandem mass spectrometry for the analysis of flavonoids in glandular trichomes of Lychnophora ericoides Mart. (Asteraceae).
PubMed:
Docking of noncompetitive inhibitors into dengue virus type 2 protease: understanding the interactions with allosteric binding sites.
PubMed:
Efficacy of extracting solvents to chemical components of kava (Piper methysticum) roots.
PubMed:
Induction of apoptosis by ginger in HEp-2 cell line is mediated by reactive oxygen species.
PubMed:
An unusual homoisoflavanone and a structurally-related dihydrochalcone from Polygonum ferrugineum (Polygonaceae).
PubMed:
Inhibitory activity of cyclohexenyl chalcone derivatives and flavonoids of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease.
PubMed:
Pinostrobin--an anti-leukemic flavonoid from Polygonum lapathifolium L. ssp. nodosum (Pers.) Dans.
PubMed:
DPPH free radical scavenger components from the fruits of Alpinia rafflesiana Wall. ex. Bak. (Zingiberaceae).
PubMed:
Antiplasmodial constituents of Cajanus cajan.
PubMed:
Trypanocidal activity of Lychnophora staavioides Mart. (Vernonieae, Asteraceae).
PubMed:
Antiprotozoal activity of the constituents of Teloxys graveolens.
PubMed:
Separation of some chiral flavanones by micellar electrokinetic chromatography.
PubMed:
Pinostrobin from honey and Thai ginger (Boesenbergia pandurata): a potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes.
PubMed:
[Flavonoids from Beijing propolis].
PubMed:
Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme.
PubMed:
Anti-inflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata.
PubMed:
Structural analysis of a novel antimutagenic compound, 4-Hydroxypanduratin A, and the antimutagenic activity of flavonoids in a Thai spice, fingerroot (Boesenbergia pandurata Schult.) against mutagenic heterocyclic amines.
PubMed:
Cytotoxic mechanism of flavonoid from Temu Kunci (Kaempferia pandurata) in cell culture of human mammary carcinoma.
PubMed:
Effects of pinostrobin on estrogen metabolism and estrogen receptor transactivation.
PubMed:
The effects of chrysin and pinostrobin, two flavonoids isolated from Teloxys graveolens leaves, on isolated guinea-pig ileum.
PubMed:
Methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate, major insecticidal principle from Piper guanacastensis.
PubMed:
Smooth muscle relaxing flavonoids and terpenoids from Conyza filaginoides.
PubMed:
Redox intermediates of flavonoids and caffeic acid esters from propolis: an EPR spectroscopy and cyclic voltammetry study.
PubMed:
[Flavonoids of Artemisia campestris, ssp. glutinosa].
PubMed:
On the local anaesthetic action of propolis and some of its constituents.