pinostrobin

4H-1-benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-methoxy-2-phenyl-, (S)-

CAS: 480-37-5 C16 H14 O4 MW: 270.28438000

Identification

Namepinostrobin
IUPAC(2S)-5-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
CAS Number480-37-5
EINECS207-548-1
FDA UNIISZD9LZS694
Molecular FormulaC16 H14 O4
Molecular Weight270.28438000
MDL NumberMFCD06858342
Nikkaji NumberJ196.197G
Beilstein270230

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for pinostrobin usage levels up tonot for fragrance use.
Recommendation for pinostrobin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

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.