kadsurenone
6(2H)-benzofuranone, 2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propen-1-yl)-, (2S,3R,3aS)-
Identification
| Name | kadsurenone |
| IUPAC | (2S,3R,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one |
| CAS Number | 95851-37-9 |
| FDA UNII | Search |
| Molecular Formula | C21 H24 O5 |
| Molecular Weight | 356.41828000 |
| MDL Number | MFCD00869351 |
| Nikkaji Number | J39.403C |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 491.10 °C. @ 760.00 mm Hg (est) |
| Flash Point | 418.00 °F. TCC ( 214.20 °C. ) (est) |
| logP (o/w) | 2.870 (est) |
| Soluble in | water, 39.51 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 kadsurenone usage levels up to | not for fragrance use. |
| Recommendation for kadsurenone flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
5-
allyl-2-(3,4-dimethoxy-phenyl)-3a-methoxy-3-methyl-3,3a-dihydro-2H-benzofuran-6-one
(2S,3R,3aS)-5-
allyl-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-3,3a-dihydro-1-benzofuran-6(2H)-one
6(2H)-
benzofuranone, 2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propen-1-yl)-, (2S,3R,3aS)-
denudatin B
(2S-(2alpha,3beta,3aalpha))-2-(3,4-
dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propenyl)-6(2H)-benzofuranone
(2S,3R,3aS)-2-(3,4-
dimethoxyphenyl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
PubMed:
Development of an LC-MS/MS method for quantification of kadsurenone in rat plasma and its application to a pharmacokinetic study.
PubMed:
Platelet-activating factor (PAF)-antagonists of natural origin.
PubMed:
[Neolignans and lignan from Piper wallichii].
PubMed:
Pharmacokinetics of kadsurenone and its interaction with cyclosporin A in rats using a combined HPLC and microdialysis system.
PubMed:
[Advances in pharmacological study of Piper kadsura (Choisy) Ohwi].
PubMed:
Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings: a convergent synthesis of diverse benzofuran neolignans.
PubMed:
Platelet-activating factor antagonists.
PubMed:
The biological activity of acetylated sphingosylphosphorylcholine derivatives.
PubMed:
[Recent progress in the study of anti-PAF (platelet activating factor) constituents of medicinal herbs].
PubMed:
[Anti-platelet activating factor constituents, 2,5-diaryltetrahydrofuran type lignans, from Piper futokadsura Sied. et Zucc].
PubMed:
Trimucytin: a collagen-like aggregating inducer isolated from Trimeresurus mucrosquamatus snake venom.
PubMed:
Stimulation of human polymorphonuclear leukocytes by leukotriene B4 and platelet-activating factor: an ultrastructural and pharmacological study.
PubMed:
[PAF antagonistic benzofuran neolignans from Piper kadsura].
PubMed:
PAF antagonism in vitro and in vivo by aglafoline from Aglaia elliptifolia Merr.
PubMed:
Stimulation of tumour necrosis factor release by cytotoxic analogues of platelet-activating factor.
PubMed:
Antagonism of platelet-activating factor-induced increase in cytosolic free calcium concentration in human endothelial cells.
PubMed:
Platelet-activating factor (PAF) receptor antagonists inhibit arachidonic acid induced platelet aggregation in rabbit whole blood.
PubMed:
Comparison of the actions of some platelet-activating factor antagonists on platelets and aortic smooth muscles.
PubMed:
Inhibition of immune complex-induced enteropathy by three different platelet-activating factor receptor antagonists.
PubMed:
The rational search for natural neolignans.
PubMed:
Pharmacologic characterization of the rabbit neutrophil receptor for platelet-activating factor.
PubMed:
Vasorelaxing effect in rat thoracic aorta caused by denudatin B, isolated from the Chinese herb, magnolia fargesii.
PubMed:
Lipophilicity force field profile: an expressive visualization of the lipophilicity molecular potential gradient.
PubMed:
Distinct stimulatory effect of platelet-activating factor on prostaglandin I2 and thromboxane A2 biosynthesis by rat dental pulp.
PubMed:
Inhibition of thrombin- and collagen-induced phosphoinositides breakdown in rabbit platelets by a PAF antagonist--denudatin B, an isomer of kadsurenone.
PubMed:
Development of specific functionally active receptors for platelet-activating factor in HL-60 cells following granulocytic differentiation.
PubMed:
Kadsurenone and other related lignans as antagonists of platelet-activating factor receptor.
PubMed:
Further characterization of PAF receptor and novel antagonists.
PubMed:
Acute microcirculatory effects of platelet-activating factor.
PubMed:
Antagonism of platelet activating factor-induced chemiluminescence in guinea-pig peritoneal macrophages in differing states of activation.
PubMed:
PAF-receptor. 1. 'Cache-oreilles' effect of selected high-potency platelet-activating factor (PAF) antagonists.
PubMed:
Pharmacologic modulation of D-49 phospholipase A2-induced paw edema in the mouse.
PubMed:
Preliminary studies on phospholipase A2-induced mouse paw edema as a model to evaluate antiinflammatory agents.
PubMed:
Antagonism of Paf-induced oedema formation in rabbit skin: a comparison of different antagonists.
PubMed:
Platelet activating factor is a potent colonic secretagogue with actions independent of specific PAF receptors.
PubMed:
Platelet-activating factor-induced calcium mobilization in human platelets and neutrophils: effects of PAF-acether antagonists.
PubMed:
[The isolation and identification of PAF inhibitors from Piper wallichii (Miq.) Hand-Mazz and P. hancei Maxim].
PubMed:
Platelet-activating factor stimulates arachidonic acid metabolism in rat liver cells (C-9 cell line) by a receptor-mediated mechanism.
PubMed:
Metabolism of kadsurenone and 9,10-dihydrokadsurenone in rhesus monkeys and rat liver microsomes.
PubMed:
Enhanced human monocyte cytotoxicity by platelet-activating factor.
PubMed:
Differential effect of platelet-activating factor (PAF) receptor antagonists on peptide and PAF-stimulated prostaglandin release in unilateral ureteral obstruction.
PubMed:
Inhibitory effect of platelet-activating factor (PAF) on luteinizing hormone-releasing hormone and somatostatin release from rat median eminence in vitro correlated with the characterization of specific PAF receptor sites in rat hypothalamus.
PubMed:
Effect of platelet activating factor on leukocyte-endothelial cell interactions.
PubMed:
Comparison of the platelet aggregation induced by three thrombin-like enzymes of snake venoms and thrombin.
PubMed:
Identification of platelet-activating factor receptors in P388D1 murine macrophages.
PubMed:
Vasoconstrictor effects of platelet-activating factor in the hamster cheek pouch microcirculation: dose-related relations and pathways of action.
PubMed:
Platelet-activating factor primes neutrophil responses to agonists: role in promoting neutrophil-mediated endothelial damage.
PubMed:
Effect of platelet-activating factor on microvascular permselectivity: dose-response relations and pathways of action in the hamster cheek pouch microcirculation.
PubMed:
Platelet activating factor receptor blockade enhances recovery after multifocal brain ischemia.
PubMed:
Effect of platelet activating factor antagonists on cultured rat mesangial cells.
PubMed:
Involvement of platelet-activating factor (PAF) in cerebral post-ischemic phase in Mongolian gerbils.
PubMed:
Specific receptor sites for platelet activating factor on rat liver plasma membranes.
PubMed:
Evaluation of PAF antagonists using human neutrophils in a microtiter plate assay.
PubMed:
Pharmacologic modulation of PAF-induced mortality in mice.
PubMed:
Pharmacological actions of WEB 2086, a new specific antagonist of platelet activating factor.
PubMed:
Pharmacologic antagonism of platelet activating factor and peptide leukotrienes inhibits guinea pig anaphylaxis.
PubMed:
Structure-activity relationships of kadsurenone analogues.
PubMed:
Species difference in the specific receptors of platelet activating factor.
PubMed:
Specific binding of [3H]dihydrokadsurenone to rabbit platelet membranes and its inhibition by the receptor agonists and antagonists of platelet-activating factor.
PubMed:
The inflammatory response of rabbit skin to topical arachidonic acid and its pharmacological modulation.
PubMed:
Characterization of platelet activating factor (PAF)-acether-induced contractions of guinea-pig lung strips by selected inhibitors of arachidonic acid metabolism and by PAF-acether antagonists.
PubMed:
Crystal and molecular structure of BN 52021, a PAF-acether antagonist. Comparison with the conformation of Kadsurenone and related compounds.
PubMed:
Relative roles of leukotrienes and platelet activating factor in experimentally-induced gastric ulceration.
PubMed:
Comparative effects of drugs on leukotrienes-, PAF-acether- and histamine- induced contractions of guinea-pig lung parenchymal strips.
PubMed:
[Neolignans from Piper hancei Maxim].
PubMed:
Specific inhibition of PAF-acether-induced platelet activation by BN 52021 and comparison with the PAF-acether inhibitors kadsurenone and CV 3988.
PubMed:
Kadsurenone distinguishes between different platelet activating factor receptor subtypes on macrophages and polymorphonuclear leucocytes.
PubMed:
Ionic and GTP regulation of binding of platelet-activating factor to receptors and platelet-activating factor-induced activation of GTPase in rabbit platelet membranes.
PubMed:
Release of platelet activating factor and its involvement in the first phase of carrageenin-induced rat foot edema.
PubMed:
Changes in cytosolic free calcium induced by platelet-activating factor in rabbit platelets: specific inhibition by BN 52021 and structurally related compounds.
PubMed:
Cardiovascular alterations in the rabbit infused with platelet activating factor (PAF): effect of kadsurenone, a PAF-receptor antagonist.
PubMed:
Inhibition of the platelet activating factor mediated component of guinea pig anaphylaxis by receptor antagonists.
PubMed:
trans-2,5-Bis-(3,4,5-trimethoxyphenyl)tetrahydrofuran. An orally active specific and competitive receptor antagonist of platelet activating factor.
PubMed:
[Antagonists of platelet activating factor].
PubMed:
Characterization of cutaneous vascular permeability induced by platelet-activating factor in guinea pigs and rats and its inhibition by a platelet-activating factor receptor antagonist.
PubMed:
Specific binding sites for platelet activating factor in human lung tissues.
PubMed:
Platelet activating factor (PAF) involvement in endotoxin-induced hypotension in rats. Studies with PAF-receptor antagonist kadsurenone.
PubMed:
Characterization of a platelet-activating factor receptor antagonist isolated from haifenteng (Piper futokadsura): specific inhibition of in vitro and in vivo platelet-activating factor-induced effects.
PubMed:
The isolation and characterization of kadsurenone from haifenteng (Piper futokadsura) as an orally active specific receptor antagonist of platelet-activating factor.