daphnetin

7,8-dihydroxycoumarin

CAS: 486-35-1 C9 H6 O4 MW: 178.14362000

Identification

Namedaphnetin
IUPAC7,8-dihydroxychromen-2-one
CAS Number486-35-1
FDA UNIIXC84571RD2
Molecular FormulaC9 H6 O4
Molecular Weight178.14362000
MDL NumberMFCD00016977
Nikkaji NumberJ6.008I
Beilstein0009372

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 262.00 °C. @ 760.00 mm Hg
Boiling Point 430.38 °C. @ 760.00 mm Hg (est)
Flash Point 364.00 °F. TCC ( 184.50 °C. ) (est)
logP (o/w) 0.884 (est)
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 429 mg/kg
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

Categorycosmetic agents
Recommendation for daphnetin usage levels up tonot for fragrance use.
Recommendation for daphnetin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

celery chickpea shoot sagina japonica watermelon seed

Synonyms

2H-1- benzopyran-2-one, 7,8-dihydroxy- 2H-1- benzopyran-2-one, 7,8-dihydroxy- (9CI) coumarin, 7,8-dihydroxy- daphnetol 7,8- dihydroxy-2H-1-benzopyran-2-one 7,8- dihydroxy-2H-chromen-2-one 7,8- dihydroxy-chromen-2-one 7,8- dihydroxy-coumarin 7,8- dihydroxychromen-2-one 7,8- dihydroxycoumarin PubMed: Immunosuppressive Activity of Daphnetin, One of Coumarin Derivatives, Is Mediated through Suppression of NF-κB and NFAT Signaling Pathways in Mouse T Cells. PubMed: Daphnetin attenuates microglial activation and proinflammatory factor production via multiple signaling pathways. PubMed: The effects of Glycyrrhizae uralenis and its major bioactive components on pharmacokinetics of daphnetin in Cortex daphnes in rats. PubMed: Protective effects of daphnetin on sodium taurocholate‑induced severe acute pancreatitis in rats. PubMed: Total synthesis of six 3,4-unsubstituted coumarins. PubMed: Daphnetin, a natural coumarin derivative, provides the neuroprotection against glutamate-induced toxicity in HT22 cells and ischemic brain injury. PubMed: Antioxidant and intestinal anti-inflammatory effects of plant-derived coumarin derivatives. PubMed: 7,8-dihydroxycoumarin may promote sciatic nerve regeneration by suppressing NF-κB expression in mice. PubMed: 7,8-Dihydroxycoumarin inhibits A549 human lung adenocarcinoma cell proliferation by inducing apoptosis via suppression of Akt/NF-κB signaling. PubMed: Coumarins of Matricaria chamomilla L.: aglycones and glycosides. PubMed: 7,8-Dihydroxy coumarin promotes chondrogenic differentiation of adipose-derived mesenchymal stem cells. PubMed: Isolation and characterization of polyphenol oxidase from Sardinian poisonous and non-poisonous chemotypes of Ferula communis (L.). PubMed: Potent α-glucosidase and protein tyrosine phosphatase 1B inhibitors from Artemisia capillaris. PubMed: [Chemical constituents from rhizome of Daphne papyracea var. crassiuscula]. PubMed: Neurotrophic effects of 7,8-dihydroxycoumarin in primary cultured rat cortical neurons. PubMed: Inhibitory activity of coumarins from Artemisia capillaris against advanced glycation endproduct formation. PubMed: Daphnetin methylation stabilizes the activity of phosphoribulokinase in wheat during cold acclimation. PubMed: Biotransformation of hydroxycoumarin derivatives by cultured suspension cells of Catharanthus roseus. PubMed: Daphnetin prevents chronic unpredictable stress-induced cognitive deficits. PubMed: The therapeutic effects of daphnetin in collagen-induced arthritis involve its regulation of Th17 cells. PubMed: Efficacy of Daphne oleoides subsp. kurdica used for wound healing: identification of active compounds through bioassay guided isolation technique. PubMed: [Analysis of metabolites of daphnetin in the intestinal wall of rats by liquid chromatography and quatrupole-time of flight mass spectrometry]. PubMed: Regulatory effect of daphnetin, a coumarin extracted from Daphne odora, on the balance of Treg and Th17 in collagen-induced arthritis. PubMed: [Chemical constituents of Daphne odora var. margirmta]. PubMed: [Effects of glycyrrhiza extract on pharmacokinetics property of daphnetin in rats]. PubMed: Differential effects of esculetin and daphnetin on in vitro cell proliferation and in vivo estrogenicity. PubMed: [Biotransformation of daphnetin by suspension transgenic hairy roots of Polygonum multiflorum]. PubMed: Potential utility of daphnetin as a novel treatment for pemphigus vulgaris. PubMed: [Studies on the chemical constituents from Daphne tangutica]. PubMed: Novel insights into the mechanism of decreased expression of type X collagen in human mesenchymal stem cells from patients with osteoarthritis cultured on nitrogen-rich plasma polymers: implication of cyclooxygenase-1. PubMed: Identification and characterization of human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of daphnetin. PubMed: [Intestinal absorption of daphnetin by rats single pass perfusion in situ]. PubMed: Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships. PubMed: Effect of chemical enhancers on percutaneous absorption of daphnetin in isopropyl myristate vehicle across rat skin in vitro. PubMed: Crystal structures of rat catechol-O-methyltransferase complexed with coumarine-based inhibitor. PubMed: Therapeutic effects of daphnetin on adjuvant-induced arthritic rats. PubMed: Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin. PubMed: In vitro potentiation of antimalarial activities by daphnetin derivatives against Plasmodium falciparum. PubMed: [In vitro effect of daphnetin on cytochrome C oxidase and ribonucleotide reductase of plasmodium falciparum]. PubMed: Determination of kava lactones and flavonoid glycoside in Scorzonera austriaca by capillary zone electrophoresis. PubMed: Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). PubMed: [Studies on the chemical constituents in roots of Daphne odora var. atrocaulis]. PubMed: Comparative study on schizontocidal activity of recrystallized or crude daphnetin against malaria parasites. PubMed: Solid-phase extraction of esculetin from the ash bark of Chinese traditional medicine by using molecularly imprinted polymers. PubMed: [Additive therapeutic effect of a combination of artemether and daphnetin against Plasmodium berghei in mice]. PubMed: Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. PubMed: Iron chelator daphnetin against Pneumocystis carinii in vitro. PubMed: Binding of the bioactive component daphnetin to human serum albumin demonstrated using tryptophan fluorescence quenching. PubMed: Bioactivity guided isolation of antifungal compounds from the liverwort Bazzania trilobata (L.) S.F. Gray. PubMed: Spectrofluorimetric study of the binding of daphnetin to bovine serum albumin. PubMed: Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase. PubMed: [Effect of daphnetin on SOD activity and DNA synthesis of Plasmodium falciparum in vitro]. PubMed: Identification and characterisation of the chinese herb Langdu by LC-MS/MS analysis. PubMed: [Effect of daphnetin on the exo-erythrocytic stage of rodent malaria]. PubMed: The schizontocidal activity of daphnetin against malaria parasites in vitro and in vivo. PubMed: In vitro antimalarial effect of daphnetin relating to its iron-chelating activity. PubMed: [Anti-hemolytic and anti-membranous lipid peroxidation effects of daphnetin]. PubMed: Daphnetin methylation by a novel O-methyltransferase is associated with cold acclimation and photosystem II excitation pressure in rye. PubMed: In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines. PubMed: Coumarin glucosides from Cruciata taurica. PubMed: Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L. PubMed: In vitro inhibitory effects of Daphne oleoides ssp. oleoides on inflammatory cytokines and activity-guided isolation of active constituents. PubMed: [Sensitization and crossreaction of simple coumarins]. PubMed: Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor. PubMed: [Scavenging effects of daphnetin and its Cu, Zn complexes on superoxide radical]. PubMed: [Chemical constituents of Stellera chamaejasme L]. PubMed: Studies on the preparation of bioactive lignans by oxidative coupling reaction. IV. Oxidative coupling reaction of methyl (E)-3-(3,4-dihydroxy-2-methoxyphenyl)propenoate and lipid peroxidation inhibitory effects of the produced lignans. PubMed: Antimalarial quinones: redox potential dependence of methemoglobin formation and heme release in erythrocytes. PubMed: [Preparation method and quality control of compound Daphne injection]. PubMed: Activated oxygen generation by a primaquine metabolite: inhibition by antioxidants derived from Chinese herbal remedies. PubMed: Daphnetin: a novel antimalarial agent with in vitro and in vivo activity. PubMed: [Effect of daphnetin on lipoprotein cholesterol content of serum]. PubMed: The sensitizing capacity of coumarins (II). PubMed: [Antithrombotic effect of daphnetin in the rat]. PubMed: Inhibition of the formation of 5-hydroxy-6,8,11,14-eicosatetraenoic acid from arachidonic acid in polymorphonuclear leukocytes by various coumarins. PubMed: [The relationship between daphnetin analgesia and central neurotransmitters of monoamines]. PubMed: [Metabolism and pharmacokinetics of daphnetin]. PubMed: Characteristics of coumarin metabolism by liver microsomes from cobalt-pretreated mice. PubMed: Isolation of daphnetin-8-beta-glucoside from Daphne acuminata. PubMed: Isolation of daphnetin-8-beta-glucoside from Daphne papyracea.