(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one

CAS: 477-90-7 C14 H16 O9 MW: 328.27432000

Identification

Namebergenin
CAS Number477-90-7
FDA UNIIL84RBE4IDC
Molecular FormulaC14 H16 O9
Molecular Weight328.27432000
MDL NumberMFCD00133120
Nikkaji NumberJ475.124H

Regulatory

Physical Properties

Appearance white needle-like crystalline powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 658.95 °C. @ 760.00 mm Hg (est)
Flash Point 483.00 °F. TCC ( 250.70 °C. ) (est)
logP (o/w) -1.398 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
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

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

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Potential Uses

None Found

Natural Occurrence

bergenia ciliata bergenia ligulata

Synonyms

bengenin cuscutin pyrano[3,2-c][2]benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, (2R,3S,4S,4aR,10bS)- (2R,3S,4S,4aR,10bS)-3,4,8,10- tetrahydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one (2R,3S,4S,4aR,10bS)-3,4,8,10- tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one (2R,3S,4S,4aR,10bS)-3,4,8,10- tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one PubMed: Comparative antioxidant and antiplasmodial activities of 11-O-galloylbergenin and bergenin isolated from Bergenia ligulata. PubMed: An LC-MS/MS method for the simultaneous determination and pharmacokinetic studies of bergenin, chlorogenic acid and four flavonoids in rat plasma after oral administration of a QingGanSanJie decotion extract. PubMed: Chemical constituents from the roots of Leea thorelii Gagnep. PubMed: In vivo and in vitro antimalarial activity of bergenin. PubMed: Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: the synthesis of bergenin. PubMed: Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition. PubMed: Extraction of quercetin from Herba Lysimachiae by molecularly imprinted-matrix solid phase dispersion. PubMed: Cancer chemopreventive effect of bergenin from Peltophorum pterocarpum wood. PubMed: Identification and characterization of human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of bergenin. PubMed: The stem bark extracts of Cenostigma macrophyllum attenuates tactile allodynia in streptozotocin-induced diabetic rats. PubMed: Evaluation of the wound healing activity of Shorea robusta, an Indian ethnomedicine, and its isolated constituent(s) in topical formulation. PubMed: Structure-activity relationships for bergenin analogues as β-secretase (BACE1) inhibitors. PubMed: In vivo metabolism study of bergenin in rats by HPLC-QTOF mass spectrometry. PubMed: A novel lactone from Tripterospermum chinense. PubMed: [Chemical constituents of Ardisia punctata]. PubMed: Chemical constituents of Caesalpinia decapetala (Roth) Alston. PubMed: Investigation of the mechanisms of improved oral bioavailability of bergenin using bergenin-phospholipid complex. PubMed: [Bergenia genus - content matters and biological activity]. PubMed: [Chemical constituents from Astilbe myriantha]. PubMed: [Chemical constituents and antibacterial activity contained in Caesalpinia millettii]. PubMed: Chemical constituents of Arisaema franchetianum tubers. PubMed: Synthesis and biological evaluation of bergenin analogues as mushroom tyrosinase inhibitors. PubMed: Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition. PubMed: [Trace chemical constituents contained in Trachelospermum jasminoides and structure identification]. PubMed: A new bergenin derivative from the rhizome of Ardisia gigantifolia. PubMed: Isolation of antitrypanosomal compounds from Vitis repens, a medicinal plant of Myanmar. PubMed: Microarray-based mRNA expression profiling of leukemia cells treated with the flavonoid, casticin. PubMed: Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α. PubMed: Antioxidant and anti-α-glucosidase compounds from the rhizome of Peltiphyllum peltatum (Torr.) Engl. PubMed: Biologically active bergenin derivatives from Bergenia stracheyi. PubMed: Formulation and evaluation of novel coated floating tablets of bergenin and cetirizine dihydrochloride for gastric delivery. PubMed: Type 2 antidiabetic activity of bergenin from the roots of Caesalpinia digyna Rottler. PubMed: Cardioprotective activity of standardized extract of Ficus racemosa stem bark against doxorubicin-induced toxicity. PubMed: Phytochemical, antioxidant and anti-α-glucosidase activity evaluations of Bergenia cordifolia. PubMed: Antinociceptive properties of bergenin. PubMed: Practical synthesis and biological evaluation of bergenin analogs. PubMed: [Studies on anti-tumor metastatic constituents from Ardisia Crenata]. PubMed: Synthesis and antiglycation potentials of bergenin derivatives. PubMed: Isointricatinol, a new antioxidant homoisoflavonoid from the roots of Caesalpinia digyna Rottler. PubMed: Chemical constituents and in vitro antioxidant activity of Phyllanthus wightianus. PubMed: Evaluation of antioxidant and antimicrobial activities of Bergenin and its derivatives obtained by chemoenzymatic synthesis. PubMed: Two new antioxidant bergenin derivatives from the stem of Rivea hypocrateriformis. PubMed: [Studies on the chemical constituents from Cissus pteroclada]. PubMed: Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica. PubMed: Chemical constituents from Astilbe chinensis. PubMed: [Comparative studies on content of arbutin, bergenin and catechin in different part of Bergenia purpurascens and B. crassifolia]. PubMed: Anti-inflammatory, cyclooxygenase inhibitory and antioxidant activities of standardized extracts of Tridax procumbens L. PubMed: Radical scavenging and angiotensin converting enzyme inhibitory activities of standardized extracts of Ficus racemosa stem bark. PubMed: Comparative in vitro bioactivities of tea extracts from six species of Ardisia and their effect on growth inhibition of HepG2 cells. PubMed: Oral characteristics of bergenin and the effect of absorption enhancers in situ, in vitro and in vivo. PubMed: A new lignan dimer from Mallotus philippensis. PubMed: Two-Step Enzymatic Modification of Solid-Supported Bergenin in Aqueous and Organic Media. PubMed: New phenolic glycosides from Securinega virosa and their antioxidant activity. PubMed: Preparation, characterization and in vivo evaluation of bergenin-phospholipid complex. PubMed: How to easily replace the independent atom model - the example of bergenin, a potential anti-HIV agent of traditional Asian medicine. PubMed: Two new megastigmane sulphonoglucosides from Mallotus anisopodus. PubMed: Differential free radical scavenging activity and radioprotection of caesalpinia digyna extracts and its active constituent. PubMed: Reactions of hydroxyl radical with bergenin, a natural poly phenol studied by pulse radiolysis. PubMed: [Studies on the chemical constituents from Cissus assamica]. PubMed: Peltophorum africanum, a traditional South African medicinal plant, contains an anti HIV-1 constituent, betulinic acid. PubMed: Quantitation of bergenin in human plasma by liquid chromatography/tandem mass spectrometry. PubMed: Determination of bergenin in human plasma after oral administration by HPLC-MS/MS method and its pharmacokinetic study. PubMed: Antioxidant activity of (+)-bergenin: a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae). PubMed: Physicochemical properties of bergenin. PubMed: Improving activity of salt-lyophilized enzymes in organic media. PubMed: Characterization of interaction between bergenin and human serum albumin in membrane mimetic environments. PubMed: [Kinetics study on intestinal absorption of bergenin in rats]. PubMed: Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb. PubMed: Separation and evaluation of free radical-scavenging activity of phenol components of green, brown, and black leaves of Bergenia crassifolia by using HPTLC-DPPH* method. PubMed: Antioxidant activity of Caesalpinia digyna root. PubMed: [Content determination of bergenin in Ardisia pusilla by HPLC]. PubMed: Electrochemical study of bergenin on a poly(4-(2-pyridylazo)-resorcinol) modified glassy carbon electrode and its determination in tablets and urine. PubMed: Determination of bergenin in rat plasma by high-performance liquid chromatography. PubMed: Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis--a flow cytometric study. PubMed: Pharmacognostical and physicochemical characteristics of roots of lesser known medicinal plant caesalpinia digyna rottl. PubMed: Chemical constituents and antioxidant activity of Mallotus roxburghianus leaves. PubMed: Direct solubilization of enzyme aggregates with enhanced activity in nonaqueous media. PubMed: Effects of Astilbe thunbergii rhizomes on wound healing Part 1. Isolation of promotional effectors from Astilbe thunbergii rhizomes on burn wound healing. PubMed: Determination and pharmacokinetic study of bergenin in rat plasma by RP-HPLC method. PubMed: Three new flavonol glycosides from the aerial parts of Rodgersia podophylla. PubMed: In vitro anti-HCV activities of Saxifraga melanocentra and its related polyphenolic compounds. PubMed: Anti-platelet aggregating and anti-oxidative activities of 11-O-(4'-O-methylgalloyl)-bergenin, a new compound isolated from Crassula cv. 'Himaturi'. PubMed: A carbon-carbon-coupled dimeric bergenin derivative biotransformed by Pleurotus ostreatus. PubMed: Evaluation of selected South African medicinal plants for inhibitory properties against human immunodeficiency virus type 1 reverse transcriptase and integrase. PubMed: PTP1B inhibitors from Ardisia japonica. PubMed: The genus Ardisia: a novel source of health-promoting compounds and phytopharmaceuticals. PubMed: [Study on constituents in rhizome of Astilbe chinensis]. PubMed: Trypanocidal activity of bergenin, the major constituent of Flueggea virosa, on Trypanosoma brucei. PubMed: Bergenin monohydrate from the rhizomae of Astilbe chinensis. PubMed: A new anti-inflammatory glucoside from Ficus racemosa L. PubMed: Antitumor effect of stilbenoids from Vateria indica against allografted sarcoma S-180 in animal model. PubMed: The influence of Sacoglottis gabonensis stem bark extract and its isolate bergenin, Nigerian alcoholic beverage additives, on the metabolic and haematological side effects of 2,4-dinitrophenyl hydrazine-induced tissue damage. PubMed: In vitro inhibitory effects of bergenin and norbergenin on bovine adrenal tyrosine hydroxylase. PubMed: [Advances in the study of Bergenia plants]. PubMed: [Studies on the chemical constituents in radix Astilbes chinensis]. PubMed: Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity. PubMed: Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata. PubMed: Short total synthesis of 8,10-di-O-methylbergenin. PubMed: Bergenin is the antiarrhythmic principle of Fluggea virosa. PubMed: Effects of bergenin, the major constituent of Mallotus japonicus against D-galactosamine-induced hepatotoxicity in rats. PubMed: Hopeafuran and a C-glucosyl resveratrol isolated from stem wood of Hopea utilis. PubMed: Protective effects of acetylbergenin against carbon tetrachloride-induced hepatotoxicity in rats. PubMed: [Bergenia crassifolia (L.) Fritsch in vitro]. PubMed: Simultaneous determination of bergenin and gallic acid in Bergenia ligulata wall by high-performance thin-layer chromatography. PubMed: Effects of acetylbergenin against D -galactosamine-induced hepatotoxicity in rats. PubMed: Hepatoprotective effects of bergenin, a major constituent of Mallotus japonicus, on carbon tetrachloride-intoxicated rats. PubMed: Host-mediated anticancer activities of tannins. PubMed: Protective effects of bergenin, the major constituent of Mallotus japonicus, on D-galactosamine-intoxicated rat hepatocytes. PubMed: Antihepatotoxic activity of bergenin, the major constituent of Mallotus japonicus, on carbon tetrachloride-intoxicated hepatocytes. PubMed: Biocatalytic combinatorial synthesis. PubMed: The evolution of biotransformation technologies. PubMed: Norepinephrine-augmenting lipolytic effectors from Astilbe thunbergii rhizomes. PubMed: Combinatorial biocatalysis: a natural approach to drug discovery. PubMed: Dammarane Triterpenes from the Leaves of Securinega melanthesoides PubMed: Antiulcer activity of naturally occurring pyrano-coumarin and isocoumarins and their effect on prostanoid synthesis using human colonic mucosa. PubMed: Constituents of Ardisia japonica and their in vitro anti-HIV activity. PubMed: Antihepatotoxic C-glycosylflavones from the leaves of Allophyllus edulis var. edulis and gracilis. PubMed: [Chemical constituents of Tibetan medicinal herb Rhodiola kirilowii (Reg.) Reg]. PubMed: The structure of bergenin. PubMed: [Quantitative analysis of bergenin in herba Ardisia japonica Bl by TLC-densitometric method]. PubMed: Synthesis of C-glycosylarenes by way of internal reactions of benzylated and benzoylated carbohydrate derivatives. PubMed: [Studies on the chemical constituents of Ardisia crenata Sims]. PubMed: Isolation of Bergenin from Barks of Syzygium cumini. PubMed: [The chemical constituents of Ardisia crenata Sims]. PubMed: [HPLC determination of bergenin in Astilbe chinensis (Maxim.) Franch. et Sav. and Bergenia purpurascens (Hook. F. et Thoms.) Engl]. PubMed: [The identification and total synthesis of aichasu, an antitussive agent (author's transl)]. PubMed: Effects of bergenin on experimental ulcers--prevention of stress induced ulcers in rats. PubMed: [Bergenin. 1. Antiulcerogenic activities of bergenin].