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gentiopicrin
1H,3H-pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)-

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Name:(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
CAS Number: 20831-76-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:244-070-2
FDA UNII: 0WE09Z21RC
Nikkaji Web:J40.726G
MDL:MFCD00075700
XlogP3-AA:-1.20 (est)
Molecular Weight:356.32820000
Formula:C16 H20 O9
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 191.00 °C. @ 760.00 mm Hg
Boiling Point: 667.80 °C. @ 760.00 mm Hg (est)
Flash Point: 477.00 °F. TCC ( 247.10 °C. ) (est)
logP (o/w): -3.170 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Gentiopicrin 98%
BOC Sciences
For experimental / research use only.
Gentiopicroside
Carbosynth
For experimental / research use only.
Gentiopicrin
ExtraSynthese
For experimental / research use only.
Gentiopicrin (HPLC) ≥95%
Glentham Life Sciences
Gentiopicroside
Shaanxi Y-Herb Biotechnology
Gentiopicrin Gentiopicroside Powder Chinese Gentian Root Extract 3% 5% 10% HPLC
Sigma-Aldrich: Sigma
For experimental / research use only.
Gentiopicrin ≥98% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for gentiopicrin usage levels up to:
 not for fragrance use.
 
Recommendation for gentiopicrin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :88708
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
Chemidplus:0020831769
 
References:
 (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):88708
Pubchem (sid):135047397
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09782
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
 gentiopicroside
1H,3H-pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)-
 

Articles:

PubMed:Evaluation of antioxidant and antibacterial activity of methanolic extracts of Gentiana kurroo royle.
PubMed:Comparative study on "long-dan", "qin-jiao" and their adulterants by HPLC analysis.
PubMed:[Optimum harvest study of Gentiana crassicaulis in Ludian].
PubMed:[Simultaneous determination of five iridoids in gentianae macrophyllae radix and their local variety by HPLC].
PubMed:Pharmacokinetic and excretion study of three secoiridoid glycosides and three flavonoid glycosides in rat by LC-MS/MS after oral administration of the Swertia pseudochinensis extract.
PubMed:Metabolic discrimination of Swertia mussotii and Swertia chirayita known as "Zangyinchen" in traditional Tibetan medicine by (1)H NMR-based metabolomics.
PubMed:Hepatoprotective effects of secoiridoid-rich extracts from Gentiana cruciata L. against carbon tetrachloride induced liver damage in rats.
PubMed:Evaluation of anticonvulsant, sedative, anxiolytic, and phytochemical profile of the methanol extract from the aerial parts of Swertia corymbosa (Griseb.) wight ex C.B. Clarke.
PubMed:Simultaneous determination of six index constituents and comparative analysis of four ethnomedicines from genus Gentiana using a UPLC-UV-MS method.
PubMed:A rapid and sensitive UFLC-MS/MS method for the simultaneous determination of gentiopicroside and swertiamarin in rat plasma and its application in pharmacokinetics.
PubMed:Application of quantitative 1H-NMR method to determination of gentiopicroside in Gentianae radix and Gentianae scabrae radix.
PubMed:Attenuation of reserpine-induced pain/depression dyad by gentiopicroside through downregulation of GluN2B receptors in the amygdala of mice.
PubMed:[Efficient method for analyzing absorbed ingredients of traditional Chinese medicine genitana macrophyllae radix].
PubMed:Combination of UHPLC/Q-TOF-MS, NMR spectroscopy, and ECD calculation for screening and identification of reactive metabolites of gentiopicroside in humans.
PubMed:Anti-diabetic activity of Swertia corymbosa (Griseb.) Wight ex C.B. Clarke aerial parts extract in streptozotocin induced diabetic rats.
PubMed:New analytical method for the study of the metabolism of gentiopicroside in rats after oral administration by LC-TOF-MS following picolinoyl derivatization.
PubMed:[Comparative study on pharmacokinetics of gentiopicroside and gentianae radix extract in rats].
PubMed:Rapid preparative separation of six bioactive compounds from Gentiana crassicaulis Duthie ex Burk. using microwave-assisted extraction coupled with high-speed counter-current chromatography.
PubMed:Microbial biotransformation of gentiopicroside by the endophytic fungus Penicillium crustosum 2T01Y01.
PubMed:Preparation, characterization, and in vivo pharmacokinetics of nanostructured lipid carriers loaded with oleanolic acid and gentiopicrin.
PubMed:Rigenolide A, a new secoiridoid glucoside with a cyclobutane skeleton, and three new acylated secoiridoid glucosides from Gentiana rigescens Franch.
PubMed:[Simultaneous determination of five constituents in eight Qingyedan species derived from Swertia plants by HPLC].
PubMed:Identification and determination of major constituents in a traditional Chinese medicine compound recipe Xiongdankaiming tablet using HPLC-PDA/ESI-MS(n) and HPLC-UV/ELSD.
PubMed:Identification of bio-active metabolites of gentiopicroside by UPLC/Q-TOF MS and NMR.
PubMed:Inhibition of vascular smooth muscle cell proliferation by Gentiana lutea root extracts.
PubMed:Spatial variation profiling of four phytochemical constituents in Gentiana straminea (Gentianaceae).
PubMed:Isolation and identification of constituents with activity of inhibiting nitric oxide production in RAW 264.7 macrophages from Gentiana triflora.
PubMed:Induction of apoptosis in human pancreatic MiaPaCa-2 cells through the loss of mitochondrial membrane potential (ΔΨm) by Gentiana kurroo root extract and LC-ESI-MS analysis of its principal constituents.
PubMed:In vitro inhibition and induction of human liver cytochrome P450 enzymes by gentiopicroside: potent effect on CYP2A6.
PubMed:[Determination and quality assessment of 10 ingredients gentiopicroside and sweroside and so on in Tibetan medicine Jia Di (Swertia chirayita)].
PubMed:Chemical profile, radical scavenging and cytotoxic activity of yellow gentian leaves (Genitaneae luteaefolium) grown in northern regions of Montenegro.
PubMed:[Callus cultivation and determination of gentiopicroside from Gentiana macrophylla].
PubMed:Hepatoprotective effects of Gentiana asclepiadea L. extracts against carbon tetrachloride induced liver injury in rats.
PubMed:[Chemical constituents of Aconitum tanguticum].
PubMed:[Transdermal behavior of effective constituents in xuanbi gel plaster].
PubMed:[Quickly investigating the absorption ingredients of Gentianae Radix et Rhizoma by SEMAC].
PubMed:Gentiopicroside attenuates morphine rewarding effect through downregulation of GluN2B receptors in nucleus accumbens.
PubMed:Inhibition of myeloperoxidase and antioxidative activity of Gentiana lutea extracts.
PubMed:An in vitro perspective to cholinesterase inhibitory and antioxidant activity of five Gentiana species and Gentianella caucasea.
PubMed:Potent Antifungal Activity of Pure Compounds from Traditional Chinese Medicine Extracts against Six Oral Candida Species and the Synergy with Fluconazole against Azole-Resistant Candida albicans.
PubMed:Determination of the plasma pharmacokinetic and tissue distributions of swertiamarin in rats by liquid chromatography with tandem mass spectrometry.
PubMed:[Study on the chemical constituents in roots of Gentiana dahurica].
PubMed:[Transdermal delivery of Gentiana macrophylla complex components system under micro-needle conditions].
PubMed:Introgression of the heterologous nuclear DNAs and efficacious compositions from Swertia tetraptera Maxim. into Bupleurum scorzonerifolium Willd. via somatic hybridization.
PubMed:Isolation of gentiopicroside from Gentianae Radix and its pharmacokinetics on liver ischemia/reperfusion rats.
PubMed:[Study on the quality and genetic diversity of Gentiana macrophylla pall of different habitats].
PubMed:Inhibitory effects of secoiridoids from the roots of Gentiana straminea on stimulus-induced superoxide generation, phosphorylation and translocation of cytosolic compounds to plasma membrane in human neutrophils.
PubMed:Development and validation of a LC-ESI-MS/MS method for the determination of swertiamarin in rat plasma and its application in pharmacokinetics.
PubMed:Introgression of Swertia mussotii gene into Bupleurum scorzonerifolium via somatic hybridization.
PubMed:Effect of Feining on bleomycin-induced pulmonary injuries in rats.
PubMed:[Preparation of gentiopicroside from the extract of Swertia mussotii Franch by preparative high performance liquid chromatography].
PubMed:Antibacterial and antifungal screening of Centaurium pulchellum crude extracts and main secoiridoid compounds.
PubMed:Analysis of iridoids, secoiridoids and xanthones in Centaurium erythraea, Frasera caroliniensis and Gentiana lutea using LC-MS and RP-HPLC.
PubMed:Concentrations of the active constituents of the Tibetan folk medicine Qinjiao (Gentiana sect. Cruciata) within and between taxonomic species across the Qinghai-Tibetan Plateau.
PubMed:[Determination of five active constituents in aerial part of Tibetan medicine Gentiana straminea by HPLC].
PubMed:New physiological function of secoiridoids: neuritogenic activity in PC12h cells.
PubMed:Anti-apoptotic activity of gentiopicroside in D-galactosamine/lipopolysaccharide-induced murine fulminant hepatic failure.
PubMed:[Simultaneous determination of four constituents in wild Gentiana lawrencei from Qinghai province by RP-HPLC].
PubMed:Simultaneous determination of four iridoid and secoiridoid glycosides and comparative analysis of Radix Gentianae Macrophyllae and their related substitutes by HPLC.
PubMed:DNA-damaging, mutagenic, and clastogenic activities of gentiopicroside isolated from Cephalaria kotschyi roots.
PubMed:[Determination of six active components in three species of genus Swertia by HPLC multiwavelength with detection].
PubMed:Sensitive determination of gentiopicroside in medicine and bio-fluids using luminol-myoglobin chemiluminescence combined with flow injection technique.
PubMed:Antimicrobial activity of Gentiana lutea L. extracts.
PubMed:Changes of gentiopicroside synthesis during somatic embryogenesis in Gentiana macrophylla.
PubMed:Further studies on the chemical constituents of Chinese folk medicine Gentiana apiata N.E. Br.
PubMed:Gentiopicrin-producing endophytic fungus isolated from Gentiana macrophylla.
PubMed:[Optimal technique of wine-processed gentian].
PubMed:[Studies on glycosides from Gentiana veitchiorum].
PubMed:[Chemical constituents from herbs of Swertia delavayi].
PubMed:Fagraldehyde, a secoiridoid isolated from Fagraea fragrans.
PubMed:Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro.
PubMed:[Enrichment process of gentiopicroside from the leaves of Gentiana macropylla with macroporous resin].
PubMed:Down-regulation of NR2B receptors partially contributes to analgesic effects of Gentiopicroside in persistent inflammatory pain.
PubMed:[Preparative separation of gentiopicrin from Radix Gentianae by high-speed counter-current chromatography with macroporous resin].
PubMed:[Determination of iridoids and triterpenes in herb of Swertia pseudochinesis by RP-HPLC].
PubMed:[Investigation on explovitage of Gentiana straminea].
PubMed:Somatic embryogenesis pathway for plant regeneration in Qinjiao (Gentiana macrophylla Pall.).
PubMed:Pharmacokinetic behavior of gentiopicroside from decoction of Radix Gentianae, Gentiana macrophylla after oral administration in rats: a pharmacokinetic comaprison with gentiopicroside after oral and intravenous administration alone.
PubMed:[Preparative separation of gentiopicrin from Gentiana scabra bunge by high speed counter current chromatography].
PubMed:[Determination of three glycosides from herbs of Swertia punicea by RP-HPLC].
PubMed:[Content of gentiopicroside and loganic acid in Radix gentianae and their fingerprints].
PubMed:Quantitative analysis of iridoids, secoiridoids, xanthones and xanthone glycosides in Gentiana lutea L. roots by RP-HPLC and LC-MS.
PubMed:Pharmacokinetics and bioavailability of gentiopicroside from decoctions of Gentianae and Longdan Xiegan Tang after oral administration in rats--comparison with gentiopicroside alone.
PubMed:In vivo pharmacokinetic and metabolism studies of ginsenoside Rd.
PubMed:Biotransformation of gentiopicroside by asexual mycelia of Cordyceps sinensis.
PubMed:[Simultaneous determination of six main constituents in Swertia of Qinghai Province and Sichuan Province by HPLC].
PubMed:Screening of plant extracts for antimicrobial activity against bacteria and yeasts with dermatological relevance.
PubMed:[Determination of ginsenoside rd in human plasma by LC/MS/MS].
PubMed:Genetic transformation of Gentiana macrophylla with Agrobacterium rhizogenes: growth and production of secoiridoid glucoside gentiopicroside in transformed hairy root cultures.
PubMed:[Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes].
PubMed:Genetic transformation of Centaurium erythraea Rafn by Agrobacterium rhizogenes and the production of secoiridoids.
PubMed:Effects of gentiopicroside, sweroside and swertiamarine, secoiridoids from gentian (Gentiana lutea ssp. symphyandra), on cultured chicken embryonic fibroblasts.
PubMed:[Studies on the chemical constituents in root of Gentiana macrophylla from Shaanxi].
PubMed:Isolation of iridoid and secoiridoid glycosides and comparative study on Radix gentianae and related adulterants by HPLC analysis.
PubMed:[HPLC fingerprinting of total glycosides of Swertia franchetiana].
PubMed:[Determination gentiopicrin in biyanqingdu granulae by SPE-HPLC].
PubMed:Mist trickling bioreactor for Centaurium erythraea Rafn growth of shoots and production of secoiridoids.
PubMed:Two new iridoid glycosides from the Tibetan folk medicine Swertia franchetiana.
PubMed:[Content determination of loganic acid and gentiopicroside in Tebitan herbal medicines Gentiana macrophylla and G. straminea by HPLC].
PubMed:[Determination of gentiopicroside in different morphological types of cultivated Gentiana manshurica population].
PubMed:[Determination and comparision of gentiopicroside of various parts of five species of genus Gentiana collected from Xinjiang by TLCS].
PubMed:Pharmacokinetics and tissue distribution of gentiopicroside following oral and intravenous administration in mice.
PubMed:[Influence of gentian leaf blight on the output and quality of Chinese gentian].
PubMed:Simultaneous determination of some active ingredients in anti-viral preparations of traditional Chinese medicine by micellar electrokinetic chromatography.
PubMed:[Comparative botanical and phytochemical investigations on the Gentiana species native to Hungary].
PubMed:Separation and determination of gentiopicroside and swertiamarin in Tibetan medicines by micellar electrokinetic electrophoresis.
PubMed:Pharmacological evaluation of several major ingredients of Chinese herbal medicines in human hepatoma Hep3B cells.
PubMed:Bioactivity of gentiopicroside from the aerial parts of Centaurium erythraea.
PubMed:[Studies on the metabolism of gentiopicroside by rat intestinal flora].
PubMed:Effects of Gentiana lutea ssp. symphyandra on the central nervous system in mice.
PubMed:Quantitative determination of secoiridoid glucosides in in vitro propagated plants of Gentiana davidii var. formosana by high performance liquid chromatography.
PubMed:Smooth muscle relaxing activity of gentiopicroside isolated from Gentiana spathacea.
PubMed:Quantitative determination of secoiridoid and gamma-pyrone compounds in Gentiana lutea cultured in vitro.
PubMed:Secoiridoid glycosides and an antifungal anthranilate derivative from Gentiana tibetica.
PubMed:Secoiridoids from Gentiana siphonantha.
PubMed:Hepatoprotective principles of Swertia japonica Makino on D-galactosamine/lipopolysaccharide-induced liver injury in mice.
PubMed:Acyl secoiridoids and antifungal constituents from Gentiana macrophylla.
PubMed:Determination of gentiopicroside, mangiferin, palmatine, berberine, baicalin, wogonin and glycyrrhizin in the traditional Chinese medicinal preparation sann-joong-kuey-jian-tang by high-performance liquid chromatography.
PubMed:[Chemical constituents of Swertia pubescens Franch].
PubMed:An acetophenone glycoside from Exacum affine.
PubMed:Suppression of chemically and immunologically induced hepatic injuries by gentiopicroside in mice.
PubMed:[Simultaneous determination of five bitter secoiridoid glycosides in nine Chinese Gentiana species used as the Chinese drug "long dan" by high performance liquid chromatography].
PubMed:Secoiridoid Glucosides Isolated from Gentiana gelida.
PubMed:Metabolism of gentiopicroside (gentiopicrin) by human intestinal bacteria.
PubMed:In vitro transformations of gentiopicroside and swertiamarin.
PubMed:6'-O-beta-D-Glucosyl Gentiopicroside: A New Secoiridoid from Gentiana asclepiadea.
PubMed:[High speed liquid chromatographic determination of gentiopicroside in radix Gentianae].
PubMed:[Isolation and identification of gentiopicroside from the roots of Gentiana triflora Pall].
PubMed:[General survey on medicinal plants of the Gentianaceae family in China].
PubMed:[Comparison of the gentiopicroside content and preparation of the root of Gentiana scabra collected in different seasons and in different growing years].
PubMed:[TLC-densitometry determination of bitter glycosides in the Chinese drug longdan, radix gentianae, and its quality evaluation].
PubMed:Desorption/Chemical ionization mass spectrometry of bitter glycosides from gentiana1.
PubMed:Gentiogenal, a conversion product of gentiopicrin (gentiopicroside)*.
PubMed:Studies on Iridoid-related Compounds III: Gentiopicral, the Aglucone of Gentiopicroside.
PubMed:A New Bitter Secoiridoid Glucoside from Gentiana scabra var. Buergeri.
PubMed:Gentiogenal, a new antimicrobial iridoid derived from gentiopicrin (gentiopicroside).
PubMed:Fungitoxic activity of the secoiridoid glucoside gentiopicrin (gentiopicroside).
PubMed:Secoiridoids and Xanthones in the genus Centaurium.
PubMed:[High-speed liquid chromatographic analysis of drugs. IX. Determination of gentiopicroside in Swertiae Herba (author's transl)].
PubMed:[High-speed liquid chromatographic analysis of drugs. VI. Rapid estimation of gentiopicroside in Gentianae scabrae radix and Gentianae radix (author's transl)].
PubMed:[Studies on crude drugs originated from Gentianaceous plants. VI. Contents of gentiopicroside in various parts of Gentiana scabra and accumulation of gentiopicroside in Gentiana triflora].
PubMed:[Studies on crude drugs originated from Gentianaceous plants. I. Determination of gentiopicroside, the bitter principle of Gentianae radix and Gentianae scabrae radix (author's transl)].
PubMed:Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis.
PubMed:[On the incorporation of loganin into gentiopicroside].
PubMed:The biological conversion of sweroside into gentiopicroside and vindoline and a biogenetic aspect of some indole alkaloids.
PubMed:Biosynthesis of gentiopicroside, a novel monoterpene.
PubMed:Studies on gentiopicrin.
PubMed:A preliminary study of the hydrolytic products of gentiopicrin by paper chromatography.
 
Notes:
a secoiridoid in gentiana with rearrangement to two pyran rings.
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