| Name: | methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-car |
| CAS Number: | 18524-94-2 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 242-398-0 |
| FDA UNII: | H7WJ16Q93C |
| Nikkaji Web: | J13.561E |
| Beilstein Number: | 0055724 |
| MDL: | MFCD00075645 |
| XlogP3-AA: | -1.40 (est) |
| Molecular Weight: | 390.38622000 |
| Formula: | C17 H26 O10 |
| 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:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 608.80 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 424.00 °F. TCC ( 217.90 °C. ) (est)
|
| logP (o/w): | -2.730 (est) |
| Soluble in: |
| | water, 1.00E+05 mg/L @ 20 °C (exp) | | | water, 3.536e+005 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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 loganin usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for loganin 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 :87691 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-car |
| Chemidplus:0018524942 |
References:
| | methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-car |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 87691 |
| Pubchem (sid): | 135042863 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | loganoside | | | methyl (1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate |
Articles:
| PubMed:Kinetic and molecular docking studies of loganin and 7-O-galloyl-D-sedoheptulose from Corni Fructus as therapeutic agents for diabetic complications through inhibition of aldose reductase. |
| PubMed:Effect of Acute Administration of loganin on Spatial Memory in Diabetic Male Rats. |
| PubMed:Effect of loganin on experimental diabetic nephropathy. |
| PubMed:Hepato-protective effects of loganin, iridoid glycoside from Corni Fructus, against hyperglycemia-activated signaling pathway in liver of type 2 diabetic db/db mice. |
| PubMed:β-Secretase (BACE1) inhibitory property of loganin isolated from Corni fructus. |
| PubMed:Loganin protects against hydrogen peroxide-induced apoptosis by inhibiting phosphorylation of JNK, p38, and ERK 1/2 MAPKs in SH-SY5Y cells. |
| PubMed:Evaluation of loganin, iridoid glycoside from Corni Fructus, on hepatic and renal glucolipotoxicity and inflammation in type 2 diabetic db/db mice. |
| PubMed:[Determination of loganin in Pterocephalus hookeri by HPLC]. |
| PubMed:The pharmacological effects of morroniside and loganin isolated from Liuweidihuang Wan, on MC3T3-E1 cells. |
| PubMed:Loganin improves learning and memory impairments induced by scopolamine in mice. |
| PubMed:Bioactive constituents of Corni Fructus: The therapeutic use of morroniside, loganin, and 7-O-galloyl-D-sedoheptulose as renoprotective agents in type 2 diabetes. |
| PubMed:Cognitive-enhancing activity of loganin isolated from Cornus officinalis in scopolamine-induced amnesic mice. |
| PubMed:Preparative purification of morroniside and loganin from Fructus corni by combination of macroporous absorption resin and HSCCC. |
| PubMed:[Comparative study on decoction and dissolution of crude and processed corni fructus]. |
| PubMed:[Determination of loganin and paeonol in Liuwei Dihuang pills by HPLC amalgamated of double UV waves]. |
| PubMed:[Studies on absorption mechanism of loganin in intestines of rats]. |
| PubMed:Bioactive compounds from Cornus officinalis fruits and their effects on diabetic nephropathy. |
| PubMed:Microbial metabolism of loganin by intestinal bacteria and identification of new metabolites in rat. |
| PubMed:Comparison of pharmacokinetic behavior of two iridoid glycosides in rat plasma after oral administration of crude Cornus officinals and its jiuzhipin by high performance liquid chromatography triple quadrupole mass spectrometry combined with multiple reactions monitoring mode. |
| PubMed:Morroniside and loganin extracted from Cornus officinalis have protective effects on rat mesangial cell proliferation exposed to advanced glycation end products by preventing oxidative stress. |
| PubMed:HPLC study of tissue distribution of loganin in rats. |
| PubMed:[Studies on pharmacokinetics of loganin and morroniside in Cornus officinalis injection in mice]. |
| PubMed:[RP-HPLC determination of loganin in mouse plasma and its pharmacokinetics]. |
| PubMed:HPLC-DAD method for comprehensive quality control of Semen Strychni. |
| PubMed:Loganin and new iridoid glucosides in Gentiana pedicellata. |
| PubMed:[Study on chemical constituents of iridoids from eucommiae folium]. |
| PubMed:Secologanin synthase which catalyzes the oxidative cleavage of loganin into secologanin is a cytochrome P450. |
| PubMed:[Chemical constituents of Dipsacus asper]. |
| PubMed:Effect of metal cationization on the low-energy collision-induced dissociation of loganin, epi-loganin and ketologanin studied by electrospray ionization tandem mass spectrometry |
| PubMed:[Determination of loganin in the fruit of Cornus officinalis Sieb. et Zucc]. |
| PubMed:[Determination of loganin in Cornus officinalis Sieb. et Zucc. by TLC scanner]. |
| PubMed:Pharmacokinetics of the main compounds absorbed into blood after oral administration of Liu Wei Di Huang Wan, a typical combinatorial intervention of Chinese medical formula. |
| PubMed:Regulation of vincamine biosynthesis and associated growth promoting effects through abiotic elicitation, cyclooxygenase inhibition, and precursor feeding of bioreactor grown Vinca minor hairy roots. |
| PubMed:Induction and analysis of the alkaloid mitragynine content of a Mitragyna speciosa suspension culture system upon elicitation and precursor feeding. |
| PubMed:Cytotoxic activity of Guettarda pohliana Müll. Arg. (Rubiaceae). |
| PubMed:[Study on the correlation between the quality of Cornus officinalis and the contents of the inorganic elements in the planting soil]. |
| PubMed:[Quickly investigating the absorption ingredients of Gentianae Radix et Rhizoma by SEMAC]. |
| PubMed:Loganin from Mytragyna parvifolia Korth. |
| PubMed:Loganin from Mytragyna parvifolia Korth. |
| PubMed:Assessing the limitations to terpenoid indole alkaloid biosynthesis in Catharanthus roseus hairy root cultures through gene expression profiling and precursor feeding. |
| PubMed:Anti-inflammatory activity of iridoids and verbascoside isolated from Castilleja tenuiflora. |
| PubMed:The Role of 9- and/or 10-oxygenated Derivatives of Geraniol, Geranial, Nerol, and Neral in the Biosynthesis of Loganin and Ajmalicine. |
| PubMed:Enzymic synthesis of loganin by carboxyl group methylation of loganic acid. |
| PubMed:[On the incorporation of loganin into gentiopicroside]. |
| PubMed:Alkaloid biosynthesis. 13. The structure, stereochemistry, and biosynthesis of loganin. |
| PubMed:[Loganin. II]. |
| PubMed:Limitation of mitragynine biosynthesis in Mitragyna speciosa (Roxb.) Korth. through tryptamine availability. |
| PubMed:[Study on the best concentration of combination of the effects of the four original constituents of liu-wei di-huang pill on the proliferation and differentiation of rat preadipocyte]. |
| PubMed:Neuroprotective iridoid glycosides from Cornus officinalis fruits against glutamate-induced toxicity in HT22 hippocampal cells. |
| PubMed:UPLC-TOF-MS Characterization and Identification of Bioactive Iridoids in Cornus mas Fruit. |
| PubMed:Geniposide and its iridoid analogs exhibit antinociception by acting at the spinal GLP-1 receptors. |
| PubMed:[Optimum harvest study of Gentiana crassicaulis in Ludian]. |
| PubMed:Isolation and screened neuroprotective active constituents from the roots and rhizomes of Valeriana amurensis. |
| PubMed:Optimization of the extraction process for the seven bioactive compounds in Yukmijihwang-tang, an herbal formula, using response surface methodology. |
| PubMed:[Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum]. |
| PubMed:LC/MS/MS determination and pharmacokinetic studies of six compounds in rat plasma following oral administration of the single and combined extracts of Eucommia ulmoides and Dipsacus asperoides. |
| PubMed:Growth inhibiting activity of lipophilic extracts from Dipsacus sylvestris Huds. roots against Borrelia burgdorferi s. s. in vitro. |
| PubMed:[UFLC-PDA fingerprint of Tibetan medicine Pterocephalus hookeir]. |
| PubMed:[Optimization of microwave-assisted extraction with RSM and HPLC determination for three iridoid glycosides in Cornus officinalis]. |
| PubMed:[Isolation and identification of nine iridoid glycosides from Lamiophlomis rotata by HPLC combining PDA and MS]. |
| PubMed:[Determination of dissolution of liuwei dihuang concentrated pills based on multi-index components]. |
| PubMed:[Studies on the chemical constituents from stems and leaves of Lonicera macranthoides]. |
| PubMed:Anti-inflammatory and analgesic activities of SKLJI, a highly purified and injectable herbal extract of Lonicera japonica. |
| PubMed:Allergy-preventive effects of chlorogenic acid and iridoid derivatives from flower buds of Lonicera japonica. |
| PubMed:Suppression of camptothecin biosynthetic genes results in metabolic modification of secondary products in hairy roots of Ophiorrhiza pumila. |
| PubMed:[Chemical constituents from twigs and leaves of Melodinus hemsleyanus]. |
| PubMed:[Chemical constituents from twigs and leaves of Melodinus hemsleyanus]. |
| PubMed:Preparative isolation and purification of iridoid glycosides from Fructus Corni by high-speed countercurrent chromatography. |
| PubMed:Rapid simultaneous identification and determination of the multiple compounds in crude Fructus Corni and its processed products by HPLC-MS/MS with multiple reaction monitoring mode. |
| PubMed:A new flavonoid and other polar compounds from Galeopsis angustifolia Ehrh. ex Hoffm. |
| PubMed:Beneficial Effect of 7-O-Galloyl-D-sedoheptulose, a Polyphenol Isolated from Corni Fructus, against Diabetes-Induced Alterations in Kidney and Adipose Tissue of Type 2 Diabetic db/db Mice. |
| PubMed:Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro. |
| PubMed:Simultaneous determination of four shanzhiside methylester derivatives in rabbit plasma by liquid chromatography/tandem mass spectrometry. |
| PubMed:Coumarin glycosides and iridoid glucosides with neuroprotective effects from Hydrangea paniculata. |
| PubMed:Analysis of the interactions of multicomponents in Cornus officinalis Sieb. et Zucc. with human serum albumin using on-line dialysis coupled with HPLC. |
| PubMed:[Chemical constituents of glucoside fraction from Liuwei Dihuang Gantang]. |
| PubMed:Simultaneous determination of four marker components in Yukmijihwang Tang by high performance liquid chromatography/diode array detector. |
| PubMed:A new iridoid glycoside from the roots of Dipsacus asper. |
| PubMed:A Review of the Ethnobotany and Pharmacological Importance of Alstonia boonei De Wild (Apocynaceae). |
| PubMed:The butanol fraction of guava (Psidium cattleianum Sabine) leaf extract suppresses MMP-2 and MMP-9 expression and activity through the suppression of the ERK1/2 MAPK signaling pathway. |
| PubMed:Lamiridosins, hepatitis C virus entry inhibitors from Lamium album. |
| PubMed:Metabolism of ginsenoside Rb1 by human intestinal microflora and cloning of its metabolizing β-D-glucosidase from Bifidobacterium longum H-1. |
| PubMed:Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters. |
| PubMed:[Function of getting rid of cores of Cornus officinalis Sieb. et Zucc. and studies on method of processing in producing area]. |
| PubMed:[Promoting effect of constituents in plasma after oral administration of liuwei dihuangwan on proliferation of rat osteoblast]. |
| PubMed:[Investigation of JinKui ShenQi pills by ultraviolet spectra and tandem mass spectrometry]. |
| PubMed:Antiprotozoal activity of Melampyrum arvense and its metabolites. |
| PubMed:The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of α,β-unsaturated enol esters. |
| PubMed:Precursor limitations in methyl jasmonate-induced Catharanthus roseus cell cultures. |
| PubMed:Effects of terpenoid precursor feeding on Catharanthus roseus hairy roots over-expressing the alpha or the alpha and beta subunits of anthranilate synthase. |
| PubMed:Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. |
| PubMed:Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii. |
| PubMed:Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique. |
| PubMed:[Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites]. |
| PubMed:Fructus Corni suppresses hepatic gluconeogenesis related gene transcription, enhances glucose responsiveness of pancreatic beta-cells, and prevents toxin induced beta-cell death. |
| PubMed:Isolation and identification of hemostatic ingredients from Lamiophlomis rotata (Benth.) Kudo. |
| PubMed:Quantitative and qualitative determination of Liuwei Dihuang tablets by HPLC-UV-MS-MS. |
| PubMed:Effect of precursor feeding on alkaloid accumulation by a tryptophan decarboxylase over-expressing transgenic cell line T22 of Catharanthus roseus. |
| PubMed:Iridoids from Gentiana loureirii. |
| PubMed:Chemical fingerprinting of Liuwei Dihuang Pill and simultaneous determination of its major bioactive constituents by HPLC coupled with multiple detections of DAD, ELSD and ESI-MS. |
| PubMed:Cornel iridoid glycoside promotes neurogenesis and angiogenesis and improves neurological function after focal cerebral ischemia in rats. |
| PubMed:[Terpenoid glycosides from stem of Luculia pinceana]. |
| PubMed:Iridoidic pattern in endemic Sardinian plants: the case of Galium species. |
| PubMed:A comparative chemotaxonomic study on Vinca sardoa steam and Vinca difformis pourret. |
| PubMed:7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures. |
| PubMed:Simultaneous determination of four bioactive constituents in Liuwei Dihuang Pills by micellar electrokinetic chromatography. |
| PubMed:Simultaneous quantification of seven bioactive components in Caulis Lonicerae Japonicae by high performance liquid chromatography. |
| PubMed:[A new indole alkaloid glycoside from stems of Nauclea officinalis]. |
| PubMed:[Determination of glycosides in traditional Chinese medicine liu-wei di-huang by RP-HPLC]. |
| PubMed:seco-iridoids from Calycophyllum spruceanum (Rubiaceae). |
| PubMed:Analysis of three effective components in Fructus corni and its preparations by micellar electrokinetic capillary chromatography. |
| PubMed:Coelobillardin, an iridoid glucoside dimer from Coelospermum billardieri. |
| PubMed:Iridoid glycosides from Lonicera quinquelocularis. |
| PubMed:2,4-D and alkaloid accumulation in periwinkle cell suspensions. |
| PubMed:Iridoids and secoiridoids from Guettarda platypoda. |
| PubMed:Phenolic and bis-iridoid glycosides from Strychnos cocculoides. |
| PubMed:Determination of sweroside in rat plasma and bile for oral bioavailability and hepatobiliary excretion. |
| PubMed:An approach based on HPLC-fingerprint and chemometrics to quality consistency evaluation of Liuwei Dihuang Pills produced by different manufacturers. |
| PubMed:Simultaneous determination of six active components in crude and processed Fructus Corni by high performance liquid chromatography. |
| PubMed:Determination of metabolic rate-limitations by precursor feeding in Catharanthus roseus hairy root cultures. |
| PubMed:Iridoids from Loasa acerifolia. |
| PubMed:Determination of five major iridoid glucosides in Flos Lonicerae by high-performance liquid chromatography coupled with evaporative light scattering detection. |
| PubMed:Response of generalist and specialist insects to qualitative allelochemical variation. |
| PubMed:On the chemical constituents of Dipsacus asper. |
| PubMed:The inhibitory effect of the components of Cornus officinalis on melanogenesis. |
| PubMed:Role of the non-mevalonate pathway in indole alkaloid production by Catharanthus roseus hairy roots. |
| PubMed:Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonauclea sessilifolia. |
| PubMed:Iridoids from Lippia graveolens. |
| PubMed:Phytochemistry and the systematics and ecology of Loasaceae and Gronoviaceae (Loasales). |
| PubMed:A new secoiridoid glycoside from Lonicera angustifolia. |
| PubMed:Pyridine monoterpene alkaloid formation from iridoid glycosides. A novel PMTA dimer from geniposide. |
| PubMed:Structural considerations on the iridoids as anti-inflammatory agents. |
| PubMed:Effect of terpenoid precursor feeding and elicitation on formation of indole alkaloids in cell suspension cultures of Catharanthus roseus. |
| PubMed:Iridoids from Scaevola racemigera1. |
| PubMed:[Further investigations regarding distribution and structure of the bitter principles from Menyanthes trifoliata]. |
| PubMed:Simultaneous qualitation and quantification of thirteen bioactive compounds in Flos lonicerae by high-performance liquid chromatography with diode array detector and mass spectrometry. |
| PubMed:Metabolomic analysis of Strychnos nux-vomica, Strychnos icaja and Strychnos ignatii extracts by 1H nuclear magnetic resonance spectrometry and multivariate analysis techniques. |
| PubMed:[Study on enrichment process of Cornus officinalis glycosides with macroporous resin and active carbon]. |
| PubMed:Iridoids from Phlomis aurea Decne growing in Egypt. |
| PubMed:Studies on the constituents of Lonicera species. XVII. New iridoid glycosides of the stems and leaves of Lonicera japonica THUNB. |
| PubMed:Cantleyoside-dimethyl-acetal and other iridoid glucosides from Pterocephalus perennis--antimicrobial activities. |
| PubMed:[Chemical investigation of genus Hedyotis. II. Isolation and identification of iridoids from Hedyotis chrysotricha]. |
| PubMed:Transformation of naturally-occurring 1,9-trans-9,5-cis sweroside to all trans sweroside during acetylation of sweroside aglycone. |
| PubMed:Influence of Precursor Availability on Alkaloid Accumulation by Transgenic Cell Line of Catharanthus roseus |
| PubMed:Analysis of several iridoid and indole precursors of terpenoid indole alkaloids with a single HPLC run. |
| PubMed:Iridoids: a new class of leishmanicidal agents from Nyctanthes arbortristis. |
| PubMed:[Plants in New Caledonia. Iridoids from Scaevola montana Labill]. |
| PubMed:4'-P-Coumaroyl Iridoid Glucosides from Gentiana pedicellata. |
| PubMed:Stereochemical studies of enzymic C-methylations. |
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