18524-94-2

Basic information

• Product Name: Loganin
• Synonyms: (1S,4aS,6S,7R,7aS)-1-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-Methylcyclopenta[c]pyran-4-carboxylic Acid Methyl Ester;NSC 606403;Meliatin;Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-Methyl-,Methyl ester, (1S,4aS,6S,7R,7aS)-;Loganin, >=98%;methyl [1S-(1alpha,4aalpha,6alpha,7alpha,7a.alpha.)]-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylate;Cuchiloside;LOGANIN hplc
• CAS NO: 18524-94-2
• Molecular Formula: C₁₇H₂₆O₁₀
• Molecular Weight: 390.38
• EINECS: 242-398-0
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Iridoids;LChromatography;Alphabetic;Chemical Class;Herbal DrugsAnalytical Standards;Life Sciences Standards;Natural Compounds;Natural CompoundsChemical Class;Natural Terpene Standards;Carbohydrates & Derivatives;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 18524-94-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 222°C
• Boiling Point: 608.8 °C at 760 mmHg
• Flash Point: 217.9 °C
• Appearance: /
• Density: 1.5 g/cm³
• Vapor Pressure: 2.31E-17mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.80±0.70(Predicted)
• Water Solubility: Completely soluble in water
• Merck: 14,5560
• BRN: 55724
• CAS DataBase Reference: Loganin(CAS DataBase Reference)
• NIST Chemistry Reference: Loganin(18524-94-2)
• EPA Substance Registry System: Loganin(18524-94-2)

Safety Data

• Statements: 22
• Safety Statements: 22-45-24/25
• RIDADR: 1544
• WGK Germany: 3
• F: 3-10-23
• Hazardous Substances Data: 18524-94-2(Hazardous Substances Data)

Usage

Uses

Loganin is an iridoid glycoside that exhibits protective effects against hepatic injury and other diabetic complications associated with abnormal metabolic states and inflammation caused by oxidative stress and advanced glycation endproduct formation.

Definition

ChEBI: An iridoid monoterpenoid isolated from the plant species of the genus Cornus.

InChI:InChI=1/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3

Upstream product

• 20586-11-2 loganin pentaacetate 
• 67-56-1 methanol 
• 82509-41-9 loganic acid 
• 389806-47-7 loganigenin-1β-O-β-D-glucopyranosyl-6'-O-β-D-glucopyranoside 
• 139501-37-4 Ligustrinoside 
• 71462-04-9 1,6-di-O-acetylloganol 
• 26660-57-1 desoxy lognanin 
• 124-41-4 sodium methylate 
• 20586-11-2 2',3',4',6',7-penta-O-acetylloganin 
• 80054-38-2 C₁₀H₁₅⁽³⁾HO₂ 
• 186581-53-3 diazomethane 

Downstream Products

• 76703-84-9 2',3',4',6'-tetra-O-acetylloganin 
• 20586-11-2 2',3',4',6',7-penta-O-acetylloganin 
• 29748-10-5 methyl-(1R,6S,7R)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate 
• 50-99-7 D-glucose 
• 938053-35-1 loganin 
• 99891-77-7 Acetic acid (4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydro-cyclopenta[c]pyran-6-yl ester 
• 99946-04-0 isoboonein 
• 132339-37-8 4-epi-Alyxialactone 
• 132237-63-9 alyxialactone 
• 82509-41-9 loganic acid 

Related news

Loganin (cas 18524-94-2) protects against hydrogen peroxide-induced apoptosis by inhibiting phosphorylation of JNK, p38, and ERK 1/2 MAPKs in SH-SY5Y cells09/27/2019

We investigated the mechanisms underlying the protective effects of loganin against hydrogen peroxide (H2O2)-induced neuronal toxicity in SH-SY5Y cells. The neuroprotective effect of loganin was investigated by treating SH-SY5Y cells with H2O2 and then measuring the reduction in H2O2-induced apo...detailed

Loganin (cas 18524-94-2) attenuates diabetic nephropathy in C57BL/6J mice with diabetes induced by streptozotocin and fed with diets containing high level of advanced glycation end products09/25/2019

AimsDiabetic nephropathy is the most common cause of end-stage renal disease in patients with diabetes. Advanced glycation end-products (AGEs) play a prominent role in the development of diabetic nephropathy. We herein evaluated the effects of loganin on diabetic nephropathy in vivo.detailed

Loganin (cas 18524-94-2) enhances long-term potentiation and recovers scopolamine-induced learning and memory impairments09/10/2019

Although the incidence rate of dementia is rapidly growing in the aged population, therapeutic and preventive reagents are still suboptimal. Various model systems are used for the development of such reagents in which scopolamine is one of the favorable pharmacological tools widely applied.Logan...detailed

Loganin (cas 18524-94-2) possesses neuroprotective properties, restores SMN protein and activates protein synthesis positive regulator Akt/mTOR in experimental models of spinal muscular atrophy09/09/2019

Spinal muscular atrophy (SMA) is an autosomal recessive neurodegenerative disease characterized by motor neurons degeneration and muscular atrophy. There is no effective SMA treatment. Loganin is a botanical candidate with anti-inflammatory, anti-oxidant, glucose-lowering and anti-diabetic nephr...detailed

Effect of Loganin (cas 18524-94-2) on experimental diabetic nephropathy09/07/2019

Connective tissue growth factor (CTGF) plays a pathogenic role in diabetic nephropathy (DN). Loganin, an iridoid glucoside compound was isolated from Cornus officinalis Sieb. et Zucc. This study was conducted to investigate the efficacy of loganin on DN and to elucidate the potential mechanism. ...detailed

Parentucellia latifolia subsp. latifolia: A potential source for Loganin (cas 18524-94-2) iridoids by HPLC-ESI-MSn technique09/06/2019

This study attempts to compare the pharmaceutical potential (antioxidant and key enzyme inhibition of clinical relevance) of organic and aqueous extracts of Parentucellia latifolia (L.) Caruel subsp. latifolia (L.) Caruel as well as phytochemical composition. The phytochemical compounds were eva...detailed

Loganin (cas 18524-94-2) inhibits the inflammatory response in mouse 3T3L1 adipocytes and mouse model☆09/05/2019

Atherosclerosis is a chronic inflammatory disease of the vascular walls. ApoCIII is an independent factor which promotes atherosclerotic processes. This study aimed to investigate whether Loganin administration inhibits the inflammatory response in vitro and in vivo. In the apoCIII-induced mouse...detailed

Relevant articles and documents

7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures

The activity of 7-deoxyloganin 7-hydroxylase, an enzyme catalyzing the conversion of 7-deoxyloganin into loganin, was detected in a microsomal preparation from the cell suspension cultures of Lonicera japonica. It was dependent on NADPH and molecular oxyg

An iridoid glucoside from Jasminum hemsleyi

A new iridoid glucoside, jashemsloside E, was isolated from the leaves of Jasminum hemsleyi. Its structure was elucidated on the basis of chemical and spectral data.

IRIDOID GLUCOSIDES FROM MELAMPYRUM

Melampyrum arvense and M. cristatum contain, besides aucubin, 8-epiloganin and melampyroside, a new natural iridoid glucoside: gardoside methyl ester.In addition, M. arvense contains mussaenoside and M. cristatum mussaenosidic acid, another novel iridoid glucoside. - Key Word Index: Melampyrum arvense; M. cristatum; Scrophulariaceae; iridoid glucosides; gardoside methyl ester; mussaenosidic acid; aucubin; 8-epiloganin; mussaenoside; melampyroside.

Ligustrinoside, a new bisiridoid glucoside from Strychnos ligustrina

A new bisiridoid glucoside, ligustrinoside (1), along with three known iridoids, loganin, loganetin and loganic acid was isolated from the wood of Strychnos ligustrina Bl. (Loganiaceae), collected in Indonesia. The structure of ligustrinoside (1) has been determined as an ester dimmer of loganin and loganic acid between C-7 and C-11.

Iridoids from Symphoricarpos albus

Twelve compounds including secologanin, loganin, the aglycon of loganin, and a new iridoid called glucologanin were isolated from fruit of common snowberry Symphoricarpos albus (L.) Blake. The structure of glucologanin was confirmed using PMR and mass spe