| Identification | Back Directory | [Name]
LOGANIC ACID | [CAS]
22255-40-9 | [Synonyms]
Loganate
Norloganin
loganicaci
LOGANIC ACID
LOGANIC ACID hplc
LOGANIC ACID WITH HPLC
Loganic acid >=95% (LC/MS-ELSD)
Loganic acid, 98%, from Cornus officinalis Sieb. & Zucc.
(1S)-1α-(β-D-Glucopyranosyloxy)-6α-hydroxy-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid
Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, (1S,4aS,6S,7R,7aS)-
[1S-(1α,4aα,6α,7α,7aα)]-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid
[1S-(1a,4aa,6a,7a,7aa)]-1-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid
[1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha)]-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid
(1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-D-Glucopyranosylox y)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carb oxylic acid | [EINECS(EC#)]
244-875-9 | [Molecular Formula]
C16H24O10 | [MDL Number]
MFCD00017417 | [MOL File]
22255-40-9.mol | [Molecular Weight]
376.36 |
| Chemical Properties | Back Directory | [Boiling point ]
646.3±55.0 °C(Predicted) | [density ]
1.60±0.1 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
Soluble in methan | [form ]
powder | [pka]
4.55±0.70(Predicted) | [color ]
White-beige | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChIKey]
JNNGEAWILNVFFD-CDJYTOATSA-N | [SMILES]
C[C@H]1[C@@H](O)C[C@H]2[C@@H]1[C@@H](OC=C2C(O)=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O | [LogP]
-2.411 (est) |
| Hazard Information | Back Directory | [Description]
Loganic acid is an iridoid glycoside that has been found in C. mas and has diverse biological activities, including antidiabetic, antiadipogenic, anti-atherosclerotic, and anti-inflammatory properties.1,2,3,4 Loganic acid (1 μM) stimulates glucagon-like peptide-1 (GLP-1) secretion by NCI H716 human enteroendocrine colorectal cancer cells.2 It inhibits dexamethasone-, 3-isobutyl-1-methylxanthine-, and insulin-induced differentiation of mouse 3T3-L1 fibroblasts into adipocytes when used at a concentration of 10 μg/ml.3 Loganic acid (20 mg/kg per day) decreases the plasma atherogenic index, a ratio of triglyceride to HDL cholesterol, and the cardiac risk ratio, a ratio of total cholesterol to HDL cholesterol, in a rabbit model of atherosclerosis induced by a cholesterol-rich diet.4 It also decreases IL-6, TNF-α, and oxidized LDL (oxLDL) plasma levels in the same model. | [Chemical Properties]
Off-white crystalline powder, soluble in methanol, derived from Gentiana macrophylla. | [Uses]
Loganic Acid is found to be present in both the fermented fruits and brines. Exhibits antioxidant activity. | [Definition]
ChEBI: A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively | [References]
[1] CARMINE J. COSCIA Luigi B Rocco Guarnaccia. Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis[J]. Biochemistry Biochemistry, 1969, 8 12: 5036-5043. DOI: 10.1021/bi00840a054
[2] HYO-WEON SUH . A bitter herbal medicine Gentiana scabra root extract stimulates glucagon-like peptide-1 secretion and regulates blood glucose in db/db mouse[J]. Journal of ethnopharmacology, 2015, 172: Pages 219-226. DOI: 10.1016/j.jep.2015.06.042
[3] EUNKUK PARK. Antiadipogenic Effects of Loganic Acid in 3T3-L1 Preadipocytes and Ovariectomized Mice.[J]. Molecules, 2018, 23 7. DOI: 10.3390/molecules23071663
[4] TOMASZ SOZA?SKI . Iridoid–loganic acid versus anthocyanins from the Cornus mas fruits (cornelian cherry): Common and different effects on diet-induced atherosclerosis, PPARs expression and inflammation[J]. Atherosclerosis, 2016, 254: Pages 151-160. DOI: 10.1016/j.atherosclerosis.2016.10.001 |
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