LOGANIC ACID Chemical Properties

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)

Safety Information

WGK Germany 

3

Storage Class

11 - Combustible Solids

LOGANIC ACID Usage And Synthesis

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. Loganic acid (1 μM) stimulates glucagon-like peptide-1 (GLP-1) secretion by NCI H716 human enteroendocrine colorectal cancer cells. 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. 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. 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

LOGANIC ACID(22255-40-9)Related Product Information

• Loganin
• Isobutyl vinyl ether
• 1,1-Dimethoxyoctane
• 1,8-Octanediol
• BUTYL-BETA-D-GLUCOPYRANOSIDE
• n-Octyl-β-D-glucopyranoside
• 1,4-Butanediol vinyl ether
• VINYLCYCLOPENTANE
• HEPTYL-BETA-D-GLUCOPYRANOSIDE
• CYCLOPENTYLACETIC ACID
• 3,4-DIHYDRO-2-METHOXY-2H-PYRAN
• 3-ETHOXYMETHACROLEIN
• HEPTANAL DIMETHYL ACETAL
• 3-ETHOXYACRYLIC ACID
• LOGANIC ACID
• HEXANAL DIMETHYL ACETAL
• N-OCTYLMONOOXYETHYLENE
• 2-ETHOXY-3,4-DIHYDRO-2H-PYRAN