Basic information
- CAS
22255-40-9- Standard SMILES
C[C@@H]1[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C(C(=O)O)[C@H]2C[C@@H]1O- InChIKey
JNNGEAWILNVFFD-CDJYTOATSA-N- Molecular formula
- C16H24O10
- Average molar mass
- 376.36 g/mol
- Monoisotopic mass
- 376.13694696
Overview
Loganic acid is 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. It has a role as a plant metabolite. It is a glucoside, a cyclopentapyran and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a loganate.
Names & identifiers
- Preferred name
- Loganic Acid
- IUPAC
- (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-carboxylic acid
- English name
- Loganic acid
- Molecular formula
- C16H24O10
- Molecular weight
- 376.36
Names & synonyms
Loganic acid22255-40-9UX3J3KK2UG(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-carboxylic acidCHEBI:30632DTXSID80944913(1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid(1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylic acid(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-carboxylic acidRefChem:153948DTXCID801373242244-875-9
Show more names
LoganateloganicaciMargannic acidLoganic acid-RMLOGANIC ACID hplcLOGANIC ACID WITH HPLCLoganic acid (Standard)Fluoroestradiol Impurity 37
Loganin acidMFCD00017417(1S,4aS,6S,7R,7aS)-6-Hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acidNorloganin(1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acidLoganic-acidEINECS 244-875-9Spectrum_001509
Properties
Computed structural properties
- XLogP
- -1.7
- Topological polar surface area
- 166 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 565
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Physicochemical properties
- Boiling point
- 646.3 · 646.3±55.0 °C(Predicted)
- Density
- 1.6 · 1.60±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in methan
- form
- powder
- pka
- 4.55 · 4.55±0.70(Predicted)
- color
- White-beige
- Major Application
- metabolomicsvitamins, 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 · -2.411 (est)
- FDA UNII
- 3 J3KK2UG · UX3J3KK2UG
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionLoganic 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.
UsesLoganic Acid is found to be present in both the fermented fruits and brines. Exhibits antioxidant activity.
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
成都市久鼎化学技术有限公司18584079237 · [email protected]
上海如吉生物科技发展有限公司
Related reactions
0 records
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Compound notes
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