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MedKoo Cat#: 599161 | Name: Loganic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Loganic acid is a naturally occurring iridoid monoterpeneglusoside with antidiabetic, antiadipogenic, anti-atherosclerotic, and anti-inflammatory properties. Loganic acid stimulates glucagon-like peptide-1 (GLP-1) secretion and inhibits dexamethasone-, 3-isobutyl-1-methylxanthine-, and insulin-induced differentiation. Loganic acid 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. It also decreases IL-6, TNF-α, and oxidized LDL (oxLDL) plasma levels in the same model.

Chemical Structure

Loganic acid
Loganic acid
CAS#22255-40-9

Theoretical Analysis

MedKoo Cat#: 599161

Name: Loganic acid

CAS#: 22255-40-9

Chemical Formula: C16H24O10

Exact Mass: 376.1369

Molecular Weight: 376.36

Elemental Analysis: C, 51.06; H, 6.43; O, 42.51

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 weeks
10mg USD 650.00 2 weeks
25mg USD 1,150.00 2 weeks
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Related CAS #
No Data
Synonym
Loganic acid; Loganin Acid, Loganate
IUPAC/Chemical Name
(1R,4aR,6R,7S,7aR)-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 acid
InChi Key
JNNGEAWILNVFFD-CAMJWXMVSA-N
InChi Code
InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9-,10+,11-,12+,13-,15-,16+/m1/s1
SMILES Code
O=C(C1=CO[C@H](O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@]3([H])[C@@]1([H])C[C@@H](O)[C@H]3C)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Loganic acid is an iridoid isolated from cornelian cherry fruits.
In vitro activity:
In vitro radical scavenging assays showed remarkable antioxidant activity of loganic acid in terms of DPPH scavenging (IC50 149 µg/ml), superoxide radical scavenging (IC50 632.43 µg/ml) and hydroxyl radical scavenging (IC50 29.78 µg/ml). Loganic acid exhibited 81% prevention of heavy metal toxicity through the mechanism of inhibiting ROS generation (2046 AU vs. 5264 AU in control) and lipid peroxidation (95.01%). Reference: Drug Chem Toxicol. 2022 Jan;45(1):239-249. https://pubmed.ncbi.nlm.nih.gov/31645139/
In vivo activity:
Loganic acid (20 mg/kg b.w.) and a mixture of anthocyanins (10 mg/kg b.w.) were administered orally for 60 days to rabbits fed with 1% cholesterol. Both loganic acid (an iridoid) and a mixture of anthocyanins diminished the formation of atherosclerotic plaques in the aorta. Reference: Adv Clin Exp Med. 2018 Nov;27(11):1505-1513. https://pubmed.ncbi.nlm.nih.gov/29790688/
Solvent mg/mL mM
Solubility
DMSO 37.5 99.64
Ethanol 20.0 53.14
PBS (pH 7.2) 10.0 26.57
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 376.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Dzydzan O, Brodyak I, Strugała-Danak P, Strach A, Kucharska AZ, Gabrielska J, Sybirna N. Biological Activity of Extracts of Red and Yellow Fruits of Cornus mas L.-An In Vitro Evaluation of Antioxidant Activity, Inhibitory Activity against α-Glucosidase, Acetylcholinesterase, and Binding Capacity to Human Serum Albumin. Molecules. 2022 Mar 30;27(7):2244. doi: 10.3390/molecules27072244. PMID: 35408646; PMCID: PMC9000679. 2. Abirami A, Sinsinwar S, Rajalakshmi P, Brindha P, Rajesh YBRD, Vadivel V. Antioxidant and cytoprotective properties of loganic acid isolated from seeds of Strychnos potatorum L. against heavy metal induced toxicity in PBMC model. Drug Chem Toxicol. 2022 Jan;45(1):239-249. doi: 10.1080/01480545.2019.1681445. Epub 2019 Oct 23. PMID: 31645139. 3. Park E, Lee CG, Lim E, Hwang S, Yun SH, Kim J, Jeong H, Yong Y, Yun SH, Choi CW, Jin HS, Jeong SY. Osteoprotective Effects of Loganic Acid on Osteoblastic and Osteoclastic Cells and Osteoporosis-Induced Mice. Int J Mol Sci. 2020 Dec 28;22(1):233. doi: 10.3390/ijms22010233. PMID: 33379387; PMCID: PMC7795511. 4. Sozański T, Kucharska AZ, Dzimira S, Magdalan J, Szumny D, Matuszewska A, Nowak B, Piórecki N, Szeląg A, Trocha M. Loganic acid and anthocyanins from cornelian cherry (Cornus mas L.) fruits modulate diet-induced atherosclerosis and redox status in rabbits. Adv Clin Exp Med. 2018 Nov;27(11):1505-1513. doi: 10.17219/acem/74638. PMID: 29790688.
In vitro protocol:
1. Dzydzan O, Brodyak I, Strugała-Danak P, Strach A, Kucharska AZ, Gabrielska J, Sybirna N. Biological Activity of Extracts of Red and Yellow Fruits of Cornus mas L.-An In Vitro Evaluation of Antioxidant Activity, Inhibitory Activity against α-Glucosidase, Acetylcholinesterase, and Binding Capacity to Human Serum Albumin. Molecules. 2022 Mar 30;27(7):2244. doi: 10.3390/molecules27072244. PMID: 35408646; PMCID: PMC9000679. 2. Abirami A, Sinsinwar S, Rajalakshmi P, Brindha P, Rajesh YBRD, Vadivel V. Antioxidant and cytoprotective properties of loganic acid isolated from seeds of Strychnos potatorum L. against heavy metal induced toxicity in PBMC model. Drug Chem Toxicol. 2022 Jan;45(1):239-249. doi: 10.1080/01480545.2019.1681445. Epub 2019 Oct 23. PMID: 31645139.
In vivo protocol:
1. Park E, Lee CG, Lim E, Hwang S, Yun SH, Kim J, Jeong H, Yong Y, Yun SH, Choi CW, Jin HS, Jeong SY. Osteoprotective Effects of Loganic Acid on Osteoblastic and Osteoclastic Cells and Osteoporosis-Induced Mice. Int J Mol Sci. 2020 Dec 28;22(1):233. doi: 10.3390/ijms22010233. PMID: 33379387; PMCID: PMC7795511. 2. Sozański T, Kucharska AZ, Dzimira S, Magdalan J, Szumny D, Matuszewska A, Nowak B, Piórecki N, Szeląg A, Trocha M. Loganic acid and anthocyanins from cornelian cherry (Cornus mas L.) fruits modulate diet-induced atherosclerosis and redox status in rabbits. Adv Clin Exp Med. 2018 Nov;27(11):1505-1513. doi: 10.17219/acem/74638. PMID: 29790688.
1. Coscia, C.J., Guarnaccia, R., and Botta, L. Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis. Biochemistry 8(12), 5036-5543 (1969). 2. Suh, H.-W., Lee, K.-B., Kim, K.-S., et al. A bitter herbal medicine Gentiana scabra root extract stimulates glucagon-like peptide-1 secretion and regulates blood glucose in db/db mouse. J. Ethnopharmacol. 172, 219-226 (2015). 3. Park, E., Kim, J., Yeo, S., et al. Antiadipogenic effects of loganic acid in 3T3-L1 preadipocytes and ovariectomized mice. Molecules 23(7), E1663 (2018). 4. Sozański, T., Kucharska, A.Z., Rapak, A., et al. Iridoid-loganic acid versus anthocyanins from the Cornus mas fruits (cornelian cherry): Common and different effects on diet-induced atherosclerosis, PPARs expression and inflammation. Atherosclerosis 254, 151-160 (2016).