An iridoid glycoside with diverse biological activities
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Loganic Acid

Item No. 28402

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-cyclopenta[c]pyran-4-carboxylic acid
CAS Number
22255-40-9
Synonyms
  • Loganate
  • Loganin Acid
Molecular Formula
C16H24O10
Formula Weight
376.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
234 nm
SMILES
OC[C@H]1O[C@@H](O[C@H]2[C@@]([C@@H](C)[C@@H](O)C3)([H])[C@@]3([H])C(C(O)=O)=CO2)[C@H](O)[C@@H](O)[C@@H]1O
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-/m0/s1
InChi Key
JNNGEAWILNVFFD-CDJYTOATSA-N
Origin
Plant/Gentianae macrophyllae
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $183

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    10 mg

    $327

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    25 mg

    $722

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    50 mg

    $1,083

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    Cayman Chemical
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    Product 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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).