A hydroxylated cyclohexane carboxylic acid with diverse biological activities
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D-(−)-Quinic Acid

Item No. 30212

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1α,3R,4α,5R-tetrahydroxy-cyclohexanecarboxylic acid
CAS Number
77-95-2
Molecular Formula
C7H12O6
Formula Weight
192.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: SolubleWater: Soluble
SMILES
OC([C@]1(O)C[C@@H](O)[C@@H](O)[C@H](O)C1)=O
InChi Code
InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1
InChi Key
AAWZDTNXLSGCEK-WYWMIBKRSA-N
Origin
Plant/Citrus limon (L.) Burm.f.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    10 g

    $40

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    25 g

    $90

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    50 g

    $139

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    100 g

    $257

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    Cayman Chemical
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    Product Description

    D-(−)-Quinic acid is a hydroxylated cyclohexane carboxylic acid that has been found in coffee beans and has diverse biological activities.1,2,3,4 It inhibits viral replication in, and viral DNA secretion from, HepG2/2.15 cells infected by hepatitis B virus (HBV; IC50s = 1.6 and 10.1 µM, respectively) without affecting cell viability (CC50 = >1,000 µM).1 D-(−)-Quinic acid (1 and 2 mg/ml) reduces cell viability in Raji lymphoma cells.2 It decreases the proliferation of isolated mouse leukocytes stimulated by LPS or concanavalin A (Item No. 14951) when used at a concentration of 2 mg/ml. D-(−)-Quinic acid (1, 2, and 4 µg/ml) inhibits radiation-induced DNA damage and cell death in isolated human lymphocytes.3 In vivo, D-(−)-quinic acid (200 or 400 mg/kg in drinking water) inhibits aluminum chloride-induced neuronal degeneration, decreases in brain acetylcholinesterase (AChE), glutathione (GSH), and superoxide dismutase (SOD) levels, brain homogenate catalase activity, and increases in time to reach the platform in the Morris water maze test in a rat model of aluminum chloride-induced neurotoxicity.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, G.-F., Shi, L.-P., Ren, Y.-D., et al. Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro. Antiviral Res. 83(2), 186-190 (2009).

    2. Akesson, C., Lindgren, H., Pero, R.W., et al. Quinic acid is a biologically active component of the Uncaria tomentosa extract C-Med 100®. Int. Immunopharmacol. 5(1), 219-229 (2005).

    3. Cinkilic, N., Cetintas, S.K., Zorlu, T., et al. Radioprotection by two phenolic compounds: Chlorogenic and quinic acid, on X-ray induced DNA damage in human blood lymphocytes in vitro. Food Chem. Toxicol. 53, 359-363 (2013).

    4. Liu, L., Liu, Y., Zhao, J., et al. Neuroprotective effects of D-(−)-quinic acid on aluminum chloride-induced dementia in rats. Evid. Based Complement. Alternat. Med. 5602597 (2020).