A polyphenol with diverse biological activities
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Lithospermic Acid

Item No. 33694

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxo-1-propen-1-yl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic acid
CAS Number
28831-65-4
Synonyms
  • (+)-Lithospermic Acid
  • Lithospermic Acid A
Molecular Formula
C27H22O12
Formula Weight
538.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
O=C(O[C@@H](C(O)=O)CC(C=C1)=CC(O)=C1O)/C=C/C(C=C2)=C3C(O[C@H](C4=CC=C(O)C(O)=C4)[C@H]3C(O)=O)=C2O
InChi Code
InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4+/t20-,23+,24-/m1/s1
InChi Key
UJZQBMQZMKFSRV-RGKBJLTCSA-N
Origin
Plant/Salvia miltiorrhiza root
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Lithospermic acid is a polyphenol that has been found in S. miltiorrhiza and has diverse biological activities.1,2 It inhibits xanthine oxidase (IC50 = 5.2 µg/ml) and scavenges DPPH (Item No. 14805) radicals in cell-free assays (IC50 = 23.2 µg/ml). It also inhibits the production of reactive oxygen species (ROS) induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in isolated human neutrophils in a concentration-dependent manner.1 Lithospermic acid inhibits 3'-processing and 3'-joining to target DNA by HIV-1 integrase in cell-free assays (IC50s = 0.83 and 0.48 µM, respectively).3 It also inhibits acute HIV-1 infection of H9 human lymphoma cells (IC50 = 2 µM) without inducing cytotoxicity. Lithospermic acid (100 mg/kg) prevents carbon tetrachloride-induced hepatic necrosis in mice.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liu, X., Chen, R., Shang, Y., et al. Lithospermic acid as a novel xanthine oxidase inhibitor has anti-inflammatory and hypouricemic effects in rats. Chem. Biol. Interact. 176(2-3), 137-142 (2008).

    2. Chan, K.W.K., and Ho, W.S. Anti-oxidative and hepatoprotective effects of lithospermic acid against carbon tetrachloride-induced liver oxidative damage in vitro and in vivo. Oncol. Rep. 34(2), 673-680 (2015).

    3. Abd-Elazem, I.S., Chen, H.S., Bates, R.B., et al. Isolation of two highly potent and non-toxic inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase from Salvia miltiorrhiza. Antiviral Res. 55(1), 91-106 (2002).