A prenylated cinnamic acid with diverse biological activities
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Artepillin C

Item No. 35666

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[4-hydroxy-3,5-bis(3-methyl-2-buten-1-yl)phenyl]-2-propenoic acid
CAS Number
72944-19-5
Synonyms
  • 3,5-Diprenyl-4-hydroxy Cinnamic Acid
  • 3,5-Diprenyl-p-hydroxy Cinnamic Acid
  • 3,5-Diprenyl-para-hydroxy Cinnamic Acid
  • 3,5-Diprenyl-4-Coumaric Acid
  • 3,5-Diprenyl-p-Coumaric Acid
  • 3,5-Diprenyl-para-Coumaric Acid
Molecular Formula
C19H24O3
Formula Weight
300.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleDMSO: Soluble
SMILES
C/C(C)=C/CC(C=C1/C=C/C(O)=O)=C(C(C/C=C(C)/C)=C1)O
InChi Code
InChI=1S/C19H24O3/c1-13(2)5-8-16-11-15(7-10-18(20)21)12-17(19(16)22)9-6-14(3)4/h5-7,10-12,22H,8-9H2,1-4H3,(H,20,21)/b10-7+
InChi Key
KABCFARPAMSXCC-JXMROGBWSA-N
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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    10 mg

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    Product Description

    Artepillin C is a prenylated cinnamic acid that has been found in B. grisebachii and has diverse biological activities.1,2,3,4,5,6 It selectively inhibits aldo-keto reductase 1C3 (AKR1C3; IC50 = 1 µM), also known as prostaglandin F synthase, over AKR1C1, AKR1C2, and AKR1C4 at 100 µM.1 It also inhibits lipid peroxidation in isolated human erythrocytes.2 Artepillin C (10 µM) induces calcium influx in HEK293T cells expressing human transient receptor potential ankyrin 1 (TRPA1), an effect that can be blocked by the TRPA1 inhibitor HC-030031 (Item No. 11923).3 It is cytotoxic to HT-1080 fibrosarcoma and 26-L5 colon cancer cells (IC50s = 45.47 and 59.32 µg/ml, respectively).4 Artepillin C is active against C. albicans, E. floccosum, T. rubrum, methicillin-sensitive S. aureus, and methicillin-resistant S. aureus (MRSA; MICs = 250, 50, 125, 250, and 250 µg/ml, respectively).5 In vivo, artepillin C (1 and 10 mg/kg) decreases carrageenan-induced peritoneal leukocyte infiltration in mice.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Endo, S., Matsunaga, T., Kanamori, A., et al. Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis. J. Nat. Prod. 75(4), 716-721 (2012).

    2. Tapia, A., Rodriguez, J., Theoduloz, C., et al. Free radical scavengers and antioxidants from Baccharis grisebachii. J. Ethnopharmacol. 95(2-3), 155-161 (2004).

    3. Hata, T., Tazawa, S., Ohta, S., et al. Artepillin C, a major ingredient of Brazilian propolis, induces a pungent taste by activating TRPA1 channels. PLoS One 7(11), e48072 (2012).

    4. Banskota, A.H., Tezuka, Y., Prasain, J.K., et al. Chemical constituents of brazilian propolis and their cytotoxic activities. J. Nat. Prod. 61(7), 896-900 (1998).

    5. Feresin, G.E., Tapia, A., Gimenez, A., et al. Constituents of the Argentinian medicinal plant Baccharis grisebachii and their antimicrobial activity. J. Ethnopharmacol. 89(1), 73-80 (2003).

    6. Paulino, N., Abreu, S.R., Uto, Y., et al. Anti-inflammatory effects of a bioavailable compound, Artepillin C, in Brazilian propolis. Eur. J. Pharmacol. 587(1-3), 296-301 (2008).