Kahweol, Diterpene molecule in coffee beans (ab141258)

Overview

  • Product name

    Kahweol, Diterpene molecule in coffee beans
  • Description

    Diterpene molecule found in coffee beans.
  • Biological description

    Diterpene molecule found in coffee beans. Increases glutathione S-transferase activity in the gut mucosa of mice and, with the diterpene cafestol, induces glutathione S-transferase expression in rat livers. Displays anti-inflammatory effects in RAW macrophages, inhibiting LPS-induced nitric oxide and prostaglandin E2 production. Antiangiogenic, blocking the proliferation of endothelial cells (IC50 = 50 μM) and inhibiting endothelial migration, invasion, and tube formation.

  • Purity

    > 97%
  • CAS Number

    6894-43-5
  • Chemical structure

    Chemical Structure

Properties

  • Molecular weight

    314.42
  • Molecular formula

    C20H26O3
  • PubChem identifier

    114778
  • Storage instructions

    Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.
  • Solubility overview

    Soluble in DMSO
  • Handling

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

  • SMILES

    C[C@@]12C=CC3=C([C@H]1CC[C@]45[C@H]2CC[C@H](C4)[C@](C5)(CO)O)C=CO3
  • Source

    Coffea arabica

References

This product has been referenced in:

  • Fumimoto R  et al. The coffee diterpene kahweol prevents osteoclastogenesis via impairment of NFATc1 expression and blocking of Erk phosphorylation. J Pharmacol Sci 118:479-86 (2012). Read more (PubMed: 22447306) »
  • Cárdenas C  et al. Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene. PLoS One 6:e23407 (2011). Read more (PubMed: 21858104) »
  • Shen T  et al. Nuclear factor-kappaB/signal transducers and activators of transcription-1-mediated inflammatory responses in lipopolysaccharide-activated macrophages are a major inhibitory target of kahweol, a coffee diterpene. Biol Pharm Bull 33:1159-64 (2010). Read more (PubMed: 20606307) »
  • Oh JH  et al. The coffee diterpene kahweol induces apoptosis in human leukemia U937 cells through down-regulation of Akt phosphorylation and activation of JNK. Apoptosis 14:1378-86 (2009). Read more (PubMed: 19768546) »
  • Cavin C  et al. The coffee-specific diterpenes cafestol and kahweol protect against aflatoxin B1-induced genotoxicity through a dual mechanism. Carcinogenesis 19:1369-75 (1998). Read more (PubMed: 9744531) »
  • Lam LK  et al. Isolation and identification of kahweol palmitate and cafestol palmitate as active constituents of green coffee beans that enhance glutathione S-transferase activity in the mouse. Cancer Res 42:1193-8 (1982). Read more (PubMed: 7059995) »

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