A fungal metabolite with diverse biological activities
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Tanzawaic Acid B

Item No. 40909

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4E)-5-[(1S,2S,4aR,6S,8R,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2,6,8-trimethyl-1-naphthalenyl]-2,4-pentadienoic acid
CAS Number
169181-33-3
Synonyms
  • (+)-Tanzawaic Acid B
Molecular Formula
C18H26O2
Formula Weight
274.4
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
OC(/C=C/C=C/[C@@H]1[C@]2([H])[C@@](C[C@H](C[C@H]2C)C)([H])C=C[C@@H]1C)=O
InChi Code
InChI=1S/C18H26O2/c1-12-10-14(3)18-15(11-12)9-8-13(2)16(18)6-4-5-7-17(19)20/h4-9,12-16,18H,10-11H2,1-3H3,(H,19,20)/b6-4+,7-5+/t12-,13-,14+,15-,16-,18-/m0/s1
InChi Key
DUGGXGNWQZWAAS-RAJPTAFASA-N
Origin
Bacterium/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $413

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    Product Description

    Tanzawaic acid B is a fungal metabolite that has been found in Penicillium and has diverse biological activities.1,2 It inhibits protein tyrosine phosphatase 1B (PTP1B) in a cell-free assay (IC50 = 8.2 µM) and LPS-induced production of nitric oxide (NO) in BV-2 microglia (IC50 = 42.5 µM).1 Tanzawaic acid B is active against chloroquine-resistant and chloroquine-sensitive P. falciparum strains (IC50s = 78.5 and 79.2 µM, respectively).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Quang, T.H., N.T.T., N., Ko, W., et al. Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities. Biooorg. Med. Chem. Lett. 24(24), 5787-5791 (2014).

    2. Matsuo, H., Hokari, R., Ishiyama, A., et al. Hatsusamides A and B: Two new metabolites produced by the deep-sea-derived fungal strain Penicillium steckii FKJ-0213. Mar Drugs 18(10), 513 (2020).