A phenol from cashew nut shell liquid
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Cardol triene

Item No. 23374

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-8Z,11Z,14-pentadecatrien-1-yl-1,3-benzenediol
CAS Number
79473-24-8
Molecular Formula
C21H30O2
Formula Weight
314.5
Purity
≥95%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 22 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
275 nm
SMILES
OC1=CC(O)=CC(CCCCCCC/C=C\C/C=C\CC=C)=C1
InChi Code
InChI=1S/C21H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h2,4-5,7-8,16-18,22-23H,1,3,6,9-15H2/b5-4-,8-7-
InChi Key
OOXBEOHCOCMKAC-UTOQUPLUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $90

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    1 mg

    $169

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    5 mg

    $755

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    10 mg

    $1,330

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    Product Description

    Cardol triene is a phenol found in cashew nut shell liquid that competitively and irreversibly inhibits mushroom tyrosinase (IC50 = 22.5 µM).1,2 It is schistosomicidal, killing 25, 75, and 100% of S. mansoni worms after 24 hours when used at concentrations of 50, 100, or 200 µM, respectively.3 It has been used as a starting material for the synthesis of bis-benzoxazines.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tyman, J.H., and Kiong, L.S. Long chain phenols: Part XI. Composition of natural cashew nutshell liquid (Anacardium occidentale) from various sources. Lipids 13(8), 525-532 (1978).

    2. Zhuang, J.-X., Hu, Y.-H., Yang, M.-H., et al. Irreversible competitive inhibitory kinetics of cardol triene on mushroom tyrosinase. J. Agric. Food Chem. 58(24), 12993-12998 (2010).

    3. Alvarenga, T.A., de Oliveira, P.F., de Souza, J.M., et al. Schistosomicidal activity of alkyl-phenols from the cashew Anacardium occidentale against Schistosoma mansoni adult worms. J. Agric. Food Chem. 64(46), 8821-8827 (2016).

    4. Attanasi, O.A., Behalo, M.S., Favi, G., et al. Solvent free synthesis of novel mono- and bis-benzoxazines from cashew nut shell liquid components. Curr. Org. Chem. 16(21), 2613-2621 (2012).