A polyunsaturated form of anacardic acid
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Anacardic Acid triene

Item No. 26611

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-hydroxy-6-(8Z,11Z)-8,11,14-pentadecatrien-1-yl-benzoic acid
CAS Number
103904-73-0
Synonyms
  • Anacardic Acid 15:3
Molecular Formula
C22H30O3
Formula Weight
342.5
Purity
≥98%
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
244, 313 nm
SMILES
OC1=CC=CC(CCCCCCC/C=C\C/C=C\CC=C)=C1C(O)=O
InChi Code
InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h2,4-5,7-8,15,17-18,23H,1,3,6,9-14,16H2,(H,24,25)/b5-4-,8-7-
InChi Key
QUVGEKPNSCFQIR-UTOQUPLUSA-N
Origin
Plant/Anacardium occidentale
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $94

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    1 mg

    $179

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    5 mg

    $748

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    10 mg

    $1,403

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    Product Description

    Anacardic acid triene is a polyunsaturated form of anacardic acid (Item No. 13144) that has been found in cashew nut shell liquid.1 It inhibits soybean lipoxygenase-1 (IC50 = 60 µM in an enzyme assay) and inhibits superoxide production by xanthine oxidase by 82% when used at a concentration of 88 µM.2,1 Anacardic acid triene is active against S. mutans and S. aureus, including the methicillin-resistant S. aureus (MRSA) strain ATCC 33591 (MICs = 1.56, 6.25, and 6.25 µg/ml, respectively).3 It also inhibits NADH oxidase (IC50 = 1.3 µg/ml), an enzyme involved in bacterial respiration. Anacardic acid triene is molluscicidal, inducing toxicity in B. glabrata (LC50 = 0.35 ppm), but is inactive against S. mansoni parasites.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Masuoka, N., and Kubo, I. Characterization of xanthine oxidase inhibition by anacardic acids. Biochim. Biophys. Acta 1688(3), 245-249 (2004).

    2. Shobha, S.V., Ramadoss, C.S., and Ravindranath, B. Inhibition of soybean lipoxygenase-1 by anacardic acids, cardols, and cardanols. J. Nat. Prod. 57(12), 1755-1757 (1994).

    3. Kubo, I., Nihei, K., and Tsujimoto, K. Antibacterial action of anacardic acids against methicillin resistant Staphylococcus aureus (MRSA). J. Agric. Food Chem. 51(26), 7624-7628 (2003).

    4. Sullivan, J.T., Richards, C.S., Lloyd, H.A., et al. Anacardic acid: Molluscicide in cashew nut shell liquid. Planta Med. 44(3), 175-177 (1982).

    5. 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).