A plant defense polyacetylene
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Falcarinol

Item No. 22407

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,9Z-heptadecadiene-4,6-diyn-3R-ol
CAS Number
21852-80-2
Molecular Formula
C17H24O
Formula Weight
244.4
Purity
≥60%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 20 mg/ml
SMILES
CCCCCCC/C=C\CC#CC#C[C@H](O)C=C
InChi Code
InChI=1S/C17H24O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h4,10-11,17-18H,2-3,5-9,12H2,1H3/b11-10-/t17-/m1/s1
InChi Key
UGJAEDFOKNAMQD-QXPKXGMISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $75

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    5 mg

    $351

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    10 mg

    $627

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    25 mg

    $1,468

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    Cayman Chemical
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    Product Description

    Falcarinol is a C17-polyacetylene produced by the Apiaceae family that has antimicrobial properties due to its inhibition of fatty acid biosynthesis.1,2 Falcarinol binds to the human recombinant cannabinoid (CB) receptors, CB1 and CB2, (Kis = 594 and 2,100 nM, respectively) in an [3H]anandamide displacement assay in HEK293 cells.3 It differentially modulates synaptic and extrasynaptic GABAA receptors in a recombinant HEK293 system.4 In vitro assays of ATPase activity demonstrate that falcarinol inhibits breast cancer resistance protein ATP-binding cassette sub-family G member 2 (ABCG2; IC50 = 79.3 μM), a drug efflux transporter and mediator of drug resistance.5 Falcarinol (6.88 μg/g feed) also inhibits aberrant crypt foci by 26.6% in azoxymethane-induced rats.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dawid, C., Dunemann, F., Schwab, W., et al. Bioactive C₁₇-polyacetylenes in carrots (Daucus carota L.): Current knowledge and future perspectives. J. Agric. Food Chem. 63(42), 9211-9222 (2015).

    2. Li, H., Cowie, A., Johnson, J.A., et al. Determining the mode of action of antimycobacterial C17 diyne natural products using expression profiling: Evidence for fatty acid biosynthesis inhibition. BMC Genomics 17(1), 621 (2016).

    3. Leonti, M., Casu, L., Raduner, S., et al. Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. Biochem. Pharmacol. 79(12), 1815-1826 (2010).

    4. Czyzewska, M.M., Chrobok, L., Kania, A., et al. Dietary acetylenic oxylipin falcarinol differentially modulates GABAA receptors. J. Nat. Prod. 77(12), 2671-2677 (2014).

    5. Tan, K.W., Killeen, D.P., Li, Y., et al. Dietary polyacetylenes of the falcarinol type are inhibitors of breast cancer resistance protein (BCRP/ABCG2). Eur. J. Pharmacol. 723, 346-352 (2014).

    6. Kobaek-Larsen, M., El-Houri, R.B., Christensen, L.P., et al. Dietary polyacetylenes, falcarinol and falcarindiol, isolated from carrots prevents the formation of neoplastic lesions in the colon of azoxymethane-induced rats. Food Funct. 8(3), 964-974 (2017).