A sesquiterpene with diverse biological activities
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Guaiazulene

Item No. 31506

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,4-dimethyl-7-(1-methylethyl)-azulene
CAS Number
489-84-9
Synonyms
  • NSC 4714
Molecular Formula
C15H18
Formula Weight
198.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:2): 0.3 mg/mlDMSO: 25 mg/mlEthanol: 25 mg/ml
λmax
244, 284 nm
SMILES
CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1
InChi Code
InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
InChi Key
FWKQNCXZGNBPFD-UHFFFAOYSA-N
Origin
Synthetic
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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    5 g

    $32

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    10 g

    $61

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    25 g

    $119

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    50 g

    $220

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    Product Description

    Guaiazulene is a sesquiterpene that has been found in M. chamomilla and has diverse biological activities.1,2,3 It inhibits lipid peroxidation in rat hepatic microsomes (IC50 = 9.8 μM), as well as scavenges hydroxyl and 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in cell-free assays.1 It inhibits LPS-induced nitric oxide production in RAW 264.7 cells (EC50 = 10.1 μM) but is cytotoxic to RAW 264.7 cells at higher concentrations with cytotoxic concentration (CC50) values of 29.8 and 30.8 μM in the presence and absence, respectively, of LPS.2 Guaiazulene is cytotoxic to N2a neuroblastoma cells and primary rat neurons in a concentration-dependent manner.3 It inhibits decreases in hepatic glutathione (GSH) levels induced by paracetamol (acetaminophen; Item No. 10024) in rats when administered at a dose of 250 mg/kg.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kourounakis, A.P., Rekka, E.A., and Kourounakis, P.N. Antioxidant activity of guaiazulene and protection against paracetamol hepatotoxicity in rats. J. Pharm. Pharmacol. 49(9), 938-942 (1997).

    2. Hashiba, K., Yokoyama, K., Wakabayashi, H., et al. Inhibition of LPS-stimulated NO production in mouse macrophage-like cells by azulenes. Anticancer Res. 24(6), 3939-3944 (2004).

    3. Togar, B., Turkez, H., Hacimuftuoglu, A., et al. Guaiazulene biochemical activity and cytotoxic and genotoxic effects on rat neuron and N2a neuroblastom cells. J. Intercult. Ethnopharmacol. 4(1), 29-33 (2015).