A sesquiterpene alcohol with diverse biological activities
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(−)-Guaiol

Item No. 23172

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,5R,8S)-1,2,3,4,5,6,7,8-octahydro-α,α,3,8-tetramethyl-5-azulenemethanol
CAS Number
489-86-1
Synonyms
  • NSC 19941
Molecular Formula
C15H26O
Formula Weight
222.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
CC(O)(C)[C@H](CC[C@@H]1C)CC2=C1CC[C@@H]2C
InChi Code
InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+/m0/s1
InChi Key
TWVJWDMOZJXUID-SDDRHHMPSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $81

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    25 mg

    $319

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    50 mg

    $479

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    100 mg

    $798

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    Product Description

    (−)-Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities.1,2,3 It selectively inhibits proliferation of A549 and H1299 non-small cell lung carcinoma (NSCLC) cells over BEAS-2B normal lung cells (IC50s = 121.7, 211.5, and 297.1 μM, respectively).1 It also dose-dependently induces formation of DNA double-strand breaks (DSBs) and autophagy in A549 and H1299 cells and increases levels of microtubule-associated protein 1 light chain 3 isoform II (LC3-II). (−)-Guaiol (8 mg/kg three times per week) inhibits tumor growth in an NSCLC mouse xenograft model. It deters A. aegypti and A. quadrimaculatus mosquitoes from feeding on a synthetic blood substitute with a biting-deterrent index (BDI) of 0.82 when used at a concentration of 25 nmol per cm2.2 (−)-Guaiol is also lethal to fourth instar M. separata and third instar P. xylostella larvae (LD50s = 0.07 and 8.9 mg/larva, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yang, Q., Wu, J., Luo, Y., et al. (−)-Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer. Oncotarget 7(38), 62585-62597 (2016).

    2. Ali, A., Tabanca, N., Demirci, B., et al. Chemical composition and biological activity of four salvia essential oils and individual compounds against two species of mosquitoes. J. Agric. Food Chem. 63(2), 447-456 (2015).

    3. Liu, T., Wang, C.-J., Xie, H.-Q., et al. Guaiol - a naturally occurring insecticidal sesquiterpene. Nat. Prod. Commun. 8(10), 1353-1354 (2013).