Guaiol

• CAT Number: R060597
• CAS Number: 489-86-1
• Molecular Formula: C15H26O
• Molecular Weight: 222.372
• Purity: ≥95%
• Target: Autophagy
• Storage: -20°C
• IUPAC Name: 2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
• InChI: 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
• InChIKey: TWVJWDMOZJXUID-SDDRHHMPSA-N
• SMILES: CC1CCC(CC2=C1CCC2C)C(C)(C)O

Guaiol (CAS 489-86-1) 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. 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).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. (−)-Guaiol is also lethal to fourth instar M. separata and third instar P. xylostella larvae (LD50s = 0.07 and 8.9 mg/larva, respectively).

Reference

1.Yang, Qingyuan, et al. "(−)-Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer." Oncotarget 7.38 (2016): 62585.
2.Ali, Abbas, et al. "Chemical composition and biological activity of four salvia essential oils and individual compounds against two species of mosquitoes." Journal of agricultural and food chemistry 63.2 (2015): 447-456.
3.Liu, Tao, et al. "Guaiol-a naturally occurring insecticidal sesquiterpene." Natural product communications 8.10 (2013): 1934578X1300801001.