(-)-PERILLYL ALCOHOL

• CAT Number: M084464
• CAS Number: 18457-55-1
• Molecular Formula: C10H16O
• Molecular Weight: 152.237
• Purity: ≥95%
• Target: Metabolic Enzyme/Protease
• Storage: Desiccate at RT
• IUPAC Name: [(4S)-4-prop-1-en-2-ylcyclohexen-1-yl]methanol
• InChI: InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1
• InChIKey: NDTYTMIUWGWIMO-SNVBAGLBSA-N
• SMILES: CC(=C)C1CCC(=CC1)CO

Perillyl alcohol, or POH, is a naturally occurring monocyclic terpenes derived from the mevalonate pathway in plants. Perillyl alcohol can be found in the essential oils of various botanicals, such as lavender, lemongrass, sage, and peppermint. It has a number of manufacturing, household, and medical applications. For example, perillyl alcohol may be used as an ingredient in cleaning products and cosmetics, and it has shown promise for inhalation therapy of patients with brain cancer.

Reference

1:A perillyl alcohol-conjugated analog of 3-bromopyruvate without cellular uptake dependency on monocarboxylate transporter 1 and with activity in 3-BP-resistant tumor cells. Chen TC, Yu J, Nouri Nigjeh E, Wang W, Myint PT, Zandi E, Hofman FM, Schönthal AH.Cancer Lett. 2017 Apr 24;400:161-174. doi: 10.1016/j.canlet.2017.04.015. [Epub ahead of print] PMID: 28450161 2:Perillyl alcohol, a pleiotropic natural compound suitable for brain tumor therapy, targets free radicals. Gomes AC, Mello AL, Ribeiro MG, Garcia DG, Da Fonseca CO, Salazar MD, Schönthal AH, Quirico-Santos T.Arch Immunol Ther Exp (Warsz). 2017 Mar 17. doi: 10.1007/s00005-017-0459-5. [Epub ahead of print] Review. PMID: 28314870 3:Orofacial antinociceptive activity of (S)-(-)-perillyl alcohol in mice: a randomized, controlled and triple-blind study. Tomaz-Morais JF, Braga RM, de Sousa FB, de Sousa DP, deM Pordeus LC, de Almeida RN, de Castro RD.Int J Oral Maxillofac Surg. 2017 May;46(5):662-667. doi: 10.1016/j.ijom.2017.01.024. Epub 2017 Feb 21. PMID: 28233648 4:Cytotoxic, Antiproliferative and Apoptotic Effects of Perillyl Alcohol and Its Biotransformation Metabolite on A549 and HepG2 Cancer Cell Lines. Oturanel CE, Kıran İ, Özşen Ö, Çiftçi GA, Atlı Ö.Anticancer Agents Med Chem. 2017 Jan 2. [Epub ahead of print] PMID: 28044940 5:Anticandidal Effect and Mechanisms of Monoterpenoid, Perillyl Alcohol against Candida albicans. Ansari MA, Fatima Z, Hameed S.PLoS One. 2016 Sep 14;11(9):e0162465. doi: 10.1371/journal.pone.0162465. eCollection 2016. PMID: 27627759 Free PMC Article6:Perillyl Alcohol and Its Drug-Conjugated Derivatives as Potential Novel Methods of Treating Brain Metastases. Chen TC, Da Fonseca CO, Schönthal AH.Int J Mol Sci. 2016 Sep 2;17(9). pii: E1463. doi: 10.3390/ijms17091463. Review. PMID: 27598140 Free PMC Article7:Perillyl alcohol efficiently scavenges activity of cellular ROS and inhibits the translational expression of hypoxia-inducible factor-1α via mTOR/4E-BP1 signaling pathways. Ma J, Li J, Wang KS, Mi C, Piao LX, Xu GH, Li X, Lee JJ, Jin X.Int Immunopharmacol. 2016 Oct;39:1-9. doi: 10.1016/j.intimp.2016.06.034. Epub 2016 Jul 6. PMID: 27394002 8:Temozolomide-perillyl alcohol conjugate induced reactive oxygen species accumulation contributes to its cytotoxicity against non-small cell lung cancer. Song X, Xie L, Wang X, Zeng Q, Chen TC, Wang W, Song X.Sci Rep. 2016 Mar 7;6:22762. doi: 10.1038/srep22762. PMID: 26949038 Free PMC Article9:Perillyl alcohol: Dynamic interactions with the lipid bilayer and implications for long-term inhalational chemotherapy for gliomas. da Fonseca CO, Khandelia H, Salazar MD, Schönthal AH, Meireles OC, Quirico-Santos T.Surg Neurol Int. 2016 Jan 5;7:1. doi: 10.4103/2152-7806.173301. eCollection 2016. PMID: 26862440 Free PMC Article10:In Vivo Anti-Tumor Activity and Toxicological Evaluations of Perillaldehyde 8,9-Epoxide, a Derivative of Perillyl Alcohol. Andrade LN, Amaral RG, Dória GA, Fonseca CS, da Silva TK, Albuquerque Júnior RL, Thomazzi SM, do Nascimento LG, Carvalho AA, de Sousa DP.Int J Mol Sci. 2016 Jan 4;17(1). pii: E32. doi: 10.3390/ijms17010032. PMID: 26742032 Free PMC Article