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MedKoo Cat#: 146355 | Name: Guaiol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Guaiol is a naturally occurring sesquiterpenoid alcohol found in various essential oils, particularly from the Guaiacum and Cannabis plants. It is known for its antimicrobial, anti-inflammatory, and potential anticancer properties. Guaiol exerts its effects by disrupting microbial cell membranes and modulating inflammatory signaling pathways, although its exact molecular mechanisms are still being explored.

Chemical Structure

Guaiol
Guaiol
CAS#489-86-1

Theoretical Analysis

MedKoo Cat#: 146355

Name: Guaiol

CAS#: 489-86-1

Chemical Formula: C15H26O

Exact Mass: 222.1984

Molecular Weight: 222.37

Elemental Analysis: C, 81.02; H, 11.79; O, 7.19

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Guaiol;
IUPAC/Chemical Name
2-((3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl)propan-2-ol
InChi Key
TWVJWDMOZJXUID-SDDRHHMPSA-N
InChi Code
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
SMILES Code
C[C@H]1CCC2=C1C[C@@H](CC[C@@H]2C)C(C)(C)O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 222.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Yang X, Yang J, Gu X, Tao Y, Ji H, Miao X, Shen S, Zang H. (-)-Guaiol triggers immunogenic cell death and inhibits tumor growth in non-small cell lung cancer. Mol Cell Biochem. 2023 Jul;478(7):1611-1620. doi: 10.1007/s11010-022-04613-y. Epub 2022 Nov 28. PMID: 36441354; PMCID: PMC10209243. 2: Cao Y, Wu Y, Tu H, Gu Z, Yu F, Huang W, Shen L, Wang L, Li Y. (-)-Guaiol inhibit epithelial-mesenchymal transition in lung cancer via suppressing M2 macrophages mediated STAT3 signaling pathway. Heliyon. 2023 Sep 7;9(9):e19817. doi: 10.1016/j.heliyon.2023.e19817. PMID: 37809930; PMCID: PMC10559221. 3: Yang X, Zhu J, Wu J, Huang N, Cui Z, Luo Y, Sun F, Pan Q, Li Y, Yang Q. (-)-Guaiol regulates autophagic cell death depending on mTOR signaling in NSCLC. Cancer Biol Ther. 2018 Aug 3;19(8):706-714. doi: 10.1080/15384047.2018.1451277. Epub 2018 Apr 19. PMID: 29611762; PMCID: PMC6067839. 4: Yang Q, Wu J, Luo Y, Huang N, Zhen N, Zhou Y, Sun F, Li Z, Pan Q, Li Y. (-)-Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer. Oncotarget. 2016 Sep 20;7(38):62585-62597. doi: 10.18632/oncotarget.11540. PMID: 27566579; PMCID: PMC5308748. 5: Waddell TG, Arp NW, Bodine KD, Pagni RM. The guaiol color reaction. Planta Med. 2002 Oct;68(10):949-50. doi: 10.1055/s-2002-34931. PMID: 12391567. 6: Liu T, Wang CJ, Xie HQ, Mu Q. Guaiol--a naturally occurring insecticidal sesquiterpene. Nat Prod Commun. 2013 Oct;8(10):1353-4. PMID: 24354171. 7: Zeng Y, Pan Y, Zhang B, Luo Y, Tian J, Wang Y, Ju X, Wu J, Li Y. Integrating Network Pharmacology, Molecular Docking, and Experimental Validation to Investigate the Mechanism of (-)-Guaiol Against Lung Adenocarcinoma. Med Sci Monit. 2022 Jul 25;28:e937131. doi: 10.12659/MSM.937131. PMID: 35871777; PMCID: PMC9336205. 8: Garcia MCF, Soares DC, Santana RC, Saraiva EM, Siani AC, Ramos MFS, Danelli MDGM, Souto-Padron TC, Pinto-da-Silva LH. The in vitro antileishmanial activity of essential oil from Aloysia gratissima and guaiol, its major sesquiterpene against Leishmania amazonensis. Parasitology. 2018 Aug;145(9):1219-1227. doi: 10.1017/S0031182017002335. Epub 2018 Jan 21. PMID: 29352826. 9: Yang M, Luo J, Li K, Hu S, Ding T, Liu H, Sheng P, Yang M. Determination and pharmacokinetic study of guaiol in rat plasma by gas chromatography-mass spectrometry with selected ion monitoring. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 May 15;1085:30-35. doi: 10.1016/j.jchromb.2018.03.041. Epub 2018 Mar 27. PMID: 29627637. 10: Miyazawa M, Sugawara A. Biotransformation of (-)-guaiol by Eurotium rubrum as a biocatalyst. Nat Prod Res. 2006 Jul 10;20(8):731-4. doi: 10.1080/14786410500185774. PMID: 16753905. 11: Choudhary MI, Batool I, Atif M, Hussain S, Atta-Ur-Rahman. Microbial transformation of (-)-guaiol and antibacterial activity of its transformed products. J Nat Prod. 2007 May;70(5):849-52. doi: 10.1021/np068052a. Epub 2007 Mar 27. PMID: 17385913. 12: Huang AC, Sumby CJ, Tiekink ER, Taylor DK. Synthesis of guaia-4(5)-en-11-ol, guaia-5(6)-en-11-ol, aciphyllene, 1-epi-melicodenones C and E, and other guaiane-type sesquiterpenoids via the diastereoselective epoxidation of guaiol. J Nat Prod. 2014 Nov 26;77(11):2522-36. doi: 10.1021/np500611z. Epub 2014 Oct 20. PMID: 25330459. 13: Zhu J, Li Z, Lu H, Liu S, Ding W, Li J, Xiong Y, Li C. New diphenyl ethers from a fungus Epicoccum sorghinum L28 and their antifungal activity against phytopathogens. Bioorg Chem. 2021 Oct;115:105232. doi: 10.1016/j.bioorg.2021.105232. Epub 2021 Aug 2. PMID: 34371373. 14: Alijar Souza M, Petry F, Vidor Morgan L, Dal Magro J, Müller LG. Biological Properties of Aloysia gratissima (Gillies & Hook.) Tronc. (Verbenaceae). Evid Based Complement Alternat Med. 2022 Jan 19;2022:1119435. doi: 10.1155/2022/1119435. PMID: 35096101; PMCID: PMC8791711. 15: Irshad H, Kulpa J, Kuehl PJ, Lefever T, McDonald JD. Characterization of aerosols from hemp-derived pre-roll joints. Inhal Toxicol. 2023 May- Jun;35(5-6):169-174. doi: 10.1080/08958378.2023.2206448. Epub 2023 May 9. PMID: 37159420. 16: Liakakou A, Angelis A, Papachristos DP, Fokialakis N, Michaelakis A, Skaltsounis LA. Isolation of Volatile Compounds with Repellent Properties against Aedes albopictus (Diptera: Culicidae) Using CPC Technology. Molecules. 2021 May 21;26(11):3072. doi: 10.3390/molecules26113072. PMID: 34063887; PMCID: PMC8196645. 17: Luns DAR, Martins R, Pombal S, Rodilla JML, Githaka NW, Vaz IDS Jr, Logullo C. Effect of essential oils against acaricide-susceptible and acaricide- resistant Rhipicephalus ticks. Exp Appl Acarol. 2021 Apr;83(4):597-608. doi: 10.1007/s10493-021-00601-x. Epub 2021 Feb 24. Erratum in: Exp Appl Acarol. 2021 Apr;83(4):609. doi: 10.1007/s10493-021-00614-6. PMID: 33625626; PMCID: PMC8041689. 18: de Moura NF, Simionatto E, Porto C, Hoelzel SC, Dessoy EC, Zanatta N, Morel AF. Quinoline alkaloids, coumarins and volatile constituents of Helietta longifoliata. Planta Med. 2002 Jul;68(7):631-4. doi: 10.1055/s-2002-32898. PMID: 12142998. 19: Carvalho VM, de Almeida FG, de Macêdo Vieira AC, Rocha ED, Cabral LM, Strongin RM. Chemical profiling of Cannabis varieties cultivated for medical purposes in southeastern Brazil. Forensic Sci Int. 2022 Jun;335:111309. doi: 10.1016/j.forsciint.2022.111309. Epub 2022 Apr 14. PMID: 35462181. 20: Kambiré DA, Kablan ACL, Yapi TA, Vincenti S, Maury J, Baldovini N, Tomi P, Paoli M, Boti JB, Tomi F. Neuropeltis acuminata (P. Beauv.): Investigation of the Chemical Variability and In Vitro Anti-inflammatory Activity of the Leaf Essential Oil from the Ivorian Species. Molecules. 2022 Jun 10;27(12):3759. doi: 10.3390/molecules27123759. PMID: 35744884; PMCID: PMC9230793.

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