Farnesol
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MedKoo CAT#: 540130

CAS#: 4602-84-0

Description: Farnesol is found in various essential oils. It regulates the volatility of odorants in perfumes. It displays a variety of biological activities, including cell cycle arrest and stimulating p21 and p27 expression in pancreatic adenocarcinoma cells, increasing latency to tumor formation in TPA-induced skin carcinogenesis, and inhibiting growth of Aspergilius and Candida.


Chemical Structure

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Farnesol
CAS# 4602-84-0

Theoretical Analysis

MedKoo Cat#: 540130
Name: Farnesol
CAS#: 4602-84-0
Chemical Formula: C15H26O
Exact Mass: 222.20
Molecular Weight: 222.370
Elemental Analysis: C, 81.02; H, 11.79; O, 7.19

Price and Availability

Size Price Availability Quantity
5g USD 150 Ready to ship
10g USD 250 Ready to ship
25g USD 550 Ready to ship
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Synonym: HSDB 445; HSDB-445; HSDB445; NSC 60597; NSC-60597; NSC60597; Farnesol

IUPAC/Chemical Name: (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

InChi Key: CRDAMVZIKSXKFV-YFVJMOTDSA-N

InChi Code: InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+

SMILES Code: C/C(C)=C\CC/C(C)=C/CC/C(C)=C/CO

Appearance: Oily liquid

Purity: >95% (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: Soluble in alcohol

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:

Biological target: Farnesol is a sesquiterpene alcohol that modulates cell-to-cell communication in Candida albicans, and has the activity in inhibiting bacteria.
In vitro activity: The present study is aimed at determining the effect of farnesol on the growth of strains of the Cryptococcus neoformans species complex, through microdilution assays. In addition, the effect of farnesol on the synthesis of phospholipase and protease - important virulence-associated enzymes - by C. neoformans and Cryptococcus gattii was also investigated. A total of 36 strains were studied, out of which 20 were from veterinary sources, 8 were from human cases and 8 were from a reference collection. The minimum inhibitory concentrations (MICs) were determined in accordance with the M27-A3 protocol as described by the CLSI and farnesol was tested at a concentration range of 0.29-150 μM. Phospholipase and protease activities were evaluated through growth on egg yolk agar and spectrophotometry, respectively, after pre-incubating the strains at different farnesol concentrations (MIC/4, MIC/2 and MIC). It was observed that farnesol presents an inhibitory activity against C. neoformans and C. gattii (MIC range: 0.29-75.0 μM). Although farnesol did not significantly alter phospholipase activity, a tendency to decrease this activity was observed. Concerning protease, no statistically significant differences were observed when comparing the production before and after pre-incubation at different farnesol concentrations. Based on these findings, it can be concluded that farnesol has in vitro inhibitory activity against C. neoformans and C. gattii, but has little impact on the production of the analyzed virulence factors. Reference: Vet Microbiol. 2012 Oct 12;159(3-4):375-80. https://linkinghub.elsevier.com/retrieve/pii/S0378-1135(12)00257-X
In vivo activity: To investigate whether farnesol induces browning of WAT in vivo as well, C57BL/6 mice were fed farnesol and a HFD. Briefly, the mice were fed a HFD for 4 weeks to induce obesity before administration of farnesol. After induction of obesity, the mice were randomly divided into two groups: a HFD group with vehicle treatment and a HFD group with farnesol (5 mg/kg/day). The HFD plus farnesol group appeared to have significantly less weight gain than that of the HFD plus vehicle group (46.08 ± 0.42 vs. 50.86 ± 0.48 g, respectively). Additionally, the tissue weights and adipocyte sizes in both iWAT and eWAT were smaller than those of the HFD-induced obese mice (Figures 3A,B). Next, we investigated the expression of the adipogenesis-related factors PPARγ, C/EBPα, and LIPIN1 and the phosphorylated level of AMPK in both the iWAT and eWAT. Farnesol administration reduced the expressions of the factors and activated the phosphorylation of AMPK significantly (p < 0.05) (Figures Figures3C3C–E). Furthermore, farnesol significantly increased the expression of UCP1, the main factor of thermogenesis, and beige adipocyte-specific markers including TMEM26, TBX1, and CD137 in the iWAT and eWAT from HFD-induced obese C57BL/6 mice (p < 0.05) (Figure Figure3F3F). Reference: Front Pharmacol. 2017 Sep 20;8:654. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/29033835/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 449.70

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
Formulation protocol:
In vitro protocol: 1. Cordeiro Rde A, Nogueira GC, Brilhante RS, Teixeira CE, Mourão CI, Castelo-Branco Dde S, Paiva Mde A, Ribeiro JF, Monteiro AJ, Sidrim JJ, Rocha MF. Farnesol inhibits in vitro growth of the Cryptococcus neoformans species complex with no significant changes in virulence-related exoenzymes. Vet Microbiol. 2012 Oct 12;159(3-4):375-80. doi: 10.1016/j.vetmic.2012.04.008. Epub 2012 Apr 19. PMID: 22580194.
In vivo protocol: 1. Kim HL, Jung Y, Park J, Youn DH, Kang J, Lim S, Lee BS, Jeong MY, Choe SK, Park R, Ahn KS, Um JY. Farnesol Has an Anti-obesity Effect in High-Fat Diet-Induced Obese Mice and Induces the Development of Beige Adipocytes in Human Adipose Tissue Derived-Mesenchymal Stem Cells. Front Pharmacol. 2017 Sep 20;8:654. doi: 10.3389/fphar.2017.00654. PMID: 29033835; PMCID: PMC5627035. 2. Ku CM, Lin JY. Farnesol, a sesquiterpene alcohol in essential oils, ameliorates serum allergic antibody titres and lipid profiles in ovalbumin-challenged mice. Allergol Immunopathol (Madr). 2016 Mar-Apr;44(2):149-59. doi: 10.1016/j.aller.2015.05.009. Epub 2015 Aug 28. PMID: 26318416.

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1: Horev B, Klein MI, Hwang G, Li Y, Kim D, Koo H, Benoit DS. pH-activated nanoparticles for controlled topical delivery of farnesol to disrupt oral biofilm virulence. ACS Nano. 2015 Mar 24;9(3):2390-404. doi: 10.1021/nn507170s. Epub 2015 Feb 13. PubMed PMID: 25661192; PubMed Central PMCID: PMC4395463.

2: Szűcs G, Murlasits Z, Török S, Kocsis GF, Pálóczi J, Görbe A, Csont T, Csonka C, Ferdinandy P. Cardioprotection by farnesol: role of the mevalonate pathway. Cardiovasc Drugs Ther. 2013 Aug;27(4):269-77. doi: 10.1007/s10557-013-6460-2. PubMed PMID: 23673412.

3: Park JS, Kwon JK, Kim HR, Kim HJ, Kim BS, Jung JY. Farnesol induces apoptosis of DU145 prostate cancer cells through the PI3K/Akt and MAPK pathways. Int J Mol Med. 2014 May;33(5):1169-76. doi: 10.3892/ijmm.2014.1679. Epub 2014 Feb 27. PubMed PMID: 24584843.

4: Strube-Bloss MF, Brown A, Spaethe J, Schmitt T, Rössler W. Extracting the Behaviorally Relevant Stimulus: Unique Neural Representation of Farnesol, a Component of the Recruitment Pheromone of Bombus terrestris. PLoS One. 2015 Sep 4;10(9):e0137413. doi: 10.1371/journal.pone.0137413. eCollection 2015. Erratum in: PLoS One. 2015;10(9):e0139296. PubMed PMID: 26340263; PubMed Central PMCID: PMC4560401.

5: Ku CM, Lin JY. Farnesol, a sesquiterpene alcohol in essential oils, ameliorates serum allergic antibody titres and lipid profiles in ovalbumin-challenged mice. Allergol Immunopathol (Madr). 2016 Mar-Apr;44(2):149-59. doi: 10.1016/j.aller.2015.05.009. Epub 2015 Aug 28. PubMed PMID: 26318416.

6: Ha J, Wang Y, Jang H, Seog H, Chen X. Determination of E,E-farnesol in Makgeolli (rice wine) using dynamic headspace sampling and stir bar sorptive extraction coupled with gas chromatography-mass spectrometry. Food Chem. 2014 Jan 1;142:79-86. doi: 10.1016/j.foodchem.2013.07.038. Epub 2013 Jul 17. PubMed PMID: 24001815.

7: Mogen AB, Chen F, Ahn SJ, Burne RA, Wang D, Rice KC. Pluronics-Formulated Farnesol Promotes Efficient Killing and Demonstrates Novel Interactions with Streptococcus mutans Biofilms. PLoS One. 2015 Jul 29;10(7):e0133886. doi: 10.1371/journal.pone.0133886. eCollection 2015. PubMed PMID: 26222384; PubMed Central PMCID: PMC4519314.

8: Bozó A, Domán M, Majoros L, Kardos G, Varga I, Kovács R. The in vitro and in vivo efficacy of fluconazole in combination with farnesol against Candida albicans isolates using a murine vulvovaginitis model. J Microbiol. 2016 Nov;54(11):753-760. Epub 2016 Oct 29. PubMed PMID: 27796932.

9: Cotoras M, Castro P, Vivanco H, Melo R, Mendoza L. Farnesol induces apoptosis-like phenotype in the phytopathogenic fungus Botrytis cinerea. Mycologia. 2013 Jan-Feb;105(1):28-33. doi: 10.3852/12-012. Epub 2012 Sep 6. PubMed PMID: 22962358.

10: Kovács R, Bozó A, Gesztelyi R, Domán M, Kardos G, Nagy F, Tóth Z, Majoros L. Effect of caspofungin and micafungin in combination with farnesol against Candida parapsilosis biofilms. Int J Antimicrob Agents. 2016 Apr;47(4):304-10. doi: 10.1016/j.ijantimicag.2016.01.007. Epub 2016 Feb 17. PubMed PMID: 26968084.

11: Cerca N, Gomes F, Bento JC, França A, Rolo J, Miragaia M, Teixeira P, Oliveira R. Farnesol induces cell detachment from established S. epidermidis biofilms. J Antibiot (Tokyo). 2013 May;66(5):255-8. doi: 10.1038/ja.2013.11. Epub 2013 Apr 3. PubMed PMID: 23549353.

12: Fernandes RA, Monteiro DR, Arias LS, Fernandes GL, Delbem AC, Barbosa DB. Biofilm formation by Candida albicans and Streptococcus mutans in the presence of farnesol: a quantitative evaluation. Biofouling. 2016;32(3):329-38. doi: 10.1080/08927014.2016.1144053. PubMed PMID: 26905659.

13: Inoue Y, Togashi N, Hamashima H. Farnesol-Induced Disruption of the Staphylococcus aureus Cytoplasmic Membrane. Biol Pharm Bull. 2016;39(5):653-6. doi: 10.1248/bpb.b15-00416. PubMed PMID: 27150138.

14: Léger T, Garcia C, Ounissi M, Lelandais G, Camadro JM. The metacaspase (Mca1p) has a dual role in farnesol-induced apoptosis in Candida albicans. Mol Cell Proteomics. 2015 Jan;14(1):93-108. doi: 10.1074/mcp.M114.041210. Epub 2014 Oct 27. PubMed PMID: 25348831; PubMed Central PMCID: PMC4288266.

15: Lee JH, Kim C, Kim SH, Sethi G, Ahn KS. Farnesol inhibits tumor growth and enhances the anticancer effects of bortezomib in multiple myeloma xenograft mouse model through the modulation of STAT3 signaling pathway. Cancer Lett. 2015 May 1;360(2):280-93. doi: 10.1016/j.canlet.2015.02.024. Epub 2015 Feb 16. PubMed PMID: 25697480.

16: Huchelmann A, Brahim MS, Gerber E, Tritsch D, Bach TJ, Hemmerlin A. Farnesol-mediated shift in the metabolic origin of prenyl groups used for protein prenylation in plants. Biochimie. 2016 Aug;127:95-102. doi: 10.1016/j.biochi.2016.04.021. Epub 2016 Apr 29. PubMed PMID: 27138105.

17: de Oliveira Júnior WM, Benedito RB, Pereira WB, de Arruda Torres P, Ramos CA, Costa JP, da Rocha Tomé A, de Sousa DP, de Freitas RM, de Fatima Formiga Melo Diniz M, de Almeida RN. Farnesol: antinociceptive effect and histopathological analysis of the striatum and hippocampus of mice. Fundam Clin Pharmacol. 2013 Aug;27(4):419-26. doi: 10.1111/j.1472-8206.2012.01030.x. Epub 2012 Feb 20. PubMed PMID: 22340189.

18: Constantino JA, Delgado-Rastrollo M, Pacha-Olivenza MA, Pérez-Giraldo C, Quiles M, González-Martín ML, Gallardo-Moreno AM. In vivo bactericidal efficacy of farnesol on Ti6Al4V implants. Rev Esp Cir Ortop Traumatol. 2016 Jul-Aug;60(4):260-6. doi: 10.1016/j.recot.2016.04.004. Epub 2016 May 26. English, Spanish. PubMed PMID: 27239017.

19: De Loof A. The essence of female-male physiological dimorphism: differential Ca2+-homeostasis enabled by the interplay between farnesol-like endogenous sesquiterpenoids and sex-steroids? The Calcigender paradigm. Gen Comp Endocrinol. 2015 Jan 15;211:131-46. doi: 10.1016/j.ygcen.2014.12.003. Epub 2014 Dec 22. Review. PubMed PMID: 25540913.

20: Lindsay AK, Deveau A, Piispanen AE, Hogan DA. Farnesol and cyclic AMP signaling effects on the hypha-to-yeast transition in Candida albicans. Eukaryot Cell. 2012 Oct;11(10):1219-25. doi: 10.1128/EC.00144-12. Epub 2012 Aug 10. PubMed PMID: 22886999; PubMed Central PMCID: PMC3485915.