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| 1g |
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| Other Sizes |
Farnesol (HSDB445; HSDB-445; HSDB 445) is an inducer of apoptosis in cell cultures. It is also used as an antimicrobial agent, and a flavoring agent.
| ln Vitro |
In Candida albicans, farnesol is a sesquiterpene alcohol that alters intercellular communication. Inhibitory activities of the compound against bacteria, Paracoccidioides brasiliensis, and non-albicans Candida species have also been demonstrated. FARNESOL was evaluated in the concentration range of 0.29-150 μM, and the minimum inhibitory concentration (MIC) was established in accordance with the M27-A3 procedure as stated. The study revealed that farnesol had inhibitory activity (MIC range: 0.29-75.0 μM) against Cryptococcus gattii and Neoformans. While farnesol does not significantly change phospholipase activity, there is a tendency for its activity to decline [1].
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Farnesol is metabolized in human tissue microsomes to farnesylglucuronide, hydroxyfarnesol, and hydroxyfarnesylglucuronide. …The metabolism of farnesol was detected using sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS). Results showed that farnesol is a good substrate for glucuronidation in human liver, kidney, and intestinal microsomes (values expressed in nmol/min/mg). Preliminary analysis using expressed human UGTs indicated that UGT 1A1 and 2B7 were the major enzymes for glucuronidation in vitro, while the activities of all other tested UGTs (UGT 1A3, 1A4, 1A6, 1A9, and 2B4) were significantly lower. Kinetic analysis and inhibition experiments showed that UGT1A1 is the major enzyme for farnesol glucuronidation in liver microsomes; however, in intestinal microsomes, UGT2B7 is likely the major isoenzyme involved, with a very low K(m) value (micromolar level). ... The known metabolites of farnesol include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(3,7,11-trimethyldodecano-2,6,10-trienoxy)oxacyclohexane-2-carboxylic acid. |
| Toxicity/Toxicokinetics |
Interactions
At time 0, pancreatic cancer in hamsters was induced using N-nitrosobis(2-oxopropyl)amine. From week 5 to week 42, animals were fed diets of control, 2% (w/w) perillyl alcohol, or 1% (w/w) farnesol, respectively. Both perillyl alcohol and farnesol reduced the incidence of pancreatic cancer. Compared with the control group, animals treated with perillyl alcohol and farnesol showed higher Bak protein expression (p < 0.05), slightly higher apoptosis rate, lower expression of the anti-apoptotic protein BCL-xL, and lower DNA synthesis rate in proliferative pancreatic duct tumors. The antigenotoxic and antioxidant efficacy of farnesol against cadmium chloride (CdCl2)-induced renal oxidative stress and genotoxicity in Swiss albino mice was evaluated. A single intraperitoneal injection of cadmium chloride (CdCl2, 5 mg/kg body weight) 24 hours later significantly increased chromosomal aberrations and micronucleus formation (p < 0.001). Two doses (1% and 2%/kg body weight) of farnesol were administered orally for seven consecutive days. The results showed that the modulator group significantly inhibited the genotoxic effects of cadmium chloride (p < 0.05). …This study evaluated the protective effect of farnesol (FL) against Fe-NTA (9 mg iron/kg body weight, intraperitoneal injection)-induced oxidative damage and early tumor-promoting markers. Pretreatment of iron-poisoned rats with FL orally for seven consecutive days at doses of 1% and 2%/kg body weight significantly reversed iron-induced increases in H₂O₂ content (p < 0.001), malondialdehyde production, xanthine oxidase activity (p < 0.001), ornithine decarboxylase activity (p < 0.001), and ³³H-thymidine incorporation in renal DNA (p < 0.005), while significantly reducing serum toxicity markers blood urea nitrogen (BUN) and creatinine levels (p < 0.001). Prophylactic treatment with farnesol significantly increased renal glutathione levels and the activities of its dependent enzymes and other phase II metabolic enzymes (such as catalase, glutathione S-transferase, and quinone reductase) in a dose-dependent manner (p < 0.001). Current findings suggest that farnesol significantly reduces oxidative damage and the appearance of tumor markers… Farnesol prolongs the sleep duration induced by barbiturates, even though it itself does not have a hypnotic effect. Non-Human Toxicity Values Oral LD50 in rats > 20 mL/kg (17742 mg/kg body weight) Oral LD50 in rats > 5000 mg/kg body weight Oral LD50 in mice 8764 mg/kg body weight |
| References | |
| Additional Infomation |
Farnesol is a colorless liquid with a faint floral scent. (NTP, 1992)
It is a colorless liquid extracted from the oils of plants such as lemongrass, orange blossom, cyclamen, and tuberose. It is an intermediate in the biosynthesis of cholesterol from mevalonic acid in vertebrates. It has a faint fragrance and is often used in perfume making. (From McGraw-Hill Dictionary of Scientific and Technical Terminology, 5th Edition) Farnesol has been reported to be found in aristolochic acid, hops, and several other organisms with relevant data. It is a colorless liquid extracted from the oils of plants such as lemongrass, orange blossom, cyclamen, and tuberose. It is an intermediate in the biosynthesis of cholesterol from mevalonic acid in vertebrates. It has a faint fragrance and is often used in perfume making. (From McGraw-Hill Dictionary of Scientific and Technical Terminology, 5th Edition) See also: Japanese chamomile (Chamaemelum nobile) flower (partial). Mechanism of Action …The effects of 20 μM farnesol on the distribution of protein kinase C (PKC) in the cytoplasm and membrane components of HeLa S3K cells and CF-3 fibroblasts were investigated. In HeLa cells, 1 hour of farnesol incubation led to the translocation of PKC from the membrane component to the cytoplasm and inhibited PMA-induced PKC translocation from the cytoplasm to the membrane. In CF-3 fibroblasts, 6 hours of incubation had no effect on PKC localization. These results suggest that protein kinase C (PKC) may be involved in the toxic effects of farnesol… In MCF-7 human breast cancer cells, farnesol induced the expression of thyroid hormone receptor (THR) β1 mRNA and protein at cell growth-inhibiting concentrations. However, changes in the expression of THR-responsive genes indicated that farnesol inhibited THR-mediated signaling. Despite higher THRβ1 levels, the protein extracts from farnesol-treated cells showed reduced binding affinity to oligodeoxynucleotides containing THR-responsive element concordant sequences, providing a mechanism to explain the decreased cellular THR transcriptional activity. Transforming cells with a plasmid encoding phosphatase LPP3 prevented farnesol-mediated apoptosis, but the LPP3 point mutant did not. In in vitro mixed micelle assays, farnesol did not directly inhibit the activity of LPP3 PA phosphatase. ... |
| Molecular Formula |
C15H26O
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|---|---|
| Molecular Weight |
222.37
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| Exact Mass |
222.198
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| CAS # |
4602-84-0
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| Related CAS # |
Farnesol-d6;166447-71-8
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| PubChem CID |
3327
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
283.4±0.0 °C at 760 mmHg
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| Melting Point |
< 25 °C
; < 25 °C
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| Flash Point |
96.1±0.0 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.485
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| LogP |
5.31
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
16
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| Complexity |
265
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C(C)=C\CC/C(C)=C/CC/C(C)=C/CO
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| InChi Key |
CRDAMVZIKSXKFV-UHFFFAOYSA-N
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| 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
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| Chemical Name |
3,7,11-trimethyldodeca-2,6,10-trien-1-ol
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| Synonyms |
HSDB445 HSDB-445 HSDB 445
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~449.70 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (11.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4970 mL | 22.4850 mL | 44.9701 mL | |
| 5 mM | 0.8994 mL | 4.4970 mL | 8.9940 mL | |
| 10 mM | 0.4497 mL | 2.2485 mL | 4.4970 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.