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1g |
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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 to farnesyl glucuronide, hydroxyfarnesol and hydroxyfarnesyl glucuronide by human tissue microsomes. ... Farnesol metabolism was examined by a sensitive LC (liquid chromatography)-MS/MS method. Results indicate that farnesol is a good substrate for glucuronidation in human liver, kidney and intestine microsomes (values in nmol/min per mg). Initial analysis using expressed human UGTs indicated that UGTs 1A1 and 2B7 were primarily responsible for glucuronidation in vitro, with significantly lower activity for all the other UGTs tested (UGTs 1A3, 1A4, 1A6, 1A9 and 2B4). Kinetic analysis and inhibition experiments indicate that, in liver microsomes, UGT1A1 is primarily responsible for farnesol glucuronidation; however, in intestine microsomes, UGT2B7 is probably the major isoform involved, with a very-low-micromolar K(m). ... Farnesol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-(3,7,11-trimethyldodeca-2,6,10-trienoxy)oxane-2-carboxylic acid. |
References | |
Additional Infomation |
Farnesol is a colorless liquid with a delicate floral odor. (NTP, 1992)
A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Farnesol has been reported in Aristolochia triangularis, Humulus lupulus, and other organisms with data available. A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) See also: Chamaemelum nobile flower (part of). Mechanism of Action ... the effect of 20 uM farnesol on the distribution of protein kinase C (PKC) between cytosolic and membrane fractions of HeLa S3K cells and fibroblasts line CF-3 was examined. In HeLa cells farnesol caused translocation of PKC from membrane fraction to cytosol after 1h of incubation and also prevented PMA-stimulated induction of PKC translocation from cytosol to membranes. Up to 6 h of incubation, there was no effect of farnesol on PKC localization in CF-3 fibroblasts. The results point to possible involvement of PKC in the toxic effect of farnesol ... ... in MCF-7 human breast cancer cells, farnesol induced the expression of thyroid hormone receptor (THR) beta1 mRNA and protein at concentrations that inhibited cell growth. Changes in the expression of THR responsive genes, however, suggested that farnesol inhibits THR-mediated signaling. Protein extracts from cells treated with farnesol displayed decreased binding to oligodeoxynucleotides containing a consensus sequence for the THR response element, despite the higher THRbeta1 content, providing a mechanism to explain the decreased transcriptional activity of cellular THRs. Farnesol-mediated apoptosis was prevented by transformation with a plasmid coding for the phosphatidic acid (PA) phosphatase LPP3, but not by an inactive LPP3 point mutant. Farnesol did not directly inhibit LPP3 PA phosphatase enzyme activity in an in vitro mixed micelle assay. ... |
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
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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.