2D Structure

3D Structure

Farnesol


Properties
PID PID00038
Mol. Weight 222.372 g/mol
LogP 4.16
Water solubility In water, 1.7 mg/L at 25 °C (est)
Hydrogen Bond Donor 1
Hydrogen Bond Acceptor 1
Rotatable Bonds 7
XLogP3-AA 4.8

Farnesol

Identifiers
Formula C15H26O
PubChem CID 445070
FEMA 2478
Flavor Profile Delicate Flowery Odor, Mild, Oily, Weak Citrus-Lime Odor, Weak Citrus-Lime Taste
Smiles CC(C)=CCC/C(C)=C/CC/C(C)=C/CO
InChl Key CRDAMVZIKSXKFV-YFVJMOTDSA-N
InChl 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+
CAS Registry Number 4602-84-0, 106-28-5
IUPAC Systematic Name (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets


Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
Clove TreeDing Xiang (丁香)Caryophylli FlosWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Dahurian AngelicaBai Zhi(白芷)Angelicae Dahuricae RadixWarm, PungentLung, Spleen, StomachView Graph
Fructus GalangaeHong Dou Kou(红豆蔻 )Galanga Galangal FruitWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Round Cardamon FruitDou Kou (豆蔻)Amomi Fructus RotundusWarm, Pungent,Spleen, Lung, StomachView Graph
Lily Magnolia Buds Equivalent plant: Magnolia liliXin Yi (辛夷)Magnoliae FlosWarm, PungentLung, Spleen, StomachView Graph
Alpinia katsumadaiCao Dou Kou(草豆蔻)Katsumada GalangalWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Cassiabarktree TwigGui Zhi (桂枝)Cinnamomi RamulusWarm, Pungent, SweetLung, Bladder, HeartView Graph
Artemisia argyiAi Ye(艾叶)Argy Wormwood Leaf Equivalent plant: Artemisia monWarm,Pungent,BitterLung,Spleen,LiverView Graph
Chinese Ephedra Equivalent plant: Ephedra equisetiMa Huang (麻黄)Ephedrae HerbaWarm, Pungent, Slightly BitterLung, BladderView Graph
Ardisiae japonicaeAi Di Cha(矮地茶)Japanese Ardisia HerbMild,Pungent,BitterSpleen,HeartView Graph
Artemisia argyiAi Ye(艾叶)Argy Wormwood Leaf Equivalent plant: Artemisia monWarm,Pungent,BitterLung,Spleen,LiverView Graph
Aromatic TurmericYu Jin (郁金)Curcumae RadixCold, Pungent, BitterLiver, Heart, LungView Graph

Pharmacological action

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is

hydrophobic, and thus insoluble in water, but miscible with oils. It is used in perfumery to emphasize the odors of sweet floral perfumes. Its method

of action for enhancing perfume scent is as a co-solvent that regulates the volatility of the odorants. It is also a flavoring ingredient. Farnesol is

a natural pesticide for mites and is a pheromone for several other insects.

Farnesol is a sesqiterpene alcohol produced by many organisms, and also found in sereval essential oils,e.g. from Pluchea dioscoridis, Zea mays and

Pittosporum undulatum, possibly these plants from parasitoc included damnges.It is used in perfumery to emphasize the odors of sweet floral perfumes.

Its method of action for enhancing perfume scent is as a co-solvent that regulates the volatility of the odorants.

Farnesol is subject to restrictions on its use in perfumery as some people may become sensitised to it, however the evidence that farnesol can

cause an allergic reaction in humans is disputed.

Farnesol is a key metabolite of the mevalonate pathway and known as an antioxidant.

Farnesol is a naturally occurring sesquiterpene that was originally isolated from essential oils found in many plants.



Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.

References

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2 Kromidas L, Perrier E, Flanagan J, et al. Release of antimicrobial actives from microcapsules by the action of axillary bacteria[J]. International journal of cosmetic science, 2006, 28(2): 103-108.

3 Navarathna D H, Hornby J M, Krishnan N, et al. Effect of farnesol on a mouse model of systemic candidiasis, determined by use of a DPP3 knockout mutant of Candida albicans[J]. Infection and immunity, 2007, 75(4): 1609-1618.

4 Brehm-Stecher B F, Johnson E A. Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone[J]. Antimicrobial agents and chemotherapy, 2003, 47(10): 3357-3360.

5 Jabra-Rizk M A, Shirtliff M, James C, et al. Effect of farnesol on Candida dubliniensis biofilm formation and fluconazole resistance[J]. FEMS yeast research, 2006, 6(7): 1063-1073.

6 Szűcs G, Murlasits Z, Török S, et al. Cardioprotection by farnesol: role of the mevalonate pathway[J]. Cardiovascular drugs and therapy, 2013, 27(4): 269-277.

7 Qamar W, Sultana S. Farnesol ameliorates massive inflammation, oxidative stress and lung injury induced by intratracheal instillation of cigarette smoke extract in rats: an initial step in lung chemoprevention[J]. Chemico-biological interactions, 2008, 176(2-3): 79-87.

8 Jahangir T, Khan T H, Prasad L, et al. Farnesol prevents Fe-NTA-mediated renal oxidative stress and early tumour promotion markers in rats[J]. Human & experimental toxicology, 2006, 25(5): 235-242.

9 Khan R, Sultana S. Farnesol attenuates 1, 2-dimethylhydrazine induced oxidative stress, inflammation and apoptotic responses in the colon of Wistar rats[J]. Chemico-Biological Interactions, 2011, 192(3): 193-200.

10 Cerca N, Gomes F, Bento J C, et al. Farnesol induces cell detachment from established S. epidermidis biofilms[J]. The Journal of antibiotics, 2013, 66(5): 255.

11 Grace M H. Chemical composition and biological activity of the volatiles of Anthemis melampodina and Pluchea dioscoridis[J]. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives, 2002, 16(2): 183-185.

12 Medeiros J R, Campos L B, Mendonça S C, et al. Composition and antimicrobial activity of the essential oils from invasive species of the Azores, Hedychium gardnerianum and Pittosporum undulatum[J]. Phytochemistry, 2003, 64(2): 561-565.

13 Schnee C, Köllner T G, Gershenzon J, et al. The maize gene terpene synthase 1 encodes a sesquiterpene synthase catalyzing the formation of (E)-β-farnesene,(E)-nerolidol, and (E, E)-farnesol after herbivore damage[J]. Plant physiology, 2002, 130(4): 2049-2060.

14 Gomes F I A, Teixeira P, Azeredo J, et al. Effect of farnesol on planktonic and biofilm cells of Staphylococcus epidermidis[J]. Current microbiology, 2009, 59(2): 118-122.

15 Gomes F, Cerca N, Azeredo J, et al. Farnesol as antibiotics adjuvant in Staphylococcus epidermidis control in vitro[J]. The American journal of the medical sciences, 2011, 341(3): 191-195.

16 https://en.wikipedia.org/wiki/Farnesol

17 Magnard J L, Roccia A, Caissard J C, et al. Biosynthesis of monoterpene scent compounds in roses[J]. Science, 2015, 349(6243): 81-83.

18 Kaneko M, Togashi N, Hamashima H, et al. Effect of farnesol on mevalonate pathway of Staphylococcus aureus[J]. The Journal of antibiotics, 2011, 64(8): 547.

19 Raner G M, Muir A Q, Lowry C W, et al. Farnesol as an inhibitor and substrate for rabbit liver microsomal P450 enzymes[J]. Biochemical and biophysical research communications, 2002, 293(1): 1-6.

20 Bozó A, Domán M, Majoros L, et al. The in vitro and in vivo efficacy of fluconazole in combination with farnesol against Candida albicans isolates using a murine vulvovaginitis model[J]. Journal of Microbiology, 2016, 54(11): 753-760.

21 Correll C C, Ng L, Edwards P A. Identification of farnesol as the non-sterol derivative of mevalonic acid required for the accelerated degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase[J]. Journal of Biological Chemistry, 1994, 269(26): 17390-17393.

22 Forman B M, Goode E, Chen J, et al. Identification of a nuclear receptor that is activated by farnesol metabolites[J]. Cell, 1995, 81(5): 687-693.

23 Duncan R E, Archer M C. Farnesol induces thyroid hormone receptor (THR) β1 but inhibits THR-mediated signaling in MCF-7 human breast cancer cells[J]. Biochemical and biophysical research communications, 2006, 343(1): 239-243.

24 Inoue Y, Shiraishi A, Hada T, et al. The antibacterial effects of terpene alcohols on Staphylococcus aureus and their mode of action[J]. FEMS microbiology letters, 2004, 237(2): 325-331.

25 Jabra-Rizk M A, Meiller T F, James C E, et al. Effect of farnesol on Staphylococcus aureus biofilm formation and antimicrobial susceptibility[J]. Antimicrobial agents and chemotherapy, 2006, 50(4): 1463-1469.

26 Peleg A Y, Hogan D A, Mylonakis E. Medically important bacterial–fungal interactions[J]. Nature reviews microbiology, 2010, 8(5): 340.

27 Bogan A A, Cohen F E, Scanlan T S. Natural ligands of nuclear receptors have conserved volumes[J]. Nature Structural and Molecular Biology, 1998, 5(8): 679.

28 Dižová S, Černáková L, Bujdáková H. The impact of farnesol in combination with fluconazole on Candida albicans biofilm: regulation of ERG20, ERG9, and ERG11 genes[J]. Folia microbiologica, 2018: 1-9.

29 Leeder A C, Palma-Guerrero J, Glass N L. The social network: deciphering fungal language[J]. Nature Reviews Microbiology, 2011, 9(6): 440.

30 Calkin A C, Tontonoz P. Transcriptional integration of metabolism by the nuclear sterol-activated receptors LXR and FXR[J]. Nature reviews Molecular cell biology, 2012, 13(4): 213.

31 https://en.wikipedia.org/wiki/Farnesol