chembox Verifiedfields changed Watchedfields changed verifiedrevid 461098987 Name Farnesol ImageFile Farnesol.png ImageSize 250px ImageName Skeletal formula of farnesol ImageFile1 Farnesol 3D balls.png ImageSize1 250px ImageName1 Ball and stick model IUPACName 2 E ,6 E 3,7,11 trimethyldodeca 2,6,10 trien 1 ol Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 3210 PubChem 3327 ChEMBL Ref ebicite changed EBI ChEMBL 25308 UNII Ref fdacite correct FDA UNII X23PI60R17 InChI 1 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 InChIKey CRDAMVZIKSXKFV UHFFFAOYAI StdInChI Ref stdinchicite correct chemspider StdInChI 1S C15H26O c1 ... C at 0.35 mmHg br 283 284.00 C at 760 mmHg Farnesol is a natural organic compound which is an acyclic ... starting compound for organic synthesis . Uses Farnesol is present in many essential oil s such as citronella .... It is especially used in lilac perfumes. Farnesol is a natural pesticide for mites and is a pheromone for several other insects. In a 1994 report released by five top cigarette companies, farnesol ... Farnesol is found in a flower extract with a long history of use in perfumery. The pure substance farnesol was named ca. 1900 1905 after Vachellia farnesiana Farnese acacia tree Vachellia farnesiana ... browse farnesol Etymology of farnesol, accessed August 27, 2009. ref The plant itself was brought ... 57, 3, March, 1885 ref Health effects Farnesol has been suggested to function as a chemopreventative ... in farnesol induced apoptosis journal Cancer Lett. volume 287 issue 2 pages 123 35 year 2009 month June pmid 19520495 doi 10.1016 j.canlet.2009.05.015 url pmc 2815016 ref Farnesol is used as a deodorant ... 28 issue 2 pages 103 108 ref Farnesol should be avoided by people with perfume allergy. ref http ... Category Perfume ingredients Category Flavors Category Insect pheromones da Farnesol de Farnesol et Farnesool fr Farn sol it Farnesolo hu Farnezol nl Farnesol ja pl Farnezol ru ... more details
enzyme Name farnesol 2 isomerase EC number 5.2.1.9 CAS number 94047 16 2 IUBMB EC number 5 2 1 9 GO code 0047885 image width caption In enzymology , a farnesol 2 isomerase EC number 5.2.1.9 is an enzyme that catalysis catalyzes the chemical reaction 2 trans,6 trans farnesol math rightleftharpoons math 2 cis,6 trans farnesol Hence, this enzyme has one substrate biochemistry substrate , 2 trans,6 trans farnesol , and one product chemistry product , 2 cis,6 trans farnesol . This enzyme belongs to the family of isomerase s, specifically Cis trans isomerism cis trans isomerases . The systematic name of this enzyme class is 2 trans,6 trans farnesol 2 cis trans isomerase . This enzyme is also called farnesol isomerase . References reflist 1 cite journal author Picken D and Swanson S date 1984 title Biosynthesis of gamma bisabolene in tissue cultures of Andrographis paniculata journal Can. J. Chem. volume 62 pages 2079&ndash 2088 doi 10.1139 v84 355 issue 10 isomerase stub Category EC 5.2.1 Category Enzymes of unknown structure ... more details
enzyme Name farnesol dehydrogenase EC number 1.1.1.216 CAS number 90804 55 0 IUBMB EC number 1 1 1 216 GO code 0047886 image width caption In enzymology , a farnesol dehydrogenase EC number 1.1.1.216 is an enzyme that catalysis catalyzes the chemical reaction 2 trans,6 trans farnesol NADP sup sup math rightleftharpoons math 2 trans,6 trans farnesal NADPH H sup sup Thus, the two substrate biochemistry substrates of this enzyme are 2 trans,6 trans farnesol and nicotinamide adenine dinucleotide phosphate NADP sup sup , whereas its 3 product chemistry products are 2 trans,6 trans farnesal , nicotinamide adenine dinucleotide phosphate NADPH , and hydrogen ion H sup sup . This enzyme belongs to the family of oxidoreductase s, specifically those acting on the CH OH group of donor with NAD or NADP as acceptor. The systematic name of this enzyme class is 2 trans,6 trans farnesol NADP 1 oxidoreductase . Other names in common use include NADP farnesol dehydrogenase , and farnesol nicotinamide adenine dinucleotide phosphate dehydrogenase . References reflist 1 cite journal author Inoue H, Tsuji H and Uritani I date 1984 title Characterization and activity change of farnesol dehydrogenase in black rot fungus infected sweet potato journal Agric. Biol. Chem. volume 48 pages 733&ndash 738 1.1.1 enzyme stub Category EC 1.1.1 Category NADPH dependent enzymes Category Enzymes of unknown structure it Farnesolo deidrogenasi ja ... more details
DISPLAYTITLE C sub 15 sub H sub 26 sub O The molecular formula C sub 15 sub H sub 26 sub O may refer to Bisabolol Carotol Cubebol Farnesol Levomenol Nerolidol Patchouli alcohol molFormDisambig fr C15H26O it C15H26O ... more details
In lipid anchored proteins , a covalently attached fatty acid such as palmitate or myristate serves to anchor them to either face of the cell membrane . Examples include G protein s and certain kinase s. It is believed that the fatty acid chain inserts and assumes a place in the lipid bilayer bilayer structure of the membrane alongside the similar fatty acid tails of the surrounding lipid molecules. Potential points of attachment include the terminal amino group of the protein backbone and the side chain of cysteine residues. Prenylation is the attachment of lipid chains to proteins to facilitate their interaction with the cell membrane . Some important prenylation chains are geranylgeraniol , farnesol and dolichol , all products of the HMG CoA reductase metabolic pathway . Other anchors include the GPI anchor see there . The bond is covalent. ref name Karp2009 cite book author Gerald Karp title Cell and Molecular Biology Concepts and Experiments url http books.google.com books?id arRGYE0GxRQC&pg PA128 accessdate 13 November 2010 year 2009 publisher John Wiley and Sons isbn 9780470483374 pages 128 ref References Reflist Cell membranes DEFAULTSORT Lipid Anchored Protein Category Membrane biology Category Membrane proteins Category Lipoproteins Category Posttranslational modification Membrane protein stub sr Lipid vezani proteini ... more details
chembox verifiedrevid 288107412 Reference ref name Merck Merck Index , 11th Edition, 6388 . ref Name trans Nerolidol small top small and cis Nerolidol small bottom small ImageFile1 Nerolidol.png ImageSize1 200px ImageName1 trans Nerolidol ImageFile2 Nerolidol cis.png ImageSize2 200px ImageName2 cis Nerolidol IUPACName 3,7,11 Trimethyl 1,6,10 dodecatrien 3 ol OtherNames Peruviol Section1 Chembox Identifiers CASNo Ref cascite CASNo 7212 44 4 CASOther unspecified br 3790 78 1 cis br 40716 66 3 trans SMILES CC C CCCC C CCCC C O C C Section2 Chembox Properties Formula C sub 15 sub H sub 26 sub O MolarMass 222.37 g mol Density 0.872 g cm sup 3 sup MeltingPt BoilingPt 122 C at 3 mmHg Nerolidol , also known as peruviol, is a naturally occurring terpene sesquiterpene found in the essential oil s of many types of plants and flowers. ref name Merck There are two isomer s of nerolidol, cis and trans , which differ in the geometry about the central double bond. Nerolidol is present in neroli , ginger , jasmine , lavender , Melaleuca tea tree and lemon grass . The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also currently under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs. ref K. Moser et al. European Journal of Pharmaceutics and Biopharmaceutics 52 2001 103 112 doi 10.1016 S0939 6411 01 00166 7 ref See also Linalool Farnesol References reflist Category Alcohols Category Alkenes Category Perfume ingredients Category Flavors Category Sesquiterpenes de Nerolidol pl Nerolidol ru ... more details
Unreferenced stub auto yes date December 2009 Chembox verifiedrevid 424660305 ImageFile Farnesyl pyrophosphate.png ImageSize 220px ImageName Skeletal formula ImageFile1 Farnesyl pyrophosphate 3D balls.png ImageSize1 250px ImageName1 Ball and stick model IUPACName OtherNames Section1 Chembox Identifiers CASNo Ref cascite correct ?? CASNo 13058 04 3 PubChem 706 SMILES MeSHName farnesyl pyrophosphate Section2 Chembox Properties Formula C sub 15 sub H sub 28 sub O sub 7 sub P sub 2 sub MolarMass 382.326 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Farnesyl pyrophosphate FPP , also known as farnesyl diphosphate FDP , is an intermediate in the HMG CoA reductase pathway used by organisms in the biosynthesis of terpene s, terpenoid s, and sterol s. It is the immediate precursor of squalene via the enzyme squalene synthase , dehydrodolichol diphosphate a precursor of dolichol , and geranylgeranyl pyrophosphate GGPP . Biosynthesis Farnesyl pyrophosphate synthase a prenyl transferase catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3 isopentenyl pyrophosphate to form farnesyl pyrophosphate, as is shown in the following two steps Dimethylallyl pyrophosphate reacts with 3 isopentenyl pyrophosphate to form geranyl pyrophosphate Image Cholesterol Synthesis Reaction8.png Geranyl pyrophosphate then reacts with another molecule of 3 isopentenyl pyrophosphate to form farnesyl pyrophosphate Image Cholesterol Synthesis Reaction9.png Regulation The above reactions are inhibited by bisphosphonate s used for osteoporosis . Related compounds Farnesene Farnesol Geranyl pyrophosphate Geranylgeranyl pyrophosphate Cholesterol metabolism intermediates DEFAULTSORT Farnesyl Pyrophosphate Category Organophosphates Category Sesquiterpenes Biochem stub fi Farnesyylipyrofosfaatti zh ... more details
Sesquiterpenes are a class of terpene s that consist of three isoprene units and have the molecular formula C sub 15 sub H sub 24 sub . Like monoterpenes , sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as redox oxidation or rearrangement reaction rearrangement produce the related sesquiterpenoids . Sesquiterpenes are found naturally in plants and insects, as semiochemical s, e.g. defensive agents or pheromones. Acyclic When geranyl pyrophosphate reacts with isopentenyl pyrophosphate , the result is the 15 carbon farnesyl pyrophosphate , which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene . Oxidation can then provide sesquiterpenoids such as farnesol . Image Farnesyl pyrophosphate.png thumb 300px none Farnesyl pyrophosphate Monocyclic With the increased chain length and additional double bond, the number of possible ways that cyclization can occur is also increased, and there exists a wide variety of cyclic sesquiterpenes. In addition to common six membered ring systems such as is found in zingiberene , a constituent of the oil from ginger , cyclization of one end of the chain to the other end can lead to macrocyclic rings such as humulene . Bicyclic image Cadinene.png thumb right 100px &delta Cadinene, a sesquiterpene In addition to common six membered rings such as in the cadinene s, one classic bicyclic sesquiterpene is caryophyllene , from the oil of clove s, which has a nine membered ring and cyclobutane ring. Additional unsaturation provides aromatic bicyclic sesquiterpenoids such as vetivazulene and guaiazulene . Tricyclic With the addition of a third ring, the possible structures become increasingly varied. Examples include longifolene , copaene and the alcohol patchoulol . External links MeshName Sesquiterpenes Category Sesquiterpenes es Sesquiterpeno fr Sesquiterp ne pl Seskwiterpeny pt Sesquiterpeno ru fi Seskviterpeeni ... more details
Drugbox verifiedrevid 447621772 IUPAC name 2 E ,6 E 3,7,11 trimethyldodeca 2,6,10 trien 1 yl 1 4 chlorobenzoyl 5 methoxy 2 methyl 1 H indol 3 yl acetate image Infree.png Clinical data tradename Drugs.com drugs.com international indometacin farnesil pregnancy AU A B1 B2 B3 C D X pregnancy US A B C D X pregnancy category legal status Rx only routes of administration Oral Pharmacokinetic data bioavailability protein bound metabolism To indometacin elimination half life 1.5 hours excretion Renal Identifiers CAS number 85801 02 1 ATC prefix ATC suffix ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 4445378 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C34H40ClNO4 c1 23 2 9 7 10 24 3 11 8 12 25 4 19 20 40 33 37 22 30 26 5 36 32 18 17 29 39 6 21 31 30 32 34 38 27 13 15 28 35 16 14 27 h9,11,13 19,21H,7 8,10,12,20,22H2,1 6H3 b24 11 ,25 19 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey CFIGYZZVJNJVDQ LMJOQDENSA N PubChem 5282183 DrugBank Ref drugbankcite correct drugbank DrugBank Chemical data C 34 H 40 Cl 1 N 1 O 4 molecular weight 562.14 g mol smiles CC1 C C2 C N1C O C3 CC C C C3 Cl C CC C2 OC CC O OCC C C CCC C C CCC C C C Indometacin farnesil International Nonproprietary Name INN is a prodrug of the non steroidal anti inflammatory drug indometacin , designed to reduce the occurrence of side effects by esterification of the carboxyl group on indometacin with farnesol . Indometacin farnesil was first approved in Japan in 1991, and is available in Japan and Indonesia , under the trade names Infree and Dialon respectively. External links http di.eisai.co.jp di EPI INF C SC EPI.pdf Infree prescribing information from Eisai Co. NSAIDs Category Non steroidal anti inflammatory drugs Category Indoles Category Prodrugs Category Sesquiterpenes musculoskeletal drug stub ja vi Indomethacin farnesil ... more details
File Sekretausscheidung zur Musth.JPG right thumb Secretion of temporins visible on an African elephant during musth 2007 . Temporins are a family of peptide s isolated originally Citation needed date June 2011 from the skin secretion of the European red frog Rana temporaria . Peptides belonging to the temporin family have been isolated also from closely related North American frogs. In elephant s, temporin is secreted by temporal bone temporal exocrine gland glands during the period of musth . It contains protein s, lipid s notably cholesterol , phenol s, cresol s and sesquiterpene s notably farnesol and its derivatives . ref cite book title The living elephants evolutionary ecology, behavior, and conservation last Sukumar first R year 2003 publisher Oxford University Press isbn 0195107780, 9780195107784 page 155 url http books.google.ca books?id P IS80OBWTgC&pg PA155&lpg PA155 accessdate 2010 12 25 ref In old Sanskrit texts, it is referred to as Rut mammalian reproduction rut fluid d na , or mada and is considered to be a symbol of potency and vigour ref Bana, Kadambari . Transl. P. Rajappa, Penguin Books 2010, p. 19 ref Wild elephants roam the forest and water the trees with their streaming rut fluid. Is it therefore any wonder that the trees in the forest have grown so very tall? However, even from the point of view of ancient Indian elephant science gaja stra ref See, e.g., http books.google.com books?id u6 41berm3IC&printsec frontcover&source gbs ge summary r&cad 0 v onepage&q&f false Franklin Edgerton, The Elephant Lore of the Hindus, Delhi 1985 repr. , pp. 29 38. ref , Temporin mada is not a direct symptom of rut. biology stub Notes reflist Category Peptide hormones Category Biomolecules Category Exocrine system ... more details
Farnesyltransferase is one of the three enzyme s in the prenyltransferase group. Farnesyltransferase FTase adds a 15 carbon isoprenoid called a farnesol farnesyl group to protein s bearing a CaaX Sequence motif motif a four amino acid sequence at the carboxyl terminus of a protein. Farnesyltransferase s targets include members of the Ras superfamily of GTPase small GTP binding proteins critical to cell cycle progression. For this reason, several Farnesyltransferase inhibitor FTase inhibitors are undergoing testing as anti cancer agents. FTase inhibitors have shown efficacy as anti parasitic agents, as well. FTase is also believed to play an important role in development of progeria and various forms of cancer s. Overview Farnesyltransferase Posttranslational modification posttranslationally modifies proteins by adding an isoprenoid lipid called a farnesol farnesyl group to the SH of the cysteine near the end of target proteins to form a thioether linkage. This process, called farnesylation which is a type of prenylation , causes farnesylated proteins to become cell membrane membrane associated due to the hydrophobic nature of the farnesyl group. Most farnesylated proteins are involved in cell signaling cellular signaling wherein membrane association is critical for function. Farnesyltransferase structure and function Farnesyltransferase has two Protein subunit subunit s a 48kDa alpha subunit and a 46kDa FNTB beta subunit . Both subunits are primarily composed of alpha helix alpha helices . The subunit is made of a double layer of paired alpha helices stacked in parallel, which wraps partly around the beta subunit like a blanket. The alpha helices of the subunit form a barrel. The active site is formed by the center of the subunit flanked by part of the subunit. Farnesyltransferase coordinates a zinc cation on its subunit at the lip of the active site. Farnesyltransferase has a hydrophobic binding pocket for farnesyl diphosphate , the lipid donor molecule. ... more details
browse farnesol Etymology of farnesol, accessed August 27, 2009. ref The plant itself was brought ... chemical farnesol , found as a basic sterol precursor in plants, and cholesterol precursor in animals ... farnesol is named. Scented ointment s from Cassie are made in India . ref name purdue Image ... more details
to be farnesol , ref name pmid8626470 cite journal author Meigs TE, Roseman DS, Simoni RD title ... metabolite farnesol in vivo journal J. Biol. Chem. volume 271 issue 14 pages 7916 22 year 1996 month ... issn ref ref name pmid9281305 cite journal author Meigs TE, Simoni RD title Farnesol as a regulator ... Keller RK, Zhao Z, Chambers C, Ness GC title Farnesol is not the nonsterol regulator mediating ... more details
Cleanup date October 2009 File Tipifarnib.png thumb Skeletal formula of tipifarnib R115777 , a farnesyltransferase inhibitor that reached Phase III clinical trials The farnesyltransferase inhibitors FTIs are a class of experimental cancer drugs that target protein farnesyltransferase with the downstream effect of preventing the proper functioning of the Ras protein , which is commonly abnormally active in cancer. Background Studies have suggested that interference with certain post translational modification processes seem to have quite a high selectivity for targeting cells displaying tumour phenotypes although the reason for this is a matter of controversy as will be explained below . After translation, Ras goes through four steps of modification isoprenylation , proteolysis , methylation and palmitoylation . Isoprenylation involves the enzyme farnesyltransferase FTase transferring a farnesol farnesyl group from farnesyl pyrophosphate FPP to the pre Ras protein. Also, a related enzyme geranylgeranyltransferase I GGTase I has the ability to transfer a geranylgeranyl group to K and N Ras the implications of this are discussed below . Farnesyl is necessary to attach Ras to the cell membrane. Without attachment to the cell membrane, Ras is not able to transfer signals from membrane receptors. ref name pmid10961860 cite journal author Reuter CW, Morgan MA, Bergmann L title Targeting the Ras signaling pathway a rational, mechanism based treatment for hematologic malignancies? journal Blood volume 96 issue 5 pages 1655 69 year 2000 month September pmid 10961860 doi url http www.bloodjournal.org cgi pmidlookup?view long&pmid 10961860 ref Development of FTIs After a program of high throughput screening of a class of medication drugs targeting the first step, the farnesyltransferase inhibitors FTIs were developed. ref name pmid10961860 A number of molecules were found to have FTI activity. Some earlier compounds were found to have major side effects, and their development w ... more details
Distinguish from Must disambiguation must . File Sekretausscheidung zur Musth.JPG thumb Temporin secretion during musth File Thai bull elephant in musth.jpg thumb An Asian Elephant bull chained during musth. Note the discharge from the temporal glands. Musth or must IPAc en icon m s t is a periodic condition in bull elephant s, characterized by highly aggressive behavior, accompanied by a large rise in reproductive hormones testosterone levels in an elephant in musth can be as much as 60 times greater than in the same elephant at other times. However, whether this hormonal surge is the sole cause of musth, or merely a contributing factor, is unknown scientific investigation of musth is problematic because during musth even elephants that are otherwise placid may try to kill humans. Cause and effects Although it has often been speculated by zoo visitors ref http www.upali.ch musth en.html ref that musth is linked to Rut mammalian reproduction rut , it is unlikely there is a biological connection because the female elephant s estrus cycle is not seasonally linked, whereas musth most often takes place in winter. Furthermore, bulls in musth have often been known to attack female elephants, regardless of whether or not the females are in heat. There has been speculation that there may be a connection between musth and dominance behaviour. Often, elephants in musth discharge a thick tar like secretion called temporin from the temporal bone temporal ducts on the sides of the head. Temporin contains proteins , lipids notably cholesterol , phenols , cresols and sesquiterpenes notably farnesol and its derivatives . ref cite book title The living elephants evolutionary ecology, behavior, and conservation last Sukumar first R authorlink coauthors year 2003 publisher Oxford University Press location USA isbn 0195107780, 9780195107784 page 155 pages 478 url http books.google.ca books?id P IS80OBWTgC&pg PA155&lpg PA155&dq temporin elephant v onepage&q temporin 20elephant&f fal ... more details
Image RoseEssentialOil.png 250px thumb right Rose Rosa damascena essential oil in clear glass vial Rose oil , meaning either rose otto attar of rose , attar of roses or rose absolute , is the essential oil extracted from the petal s of various types of rose . Rose ottos are extracted through steam distillation , while rose absolutes are obtained through solvent extraction or supercritical carbon dioxide supercritical carbon dioxide extraction , with the absolute being used more commonly in perfumery . Even with their high price and the advent of organic synthesis , rose oils are still perhaps the most widely used essential oil in perfumery. Components wiktionary rose oil Two major species of rose are cultivated for the production of rose oil Rosa damascena , the damask rose, which is widely grown in Bulgaria , Turkey , Russia , Pakistan , India , Uzbekistan , Iran and China Rosa centifolia , the cabbage rose, which is more commonly grown in Morocco , France and Egypt Bulgaria produces about 70 of all rose oil in the world. ref http www.centcom.mil bulgaria Bulgaria U.S. Central Command Factbook ref Other significant producers are Morocco, Iran and Turkey. Recently, China has begun producing rose oil as well. Citation needed date October 2008 The most common chemical compounds present in rose oil are citronellol , geraniol , nerol , linalool , phenyl ethyl alcohol , farnesol , stearoptene , pinene , pinene , terpinene , limonene , p cymene , camphene , caryophyllene , Citral neral , citronellyl acetate , geranyl acetate , neryl acetate , eugenol , methyl eugenol , rose oxide , damascenone , damascenone , benzaldehyde , benzyl alcohol , rhodinyl acetate , phenyl ethyl formate The key flavor compounds that contribute to the distinctive scent of rose oil, however, are beta damascenone , beta damascone , beta ionone , and rose oxide . Beta damascenone presence and quantity is considered as the marker for the quality of rose oil. Even though these compounds ex ... more details
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